plants

Review
Phytochemical and Pharmacological Study of the
Eysenhardtia Genus
Abraham Garcia-Campoy 1 , Efrén Garcia 2 and Alethia Muñiz-Ramirez 3, *
1 Laboratorio de Investigación de Productos Naturales, Escuela Superior de Ingeniería Química e Industrias
extractivas Instituto Politécnico Nacional, Av. Instituto Politécnico Nacional S/N, Unidad Profesional Adolfo
López Mateos, Ciudad de Mexico CP 07708, Mexico; abrahamhgc27@hotmail.com
2 Laboratorio de Química Supramolecular y Nanociencias, Instituto Politécnico Nacional, Acueducto S/N,
Barrio la laguna Ticomán, Ciudad de Mexico CP 07340, Mexico; efren1003@yahoo.com.mx
3 CONACYT-IPICYT/CIIDZA, Camino a la Presa de San José 2055, Col. Lomas 4 Sección,
San Luis Potosí S.L.P CP 78216, Mexico
* Correspondence: alethia.muniz@ipicyt.edu.mx




Received: 29 July 2020; Accepted: 18 August 2020; Published: 31 August 2020


Abstract: The participation of natural products in health care has been remarkable, and today they
continue to play a key role in the discovery and development of new treatments. Phytochemical
studies together with pharmacological tests have managed to integrate bioactive agents as an
alternative solution to reduce or regulate the problems caused by diseases. The Eysenhardtia genus
is a family of plants that are rich in secondary metabolites, which have shown potential activity
in the control and mitigation of urinary disorders, diabetes, oxidative stress, protein glycosylation,
microbial infections, inflammation, pain or discomfort, muscle contractions, cytotoxicity, or as a
cellular or neuronal signaling modulator. These conditions generally appear in comorbid diseases,
which motivated the bibliographic review associated with the plant. This document presents the
beneficial actions produced by Eysenhardtia extracts and/or bioactives to inhibit, control, or reduce the
complications or discomfort of degenerative diseases and thus generate new therapeutic alternatives.

Keywords: Eysenhardtia; phytochemical; pharmacological

1. Introduction
The relationship between humanity and medicinal plants goes back to ancient times. The oldest
records found correspond to the Sumerians, approximately 5000 years ago [1]. The growth and
development of civilizations have been closely linked to the use and exploitation of the healing properties
of medicinal plants [2]. The process of recognition and use of herbalism in the preparation of remedies,
infusions, or concoctions for the treatment of disease has been carried out by trial and error [3]. There are
countries with a long tradition of using herbal medicine such as China, India, Japan, Pakistan, and Mexico.
Ethnopharmacological studies have contributed to the amplification of knowledge and the discovery of
new drugs or effective bioactive compounds for the control of diseases [4].
Mexico has a history of using ethnomedicine, whose origins go back to pre-Hispanic cultures
where archaeological findings have shown its anthropological influence and impact on Mexican
culture [5]. One of the plants with antecedents is Eysenhardtia polystachya (EP), dating back to the
era of New Spain where Nicolas B. Monardes (1565) relates the use of a tree to treat kidney and
urinary diseases; he describes that they drank a blue-colored infusion which was obtained by placing
thin slices of a wood (bark) into water for a period of time [6]. Furthermore, in the Florentine
Codex, Fray Bernardino de Sahagún refers to the use of “Coatli” for fever or retention of urine [7].
In the following centuries (XVI and XVII), it was taken to Europe where it was known as Lignum

Plants 2020, 9, 1124; doi:10.3390/plants9091124 www.mdpi.com/journal/plants

Plants 2020, 9, 1124 2 of 33

nephriticum [8,9]. Later, it continued to be consumed in a traditional way by Mexicans for the control
of urinary, contraceptive [10], antidiarrheal, and antiseptic disorders, as well as for the control of
diabetes [11,12].
In recent decades, the Eysenhardtia genus has attracted attention due to its medicinal properties.
This triggered a series of phytochemical and pharmacological studies linked to the identification of
health benefits. Among the actions determined are its diuretic [13], antidiabetic, antiglycation [14],
antioxidant [15], anti-inflammatory [16], and antimicrobial [17] potential. It also has cytotoxic
properties [8], is cardioprotective, and inhibits neurodegeneration and modulators of cell signaling [15].
This article presents a bibliographic review focused on the diverse activities that have been
attributed to the Eysenhardtia genus, which is made up of fourteen species [18].

2. Taxonomic Classification
Kingdom: Plantae
Phyllum: Tracheophyta
Class: Magnoliopsida
Orden: Fabales
Family: Fabaceae
Species: E. adenostylis, E. platycarpa, E. punctata, E. subcoriacea, E. cobriformis, E. reticulata, E. orthocarpa,
E. polystachya, E. texana, E. angustifolia, E. spinosa, E. peninsularis, E. parvifolia, E. schizocalyx.
Common names in Mexico: Cuate (Jal.), Coatillo (Pue.), Coatl (l. náhuatl), Cohuatli, Cuatle (Oax.),
Lanaé (l. chontalpa, Oax.), Palo cuate, Rosilla (Sin.), Palo dulce (Sin., Mex., Hgo., Pue., Mich.), Palo azul
(Mex), Taray (N.L., Dgo.), Tlapahuaxpatli; Ursa (l. otomí, Hgo.), Vara dulce, Varaduz (Dgo.).
Common names in English: Kidneywood, Mexican Kidneywood [19–21].

2.1. Description of the Eysenhardtia Genus

The Eysenhardtia genus is a deciduous tree or shrub 3 to 9 m high with a diameter of 15 to
35 cm [20]. It has a crown and alternate, compound, pinnate leaves, elliptical leaflets, and aromatic
resins. Its wood is branched brown [19]. The bark is rough and scaly with a dark coloration on the
outside and reddish-brown on the inside [20]. It shows inflorescences in spiky clusters lobed with
white corolla. Its fruit is shown in a curved pod that houses a thin seed susceptible to water, and it is a
hermaphrodite (Figure
Plants 2020, 9, x FOR 1) [17].
PEER REVIEW 3 of 27

Figure
Figure 1. Eysenhardtia genus.
1. Eysenhardtia genus.

2.2. Geographical Distribution of the Eysenhardtia Genus

It is found throughout Mexico, mainly in the states of Colima, Chiapas, Chihuahua, Coahuila,
Mexico City, Durango, Guanajuato, Guerrero, Hidalgo, Jalisco, State of Mexico, Morelos, Oaxaca,
Puebla, Querétaro, San Luis Potosí, Sinaloa, Sonora, Tamaulipas, Tlaxcala, Veracruz, and
Plants 2020, 9, 1124 3 of 33
Figure 1. Eysenhardtia genus.

2.2.
2.2.Geographical
GeographicalDistribution
Distributionofofthe
theEysenhardtia
EysenhardtiaGenus
Genus
ItItisisfound
foundthroughout
throughout Mexico,
Mexico, mainly in the
mainly in the states
statesofofColima,
Colima,Chiapas,
Chiapas,Chihuahua,
Chihuahua,Coahuila,
Coahuila,
Mexico City, Durango, Guanajuato, Guerrero, Hidalgo, Jalisco, State of Mexico, Morelos,
Mexico City, Durango, Guanajuato, Guerrero, Hidalgo, Jalisco, State of Mexico, Morelos, Oaxaca, Oaxaca,
Puebla,
Puebla,Querétaro,
Querétaro,SanSanLuisLuis
Potosí, Sinaloa,
Potosí, Sonora,
Sinaloa, Tamaulipas,
Sonora, Tlaxcala,
Tamaulipas, Veracruz,
Tlaxcala, and Zacatecas.
Veracruz, and
ItZacatecas.
has also been found in the southeastern United States (Figure 2) [22,23].
It has also been found in the southeastern United States (Figure 2) [22,23].

Figure 2. Geographical distribution of Eysenhardtia [22,23].

Figure 2. Geographical distribution of Eysenhardtia [22,23].

3.3.Secondary
SecondaryMetabolites
MetabolitesIsolated
Isolatedfrom
fromthe
theEysenhardtia
EysenhardtiaGenus
Genus
TheEysenhardtia
The Eysenhardtia genus
genus has
has shown to be an an excellent
excellent source
source ofof secondary
secondarymetabolites
metaboliteswith
with
flavonoids, flavones, isoflavones, flavonones, phenolic compounds, chalcones, dihydrochalcones,
flavonoids, flavones, isoflavones, flavonones, phenolic compounds, chalcones, dihydrochalcones,
coumarins,pterocarpan,
coumarins, pterocarpan,sugars,
sugars,and
andfatty
fattyacids,
acids,among
amongothers,
others,
inin
itsits composition.
composition. Table
Table 1 shows
1 shows the
the phytochemical
phytochemical compounds
compounds identified
identified from
from the the different
different parts (leaves,
parts (leaves, branches,
branches, heartwood,
heartwood, and bark)
ofand
thebark) of the genus.
genus.
 Plants 2020, 9, 1124 4 of 33
Part Used
Referenc
Number Compound Structure Species (Type of
e(s)
lants 2020, 9, x FOR PEER REVIEW Extract) 5 of 43
Table 1. Phytochemical compounds identified in the species Eysenhardtia.

Phenolic Compounds
Part Used (Type
Number Compound Structure Species Reference(s)
Plants 2020, 9, x FOR PEER REVIEW of Extract) 5 of 43

coatline B (3′-C-β-glucopyranosyl-α,2′,4′,3,4- Wood

2 E. polystachya [13]
pentahydroxydihydrochalcone)
coatline coatline A (30 -C-β-glucopyranosyl-
A (3′-C-β-glucopyranosyl-α,2′,4′,4- (aqueous)
Wood
Plants 2020,
1 9, x FOR PEER REVIEW
1 E.E.polystachya
polystachya Wood (aqueous) [13]5 of[13]
43
α,20 ,40 ,4-tetrahydroxydihydrochalcone)
tetrahydroxydihydrochalcone) (aqueous)

coatline B (3′-C-β-glucopyranosyl-α,2′,4′,3,4- Wood

2 E. polystachya [13]
pentahydroxydihydrochalcone) (aqueous)

coatline B (30 -C-β-glucopyranosyl-α,

coatline B (3′-C-β-glucopyranosyl-α,2′,4′,3,4- Wood
2 2 E.E.polystachya
polystachya Wood (aqueous) [13] [13]
2 ,40 ,3,4-pentahydroxydihydrochalcone)
0
pentahydroxydihydrochalcone) (aqueous)

Wood
3 matlaline E. polystachya [7]
(aqueous)

Wood
3 3 matlaline matlaline E.polystachya
E. polystachya Wood (aqueous) [7] [7]
(aqueous)

Wood
3 matlaline E. polystachya [7]
(aqueous)

Wood
4 4 octa-acetyl coatline A
octa-acetyl coatline A E. polystachya
E. polystachya Wood (aqueous) [13] [13]
(aqueous)

Wood
4 octa-acetyl coatline A E. polystachya [13]
(aqueous)

Wood
4 octa-acetyl coatline A E. polystachya [13]
(aqueous)
Plants 2020, Plants 2020, 9, 1124 nona-acetyl coatline B Wood 5 of 33
5 9, x FOR PEER REVIEW E. polystachya [13]6 of 43
(aqueous)

Table 1. Cont.
Plants 2020, 9, x FOR PEER REVIEW 6 of 43
Phenolic Compounds
Part Used (Type
Number Compound Structure Species Wood Reference(s)
5 nona-acetyl coatline B E. polystachya of Extract) [13]
(aqueous)

Wood
Wood
65 5 nona-acetyldihydrocoatline
nona-acetyl coatline B B coatline B
nona-acetyl E.
E. polystachya
E. polystachya
polystachya Wood (aqueous) [13]
[13] [13]
(aqueous)
(aqueous)

Wood
6 6 nona-acetyldihydrocoatline B
nona-acetyldihydrocoatline B E. polystachya
E. polystachya Wood (aqueous) [13] [13]
(aqueous)
Heartwood
(methanol)
Wood
6 nona-acetyldihydrocoatline B E. polystachya [13]
(aqueous)
Heartwood
Plants 2020, 9, x FOR PEER REVIEW 7 of 43
7 3,4-dimethoxy-8,9-methylenedioxypterocarpan (methanol)
Bark [8,24]
7 3,4-dimethoxy-8,9-methylenedioxypterocarpan E. polystachya [8,24]
Bark
(CHCl3 -MeOH)
Heartwood
(methanol)
(CHCl3-
MeOH)
O O
Heartwood
O Heartwood
Heartwood
87 3,4-dimethoxy-8,9-methylenedioxypterocarpan
8 dehydrorotenone
dehydrorotenone E. polystachya
E. polystachya Bark
(methanol) [8,24]
[24] [24]
(methanol)
(methanol)
O
OMe

OMe
7 3,4-dimethoxy-8,9-methylenedioxypterocarpan E. polystachya (CHCl
Bark 3- [8,24]
MeOH)

(CHCl3-
MeOH)

Heartwood
9 angustlegor-retoside E. polystachya [24]
(Methanol)
 O Heartwood
8 dehydrorotenone E. polystachya [24]
(methanol)
O
OMe
O O
OMe
O Heartwood
8 dehydrorotenone E. polystachya [24]
Plants 2020, 9, 1124 (methanol) 6 of 33
O
OMe

Table 1. Cont. OMe

Phenolic Compounds
Heartwood
Part Used (Type
9 Number angustlegor-retoside
Compound Structure E. Species
polystachya [24]Reference(s)
(Methanol)
of Extract)

Heartwood
Heartwood
9 9 angustlegor-retoside
angustlegor-retoside E.polystachya
E. polystachya [24] [24]
(Methanol)
(Methanol)

Plants 2020, 9, x FOR PEER REVIEW 8 of 43

Bark

Bark
Plants 2020, REVIEW10 (3S)-7-hydroxy-20 ,30 ,40 ,50 ,8-pentamethoxyisoflavan
10 9, x FOR PEER (3S)-7-hydroxy-2′,3′,4′,5′,8-pentamethoxyisoflavan E.polystachya
E. polystachya [8] 8 of 43[8]
(CHCl3 -MeOH)
Bark 3-
(CHCl
Bark
MeOH)
11 (3S)-3′,7-dihydroxy-2′,4′,5′,8-tetramethoxyisoflavan E. polystachya [8]
10 (3S)-7-hydroxy-2′,3′,4′,5′,8-pentamethoxyisoflavan E. polystachya [8]
(CHCl3-
Bark 3-
(CHCl
MeOH)
MeOH)
Bark
11 11 (3S)-30 ,7-dihydroxy-20 ,40 ,50 ,8-tetramethoxyisoflavan
(3S)-3′,7-dihydroxy-2′,4′,5′,8-tetramethoxyisoflavan E.polystachya
E. polystachya [8] [8]
(CHCl3 -MeOH)
(CHCl3-
MeOH)

Bark

Bark
12 12 (3S)-20 ,30 ,40 ,50 ,8-pentamethoxy-7-O-acetylisoflavan
(3S)-2′,3′,4′,5′,8-pentamethoxy-7-O-acetylisoflavan E. polystachya
E. polystachya [8] [8]
(CHCl3 -MeOH)
(CHCl3-
Bark
MeOH)

12 (3S)-2′,3′,4′,5′,8-pentamethoxy-7-O-acetylisoflavan E. polystachya [8]

(CHCl3-
MeOH)

Bark

13 (3S)-2′,4′,5′,8-tetramethoxy-3′,7-O-diacetylisoflavan E. polystachya [8]

(CHCl3-
Bark
MeOH)
Plants 2020, 9, x FOR PEER REVIEW Bark 9 of 43

12 (3S)-2′,3′,4′,5′,8-pentamethoxy-7-O-acetylisoflavan
Plants 2020, 9, 1124 E. polystachya [8] 7 of 33
(CHCl3-
MeOH)
Table 1. Cont. Bark

Phenolic Compounds
14 isoduartin (2′,7-dihydroxy-3′,4′,8-trimethoxyisoflavan) E. polystachya [8]
Part Used (Type
Number
Plants 2020, 9, x FOR PEER REVIEW Compound Structure Species (CHCl3- Reference(s)
9 of 43
of Extract)
MeOH)
Bark

lants 2020, (3S)-20 ,40 ,50 ,8-tetramethoxy-30 ,7- Bark

13 9, x FOR PEER(3S)-2′,4′,5′,8-tetramethoxy-3′,7-O-diacetylisoflavan
REVIEW
13 E.polystachya
E. polystachya [8]9 of 43[8]
O-diacetylisoflavan (CHCl 3 -MeOH)
Bark
(CHCl3-
MeOH)
14 isoduartin (2′,7-dihydroxy-3′,4′,8-trimethoxyisoflavan) E. polystachya [8]
Bark
(CHCl3-
Bark
MeOH)
15 cuneatin (7-hydroxy-2′-methoxy-4′,5′-(methylendioxy)isoflavone) E. polystachya [8]
isoduartin Bark
14 isoduartin
14 (2′,7-dihydroxy-3′,4′,8-trimethoxyisoflavan) E. polystachya
E. polystachya (CHCl3- [8] [8]
(20 ,7-dihydroxy-30 ,40 ,8-trimethoxyisoflavan) (CHCl3 -MeOH)
MeOH)
(CHCl 3-

MeOH)

cuneatin (7-hydroxy-20 -methoxy-40 ,50 - Bark

Bark
15 E. polystachya [8]
(methylendioxy)isoflavone) (CHCl3 -MeOH)
15 cuneatin (7-hydroxy-2′-methoxy-4′,5′-(methylendioxy)isoflavone) E. polystachya [8]
Bark
(CHCl3-
Bark
lants 2020, 9, x FOR PEER REVIEW MeOH)
Bark 10 of 43

16 (CHCl3 -MeOH)
15 16 7-hydroxy-20 ,40 ,50 -trimethoxyisoflavone
7-hydroxy-2′,4′,5′-trimethoxyisoflavone
cuneatin (7-hydroxy-2′-methoxy-4′,5′-(methylendioxy)isoflavone) E.polystachya
E.
E. polystachya
polystachya (CHCl 3-
[8]
[8] [8]
Heartwood
MeOH)
(Aqueous)
(CHCl 3-
Heartwood
MeOH)
(Aqueous)
Bark

Bark
17 17 (α-R)-α,3,4,20 ,40 -pentahydroxydihydrochalcone
(α-R)-α,3,4,2′,4′-pentahydroxydihydrochalcone E.
E. polystachya
polystachya Bark [25] [25]
(CHCl3 -MeOH)
(CHCl3-
MeOH)
16 7-hydroxy-2′,4′,5′-trimethoxyisoflavone E. polystachya (CHCl3- [8]
Bark
MeOH)
Heartwood
(Aqueous)
16 7-hydroxy-2′,4′,5′-trimethoxyisoflavone E. polystachya (CHCl3- [8]
Bark
MeOH)
 17 (α-R)-α,3,4,2′,4′-pentahydroxydihydrochalcone E. polystachya [25]
(CHCl3-
MeOH)
Bark

17 Plants 2020,(α-R)-α,3,4,2′,4′-pentahydroxydihydrochalcone
9, 1124 E. polystachya [25] 8 of 33
(CHCl3-
MeOH)
Table 1. Cont. Bark

(αR)-3′-C-β-D-xylopyranosyl-α,3,4,2′,4′- Phenolic Compounds

18 E. polystachya [25]
pentahydroxydihydrochalcone
Part
(CHClUsed
3-
(Type
Number Compound Structure Species Reference(s)
of Extract)
MeOH)
Bark

(αR)-30 -C-β-D-xylopyranosyl-α,3,4,20 ,40 -

Plants 2020, 9, x FOR PEER REVIEW (αR)-3′-C-β-D-xylopyranosyl-α,3,4,2′,4′- Bark 11 of 43
18 18 E. polystachya
polystachya [25] [25]
pentahydroxydihydrochalcone
pentahydroxydihydrochalcone (CHCl3 -MeOH)
(CHCl3-
MeOH)
Bark
Plants 2020, 9, x FOR PEER REVIEW 11 of 43
(αR)-30 -O-β-D-xylopyranosyl-α,3,4,20 ,40 - Bark
19 (αR)-3′-O-β-D-xylopyranosyl-α,3,4,2′,4′- E. polystachya [25]
19 pentahydroxydihydrochalcone E. polystachya (CHCl3 -MeOH) [25]
pentahydroxydihydrochalcone Aerial parts
(CHCl3-
20 4′,5,7-trihydroxy-8-methyl-6-(3-methyl-[2-butenyl])-(2S)-flavanone E. texana (CH2Cl2- [26,27]
MeOH)
Bark
MeOH)
(αR)-3′-O-β-D-xylopyranosyl-α,3,4,2′,4′-
19 E. polystachya Aerial parts [25]
40 ,5,7-trihydroxy-8-methyl-6-(3-methyl-
pentahydroxydihydrochalcone Aerial parts
20 4′,5,7-trihydroxy-8-methyl-6-(3-methyl-[2-butenyl])-(2S)-flavanone
20 E.
E.texana
texana (CH23Cl
(CHCl - 2- [26,27] [26,27]
[2-butenyl])-(2S)-flavanone (CH2 Cl2 -MeOH)
MeOH)
MeOH)

Aerial parts
21 40 ,5,7-trihydroxy-6-methyl-8-(3-methyl-
4′,5,7-trihydroxy-6-methyl-8-(3-methyl-[2-butenyl])-(2S)-flavanone E.texana
texana Aerial
(CH parts
2Cl2- [26,27] [26,27]
21 E.
[2-butenyl])-(2S)-flavanone (CH2 Cl2 -MeOH)
MeOH)

Aerial parts
21 4′,5,7-trihydroxy-6-methyl-8-(3-methyl-[2-butenyl])-(2S)-flavanone E. texana (CH2Cl2- [26,27]
MeOH)
Plants 2020, 9, x FOR PEER REVIEW 12 of 43

Plants
lants 2020, 9, x FOR PEER 2020, 9, 1124
REVIEW 12 of 43 9 of 33

Table 1. Cont.
Plants 2020, 9, x FOR PEER REVIEW 12 of 43
Aerial parts
Phenolic Compounds
22 4′,5-dihydroxy-7-methoxy-6-(3-methyl-[2-butenyl])-(2S)-flavanone E. texana (CH2Cl2- [26,27]
Part Used (Type
MeOH)
Number Compound Structure Species Reference(s)
of Extract)
Aerial parts
22 4′,5-dihydroxy-7-methoxy-6-(3-methyl-[2-butenyl])-(2S)-flavanone E. texana (CH2Cl2- [26,27]
MeOH)

Aerial parts
40 ,5-dihydroxy-7-methoxy-6-(3-methyl- Aerial parts
22 4′,5-dihydroxy-7-methoxy-6-(3-methyl-[2-butenyl])-(2S)-flavanone
22 E.texana
E. texana (CH2Cl2- [26,27] [26,27]
[2-butenyl])-(2S)-flavanone (CH2 Cl2 -MeOH)
MeOH)

Heartwood
23 7-hydroxy-4′-methoxyisoflavone E. polystachya [28,29]
(Aqueous)

Heartwood
Heartwood
23 7-hydroxy-40 -methoxyisoflavone
23 7-hydroxy-4′-methoxyisoflavone E.
E. polystachya
polystachya [28,29] [28,29]
(Aqueous)
(Aqueous)

Heartwood
23 7-hydroxy-4′-methoxyisoflavone E. polystachya [28,29]
(Aqueous)

Leaves
Leaves
24 9, x FOR PEER REVIEW
Plants 2020, 40 -O-methyl-8-prenylnaringenin
24 4′-O-methyl-8-prenylnaringenin E.platycarpa
E. platycarpa [30] [30]
13 of 43
(Methanolic)
(Methanolic)

Leaves
24 4′-O-methyl-8-prenylnaringenin E. platycarpa [30]
(Methanolic)

25 5,40 ,1”-trihydroxy-6,7-(3”,3”-
5,4′,1′′-trihydroxy-6,7-(3′′,3′′-dimethylchroman)flavone E.platycarpa
platycarpa
Branches
Branches [30]
25 E. Leaves [30]
24 dimethylchroman)flavone
4′-O-methyl-8-prenylnaringenin E. platycarpa (Methanolic)
(Methanolic) [30]
(Methanolic)

Branches and
 Branches
25 5,4′,1′′-trihydroxy-6,7-(3′′,3′′-dimethylchroman)flavone E. platycarpa [30]
(Methanolic)

Plants 2020, 9, 1124 Branches 10 of 33

25 5,4′,1′′-trihydroxy-6,7-(3′′,3′′-dimethylchroman)flavone E. platycarpa [30]
(Methanolic)

Table 1. Cont.

Phenolic Compounds
Branches
Part Usedand
(Type
26 Number Compound
(2S)-4′-O-methyl-6-methyl-8-prenylnaringenin Structure E.Species
platycarpa leaves [30]Reference(s)
of Extract)
(Methanolic)

Branches and
Branches and
26 26 (2S)-40 -O-methyl-6-methyl-8-prenylnaringenin
(2S)-4′-O-methyl-6-methyl-8-prenylnaringenin E.platycarpa
E. platycarpa leaves
leaves [30] [30]
Plants 2020, 9, x FOR PEER REVIEW (Methanolic)
(Methanolic) 14 of 43

Plants 2020, 9, x FOR PEER REVIEW Branches and 14 of 43

Branches and
27 5,7-dihydroxy-6-methyl-8-prenylflavanone
27 5,7-dihydroxy-6-methyl-8-prenylflavanone E.platycarpa
E. platycarpa leaves
leaves [30] [30]
(Methanolic)
(Methanolic)
Branches and
28 5,7-dihydroxy-8-methyl-6-prenylflavanone E. platycarpa leaves [30]
Branches and
(Methanolic)
27 5,7-dihydroxy-6-methyl-8-prenylflavanone E. platycarpa leaves [30]
(Methanolic)
Branches
Branchesand
and
28 5,7-dihydroxy-8-methyl-6-prenylflavanone
28 5,7-dihydroxy-8-methyl-6-prenylflavanone E.platycarpa
E. platycarpa leaves
leaves [30] [30]
(Methanolic)
(Methanolic)

Branches
Branches
29 29 5,7-dihydroxy-6-prenylflavanone
5,7-dihydroxy-6-prenylflavanone E. platycarpa
E. platycarpa [30] [30]
(Methanolic)
(Methanolic)

Branches
29 5,7-dihydroxy-6-prenylflavanone E. platycarpa [30]
(Methanolic)

Leaves
30 5-hydroxy-7-methoxy-8-prenylflavanone E. platycarpa [30]
(Methanolic)

Leaves
 Plants 2020, 9, 1124 Branches 11 of 33
29 5,7-dihydroxy-6-prenylflavanone E. platycarpa [30]
(Methanolic)

Table 1. Cont.
lants 2020, 9, x FOR PEER REVIEW 15 of 43
Phenolic Compounds
Part Used (Type
Number Compound Structure Species Reference(s)
of Extract)
lants 2020, 9, x FOR PEER REVIEW 15 of 43

Branches
31 5,7-dihydroxy-8-prenylflavanone E. platycarpa Leaves
Leaves [30]
30 9, x FOR PEER REVIEW
lants 2020, 5-hydroxy-7-methoxy-8-prenylflavanone
30 5-hydroxy-7-methoxy-8-prenylflavanone E. platycarpa
E. platycarpa (Methanolic) [30] [30]
15 of 43
(Methanolic)
(Methanolic)

Branches
31 5,7-dihydroxy-8-prenylflavanone E. platycarpa [30]
(Methanolic)

Branches
Branches
31 31 5,7-dihydroxy-8-prenylflavanone
5,7-dihydroxy-8-prenylflavanone E.platycarpa
E. platycarpa [30] [30]
(Methanolic)
(Methanolic)
Bark
subcoriacin (3-(2′-hydroxy-4′,5′-methylendioxyphenyl)-6-(3′′-
32 E. subcoriacea [31,32]
hydroxymethyl-4′′-hydroxybut-2′′-enyl)-7-hydroxycoumarin)
(Methanolic)
Bark
subcoriacin (3-(20 -hydroxy-40 ,50 -
subcoriacin (3-(2′-hydroxy-4′,5′-methylendioxyphenyl)-6-(3′′- Bark
32 32 methylendioxyphenyl)-6-(3”-hydroxymethyl-4” subcoriacea
E. subcoriacea [31,32] [31,32]
hydroxymethyl-4′′-hydroxybut-2′′-enyl)-7-hydroxycoumarin) (Methanolic)
-hydroxybut-2”-enyl)-7-hydroxycoumarin)
(Methanolic)
Bark
subcoriacin (3-(2′-hydroxy-4′,5′-methylendioxyphenyl)-6-(3′′-
32 E. subcoriacea [31,32]
hydroxymethyl-4′′-hydroxybut-2′′-enyl)-7-hydroxycoumarin) Bark
E. platycarpa,
platycarpa, (Methanolic)
33 (+)-cathechin (+)-cathechin E. Bark [30,31,33]
33 [30,31,33]
E.subcoriacea
E. subcoriacea (Methanolic)
(Methanolic)
Bark
E. platycarpa,
33 (+)-cathechin [30,31,33]
E. subcoriacea
(Methanolic)
Bark
E. platycarpa,
33 (+)-cathechin [30,31,33]
E. subcoriacea
(Methanolic)
lants 2020, 9, x FOR PEER REVIEW 16 of 43

lants 2020, 9, x FOR PEER REVIEW 16 of 43

Plants 2020, 9, 1124 12 of 33
Bark
E. platycarpa,
34 (−)-epicatechin Table 1. Cont. [30,31,33]
E. subcoriacea
lants 2020, 9, x FOR PEER REVIEW 16 of 43
Phenolic Compounds (Methanolic)
Bark
E. platycarpa, Part Used (Type
34 Number (−)-epicatechin Compound Structure Species Reference(s)
E. subcoriacea of Extract) [30,31,33]
(Methanolic)
Bark
E. platycarpa,
E. platycarpa, Bark
34 34 (−)-epicatechin
(−)-epicatechin [30,31,33]
[30,31,33]
E. subcoriacea
E. subcoriacea (Methanolic)
Bark
E. platycarpa, (Methanolic)
35 (+)-afzelechin [30,31,33]
E. subcoriacea
(Methanolic)
Bark
E. platycarpa,
platycarpa, Bark
35 35 (+)-afzelechin (+)-afzelechin [30,31,33]
[30,31,33]
E. subcoriacea
E. subcoriacea (Methanolic)
(Methanolic)
Bark
E. platycarpa,
35 (+)-afzelechin [30,31,33]
E. subcoriacea
Bark
(Methanolic)
lants 2020, E. platycarpa,
E. platycarpa, Bark
36 9, x FOR PEER REVIEW
36 eriodictyol eriodictyol 17 of
[30,31,33] 43
[30,31,33]
E.subcoriacea
E. subcoriacea (Methanolic)
(Methanolic)
Bark
E. platycarpa,
36 eriodictyol [30,31,33]
E. subcoriacea
Bark
(Methanolic)
E. platycarpa,
E. platycarpa, Bark
Bark
37 (+)-catechin-3-O-β-D-galactopyranoside
37 (+)-catechin-3-O-β-D-galactopyranoside [30,31,33]
[30,31,33]
E.
E. subcoriacea
E.subcoriacea
platycarpa, (Methanolic)
36 eriodictyol (Methanolic) [30,31,33]
E. subcoriacea
(Methanolic)

Bark
E. platycarpa,
38 quercetin-3-O-β-D-galactopyranoside [30,31,33]
E. subcoriacea
(Methanolic)
 E. platycarpa,
37 (+)-catechin-3-O-β-D-galactopyranoside [30,31,33]
E. subcoriacea
(Methanolic)
Bark
Plants 2020, 9, 1124 E. platycarpa, 13 of 33
37 (+)-catechin-3-O-β-D-galactopyranoside [30,31,33]
E. subcoriacea
(Methanolic)
Table 1. Cont.

Phenolic Compounds
Bark
E.Species
platycarpa, Part Used (Type
Number Compound Structure Reference(s)
38 quercetin-3-O-β-D-galactopyranoside of Extract) [30,31,33]
E. subcoriacea
(Methanolic)
Bark
platycarpa,
E. platycarpa, Bark
38 quercetin-3-O-β-D-galactopyranoside
38 quercetin-3-O-β-D-galactopyranoside [30,31,33]
[30,31,33]
E. subcoriacea
E. subcoriacea (Methanolic)
(Methanolic)

lants 2020, 9, x FOR PEER REVIEW 18 of 43

Bark

Bark
39 39
lants 2020, 9, x FOR PEER REVIEW
20 ,40 -dihydroxychalcone-60 -O-β-D-glucopyranoside
2′,4′-dihydroxychalcone-6′-O-β-D-glucopyranoside E.polystachya
E. polystachya [34]
18 of 43
[34]
(Water/MeOH)
(Water/MeOH
Bark
)
α,3,2′,4′-tetrahydroxy-4-methoxy-dihydrochalcone-3′-C-β-
40
39 2′,4′-dihydroxychalcone-6′-O-β-D-glucopyranoside E. polystachya [34]
glucopyranosy-6′-O-β-D-glucopyranoside
(Water/MeOH
Bark
)
α,3,2 ,4 -tetrahydroxy-4-methoxy-
0 0
α,3,2′,4′-tetrahydroxy-4-methoxy-dihydrochalcone-3′-C-β-
0 Bark
40 40 dihydrochalcone-3 -C-β-glucopyranosy- E.polystachya
E. polystachya [34] [34]
glucopyranosy-6′-O-β-D-glucopyranoside (Water/MeOH)
60 -O-β-D-glucopyranoside (Water/MeOH
)

Bark
7-hydroxy-5,80 -dimethoxy-60 α-L-
7-hydroxy-5,8′-dimethoxy-6′ -L-rhamnopyranosyl-8-(3-phenyl- Bark
41 41 rhamnopyranosyl-8-(3-phenyl-transacryloyl)- E. polystachya
E. polystachya [34] [34]
transacryloyl)-1-benzopyran-2-one (Water/MeOH)
1-benzopyran-2-one (Water/MeOH
Bark
)

7-hydroxy-5,8′-dimethoxy-6′ -L-rhamnopyranosyl-8-(3-phenyl-
41 E. polystachya [34]
transacryloyl)-1-benzopyran-2-one
(Water/MeOH
)

Bark

6′,7-dihydroxy-5,8-dimethoxy-8(3-phenyl-trans-acryloyl)-1-
42 E. polystachya [34]
 Bark

7-hydroxy-5,8′-dimethoxy-6′ -L-rhamnopyranosyl-8-(3-phenyl-
41 Plants 2020, 9, 1124 E. polystachya [34] 14 of 33
lants 2020, 9, x FOR PEER REVIEW transacryloyl)-1-benzopyran-2-one 19 of 43
(Water/MeOH
)
Table 1. Cont.

Phenolic Compounds
lants 2020, 9, x FOR PEER REVIEW 19 of 43
PartBark
Used (Type
Number Compound Structure Species Reference(s)
of Extract)
43 9-hydroxy-3,8-dimethoxy-4-prenylpterocarpan E. polystachya Bark [34]
(Water/MeOH
lants 2020, 9, x FOR PEER REVIEW 0
6′,7-dihydroxy-5,8-dimethoxy-8(3-phenyl-trans-acryloyl)-1- 19 of 43
6 ,7-dihydroxy-5,8-dimethoxy-8(3-phenyl-trans- )Bark
Bark
42 42 E.polystachya
E. polystachya [34] [34]
benzopyran-2-one
acryloyl)-1-benzopyran-2-one (Water/MeOH)
(Water/MeOH
43 9-hydroxy-3,8-dimethoxy-4-prenylpterocarpan E. polystachya ) [34]
(Water/MeOH
)
Bark

Bark
Bark
43 9-hydroxy-3,8-dimethoxy-4-prenylpterocarpan
43 9-hydroxy-3,8-dimethoxy-4-prenylpterocarpan E.polystachya
E. polystachya [34] [34]
(Water/MeOH)
(Water/MeOH
44 5,4′-dihydroxy-7,2′-dimethoxyl-isoflavone E. polystachya [34]
)
(Water/MeOH
)
Bark

Bark
44 5,40 -dihydroxy-7,20 -dimethoxyl-isoflavone
5,4′-dihydroxy-7,2′-dimethoxyl-isoflavone
44 E.
E.polystachya
polystachya [34] [34]
(Water/MeOH)
(Water/MeOH
)
Bark

44 5,4′-dihydroxy-7,2′-dimethoxyl-isoflavone E. polystachya Bark [34]

(Water/MeOH
α,4,40 -trihydroxy-dihydrochalcone-20 - Bark
45 α,4,4′-trihydroxy-dihydrochalcone-2′-O-β-D-glucopyranoside
45 E.
E. polystachya
polystachya ) [34] [34]
O-β-D-glucopyranoside (Water/MeOH)
(Water/MeOH
)
Bark

45 α,4,4′-trihydroxy-dihydrochalcone-2′-O-β-D-glucopyranoside E. polystachya [34]

(Water/MeOH
)
Bark

45 α,4,4′-trihydroxy-dihydrochalcone-2′-O-β-D-glucopyranoside E. polystachya [34]

(Water/MeOH
)
lants 2020, 9, x FOR PEER REVIEW Bark 20 of 43

46 (3R)-5,7-2′,4′-tetrahydroxyl-3′-methoxyl-isoflavanone E. polystachya [34]

Plants 2020, 9, 1124 15 of 33
(Water/MeOH
)
Bark
lants 2020, 9, x FOR PEER REVIEW Table 1. Cont. 20 of 43
46 (3R)-5,7-2′,4′-tetrahydroxyl-3′-methoxyl-isoflavanone Phenolic Compounds E. polystachya [34]
(Water/MeOH
Part Used (Type
Number Compound Structure Species Reference(s)
of )Extract)
Bark

(3R)-5,7-20 ,40 -tetrahydroxyl-30 - Bark

46
47 (3R)-5,7-2′,4′-tetrahydroxyl-3′-methoxyl-isoflavanone
46 C (9-methoxy-2,3-methylenedioxycoumestan)
flemichapparin E.polystachya
E. polystachya [34] [34]
methoxyl-isoflavanone (Water/MeOH)
(Water/MeOH
)
Bark

flemichapparin C Bark
47 9, x FORflemichapparin
lants 2020, 47 C (9-methoxy-2,3-methylenedioxycoumestan)
PEER REVIEW E. polystachya
E. polystachya [34] [34]
21 of 43
(9-methoxy-2,3-methylenedioxycoumestan) (Water/MeOH)
(Water/MeOH
)
Bark
Bark
lants 2020, 9, x FOR PEER REVIEW Bark 21 of 43
47 flemichapparin C (9-methoxy-2,3-methylenedioxycoumestan) E. polystachya Bark [34]
48 neohesperidin-dihydrochalcone
48 neohesperidin-dihydrochalcone E.
E.polystachya
polystachya [34] [34]
(Water/MeOH)
49 hesperetin dihydrochalcone glucoside E. polystachya (Water/MeOH
(Water/MeOH [34]
))
(Water/MeOH
Bark
)
Bark
48 neohesperidin-dihydrochalcone E. polystachya [34]
49 hesperetin dihydrochalcone glucoside polystachya Bark
(Water/MeOH [34]
49 hesperetin dihydrochalcone glucoside E. polystachya [34]
(Water/MeOH)
)
(Water/MeOH
Bark
)
Bark
48 neohesperidin-dihydrochalcone E. polystachya [34]
Bark
50 50 aspalathin aspalathin E.
E. polystachya
polystachya (Water/MeOH [34] [34]
(Water/MeOH)
)
(Water/MeOH
)
Bark

50 aspalathin E. polystachya [34]

(Water/MeOH
)

Bark

51 sandwicensin E. polystachya [34]

 Bark

50 Plants 2020, 9, 1124 aspalathin E. polystachya [34] 16 of 33

(Water/MeOH
Table 1. Cont. )

Phenolic Compounds
Part Used (Type
Number Compound Structure Species Reference(s)
lants 2020, 9, x FOR PEER REVIEW of Extract) 22 of 43

Bark

Bark
51 9, x FOR PEER REVIEW
Plants 2020, 51 sandwicensinsandwicensin E.polystachya
E. polystachya [34] [34]
22 of 43
(Water/MeOH)
(Water/MeOH
Bark
)
2′-O-α-L-rhamnopyranosyl- α,6′-dihydroxy-4′-acetyl-4-
52 E. polystachya [35]
methoxydihydrochalcone
(Water/MeOH
)
Bark

20 -O-α-L-rhamnopyranosyl-
2′-O-α-L-rhamnopyranosyl- α,60 -dihydroxy-
α,6′-dihydroxy-4′-acetyl-4- Bark
52 52 0 E.
E.polystachya
polystachya [35] [35]
4 -acetyl-4-methoxydihydrochalcone
methoxydihydrochalcone (Water/MeOH)
(Water/MeOH
)

Bark
lants 2020, 9, x FOR PEER REVIEW 22 of 43
Bark
53 53 60 methoxy-sieboldin
6′methoxy-sieboldin E.polystachya
E. polystachya [35] [35]
(Water/MeOH)
(Water/MeOH
)
Bark

53 6′methoxy-sieboldin E. polystachya Bark [35]

(Water/MeOH
20 -O-β-D-glucopyranosyl-4
2′-O-α-L-rhamnopyranosyl- 0 -methoxy-4-
α,6′-dihydroxy-4′-acetyl-4- Bark
52 54 E.polystachya
E. polystachya ) [35] [35]
methoxydihydrochalcone
hydroxy-3-isoprenyldihydrochalcone (Water/MeOH)
(Water/MeOH
Bark
)

2′-O-β-D-glucopyranosyl-4′-methoxy-4-hydroxy-3-
54 E. polystachya [35]
isoprenyldihydrochalcone
(Water/MeOH
)
Bark

2′-O-β-D-glucopyranosyl-4′-methoxy-4-hydroxy-3-
54 E. polystachya Bark [35]
isoprenyldihydrochalcone
(Water/MeOH
lants 2020, 9, x FOR PEER REVIEW 23 of 43

lants 2020, 9, x FOR PEER REVIEW 23 of 43

Plants 2020, 9, 1124 Bark 17 of 33

55 2′,4′,6′-trihydroxy-4,5-dimethoxy-3-isoprenyldihydrochalcone E. polystachya [35]

Table 1. Cont.
lants 2020, 9, x FOR PEER REVIEW (Water/MeOH 23 of 43
Bark
Phenolic Compounds )
Part Used (Type
55 Number Compound
2′,4′,6′-trihydroxy-4,5-dimethoxy-3-isoprenyldihydrochalcone Structure E. Species
polystachya [35]Reference(s)
of Extract)
(Water/MeOH
Bark
)

20 ,40 ,60 -trihydroxy-4,5-dimethoxy- Bark

55 2′,4′,6′-trihydroxy-4,5-dimethoxy-3-isoprenyldihydrochalcone
55 E. polystachya
E. polystachya [35] [35]
3-isoprenyldihydrochalcone (Water/MeOH)
Bark
(Water/MeOH
3′-C-β-glucopyranosyl-α, 2′,4′,6′-trihydroxy-4- )
56 E. polystachya [35]
methoxydihydrochalcone
(Water/MeOH
Bark
)
3′-C-β-glucopyranosyl-α,302′,4′,6′-trihydroxy-4-
-C-β-glucopyranosyl-α, Bark
56 56 E. polystachya
E. polystachya [35] [35]
20 ,40 ,60 -trihydroxy-4-methoxydihydrochalcone
methoxydihydrochalcone (Water/MeOH)
(Water/MeOH
Bark
)
3′-C-β-glucopyranosyl-α, 2′,4′,6′-trihydroxy-4-
56 E. polystachya [35]
methoxydihydrochalcone
(Water/MeOH
Bark
)
3′-C-β-glucopyranosyl-α,302′,4-trihydroxy-4′,6′-
-C-β-glucopyranosyl-α, Bark
57 9, x FOR PEER REVIEW
lants 2020, 57 E. polystachya
E. polystachya [35]
24 of 43
[35]
20 ,4-trihydroxy-40 ,60 -dimethoxydihydrochalcone
dimethoxydihydrochalcone (Water/MeOH)
(Water/MeOH
Bark
)
3′-C-β-glucopyranosyl-α, 2′,4-trihydroxy-4′,6′-
57 E. polystachya [35]
dimethoxydihydrochalcone Bark
(Water/MeOH
Bark
)Bark
58 58 3-hydroxyphloretin-40 -O-β-D-glucopyranoside
3-hydroxyphloretin-4′-O-β-D-glucopyranoside E.polystachya
E. polystachya [35] [35]
3′-C-β-glucopyranosyl-α, 2′,4-trihydroxy-4′,6′- (Water/MeOH)
57 E. polystachya (Water/MeOH [35]
dimethoxydihydrochalcone
)
(Water/MeOH
)

Bark

59 3,4′-dihydroxy-2,4,6-trimethoxydihydrochalcone E. polystachya [35]

(Water/MeOH
 58 3-hydroxyphloretin-4′-O-β-D-glucopyranoside E. polystachya [35]
(Water/MeOH
)
Bark

58 Plants3-hydroxyphloretin-4′-O-β-D-glucopyranoside
2020, 9, 1124 E. polystachya [35] 18 of 33
(Water/MeOH
)
Table 1. Cont.
Bark
Phenolic Compounds
59 3,4′-dihydroxy-2,4,6-trimethoxydihydrochalcone E. polystachya Part Used (Type [35]
Number Compound Structure Species Reference(s)
of Extract)
(Water/MeOH
)
Bark

Bark
59 59 3,40 -dihydroxy-2,4,6-trimethoxydihydrochalcone
3,4′-dihydroxy-2,4,6-trimethoxydihydrochalcone E. polystachya
E. polystachya [35] [35]
(Water/MeOH)
ants 2020, 9, x FOR PEER REVIEW (Water/MeOH 25 of 43
)
Bark

ants 2020, 9, x FOR PEER REVIEW Bark 25 of 43

60 60 20 ,40 ,4-trihydroxy-30 -methoxydihydrochalcone
2′,4′,4-trihydroxy-3′-methoxydihydrochalcone E.polystachya
E. polystachya [35] [35]
(Water/MeOH)
Bark
(Water/MeOH
)
Bark
61 2′,4′,6′,4-tetrahydroxy-3,5-diisoprenyldihydrochalcone E. polystachya [35]
60 2′,4′,4-trihydroxy-3′-methoxydihydrochalcone E. polystachya (Water/MeOH
Bark [35]
)
(Water/MeOH
20 ,40 ,60 ,4-tetrahydroxy-3,5- )Bark
61 61
2′,4′,6′,4-tetrahydroxy-3,5-diisoprenyldihydrochalcone E. polystachya [35] [35]
diisoprenyldihydrochalcone (Water/MeOH)
(Water/MeOH
)

Bark

30 -C-β-glucopyranosyl-α,20 ,40 ,3,4- Bark

62 62
3′-C-β-glucopyranosyl-α,2′,4′,3,4-pentahydroxydihydroxychalcone E. polystachya [35] [35]
pentahydroxydihydroxychalcone (Water/MeOH)
(Water/MeOH
Bark
)

62 3′-C-β-glucopyranosyl-α,2′,4′,3,4-pentahydroxydihydroxychalcone E. polystachya [35]

(Water/MeOH
)

Bark

63 3′-O-β-D-glucopyranosyl-α,4,2′,4′,6′-pentahydroxydihydrochalcone E. polystachya [36]

(Water/MeOH
 Bark

62 3′-C-β-glucopyranosyl-α,2′,4′,3,4-pentahydroxydihydroxychalcone
Plants 2020, 9, 1124 E. polystachya [35] 19 of 33

lants 2020, 9, x FOR PEER REVIEW

(Water/MeOH 26 of 43
)
Table 1. Cont.

Phenolic Compounds
Plants 2020, 9, x FOR PEER REVIEW Part Used (Type 26 of 43
Number Compound Sterols and terpenoids Structure Species Reference(s)
of Extract)

Bark

30 -O-β-D-glucopyranosyl-α,4,20 ,40 ,6Sterols

0- and terpenoids Bark
63 3′-O-β-D-glucopyranosyl-α,4,2′,4′,6′-pentahydroxydihydrochalcone
63 E. polystachya
polystachya [36] [36]
pentahydroxydihydrochalcone (Water/MeOH)
(Water/MeOH
)

Sterols and terpenoids Branches

64 oleanolic acid E. platycarpa [30]
(Methanolic)

Branches
Branches
64 64 oleanolic acidoleanolic acid E.E.platycarpa
platycarpa [30] [30]
(Methanolic)
(Methanolic)

Branches
Branches
65 65 β-sitosterol β-sitosterol E. platycarpa
platycarpa [30] [30]
(methanolic)
(methanolic)

Branches
65 β-sitosterol E. platycarpa [30]
(methanolic)
lants 2020, 9, x FOR PEER REVIEW 27 of 43

Plants 2020, 9, x FOR Plants

PEER REVIEW
2020, 9, 1124 27 of 43 20 of 33

Table 1. Cont.
lants 2020, 9, x FOR PEER REVIEW Branches 27 of 43
66 β-sitosteryl β-D-glucopyranoside Sterols and terpenoids E. platycarpa [30]
(Methanolic)
Part Used (Type
Number Compound Structure Species Reference(s)
of Extract)
Branches
66 β-sitosteryl β-D-glucopyranoside E. platycarpa [30]
(Methanolic)

Branches
Branches
66 β-sitosteryl β-D-glucopyranoside
66 β-sitosteryl β-D-glucopyranoside E.
E. platycarpa
platycarpa [30] [30]
(Methanolic)
(Methanolic)

Branches
67 β-sitosteryl palmitate E. platycarpa [30]
(Methanolic)

Branches
Branches
67 67 β-sitosteryl palmitate
β-sitosteryl palmitate E. E. platycarpa
platycarpa [30] [30]
(Methanolic)
(Methanolic)

Branches
67 β-sitosteryl palmitate E. platycarpa Bark [30]
(Methanolic)

68 stigmasterol stigmasterol E. polystachya

polystachya Bark [8]
68 E. [8]
(CHCl3 -MeOH)
(CHCl3-
Bark
MeOH)

68 stigmasterol E. polystachya [8]

(CHCl3-
Bark
MeOH)

68 stigmasterol E. polystachya [8]

(CHCl3-
MeOH)
lants 2020, 9, x FOR PEER REVIEW 28 of 43

lants 2020, 9, x FOR PEER REVIEW

Plants 2020, 9, 1124 28 of 43 21 of 33

Table 1. Cont. Branches

69 3-O-acetyl-11α,12α-epoxy-oleanan-28,13β-olide
lants 2020, 9, x FOR PEER REVIEW E. platycarpa [30,33]
28 of 43
(Methanolic)
Sterols and terpenoids
Part Used (Type
Number Compound Structure Species Reference(s)
of Extract)
Branches
69 3-O-acetyl-11α,12α-epoxy-oleanan-28,13β-olide E. platycarpa [30,33]
(Methanolic)

Branches
Branches
69 69 3-O-acetyl-11α,12α-epoxy-oleanan-28,13β-olide
3-O-acetyl-11α,12α-epoxy-oleanan-28,13β-olide E.
E.platycarpa
platycarpa [30,33] [30,33]
(Methanolic)
(Methanolic)

Branches
70 lupeol E. platycarpa [30]
(Methanolic)

Branches
Branches
70 70 lupeol lupeol E.platycarpa
E. platycarpa [30] [30]
(Methanolic)
(Methanolic)

Branches
70 lupeol E. platycarpa [30]
(Methanolic)

Branches
Branches
71 71 betulinic acid betulinic acid platycarpa
E. platycarpa [30] [30]
(Methanolic)
(Methanolic)

Branches
71 betulinic acid E. platycarpa [30]
(Methanolic)

Branches
71 betulinic acid E. platycarpa [30]
(Methanolic)
 72 3-O-acetyloleanolic acid E. platycarpa leaves [30]
(Methanolic)

Plants 2020, 9, 1124 Branches and 22 of 33

72 3-O-acetyloleanolic acid E. platycarpa leaves [30]
(Methanolic)
Table 1. Cont.
lants 2020, 9, x FOR PEER REVIEW 29 of 43
Fatty acidsSterols and terpenoids

Part Used (Type

Number Compound Structure Species Reference(s)
of Extract)
lants 2020, 9, x FOR PEER REVIEW 30 of 43

Fatty acids Branches and

Branches
Branches and
and
(Ethanolic)
72 72 3-O-acetyloleanolic acid
3-O-acetyloleanolic acid E. platycarpa
E. platycarpa leaves
leaves
leaves [30] [30]
(Methanolic)
(Methanolic)
73 stearic acid E. polystachya [12]

(Ethanolic)
Plants 2020, 9, x FOR PEER REVIEW Fatty acids Branches and 30 of 43
Branches and
leaves
Branches
leaves and
73 73 stearic acid stearic acid E.E.
polystachya
polystachya (Ethanolic)
leaves [12] [12]
75 palmitic acid E. polystachya (Ethanolic) [12]
Fatty acids
(Ethanolic)
Branches and
Branches and
(Ethanolic)
74 74 arachidic acidarachidic acid E.E.polystachya
polystachya leaves [12] [12]
leaves
(Ethanolic)
Branchesand
Branches and
75 palmitic acid E. polystachya leaves [12]
leaves
(Ethanolic)
75 palmitic acid E. polystachya Branches and [12]
Branches and
74 arachidic acid E. polystachya leaves [12]
leaves
Branches and
73 stearic acid E. polystachya (Ethanolic) [12]
leaves
Branches and
76 76 linoleic acid linoleic acid E.E.polystachya
polystachya leaves [12] [12]
(Ethanolic)
(Ethanolic)
(Ethanolic)

Branches and
leavesand
Branches
74 arachidic acid E. polystachya [12]
76 linoleic acid E. polystachya leaves [12]

Hydroxybenzene
(Ethanolic)
 (Ethanolic)
lants 2020, 9, x FOR PEER REVIEW 31 of 43

Plants 2020, 9, 1124 23 of 33

Branches and
Table 1. Cont. Branches and
lants 2020, 9, x FOR PEER REVIEW leaves 31 of 43
leaves
77 syringol Hydroxybenzene E. polystachya [12]
78 catechol E. polystachya [12]
Part Used (Type
Number Compound Structure Species (Ethanolic) Reference(s)
of Extract)
(Ethanolic)
ants 2020, 9, x FOR PEER REVIEW Branches and 32 of 43
leaves
Branches and
77 77 syringol syringol E.E.polystachya
polystachya leaves [12] [12]
(Ethanolic)
(Ethanolic)
Branches
Branches and
and
Cyclohexane leaves
leaves
lants 2020, 9, x FOR PEER REVIEW
Branches and 32 of 43
80
78 78 D-pinitol
catechol catechol E. polystachya
E.polystachya
E. polystachya leaves [12]
[12] [12]
(Ethanolic)
(Ethanolic)
(Ethanolic)
Cyclohexane
Branches and
Branches
leavesand
lants 2020, 9, x FOR PEER REVIEW leaves 32 of 43
78 catechol E. Branches
Branches
79 3-O-methyl-myo-inositol E.polystachya
E. platycarpa [12]
[30]
80 79 3-O-methyl-myo-inositol
D-pinitol E. platycarpa
polystachya (Methanolic)
(Methanolic) [12] [30]

Cyclohexane (Ethanolic)
Branches and
(Ethanolic)
leaves
Branches and
81 lactic acid E. polystachya leaves [12]
Branches and
80 80 D-pinitol D-pinitol E.E.polystachya
polystachya leaves [12] [12]
(Ethanolic)
(Ethanolic)
Cyclohexane (Ethanolic)
Branches and
Branches
leaves
79 3-O-methyl-myo-inositol E. platycarpa Branches and [30]
(Methanolic)
81 81 lactic acid lactic acid E.E.polystachya
polystachya leaves [12] [12]
(Ethanolic)
Branches and
(Ethanolic)
leaves
Branches
Branches andand
82 82 2-furoic acid 2-furoic acid E. polystachya
E. polystachya leaves
leaves [12] [12]
Branches
79 3-O-methyl-myo-inositol E. platycarpa (Ethanolic) [30]
81 lactic acid E. polystachya (Methanolic) [12]
(Ethanolic)

(Ethanolic)
Branches and
leaves
82 2-furoic acid E. polystachya [12]

(Ethanolic)
Branches and
lants 2020, 9, x FOR PEER REVIEW Branches and 33 of 43
leaves
83 succinic acid E. polystachya [12]

Plants 2020, 9, 1124 (Ethanolic) 24 of 33

Branches and
lants 2020, 9, x FOR PEER REVIEW 34 of 43
leaves
lants 2020, 9, x FOR PEER REVIEW 33 of 43
83 succinic acid Table 1. Cont. E. polystachya [12]

Cyclohexane
(Ethanolic)
Branches
Part Used
Branches and
(Type
and
Number
lants 2020, 9, x FOR PEER REVIEW Compound Structure Species leaves 34Reference(s)
of 43
of Extract)
leaves
Branches and
86
84 N,N-diethyl
fumariccarbamate
acid E. polystachya
E. polystachya leaves [12]
[12]
Branches and
83 83 succinic acid succinic acid E.E.polystachya
polystachya leaves [12] [12]
(Ethanolic)
(Ethanolic)
(Ethanolic)
Branches
Branches and
and
(Ethanolic)
leaves
leaves
Branches and
84
86 84 acid fumaric acid
fumariccarbamate
N,N-diethyl E.E.
E.polystachya
polystachya
polystachya leaves [12]
[12] [12]
(Ethanolic)
(Ethanolic)
(Ethanolic)
Carbohydrates or saccharides
Branches and
lants 2020, 9, x FOR PEER REVIEW Branches
leavesandand 34 of 43
Branches
leaves
85 85 sinapic acid sinapic acid E.E.polystachya
polystachya leaves [12] [12]
84 fumaric acid E. polystachya (Ethanolic) [12]
(Ethanolic)
Carbohydrates or saccharides Branches and
(Ethanolic)
Branches
leavesand
leaves
85 sinapic acid E. polystachya Branches and [12]
86
87 86 N,N-diethyl N,N-diethyl carbamate
carbamate
D-erythrose E.E.polystachya
polystachya leaves [12] [12]
(Ethanolic)
(Ethanolic)
(Ethanolic)
Carbohydrates or saccharides Branches
Branches and
and
leaves
leaves
Branches and
87 E.E.
85 87 D-erythrose
sinapic acid D-erythrose E.polystachya
polystachya
polystachya leaves [12]
[12] [12]
(Ethanolic)
(Ethanolic)
(Ethanolic)
Carbohydrates or saccharides Branches and
leaves and
Branches
88 88 D-mannose D-mannose E.E.polystachya
polystachya leaves [12] [12]
(Ethanolic)
(Ethanolic)
Branches and
Branches and
leaves
leaves
88 D-mannose E. polystachya [12]
87 D-erythrose E. polystachya [12]

(Ethanolic)
(Ethanolic)
 89 D-arabinose E. polystachya Branches and [12]
Plants 2020, 9, x FOR PEER REVIEW leaves 35 of 43

Plants 2020, 9, 1124 25 of 33

(Ethanolic)
89 D-arabinose E. polystachya Branches and [12]
Table 1. Cont. leaves
Plants 2020, 9, x FOR PEER REVIEW 35 of 43
Carbohydrates or saccharides
Part Used (Type
Number Compound Structure Species (Ethanolic) Reference(s)
90 xilose E. polystachya of Extract)
Branches and [12]
leaves
89 D-arabinose E. polystachya Branches andand
Branches [12]
89 D-arabinose E. polystachya leaves
leaves [12]
(Ethanolic)
(Ethanolic)
90 xilose E. polystachya Branches and
(Ethanolic) [12]
Branches and
leaves
90 xilose E. polystachya leaves [12]
(Ethanolic)

91
OH OH (Ethanolic)
trehalose E. polystachya Branches and [12]
OH
leaves
90 xilose O
E. polystachya Branches and [12]
OH Branches
leaves and
91 trehalose E. polystachya leaves [12]
O O
HO (Ethanolic)
(Ethanolic)
HO OH OH
OH
91 trehalose E. polystachya Branches and
(Ethanolic) [12]
OH OH
leaves
O
OH

O O
HO
(Ethanolic)
HO OH
OH OH
91 trehalose OH E. polystachya Branches and [12]
OH
leaves
O
OH

O O
HO
(Ethanolic)
HO OH

OH
Plants 2020, 9, 1124 26 of 33

4. Pharmacological Activities
The pharmacological activities were described chronologically in order to encapsulate the research
carried out on Eysenhardtia gender through the years.

4.1. Urinary Disorders

As previously mentioned, the plant was analyzed for its beneficial effects on kidney or urinary
tract problems. In 1998 carried out a study to test the diuretic and antilytic effect of the aqueous extract
of Eysenhardtia polystachya bark in rats [37]. The model animals were induced with urolithiasis by
implanting a zinc disk in the bladder. As a result, they observed a significant reduction in the weight
of the uroliths after the administration of the aqueous extract of E. polystachya in the affected animals
compared to the control group. Diuretic action was also verified by identifying an increase in the
volume of urine [37], as well as favoring the retention of potassium [38].
In the year 2000, the compounds responsible for the antiurolithiatic (antilithiatic) and diuretic
activity were identified, which correspond to 7-hydroxy-20 ,40 ,50 -trimethoxyisoflavone (16) and
7-hydroxy-40 -methoxyisoflavone (23) [28,39].
Later, in 2002, the effect of isoflavones isolated from the bark of Eysenhardtia polystachya on the
formation of oxalate and calcium phosphate (COM) stones in urine was analyzed and reported in a
preclinical trial. From this study, it was found that the phenolics compounds reported were able to
inhibit the formation and growth of COM, consequently reducing the appearance of kidney stones and
suggesting the use of isoflavones as a preventive treatment [29].

4.2. Antimicrobial Activity

The inappropriate use of treatments and the ability of microorganisms to adapt have led them to
develop tolerance to various antimicrobial drugs; this has prompted the continued search for new drugs
that offer other options, possible sources thereof being plants. In the case of the genus Eysenhardtia, the
first report found on antimicrobial activity was published in 1997, in which an antimicrobial scan was
performed using minimal inhibitory concentration (MIC) tests. The microorganisms used were Sarcina
lutea, Proteus vulgaris, Staphylococcus aureus, Escherichia coli, and Candida albicans. The information
obtained showed that the E. polystachya methanol extract had an effect on inhibiting the different strains
studied; this inhibitory action was shown to have potential against Gram positive and Gram negative
bacteria [40].
In 1998, the antimicrobial action of the compounds (3S)-7-hydroxy-20 ,30 ,40 ,50 ,8-pentamethoxyisoflavan
(10), (3S)-30 ,7-dihydroxy-20 ,40 ,50 ,8-tetramethoxyisoflavan (11), stigmasterol (68), isoduartin (14), cuneatin
(15), 7-hydroxy-20 ,40 ,50 -trimethoxyisoflavone (16) and 3,4-dimethoxy-8,9-methylenedioxypterocarpan (7),
isolated from the bark E. polystachya was analyzed for each of it. The results showed that they had no
action against Escherichia coli, Pseudomonas aeroginosa, Streptococcus aureus, Bacillus subtilis, Shigella smiled,
and Candida albicans at a concentration of 200 µg/mL [8].
In 1999, the compounds (α-hydroxydihydrochalcones, (αR)-α,3,4,20,40-pentahydroxydihydrochalcone
(17), (αR)-30-C-β-D-xylopyranosyl-α,3,4,20,40-pentahydroxydihydrochalcone (18), (αR)-30-O-β-D-
0 0 0
xylopyranosyl-α,3,4,2 ,4 -pentahydroxydihydrochalcone (19) and coatline B [(αR)-3 -C-β- D-glucopyranosyl-α,
20,3,40,4-pentahydroxydihydrochalcone]) (2) isolated from the bark of E. polystachya. They did not show
activity against Escherichia coli, Pseudomonas aeroginosa, Streptococcus aureus, Bacillus subtilis, Shigella
smiled, and Candida albicans [25]. Likewise, in 1999 were evaluated the compounds 40,5,7-trihydroxy-
8-methyl-6-(3-methyl-[2-butenyl])-(2S)-flavanone (20), 40,5,7-trihydroxy-6-methyl-8-(3-methyl- [2-butenyl])-
(2S)-flavanone (21) and 40,5-dihydroxy-7-methoxy-6-(3-methyl-[2-butenyl])-(2S)-flavanone (22), from the
aerial zone of Eysenhardtia texana Kunth from an extract of methanol and dichloromethane. The flavonones
were active in inhibiting the growth of Staphylococcus aureus, and one of them also reduced the proliferation of
Candida albicans [26,27].
Plants 2020, 9, 1124 27 of 33

Subsequently, the antimicrobial action of the methanol extracts of E. polystachya and E texana
were studied to mitigate nine strains of bacteria and a yeast linked to urinary infections; the species
evaluated were Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella pneumoniae, Enterobacter
aerogenes, Pseudomonas aeruginosa, Serratia marcescens, Staphylococcus aureus, Staphylococcus epidermidis,
and Candida albicans. The results showed that E. texana had limited antibacterial activity; in contrast,
E. polystachya showed a broad-spectrum antimicrobial effect against the microorganisms evaluated.
The authors suggest its use as a possible alternative for the inhibition of Gram positive and Gram
negative bacteria, since it exists there is a shortlist of appropriate drugs to inhibit these families of
microorganisms [18].
In 2012, the antibacterial potential of 47 plants in oral infections was researched by analyzing
ethanolic and aqueous extracts. E. polystachya, showed a reduction in the proliferation of Streptococcus
mutans and Porphyromonas gingivalis [41].
Subsequently, the ethanol extract from the leaves and branches of E. polystachya was analyzed
using the MTT test, as well as the lowest inhibitory concentration (MIC). The data showed activity
for Escherichia coli (MIC = 1.56 µg/mL), Staphylococcus aureus (MIC = 0.78 µg/mL), and multi-resistant
organisms (MIC > 100 µg/mL) [12].

4.3. Antidiabetic Activity

Diabetes is a chronic degenerative disease related to hyperglycemia. Excess glucose in the
blood causes health problems related to the generation of reactive oxidant species, the glycation of
proteins, lipoperoxidation, difficulty in recognizing, sensitivity, and secretion of insulin, among others;
this results in a diabetic pathology.
In 1998, the hypoglycemic capacity of 28 plants was evaluated; among the species analyzed
was E. polystachya, which was considered an appropriate candidate to regulate glycemic levels in a
pre-clinical study [11].
Subsequently, the antihyperglycemic activity of the methanolic extracts of the leaves (LEP),
branches (BEP), and bark (REP) of Eysenhardtia platycarpa was studied in diabetic rats induced with
streptozotocin, as well as in healthy animals. It was observed that the REP extract did not exhibit
antihyperglycemic action compared to LEP and BEP. Additionally, the effect of 3-O-acetyloleanolic (72)
acid (isolated from BEP) was observed in reducing blood glucose levels in diabetic rats.
In 2007, a study was published evaluating the antioxidant activity of the methanol extracts of E.
platycarpa, E. puntacta, and E. subcoriacea in a murine pancreatic model. The tests showed that these
species were protected from the damage induced by 2,2-azo-bis(2-amidinopropane)dihydrochloride
(AAPH). Furthermore, some bioactives, (3-O-acetyl-11α,12α-epoxy-oleanan-28,13β-olide (69),
(+)-catechin (33), and (+)-catechin-3-O-β-D-galactopyranoside (37)) isolated from the branches of
E. platycarpa, showed radical scavenging capacity 2,2-diphenyl-1-picrylhydrazyl (DPPH), increase
the concentration of pancreatic glutathione (GSH), the activity of glutathione peroxidase (GSHPx)
and catalase (CAT), as well as regulating the gain in levels of glucose in diabetic rats induced with
streptozotocin after five days of administration [33].
In 2008, the antioxidant activity of secondary metabolites identified in the aerial zone of E. subcoriacea
was reported. Among the bioactive drugs described are 3-(20 -hydroxy-40 ,50 -methylendioxyphenyl)-
6-(30 ’-hydroxymethyl-40 ’-hydroxybut-20 ’-enyl)-7-hydroxycoumarin (32), (+)-catechin (33), (-)-epicatechin
(34), (+)-afzelechin (35), eriodictyol (36), (+)-catechin 3-O-β-D-galactopyranoside (37), and quercetin
3-O-β-D-galactopyranoside (38), all of which countered the presence and development of free radicals
(DPPH and AAPH) and can be used to suppress diabetic pathology [31].
In 2010, the antihyperglycemic and antioxidant effect of subcoriacin (3-aryl-6prenylcoumarin),
a secondary metabolite from E subcoriacea, was researched. The administration of the bioactive
compound to streptozotocin-induced diabetic rats for five days showed a reduction in blood glucose
levels, increased activity of the enzymes (glutathione peroxidase (GSHPx), superoxide dismutase (SOD)
Plants 2020, 9, 1124 28 of 33

and catalase (CAT)) of the endogenous system. For this reason, the protective action of Subcoriacin
against pancreatic damage induced by free radicals under a diabetic condition [32] was suggested.
In 2014, the antioxidant, antidiabetic and antiglycation properties of the aqueous-methanolic
extract of Eysenhardtia polystachya were analyzed. The ability to decrease and/or eliminate free radicals
DPPH, ABTS, was noted, as well as the reactive oxygen species (RO2 , −O2 , H2 O2 , −OH, ONOO−,
NO−, HOCl, 1 O2 ), and the ability to absorb oxygen radicals (ORAC) by donating electrons (H+ ).
The ability to sequester metals for the formation of chelates and decreased lipoperoxidation was
also examined. At the same time, the activity to inhibit fluorescent AGEs, glycation of hemoglobin,
and methylglyoxal products was determined. As for in vivo tests with strepzotocin-induced diabetic
murine models, a decrease was observed in blood glucose levels, triglycerides (TG), total cholesterol
(TC), thiobarbituric acid reactives substances (TBARS), and low-density lipoprotein (LDL). At the same
time, an increase in serum insulin, body weight, and liver biomarkers were induced. Consequently,
the methanolic-aqueous extract of EP demonstrated the ability to interact at the different points
evaluated, exercising beneficial actions in the control of disorders associated with diabetes based on
the presence of phenolic compounds [14].
In 2016, were analyzed six compounds (20 ,40 -dihydroxychalcone-60 -O-β-D-glucopyranoside
(39), α,3,20 ,40 -tetrahydroxy-4-methoxy-dihydrochalcone-30 -C-β-glucopyranosi-60 -O-β-D-glucopyranoside
(40), 7-hydroxy-5,80 -dimethoxy-60 α-L-rhamnopyranosyl-8-(3-phenyl-transacryloyl)-1-benzopyran-2-one
(41), 60 7-dihydroxy-5,8-dimethoxy-8(3-phenyl-trans-acryloyl)-1-benzopyran-2-one (42), 9-hydroxy-3,8-
dimethoxy-4-prenylterocarpan (43), and α,4,40 -trihydroxy-dihydrochalcone-20 -O-β-D-glucopyranoside
(45)) from the aqueous-methanol extract of the bark of Eysenhardtia polystachya, for their possible
antioxidant potential, in streptozotocin-induced diabetic mice. The first five flavonoids showed favorable
effects on the regulation and protection of hepatic and cellular biomarkers associated with disorders
caused by oxidative stress in diabetes [34].
Furthermore, the inhibition capacity of 11 dihydrochalcones from the methanolic extract of the E.
polystachya bark in the formation of advanced glycation end products (AGEs) was studied in their multiple
stages (early, intermediate, and final). Protein glycation corresponds to the interaction of proteins with
excess sugars in the body; this hyperglycemic condition occurs during diabetes. The tests carried out were
in vitro, and it was concluded that each of the isolated bioactives were capable of inhibiting and protecting
from the formation and accumulation of AGEs. The biocomposites analyzed were: (60 methoxy-sieboldin
(53), 20 -O-α-L-rhamnopyranosyl-α,60 ,dihydroxy-40 acetyl-4-methoxy-dihydrochalcone (52), 20 -O-β-D-
glucopyranosyl-40 -methoxy-4-hydroxy-3-isoprenyl-dihydrochalcone (54), 20 ,40 ,60 trihydroxy-4,5-
0 0 0 0
dimethoxy-3-isoprenyl-dihydrochalcone (55), 3 -C-β-glucopyranosyl-α,2 ,4 ,6 - trihydroxy-4- methoxy-
dihydrochalcone (56) and 30 -C-β-glucopyranosyl-α,20 ,4-trihydroxy-40 ,60 -dimethoxy- dihydrochalcone)
(57) the rest (3-hydroxyphloretin-40 -O-β-D-glucopyranoside (58), 3,40 -dihydroxy-2,4,6-trimethoxy-
dihydrochalcone (59), 20 ,40 ,4-trihydroxy-30 -methoxy-dihydrochalcone (60), 20 ,40 ,60 ,4-tetrahydroxy-3,
5-diisoprenyl-dihydrochalcone (61), and 30 -C-β-glucopyranosyl-α,20 ,40 ,3,4-penta-hydroxy-
dihydroxychalcone (62)) had previously been elucidated [35].
In 2019, it was demonstrated that the bioactive 30 -O-β-D-glucopyranosyl α,4,20 ,40 ,60 -
pentahydroxy–dihydrochalcone (63) isolated from Eysenhardtia polystachya is an excellent antiglycation
compound capable of reducing glycation of proteins responsible for diabetic nephropathy in diabetic
individuals. Tests were carried out using diabetic mice with kidney problems induced with stretozotocin;
levels of glycated hemoglobin (HbA1c), the concentration of glycation end products advances in the
kidney and circulatory system, as well as in pro-inflammatory markers ICAM-1 were then analyzed.
The bioactive (63) was administered for five weeks at different concentrations (25, 50, and 100 mg/kg);
at the end of the dosing period the diabetic animals showed a significant improvement, suggesting the
ability of the bioactive to react and inhibit early and intermediate precursors in the formation of AGEs,
responsible for damaging the structure of the kidneys [36].
Plants 2020, 9, 1124 29 of 33

4.4. Anti-Inflammatory Activity

In 2015, the anti-inflammatory potential of the Eysenhardtia polystachya bark from hexane (PAH),
chloroform (PAC), and methanol (PAM) extracts was researched. The extracts were evaluated using
Wistar rats as an experimental model. To determine the anti-inflammatory activity of the extracts,
different tests were used such as: carrageenan and croton oil induced edema. The tumor necrosis
factor α (TNF-α), interleukin-1-β (1L-1β), prostaglandin E2 (PGE2) and leukotriene B4 (LTB4) were
also quantified. The PAM extract showed anti-inflammatory activity in the different induced edema
inhibited the expression of the cytokines (TNF-α, 1L-1β, PGE2 and LTB4), and the enzymes lipoxygenase
and xanthine-oxidase linked to inflammatory problems [15].
Furthermore, in 2018 the properties of the ethanolic extract from the bark of E. polystachya
to mitigate rheumatoid arthritis were analyzed. To do this, the antiarthritic activity induced by
Complete Freund’s Adjuvant (CFA) in rats was determined. Trials showed that secondary metabolites
of E. polystachya, mainly flavonoids, inhibited secondary inflammatory processes in arthritic rats,
encouraged histopathological changes, and reduced serum levels of inflammatory cytokines [16].
Additionally, in that same year, the anti-inflammatory effect of ethanol extract from the leaves
and branches of E. polystachya was examined using in vitro tests stimulating macrophages using LPS.
The results demonstrated a decrease in the production of H2 O2 (IC50 = 43.9 ± 3.8 µg/mL) and IL-6
(73.3 ± 6.9 µg/mL) [12].

4.5. Antinociceptive Activity

The importance of reducing or mitigating the sensation of pain has been fundamental for the
control and treatment of different conditions, this has prompted the search for natural alternatives.
In 2018, the ethanolic extract of the bark of E. polystachya was evaluated, using the acetic acid-induced
abdominal contraction test and the hot-plate test, which were performed on mice. A decrease in
the spasms generated by acetic acid and a prolonged sensitivity time at the peripheral and central
levels [16] were observed.
Furthermore, in that same year, D-pinitol (80) isolated from ethanolic extract of Eysenhardia
polystachya was examined to find out if it had the property to block or reduce pain. It was found
that D-pinitol inhibited 67.58% with an effective dose of 10.7 mg/kg; its activity is associated with the
serotoninergic system (5-HT3) and nitric oxide [42].
Additionally, the antinociceptive effect of the ethanolic extract from leaves and branches
of E. polystachya (EPE) was also studied, following the acetic acid, formalin, and hot plate test.
It was identified that the extract contained 26.93% D-pinitol, the bioactive responsible for an action.
EPE presented an effective dose of 117 ± 14.5 mg/kg and 33 ± 3.2 mg/kg for D-pinitol in acetic acid test;
in the case of formalin it was 48.9 ± 3.9 mg/kg. The action of EPE is probably due to the involvement of
ATP-sensitive K+ channels. As for D-pinitol, its route of action is considered to occur at nitric oxide
receptors and 5-hydroxytryptamine 3 (5-HT3) [12].

4.6. Antidiarrheal
The ability to stop diarrhea was analyzed from the ethanolic extract of the leaves and branches of
E. polystachya (EPE) and the compound D-pinitol (80) isolated from E. polystachya. The results showed
that the EPE extract had an effective dose of 7.5 ± 0.9 µg/mL and the D-pinitol 0.1 ± 0.03 µg/mL.
The results suggest that this was due to the elimination of intestinal fluid [12].

4.7. Muscle Relaxant

The pharmacological potential in Jejunum muscle contraction was explored using chloroform
extract from the stems of E. polystachya in muscle tissue extracted from rabbits. The test showed that
the extract presents an effect on jejunum contractility [43].
Plants 2020, 9, 1124 30 of 33

4.8. Cytotoxic Activity

In 1998, the cytotoxic activity of the bioactives ((3S) -7-hydroxy-20 ,30 ,40 ,50 ,8-pentamethoxyisoflavan
(10), (3S)-30 ,7-dihydroxy-20 ,40 ,50 ,8-tetramethoxyisoflavan (11), isoduartine (20 ,7-dihydroxy-30 ,40 ,8-
trimethoxyisoflavan)(14)) was evaluated; these were isolated from the chloroform-methanol extract
of the bark of E. polystachya. The identified metabolites showed slight cytotoxic activity against the
cell lines (KB (nasopharyngeal carcinoma), P388 (murine leukemia) and SQC-1 UISO (squamous cell
carcinoma of the cervix)) [8].

4.9. Nanoparticles and Eysenhardtia

Furthermore, in 2018 silver nanoparticles were synthesized with the aqueous methanol extract
of Eysendhartia polystachya and their performance in inhibiting AGEs in vitro tests cell viability with
RAW-264.7 cells was analyzed and in vivo tests with diabetic zebrafish induced by glucose exposure
were performed. It was found that the bioactives present in the nanostructures can counteract
protein glycosylation through their intervention in the neutralization and elimination of fluorescent,
non-fluorescent, free radical AGEs, and the catchment of methylglyoxal together with its derivatives.
Regarding diabetic fish, these showed a decrease in the conditions caused by chronic hyperglycemia.
Their results suggest the use of nanoparticles for diabetic pathology [44].
Also, in 2018, silver nanoparticles biosynthesized with the aqueous methanolic extract from the
bark of E. polystachya were used as delivery and transport systems for polyphenolic constituents.
The cell viability (murine RAW-264.7 macrophage cells) and biocompatibility of nanostructures was
determined, as well as the E. polystachya extract. The antioxidant effect of the synthesized nanometric
material on the biomarkers of zebrafish embryos exposed to a medium with high glucose concentrations
was also studied. Treatments using nanoparticles and plant extracts increased the activity of the
antioxidant enzymes (SOD, CAT, and GPx) and reduced the damage caused by the formation of
reactive oxidative species, positively influencing the total protein concentration while decreasing the
formation of malondialdehyde (MDA) and lipoperoxidation. Consequently, nanostructures with a high
content of phenolic compounds could be a viable alternative in minimizing the diabetic complications
associated with oxidative stress [45].
In that same year, the antidiabetic properties (qualities) of the bio-nanofabricated silver
nanoparticles were evaluated using the hydroalcoholic extract of Eysenhardtia polystachya (EP/AgNPs).
They demonstrated the protective action of EP/AgNPs against damage caused by hydrogen peroxide to
INS-I cells, minimizing cell mortality, also having a cytoprotective action against oxidative laceration.
Furthermore, it was observed that when administering the EP/AgNPs to glucose-induced diabetic
zebrafish (111 mM), they showed an improvement in the levels of blood glucose, insulin, triglycerides,
and cholesterol; helping to regulate hyperglycemic, hyperlipidemic, and insulin sensitivity. The authors
suggest the possibility of using E. polystachya nanostructures as an alternative therapy for the control of
diabetes due to their high concentration of chalcones, dihydrochalcones, and flavonoids [46].
Furthermore, nanoparticles have been synthesized and functionalized with the extract of
E. polystachya using biological applications by taking advantage of the composition of the plant’s
fluorescent biocomposites; these can then be used as a fluorescent cell nanomarker to detect cancer or
pathogenic microorganisms [47].

4.10. Other Applications

The bioactive molecules responsible for the fluorescence of E. polystachya were isolated
and elucidated from the methanol extract of the heartwood. Among the bioactives isolated
are; 7-hydroxy-20 ,40 ,50 -trimethoxyisoflavone (16) and 9-methoxy-2,3-methylenedioxycoumestan (47)
corresponding to Robert Boyle’s acid-base fluorescent indicator used in the 17th century [24].
Plants 2020, 9, 1124 31 of 33

Also, the activity of the extracts of ethyl acetate, dichloromethane, hexane, and methanol was
determined from calluses and suspended cells of E. polystachya for the control of fungal phytopathogens.
The information obtained provided an opportunity to propose plant extracts as a fungicide option [48].
Nine fractions of the E. polystachya ethanolic extract were also evaluated for use as fluorescent
biosensors. Six of the nine fractions tested positive for photoluminescence and only two were stable
for use in the functionalization of silica nanoparticles. The G2 subfraction demonstrated appropriate
fluorescence qualities at a physiological pH and its detection also did not show toxicity, allowing cell
viability [49].

5. Conclusions
Currently, there are many diseases linked to factors related to metabolic syndrome. This condition
has caused people to develop various health problems and increases their risk of mortality. This has
caused a large part of society to live under a constant medication scheme that attempts to regulate
the ailments that afflict them, which in turn stimulates the consumption of natural alternatives that
have shown to help control symptoms. In this paper, we present the potential of the extracts and/or
bioactives of the Eysenhardtia genus to limit the proliferation of microbial infections, urinary disorders,
oxidative stress, protein glycation, lipoperoxidation, increase in blood sugar levels, inflammation,
or the development of bodily discomfort. Furthermore, the introspection performed made it clear that
the composition of phytochemical compounds and their diversity of secondary metabolites could be a
complementary solution for individuals affected by comorbidity.

Author Contributions: Writing—original draft preparation, A.G.-C. and A.M.-R.; writing—review and editing,
E.G. and A.M.-R. All authors have read and agreed to the published version of the manuscript.
Funding: Consejo Nacional de Ciencia y Tecnología (CONACYT), project FORDECYT-CIIDZA: 296354.
Acknowledgments: We acknowledge the funding from CONACYT (FORDECYT-CIIDZA: 296354). The authors
thank Biologist Juan Pablo Brunei, for providing the images of the plant for publication.
Conflicts of Interest: The authors declare no conflict of interest.

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