Natural Product Research

Formerly Natural Product Letters

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Alkaloids of genus Erythrina: An updated review

Nouran M. Fahmy, Eman Al-Sayed, Mohamed El-Shazly & Abdel Nasser

Singab

To cite this article: Nouran M. Fahmy, Eman Al-Sayed, Mohamed El-Shazly & Abdel Nasser
Singab (2019): Alkaloids of genus Erythrina: An updated review, Natural Product Research, DOI:
10.1080/14786419.2018.1564300

To link to this article: https://doi.org/10.1080/14786419.2018.1564300

Published online: 21 Jun 2019.

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NATURAL PRODUCT RESEARCH
https://doi.org/10.1080/14786419.2018.1564300

REVIEW

Alkaloids of genus Erythrina: An updated review

Nouran M. Fahmya, Eman Al-Sayeda , Mohamed El-Shazlya,b and
Abdel Nasser Singaba,c
a
Department of Pharmacognosy Faculty of Pharmacy, Ain-Shams University, Cairo, Egypt;
b
Department of Pharmaceutical Biology Faculty of Pharmacy and Biotechnology, German University
in Cairo, Cairo, Egypt; cCenter for Drug Discovery and Development Research, Ain-Shams University,
Cairo, Egypt

ABSTRACT ARTICLE HISTORY

Genus Erythrina (Fabaceae) comprises several species, which are Received 14 October 2018
widely distributed in tropical and subtropical regions of the world. Accepted 19 December 2018
The plants of this genus exhibited significant role in traditional
medicine targeting different diseases. Alkaloids and flavonoids KEYWORDS
were reported as the chief bioactive constituents of this genus Erythrina; alkaloids;
erythroidine; curare;
with a wide range of biological activities. About 143 alkaloids anticonvulsant; erysodine
were isolated from Erythrina sp. Anticonvulsant, anxiolytic, curare-
like activity, insecticidal and cytotoxic activities were reported for
Erythrina sp. alkaloids. The present work is an overview of the iso-
lated alkaloids from Erythrina sp. with their reported biological
activities.

Abbreviations: CHCl3: Chloroform; CNS: Central nervous

system; DCM: Methylene chloride; DPPH: 2,2-Diphenyl-1-pic-
rylhydrazyl; E.: Erythrina; ERa/b: Estrogen receptors a/b;
EtOAc: Ethyl acetate; EtOH: Ethanol; Hep-G2: Human liver
carcinoma cell lines; HIV: Human immunodeficiency virus;
HL-60: Human promyelocytic leukemia cells; K-562: Human
immortalized myelogenous leukemia cell line; LPS:
Lipopolysaccharide; MeOH: Methanol; MOLT-4: Acute
lymphoblastic leukemia cell line; nAChRs: nicotinic acetyl-
choline receptors; NO: Nitric oxide; NREM: non-rapid eye
movement; Pet. ether: Petroleum ether; RBA: Receptor
binder affinity; TRAIL: Tumor necrosis factor (TNF)-related
apoptosis-inducing ligand

CONTACT Abdel Nasser Singab dean@pharma.asu.edu.eg Department of Pharmacognosy, Faculty of

Pharmacy, Ain Shams University, Organization of African Unity Street, Abassia, Cairo 11566, Egypt; Mohamed El-
Shazly mohamed.elshazly@pharma.asu.edu.eg Department of Pharmacognosy, Faculty of Pharmacy, Ain-
Shams University, Organization of African Unity Street, Abassia, Cairo 11566, Egypt
ß 2019 Informa UK Limited, trading as Taylor & Francis Group
2 N. M. FAHMY ET AL.

Introduction
The genus Erythrina found throughout the tropical and subtropical regions of the
world, belongs to family Fabaceae (Leguminosae). Erythrina comprises over 130 spe-
cies of orange and/or red flowering trees, shrubs and herbaceous plants. Some
Erythrina sp. are used for ornamental purposes, as a shade and for soil improvement
in gardens and streets (Jackson 1985; Mohammed et al. 2012). The name “coral tree”
is used as a collective term for these plants (Kumar et al. 2010). Erythrina sp. have
been used in traditional medicine for the treatment of various diseases, for example E.
herbacea is used by the Tenek tribe of San Luis Potosi, Mexico, as a tranquilizer agent,
due to its alkaloids (Tanaka et al. 2010). In Indonesia, the decoction of the bark or
leaves were used for malaria (Tjahjandarie et al. 2014). Erythrina sp. are a rich source
of secondary metabolites with alkaloids and flavonoids as their main bioactive constit-
uents (Fahmy et al. 2018). Reviews on Erythrina alkaloids were traced and we found
that authors focused on the alkaloids structural features and biosynthesis (Jackson
1985; Chawla and Kapoor 1995). These reviews were published more than two deca-
des ago in 1985, 1991 and 1995. Literature survey on Erythrina alkaloids revealed that
no updated review was published reporting most of the isolated Erythrina alkaloids
with their biological activity. Only Hussain et al. in 2016 highlighted briefly Erythrina
chemical constituents reporting 47 alkaloids (Hussain et al. 2016). The present work is
an overview of Erythrina sp. alkaloids isolated in the period between the early 1936
and the late 2018 with their reported biological activities.

Literature survey databases

All information on Erythrina alkaloids was compiled from electronic databases such as
Medline, Google Scholar, PubMed, ScienceDirect, SCOPUS, SciFinder and Springer Link.

Results
Erythrina alkaloids
About 143 alkaloids were isolated from the genus Erythrina, distributed mainly in the
seeds as well as the stem, bark, leaves and flowers (Chawla and Kapoor 1995).
Erythrina alkaloids are characterized by a tetracyclic spiroamine system with four linked
rings, labeled A, B, C, and D, known as the erythrinane skeleton. The Erythrina alkaloids
can be categorized into three main classes known as dienoid, alkenoid and lactonic
alkaloids. The dienoid alkaloids possess a conjugated diene system in ring A and B,
whereas the alkenoid have a 1,6-double bond in the A-ring, the lactonic alkaloids
have a lactone ring instead of the benzene ring (Jackson 1985). Other alkaloids were
reported from this genus, including 16-Azoerythrinanes, tetrahydroisoquinolines, ben-
zylisoquinoline, quinolizidine, indole and dimeric alkaloids. Few alkaloid glycosides
were also reported from Erythrina sp. Recently, trimeric dienoid alkaloids were isolated
from E. variegata flowers (Zhang B-J et al. 2016). Table 1 highlights the structural
diversity of Erythrina alkaloids Figures (1–8).
Table 1. Alkaloids isolated from genus Erythrina.
No. Compound Name Occurrence (Solvent used for extraction) Reference
1. Dienoid alkaloids
1. Erysodine E. crista galli leaves (Deulofeu and Labriola 1947; Ito et al. 1973a)
E. crista galli seeds (Wang et al. 2017)
E. suberosa seeds (EtOH) (Singh and Chawla 1969)
E. abyssinica seeds (Folkers and Koniuszy 1940)
E. sandwicensin seeds E. americana seeds E. poeppigiana seeds E. her- (Folkers and Koniuszy 1940) (Folkers and Koniuszy 1940)
bacea seeds E. flubelliformis seeds (Folkers and Koniuszy 1940) (Folkers and Koniuszy 1940)
(Folkers and Koniuszy 1940)
E. folkersii (Millington et al. 1974)
E. velutina seeds (MeOH) (Ozawa et al. 2009)
E. variegata bark, leaves and seeds (Ghosal et al. 1972; Chawla etal. 1988)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004)
E. chiriquensis E. caribea (Jackson 1985) (Jackson 1985)
E. senegalensis seeds (MeOH) (Wandji et al. 1995)
E. latissima seed pods (DCM:MeOH) (Wanjala et al. 2002)
E. arborescens leaves and flowers (MeOH) (Ito et al. 1973b; Wu et al. 2017)
E. addisoniae seeds (EtOAc) (Cui et al. 2009)
E. caffra E. zeyheri E. livingstoniana E. fusca E. coralloides E. goldmanii (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. coralloides E. atitlanensis E. macrophylla E. tajumulcensis E. gua- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
temalensis E. steyermarkii E. oliviae E. mulungu (Synonyms of E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
verna Vell.) (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
2. Erysovine E. crista galli seeds and bark (MeOH) (Deulofeu and Labriola 1947; Ozawa et al. 2010)
E. crista galli seeds (Wang et al. 2017)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. variegata bark (pet. ether) and seeds (Singh et al. 1975; Singh et al. 1981)
E. sandwicensin seeds (Folkers and Koniuszy 1940)
E. berteroana seeds E. poeppigiana seeds E. flubelliformis seeds (Folkers and Koniuszy 1940) (Folkers and Koniuszy 1940)
(Folkers and Koniuszy 1940)
E. folkersii (Millington et al. 1974)
E. velutina seeds (MeOH) (Ozawa et al. 2009)
E. latissima seeds (Wanjala and Majinda 2000)
E. addisoniae seeds (EtOAc) and flowers (MeOH) (Cui et al. 2009; Wu et al. 2017)
E. chiriquensis E. caribea (Jackson 1985) (Jackson 1985)
E. caffra E. zeyheri E. senegalensis E. livingstoniana E. abyssinica E. sub- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
erosa E. arborescens E. fucosa E. coralloides E. goldmanii E. atitla- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
nensis E. macrophylla E. tajumulcensis E. guatemalensis E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
steyermarkii E. oliviae E. mulungu E. lysistemon (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
NATURAL PRODUCT RESEARCH

3. Erysopine E. crista galli seeds (Deulofeu and Labriola 1947)

E. abyssinica seeds (Folkers and Koniuszy 1940)
(continued)
3
 4

Table 1. Continued.
No. Compound Name Occurrence (Solvent used for extraction) Reference
E. sandwicensin seeds E. herbacea seeds E. flubelliformis (Folkers and Koniuszy 1940) (Folkers and Koniuszy 1940)
(Folkers and Koniuszy 1940)
E. variegata bark, leaves, and seeds ( Chawla et al. 1988)
E. addisoniae seeds (EtOAc) (Cui et al. 2009)
E. chiriquensis E. caribea (Jackson 1985) (Jackson 1985)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
4. Erysoline E. melanacantha E. merilliana (Jackson 1985) (Jackson 1985)
E. folkersii (Millington et al. 1974)
E. berteroana E. guatemalensis E. steyermarkii E. subumbrans E. lanata (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
N. M. FAHMY ET AL.

E. acantbocarpa E. caribea (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
5. Erysonine E. melanacantha E. merilliana (Jackson 1985) (Jackson 1985)
E. folkersii (Millington et al. 1974)
E. variegata bark ( Chawla et al. 1988)
E, caribea E. guatemalensis E. steyermarkii E. berteroana E. costaricensis (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. folkersii E. melanacantha (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
6. Erysotrine (Erysothrine) E. suberosa seeds (EtOH) (Singh and Chawla 1969)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. crista galli leaves (Ito et al. 1973c)
E. crista galli seeds (Wang et al. 2017)
E. chiriquensis (Jackson 1985)
E. folkersii (Millington et al. 1974)
E. vespertilio fruits (Iranshahi et al. 2012)
E. velutina seeds (MeOH) (Ozawa et al. 2009)
E. variegata bark, leaves and seeds (Ghosal et al. 1972; Chawla et al. 1988)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004)
E. latissima seed pods (DCM:MeOH) (Wanjala et al. 2002)
E. arborescens leaves and flowers (Ito et al. 1973a; Wu et al. 2017)
E. addisoniae seeds (EtOAc) (Cui et al. 2009)
E. abyssinica seeds (CHCl3) (Mohammed et al. 2012)
E. caffra E. zeheri E. senegalensis E. livingstoniana E. fucosa, E. flabelli- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
formis E. poeppigiana E. coralloides E. goldmanii E. atitlanensis E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
macrophylla E. tajumulcensis E. guatemalensis E. steyermarkii E. oli- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
viae E. mulungu flowers (EtOH) E. speciosa flowers (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991; Amorim et al. 2018) (Faria
et al. 2007)
7. Erythravine E. folkersii (Millington et al. 1974)
E. mulungu flowers (70% EtOH) (Flausino et al. 2007; Faggion et al. 2011; Setti-Perdigao
et al. 2013)
E. lysistemon E. abyssinica E. steyermarkii E. eggersii (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
8. Erythrascine E. arborescens (Amer et al. 1991)
(continued)
Table 1. Continued.
No. Compound Name Occurrence (Solvent used for extraction) Reference
9. 11-b-Hydroxyerysotrine (Erythrartine) E. arborescens leaves (Ito et al. 1973b)
E. variegata E. poeppigiana E. mulungu (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004)
E. herbacea flowers (MeOH) E. speciosa flowers (Tanaka et al. 2008) (Faria et al. 2007)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
10. Erythristemine E. lysistemon flowers, stem wood and leaves (DCM:MeOH) (Juma and Majinda 2004)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
11. 11-b-Hydroxyerysodine E. lysistemon seeds E. senegalensis E. livingstoniana E. latissima (Jackson 1985) (Jackson 1985) (Jackson 1985)
(Jackson 1985)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
12. 11-a-Hydroxyerysodine E. lysistemon seeds and flowers (Jackson 1985; Juma and Majinda 2004)
13. 11-a-Hydroxyerysotrine E. suberosa stem bark (DCM:MeOH) (Kumar S et al. 2013)
E. mulungu flowers (70% EtOH) (Flausino et al. 2007; Setti-Perdigao et al. 2013)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
14. 11-a-Hydroxyerythravine E. mulungu flowers (70% EtOH) (Flausino et al. 2007; Faggion et al. 2011; Setti-Perdigao
et al. 2013)
15. 11-b-Hydroxyerysovine E. arborescens E. lysistemon E. senegalensis (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
16. 11-b-Methoxyerysodine E. lysistemon seeds (Jackson 1985)
E. abyssinica seeds (CHCl3) (Mohammed et al. 2012)
17. 11-b-Methoxyerysovine E. lysistemon E. abyssinica (Amer et al. 1991)
18. 11-Oxoerysodine E. senegalensis E. excelsa E. tabitensis (Synonyms of E. sandwicensin) E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
arborescens E. caffra E. livingstoniana E. abyssinica (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
19. 11-Oxyerysovine E. tabitensis (Synonyms of E. sandwicensin) E. arborescens E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
livingstoniana
20. 11-Oxoerysopine E. tabitensis (Synonyms of E. sandwicensin) E. arborescens (Amer et al. 1991) (Amer et al. 1991)
21. 11-Methoxyerysopine E. caffra (Amer et al. 1991)
22. Erysotramidine E. arborescens leaves and flowers (MeOH) (Ito et al. 1973c; Wu et al. 2017)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004)
E. latissima seeds (Wanjala and Majinda 2000)
E. herbacea flowers (MeOH) (Tanaka et al. 2008)
E. variegata (Kumar A et al. 2010)
23. 8-Oxoerysodine E. tabitensis (Synonyms of E. sandwicensin) (Amer et al. 1991)
24. 11-b-Hydroxyerysotramidine E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004; Armwood et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. arborescens flowers (MeOH) (Wu et al. 2017)
25. 11-b-Methoxyerysotramidine E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004; Armwood et al. 2018)
26. 11-a-Methoxyerysotramidine E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
27. 10,11-Dehydroerysovine (Dyke and Quessy 1981)
28. 10,11-Dehydroerysovine (Dyke and Quessy 1981)
29. Erythraline E. crista galli leaves, seeds, flowers and bark (MeOH) (Deulofeu and Labriola 1947; Ito et al. 1973a; Chawla A. S.,
NATURAL PRODUCT RESEARCH

Gupta, et al. 1988; Etoh et al. 2013)

E. corallodendron flowers (MeOH) (Zhao et al. 2018)
(continued)
5
 6

Table 1. Continued.
No. Compound Name Occurrence (Solvent used for extraction) Reference
E. brucei root bark (DCM:MeOH) (Gurmessa et al. 2018)
E. glauca wild seeds (Synonyms E. fusca Lour.) (Folkers and Koniuszy 1940)
E. variegata seeds and bark (Singh et al. 1981; Chawla et al. 1988)
E. chiriquensis (Jackson 1985)
E. verna (Synonyms E. mulungu Benth.) (Guaratini et al. 2014)
E. velutina seeds (MeOH) (Ozawa et al. 2009)
E. latissima seeds (Wanjala and Majinda 2000)
E. addisoniae seeds (EtOAc) and flowers (MeOH) (Cui et al. 2009; Wu et al. 2017)
E. abyssinica seeds (CHCl3) (Mohammed et al. 2012)
N. M. FAHMY ET AL.

E. coralloides E. tajumulcensis E. macrophylla E. guatemalensis E. glo- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
bocalyx E. steyermarkii E. oliviae E. huehuetenangensis E. lanceolate (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. barqueroana E. folkersii E. stricta E. lysistemon E. zeyheri E. sene- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
galensis E. excelsa E. latissima E. tabitensis (Synonyms of E. sandwi- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
censin) E. vespertilio E. burana E. suberosa E.
bidwillii E. caffra (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991)
30. 11-b-Methoxyerythraline E. vespertilio E. caffra E. lysistemon (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
31. Erythrinine E.
bidwillii (Ito et al. 1973b)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. crista galli leaves, bark and flowers (MeOH) ( Chawla et al. 1988; Ozawa et al. 2010)
E. arborescens flowers (MeOH) (Wu et al. 2017)
E. variegata E. glauca E. brucei E. lithosperma (Synonyms of E. varie- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
gata) E. stricta E. vespertilio E. burana E. macrophylla E. caffra (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
32. Erythrocarine E. caribea (Jackson 1985)
33. 11-Oxoerythraline E. zeheri (Amer et al. 1991)
34. 10-Oxoerythrinine E. corallodendron flowers (MeOH) (Zhao et al. 2018)
35. 10,11-Dioxoerythraline E. corallodendron flowers (MeOH) (Zhao et al. 2018)
36. 8-Oxoerythrinine E. brucei (Amer et al. 1991)
E. crista galli bark and flowers (MeOH) (Ozawa et al. 2010)
E. arborescens flowers (MeOH) (Wu et al. 2017)
E. stricta roots (DCM) (Rukachaisirikulet al. 2007)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
37. 8-Oxoerythraline E. velutina seeds (MeOH) (Ozawa et al. 2009)
E. latissima seeds (Wanjala and Majinda 2000)
E. crista galli bark (MeOH) (Ozawa et al. 2010)
E. abyssinica seeds (CHCl3) (Mohammed et al. 2012)
E. arborescens flowers (MeOH) (Wu et al. 2017)
E. lysistemon E. chiriquensis E. tahitensis E. brucei (Jackson 1985; Amer et al. 1991) (Amer et al. 1991) (Amer
et al. 1991) (Amer et al. 1991)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
(continued)
Table 1. Continued.
No. Compound Name Occurrence (Solvent used for extraction) Reference
38. 8-Oxo-11-b-methoxyerythraline E. lysistemon seeds (Jackson 1985)
39. Crystamidine E. crista galli bark and leaves (MeOH) (Ito et al. 1973c; Ozawa et al. 2010)
E. brucei (Amer et al. 1991)
40. Erysodine-N-oxide E. velutina seeds (MeOH) (Ozawa et al. 2009)
41. Erysotrine-N-oxide E.
bidwillii E. mulungu flowers (EtOH) (Amer et al. 1991) (Amer et al. 1991; Amorim et al. 2018)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004)
E. herbacea flowers (MeOH) (Tanaka et al. 2008)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
42. 11-b-Hydroxyerysotrine-N-oxide E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004; Armwood et al. 2018)
(Erythrartine N-oxide) E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. arborescens flowers (MeOH) (Wu et al. 2017)
43. 11-a-Hydroxyerysotrine-N-oxide E. mulungu (Amer et al. 1991)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004; Armwood et al. 2018)
44. O-Methylerythrartine-N-oxide E. lysistemon flowers (DCM:MeOH) E.
bidwillii (Juma and Majinda 2004) (Amer et al. 1991)
(Erythristemine-N-oxide)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
45. Erysovine-N-oxide E. addisoniae seeds (EtOAc) (Cui et al. 2009)
46. 11-b-Methoxyerythraline-N-oxide E. crista galli flowers (MeOH) ( Chawla et al. 1988)
E. suberosa (Chawlaand Kapoor 1995)
47. Erythraline N-oxide (Cristanine A) E. crista galli bark (MeOH) (Ozawa et al. 2010)
E. arborescens flowers (MeOH) (Wu et al. 2017)
E. brucei root bark (DCM:MeOH) (Gurmessa et al. 2018)
48. Erythrinine N-oxide E. corallodendron flowers (MeOH) (Zhao et al. 2018)
49. Erytharbine E. arborescens leaves and flowers (MeOH) (Ito et al. 1973a; Wu et al. 2017)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. herbacea flowers (MeOH) (Tanaka et al. 2008)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004)
50. 10,11-Dioxoerysotrine E. latissima seed pods (DCM:MeOH) (Wanjala et al. 2002)
E. herbacea flowers (MeOH) (Tanaka et al. 2008)
E. arborescens flowers (MeOH) (Wu et al. 2017)
51. 10-Hydroxy-11-oxoerysotrine E. herbacea flowers (MeOH) (Tanaka et al. 2008)
52. Erytharborine H E. arborescens flowers (MeOH) (Wu et al. 2017)
53. 11-b-Methoxy-10-oxoerysotramidine E. latissima seed flowers (CHCl3:MeOH) (Cornelius et al. 2009)
54. 10,11-Dioxoerysotramidine E. latissima seed flowers (CHCl3:MeOH) (Cornelius et al. 2009)
55. Erytharborine A E. arborescens flowers (MeOH) (Wu et al. 2017)
56. Erytharborine B E. arborescens flowers (MeOH) (Wu et al. 2017)
57. Erysothiovine E. glauca E. pallida E. poeppigiana (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
58. Erysothiopine E. glauca (Amer et al. 1991)
59. Sodium erysovine 15-O-sulfate E. velutina seeds (MeOH) (Ozawa et al. 2011)
60. Erysopine 15-O-sulfate E. velutina seeds (MeOH) (Ozawa et al. 2011)
61. Sodium erysovine-N-oxy-15-O-sulfate E. velutina seeds (MeOH) (Ozawa et al. 2011)
2. Dienoid glycoside alkaloids
62. 11-b-Methoxyglucoerysovine E. lysistemon (Amer et al. 1991)
NATURAL PRODUCT RESEARCH

E. vespertilio fruits (Iranshahi et al. 2012)

63. b-Glucoerysodine E. lysistemon (Amer et al. 1991)
(continued)
7
 8

Table 1. Continued.
No. Compound Name Occurrence (Solvent used for extraction) Reference
E. velutina seeds (MeOH) (Ozawa et al. 2009)
E. senegalensis seeds (MeOH) (Wandji et al. 1995)
E. latissima seeds (Wanjala and Majinda 2000)
E. addisoniae seeds (EtOAc) (Cui et al. 2009)
64. 11-b-Methoxy glucoerysodine E. lysistemon (Amer et al. 1991)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
65. Rhamnoerysodine E. lysistemon (Amer et al. 1991)
66. 15-O-b-Glucoerysopine E. latissima seeds (Wanjala and Majinda 2000)
67. 16-O-b-Glucoerysopine E. latissima seeds (Wanjala and Majinda 2000)
N. M. FAHMY ET AL.

E. crista galli seeds (MeOH) (Tan et al. 2017)

68. 11-O-b-Glucoerythraline
69. 16-O-b-Glucococcoline
3. Alkenoid alkaloids
70. Erythratidine
71. Epierythratidine
72. 11-Hydroxyerythratidine
73. 11-Hydroxyepierythratidine
74. 11-Methoxyerythratidine
75. Erysosalvine
76. 11-Hydroxyerysosalvine
77. Erysotine
78. 11-Hydroxyerysotine
79. Erysopitine
80. 11-b-Hydroxyerythratidine N-oxide
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. crista galli seeds (MeOH) (Tan et al. 2017)
E. velutina seeds (MeOH) (Ozawa et al. 2011)
E. salviiflora (Millington et al. 1974)
E. caribea (Jackson 1985)
E. crista galli bark (MeOH) (Ozawa et al. 2010)
E. arborescens leaves (Ito et al. 1973c)
E. poeppigiana E. coralloides E. goldmanii E. guatemalensis E. steyer- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
markii E. barqueroana E. oliviae E. senegalensis E. excelsa E. living- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
stoniana E. abyssinica E. falcata E. latissima E. tahitensis E. burana (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. lysistemon E. variegata E. macrophylla E. melanacantha (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
E. fusca E. variegata (Amer et al. 1991) (Amer et al. 1991)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. crista galli bark (MeOH) (Ozawa et al. 2010)
E. poeppigiana E. berteroana (Amer et al. 1991) (Amer et al. 1991)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. variegata E. poeppigiana E. subumrans (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. subumbrans E. macrophylla E. brucei E. cochleata (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. sulciiflora E. salviiflora (Millington et al. 1974) (Millington et al. 1974)
E. latissima E. arborescens E. livingstoniana E. tahitensis E. burana E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
salviiflora E. oliviae E. melanacantha (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991)
E. berteroana (Amer et al. 1991)
E. sulciiflora E. salviiflora (Millington et al. 1974) (Millington et al. 1974)
E. oliviae E. melanacantha E. variegata E. thollonia (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
E. berteroana (Amer et al. 1991)
E. variegata bark ( Chawla et al. 1988)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
(continued)
Table 1. Continued.
No. Compound Name Occurrence (Solvent used for extraction) Reference
81. Erythratidinone E. variegata (Kumar A et al. 2010)
E. arborescens flowers (MeOH) (Wu et al. 2017)
82. Erysosalvinone E. salviiflora (Amer et al. 1991)
E. addisoniae seeds (EtOAc) (Cui et al. 2009)
83. Erysotinone E. salviiflora (Millington et al. 1974)
84. 11-Hydroxyerysotinone E. macrophylla (Amer et al. 1991)
85. Erysoflorinone E. salviiflora E. subumbrans (Amer et al. 1991) (Amer et al. 1991)
86. 3-Demethoxyerythratidinone E. variegata (Kumar A et al. 2010)
87. 10,11-Dioxoerythratine E. subumbrans bark (MeOH) (Rukachaisirikul et al.2008)
88. 10,11-Dioxoepierythratidine E. subumbrans bark (MeOH) (Rukachaisirikul et al.2008)
89. Erytharborine F E. arborescens flowers (MeOH) (Wu et al. 2017)
90. 10,11-Dioxoerythratidinone E. subumbrans bark (MeOH) (Rukachaisirikul et al. 2008)
91. Erytharborine G E. arborescens flowers (MeOH) (Wu et al. 2017)
92. Erythramine E. crista galli seeds (Deulofeu and Labriola 1947)
E. glauca seeds (Folkers and Koniuszy 1940)
E. variegata (Kumar A et al. 2010)
E. subumbrans E. variegata E. arborescens E. sandwicensis (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
93. Erythratine E. crista galli leaves, and bark (MeOH) (Deulofeu and Labriola 1947; Ito et al. 1973a; Ozawa
et al. 2010)
E. crista galli seeds (MeOH) (Tan et al. 2017)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. glauca seeds (Folkers and Koniuszy 1940)
E. arborescens flowers (MeOH) (Wu et al. 2017)
E. macrophylla E. subumbrans E. variegata E. velutina E. caffra E. folk- (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
ersii E. abyssinica (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
94. Epierythratine E. subumbrans (Amer et al. 1991)
95. 11-Hydroxyerythratine E. macrophylla E. subumbrans (Amer et al. 1991) (Amer et al. 1991)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
96. 11-Hydroxyepierythratine E. subumbrans (Amer et al. 1991)
97. Erythratinone E. glauca E. crista galli E. lithosperma (Synonyms of E. variegata) (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
98. 11-Methoxyerythratine E. crista galli flowers (MeOH) ( Chawla et al. 1988)
99. Cristanines B E. crista galli bark (MeOH) (Ozawa et al. 2010)
100. 8-Oxoerythraline E. poeppigiana wood (DCM) (Tanaka et al. 2001)
epoxide E. arborescens flowers (MeOH) (Wu et al. 2017)
101. Erytharborine E E. arborescens flowers (MeOH) (Wu et al. 2017)
102. Erysodienone E. variegata bark ( Chawla et al. 1988)
103. Erythritol E. variegata (Kumar A et al. 2010)
104. Erytharborine C E. arborescens flowers (MeOH) (Wu et al. 2017)
105. Erytharborine D E. arborescens flowers (MeOH) (Wu et al. 2017)
4. Lactonic alkaloids
NATURAL PRODUCT RESEARCH

106. a-Erythroidine E. poeppigiana stem bark (MeOH) (Djiogue et al. 2014)

E. americana (Folkers and Major 1937)
(continued)
9

Table 1. Continued.
No. Compound Name
107. b-Erythroidine
108. 8-Oxo-a-erythroidine
109. 8-Oxo-b-erythroidine
110. Dihydro-b-erythroidine
111. 8-Oxo-a-erythroidine epoxide
5. 16-Azoerythrinanes alkaloids
112. Erymelanthine
113. Melanacanthine (8-
Oxoerymelanthine)
6. Tetrahydroisoquinolines alkaloids
114. Protosinomenine
115. N-Norprotosinomenine
116. Orientaline
117. N-Nororientaline
118. Norisoorientaline
7. Benzylisoquinoline alkaloids
119. Cristadine
8. Quinolizidine alkaloids
120. Scoulerine
121. Coreximine
9. Indole alkaloids
122. Hypaphorine
10
Occurrence (Solvent used for extraction) Reference
E. coralloides E. oliviae E. berteroana E. standleyana E. chiapasana E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
globocalyx E. thollonia (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991)
E. poeppigiana stem bark (MeOH) (Djiogue et al. 2014)
E. americana (Folkers and Major 1937)
E. coralloides E. oliviae E. berteroana E. standleyana E. chiapasana E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
globocalyx E. thollonia E. arborescens E. lithosperma (Synonyms of (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. variegata) (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. poeppigiana stem bark (MeOH) and wood (DCM) (Tanaka et al. 2001; Djiogue et al. 2014)
N. M. FAHMY ET AL.
E. berteroana E. thollonia (Amer et al. 1991) (Amer et al. 1991)
E. poeppigiana stem bark (MeOH) (Djiogue et al. 2014)
E. berteroana E. thollonia (Amer et al. 1991) (Amer et al. 1991)
(Unna et al. 1944)
E. poeppigiana wood (DCM) (Tanaka et al. 2001)
E. melanacantha seeds (Jackson 1985; Hussain et al. 2016)
E. merilliana
E. velutina seeds (MeOH) (Ozawa et al. 2009) (Ozawa et al. 2009)
E. variegata
E. melanacantha (Jackson 1985; Hussain et al. 2016)
E. lithosperma (Synonyms of E. variegata) (Chawlaand Kapoor 1995)
E. lithosperma (Synonyms of E. variegata) (Chawlaand Kapoor 1995)
(Chawlaand Kapoor 1995)
E. crista galli leaves (MeOH) (Ito et al. 1973a; Chawlaand Kapoor 1995)
E. arborescens leaves E. speciosa leaves (Ito et al. 1973a) (Graca-De-Souza et al. 2011)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. crista galli (Chawlaand Kapoor 1995)
E. variegata leaves (Kumar A et al. 2010)
E. variegata leaves (Kumar A et al. 2010)
E. suberosa leaves, and seeds (EtOH) (Singh and Chawla 1969, 1971)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. velutina seeds (MeOH) (Ozawa et al. 2008)
E. variegata bark, leaves and seeds (Singh and Chawla 1970; Ghosal et al. 1972)
E. caffra stem bark (CHCl3) (El-Masry et al. 2010)
E. herbacea seeds (Folkers and Koniuszy 1940) (Folkers and Koniuszy 1940)
E. abyssinica seeds (Folkers and Koniuszy 1940)
E. americana seeds
E. vespertilio fruits (Iranshahi et al. 2012)
E. senegalensis seeds (MeOH) (Wandji et al. 1995)
(continued)
Table 1. Continued.
No. Compound Name Occurrence (Solvent used for extraction) Reference
E. crista galli bark (MeOH) (Ozawa et al. 2010)
E. crista galli seeds (MeOH) (Tan et al. 2017)
E. flubelliformis seeds E. mulungu flowers (EtOH) (Folkers and Koniuszy 1940) (Amorim et al. 2018)
123. Hypaphorine methyl ester E. variegata bark, leaves and seeds (Ghosal et al. 1972)
124. Abrine E. caffra stem bark (CHCl3) (El-Masry et al. 2010)
125. N,N-Dimethyltryptophan E. variegata bark, leaves and seeds (Ghosal et al. 1972)
methyl ester
126. 1H-Indole-3-propanamide E. addisoniae seeds (EtOAc) (Cui et al. 2009)
10. Dimeric dienoids alkaloids
127. Erysophorine chloride E. arborescens (Amer et al. 1991)
128. Erysodinophorine hydroxide E. arborescens (Amer et al. 1991)
129. Erysopinophorine hydroxide E. arborescens (Amer et al. 1991)
130. Isoerysopinophorin hydroxide E. arborescens (Amer et al. 1991)
131. Erythrivarine A E. variegata (Zhang BJ et al. 2014)
132. Erythrivarine B E. variegata (Zhang BJ et al. 2014)
11. Dimeric dienoids glycoside alkaloids
133. Erythrivarine C E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
134. Erythrivarine D E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
12. Timeric dienoids alkaloids
135. Erythrivarine E E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
136. Erythrivarine F E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
137. Erythrivarine G E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
13. Other Erythrina alkaloids
138. Erythrinarbine E. stricta leaves and stems (80% MeOH) E. arborescens stems (Wu et al. 2018) (Dong Lei et al. 1999)
139. Stachydrine E. variegata leaves and bark (pet. ether) (Singh et al. 1975)
140. Erybidine E. crista galli leaves (MeOH) (Ito et al. 1973)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. arborescens leaves (Ito et al. 1973)
E. herbacea E. poeppigiana leaves (Chawla Amrik Singh and Kapoor 1995)
E.
bidwillii (Ito and Tanaka 1974)
141. Isoboldine E. abyssinica E. poeppigiana (Chawla Amrik Singh and Kapoor 1995) (Chawla Amrik
Singh and Kapoor 1995)
142. Reticuline E. variegata leaves (Kumar A et al. 2010)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
143. Norreticuline E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
NATURAL PRODUCT RESEARCH
11
12 N. M. FAHMY ET AL.

Figure 1. Chemical structures of dienoid alkaloids isolated from genus Erythrina.

Biological activity of Erythrina alkaloids

The anticonvulsant activity of Erythrina species was reported long ago, supporting
their traditional use as antiepileptic, anticonvulsant, and tranquilizing agents. The early
work on Erythrina in the 1930’s showed the curare-like action of the seeds extracts of
various species, which was attributed to the alkaloid content of these species (Folkers
and Major 1937; Folkers and Unna 1939). However, there were a widespread variation
 NATURAL PRODUCT RESEARCH 13

Figure 2. Chemical structures of dienoid glycoside alkaloids isolated from genus Erythrina.

in the potency of the seeds of different species. For example, E. variegata showed a
low paralysis potency value. Similarly, the large soft seeds of E. edulis, consumed
extensively by people in Colombia, either cooked or fried, demonstrated low activity.
On the other hand, the seeds of E. eggersii showed the highest paralysis potency value
compared to the seeds of any other tested species (Folkers and Unna 1939).
Erythroidine (106) isolated from the seeds of E. americana at a dose of 0.1–0.15 mg
per frog caused complete motor paralysis when injected into the lymph sac (Folkers
and Major 1937). However, Garin-Aguilar et al. 2000 studied the tranquilizer effect of
three alkaloidal fractions obtained from the seeds of E. americana, the free alkaloids in
hexane, free alkaloids in methanol and liberated alkaloids fractions (Garin-Aguilar et al.
2000). Results revealed that the three fractions diminished the aggressive behavior in
rats at a dose of 3 mg/kg, which was comparable to the positive control, diazepam.
They attributed this activity to the interaction between the cholinergic and GABAergic
system (Garin-Aguilar et al. 2000). The total alkaloid fraction of E. variegata bark exhib-
ited potent effect on the nervous system including neuromuscular blocking, smooth
muscle relaxant, CNS depressant, and anticonvulsant activities (Ghosal et al. 1972).
Further studies in the following years were done to determine the secondary metabo-
lites behind these activities. Flausino et al. 2007 and Faggion et al. 2011 attributed the
anxiolytic effect observed with the crude extract of E. mulungu to its alkaloid content
11-a-hydroxyerythravine (14), erythravine (7), and 11-a-hydroxyerysotrine (13)
(Flausino et al. 2007; Faggion et al. 2011).
The neuronal nicotinic acetylcholine receptors (nAChRs) became a popular target in
drug discovery. This might be attributed to its involvement in many diseases of the
central nervous system such as depression, schizophrenia, Alzheimer’s and Parkinson’s
diseases. Natural product chemists’ efforts over the past decade have extended to the
identification of several nicotine bioisosteres from natural sources as novel drug tar-
gets including erysodine (1) and dihydro-b-erythroidine (110) isolated from different
species of Erythrina sp. These isolated compounds were found to be competitive
nAChR antagonists. They showed selectivity for b2-containing nAChRs, particularly the
a4b2 subtype (Lloyd and Williams 2000). On the other hand, Santos et al. 2012,
14 N. M. FAHMY ET AL.

Figure 3. Chemical structures of alkenoid alkaloids isolated from genus Erythrina.

investigated the anticholinesterase activity of E. velutina leaves aqueous and alkaloid-

rich extracts. In vitro assays revealed that the alkaloid-rich extract significantly inhibited
mouse brain cholinesterase in a concentration-dependent manner (Santos et al. 2012).
The anti-HIV-1 activity of the alkaloid rich fraction from abyssinica seeds was studied,
results showed a reduction in the viability of mock-infected MT-4 cells by CC50 = 53
lM and MT-4 cells protection from HIV-1-induced cytopathogenicity by 50% (EC50 
53 lM). Furthermore, the alkaloids isolated from E. abyssinica seeds exhibited moder-
ate cytotoxic activity against Hep-G2 and Hep-2 cell lines (Mohammed et al. 2012).
Juma and Majinda 2004 isolated fourteen different erythrinaline alkaloids from the
flowers and pods of E. lysistemon and assessed their DPPH radical scavenging activity,
 NATURAL PRODUCT RESEARCH 15

Figure 4. Chemical structures of lactonic alkaloids isolated from genus Erythrina.

Figure 5. Chemical structures of 16-azoerythrinanes, tetrahydroisoquinolines, benzylisoquinoline,

and quinolizidine alkaloids isolated from genus Erythrina.

Figure 6. Chemical structures of indole alkaloids isolated from genus Erythrina.

only erysodine (1) and 11-a-hydroxyerysodine (12) showed moderate radical scaveng-
ing activity (Juma and Majinda 2004). The aphicidal activity of Erythrina alkaloids iso-
lated from E. crista-galli was studied. The results revealed that erysodine (1), erysovine
16 N. M. FAHMY ET AL.

Figure 7. Chemical structures of dimeric dienoids, dimeric dienoids glycoside, and timeric dienoids
alkaloids isolated from genus Erythrina.

Figure 8. Chemical structures of other alkaloids isolated from genus Erythrina.

(2), erysotrine (6) and erythraline (29) could potentially be used as a botanical aphi-
cides or as a candidate for the development of new insecticidal agents (Wang et al.
2017). Surprisingly, in 2014 Djiogue et al. reported the erythroidine alkaloids as a novel
class of phytoestrogens. The estrogenicity of a and b-Erythroidine (106 and 107) was
due to their induction of the enhanced expression of the specific ERa-dependent
genes trefoil factor-1 and serum glucocorticoid regulated kinase 3 in MCF-7 cells. This
Table 2. Reported biological activity of Erythrina alkaloids.
Biological Activity Compound Name Compound Number Effect Reference
Cytotoxic activity Erysodine (1) Cytotoxic against Hep-G2 (IC50 ¼ 11.8 lg/ml) and (Mohammed et al. 2012)
Hep-2 (IC50 ¼ 19.9 lg/ml) cell lines
Cytotoxic against Jurcat cell lines (IC50 ¼ 10.8 lg/ (Ozawa et al. 2009)
ml) and enhanced cytotoxicity by the addition of
TRAIL (IC50 ¼ 4.6 lg/ml)
Erysovine (2) Cytotoxic against Jurcat cell lines (IC50 ¼ 24.0 lg/ (Ozawa et al. 2009)
ml) and enhanced cytotoxicity by the addition of
TRAIL (IC50 ¼ 14.2 lg/ml)
Erysotrine (6) Cytotoxic against Hep-G2 (IC50 ¼ 15.8 lg/ml) and (Mohammed et al. 2012)
Hep-2 (IC50 ¼ 21.6 lg/ml) cell lines
11-a-Hydroxyerysotrine (13) Week cytotoxic activity against HL-60, K-562 and (Kumar S et al. 2013)
MOLT-4 (IC50 >70 lM)
11-b-Methoxyerysodine (16) Cytotoxic against Hep-G2 (IC50 ¼ 11.4 lg/ml) and (Mohammed et al. 2012)
Hep-2 (IC50 ¼ 11.5 lg/ml) cell lines
Erythraline (29) Cytotoxic against Hep-G2 (IC50 ¼ 17.6 lg/ml) and (Mohammed et al. 2012)
Hep-2 (IC50 ¼ 15.9 lg/ml) cell lines
Cytotoxic against Jurcat cell lines (IC50 ¼ 23.0 lg/ (Ozawa et al. 2009)
ml) and enhanced cytotoxicity by the addition of
TRAIL (IC50 ¼ 5.0 lg/ml)
8-Oxoerythraline (37) Cytotoxic against Hep-G2 (IC50 ¼ 3.89 lg/ml) and (Mohammed et al. 2012)
Hep-2 (IC50 ¼ 18.5 lg/ml) cell lines
Estrogenic activity a-Erythroidine (106) RBA on ERa (0.015 ± 0.010) and no RBA on ERb (Djiogue et al. 2014)
b-Erythroidine (107) Week RBA on ERa (0.005 ± 0.010) and (Djiogue et al. 2014)
ERb (0.006 ± 0.010)
Nervous system Erysodine (1) Competitive, reversible antagonist of (-)-nicotine- (Decker et al. 1995)
related activities induced dopamine release from striatal slices and
inhibited (-)-nicotine-induced 86Rb þ efflux from
IMR-32 cells
Competitive antagonist for a4b2 nAChRs (Mansbach et al. 2000)
Erythravine (7) Anxiolytic activity by significantly impairing the (Flausino et al. 2007;
inhibitory avoidance task in the elevated T-maze Faggion et al. 2011)
test at a dose of 3 and 10 mg/kg mice
Inhibition of CNS nicotinic acetylcholine receptors, (Setti-Perdigao et al. 2013)
particularly the a4b2 subtype (IC50 ¼ 13 nm)
11-a-Hydroxyerysotrine (13) Anxiolytic activity by significantly impairing the (Flausino et al., 2007)
NATURAL PRODUCT RESEARCH

inhibitory avoidance task in the elevated T-maze

test at a dose of 3 and 10 mg/kg mice
(continued)
17
Table 2. Continued.
18

Biological Activity Compound Name Compound Number Effect Reference

Low inhibition of CNS nicotinic acetylcho- (Setti-Perdigao et al. 2013)
line receptors
11-a-Hydroxyerythravine (14) Anxiolytic activity by significantly impairing the (Flausino et al. 2007; Faggion et al. 2011)
inhibitory avoidance task in the elevated T-maze
test at a dose of 3 and 10 mg/kg mice
Inhibition of CNS nicotinic acetylcholine receptors, (Setti-Perdigao et al. 2013)
particularly the a4b2 subtype (IC50 ¼ 4 nm)
Erythraline (29) Curare-like action in frogs at 8 mg/kg frog. (Folkers and Koniuszy1940)
N. M. FAHMY ET AL.

Erythramine (92) Curare-like action in frogs at 7 mg/kg frog. (Folkers and Koniuszy1940)
a/b -Erythroidine (106/107) Complete motor paralysis at 0.1-0.15 mg/frog when (Folkers and Major1937)
injected into the lymph sac
Dihydro-b-erythroidine (110) Potent curare-like action (Unna et al. 1944)
Hypaphorine (122) Increased non-rapid eye movement (NREM) sleep (Ozawa et al. 2008)
time during the first hour after its administration.
Enhancement of the NREM sleep time by 33%.
Erythrivarine F (136) Acetylcholinesterase inhibitory activity (IC50 (Zhang B-J et al. 2016)
¼ 12.5 lM)
Anti-inflamma- Erythraline (29) Inhibition of LPS-induced NO production (IC50 ¼ (Ozawa et al. 2010)
tory activity 8.8 lg/ml)
Erythrinine (31) Inhibition of LPS-induced NO production (IC50 ¼ (Ozawa et al. 2010)
3.4 lg/ml)
Hypaphorine (122) Inhibition of LPS-induced NO production (IC50 ¼ (Ozawa et al. 2010)
11.2 lg/ml)
Antiviral activity against Erysodine (1) IC50 ¼ 1.48 mM (Tan et al. 2017)
tobacco mosaic virus Erysotrine (6) IC50 ¼ 1.28 mM (Tan et al. 2017)
Erythraline (29) IC50 ¼ 1.52 mM (Tan et al. 2017)
16-O-b-Glucoerysopine (67) IC50 ¼ 0.74 mM (Tan et al. 2017)
11-O-b-Glucoerythraline (68) IC50 ¼ 0.59 mM (Tan et al. 2017)
Erythratine (93) IC50 ¼ 1.04 mM (Tan et al. 2017)
Hypaphorine (122) IC50 ¼ 1.69 mM (Tan et al. 2017)
Insecticidal activity Erysodine (1) Against aphid Aphis gossypii (LD50 ¼ 7.48 ng/aphid) (Wang et al. 2017)
Erysovine (2) Against aphid Aphis gossypii (LD50 ¼ 6.68 ng/aphid) (Wang et al. 2017)
Erysotrine (6) Against aphid Aphis gossypii (LD50 ¼ 5.13 ng/aphid) (Wang et al. 2017)
Erythraline (29) Against aphid Aphis gossypii (LD50 ¼ 4.67 ng/aphid) (Wang et al. 2017)
Erythrivarine C (133) Against aphid Rhodobium porosum (IC50 (Zhang B-J et al. 2016)
¼ 121.8 lM)
Erythrivarine D (134) Against aphid Rhodobium porosum (IC50 ¼ 77.1 lM) (Zhang B-J et al. 2016)
 NATURAL PRODUCT RESEARCH 19

proposed estrogenic activity was confirmed using molecular docking studies, showing
a potential mode of binding on ERa (Djiogue et al. 2014). Table 2 summarizes the
reported biological activity of Erythrina alkaloids.

Conclusion
This work reviews the alkaloid content of genus Erythrina and their reported biological
activity. Numerous species were studied since 1930’s with a great interest in their
alkaloid compounds. About 143 alkaloids were reported from different Erythrina sp.,
and in the current review we categorized them into 13 classes. The dienoid alkaloids
were the most prominent alkaloids in Erythrina followed by the alkenoid, then the lac-
tonic alkaloids. Tetrahydroisoquinolines, benzylisoquinoline, quinolizidine and indole
were also reported. In addition, few reports showed the isolation of alkaloidal glyco-
sides from Erythrina. The dienoid alkaloids erysodine (1), erysovine (2), erysotrine (6),
erythraline (29), the alkenoid alkaloids erythratidine (70), and the indole alkaloid hypa-
phorine (122) were the most widely spread alkaloid in the genus and were isolated
from several Erythrina sp. Erythrina alkaloids biological activities were focused mainly
on its effect on the neuronal nicotinic acetylcholine receptors to understand the
mechanism by which it produces its antiepileptic, anticonvulsant, and tranquilizing
effect. Most of the biological reports were focused on the alkaloid rich fraction, and
only few reports studied the activities of pure single compounds. However, some com-
pounds revealed a promising curare-like action, insecticidal, and cytotoxic activities.
We hope this review will enlighten researchers to reveal the full potential of this class
of compounds, that may serve as lead compounds in the discovery of new alternative
medications for the management of various nervous health conditions.

Conflict of interest
The authors declare that they have no competing interests.

ORCID
Eman Al-Sayed http://orcid.org/0000-0001-7869-2009
Mohamed El-Shazly http://orcid.org//0000-0003-0050-8288
Abdel Nasser Singab http://orcid.org//0000-0001-7445-963X

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