Natural Product Research

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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 Accepted 19 December 2018
world. The plants of this genus exhibited significant role in
traditional medicine targeting different diseases. Alkaloids and KEYWORDS
flavonoids were reported as the chief bioactive constituents of Erythrina; alkaloids;
this genus with a wide range of biological activities. About 143 erythroidine; curare;
anticonvulsant; erysodine
alkaloids 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
© 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) NA
(Folkers and Koniuszy 1940) TU
E. folkersii (Millington et al. 1974) RA
E. velutina seeds (MeOH) (Ozawa et al. 2009)
E. latissima seeds (Wanjala and Majinda 2000)
L
E. addisoniae seeds (EtOAc) and flowers (MeOH) (Cui et al. 2009; Wu et al. 2017) PR
E. chiriquensis E. caribea (Jackson 1985) (Jackson 1985) O
E. caffra E. zeyheri E. senegalensis E. livingstoniana E. abyssinica E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991) DU
sub- erosa E. arborescens E. fucosa E. coralloides E. goldmanii (Amer et al. 1991) (Amer et al. 1991) (Amer et al. CT
E. atitla- nensis E. macrophylla E. tajumulcensis E. 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer et RE
guatemalensis E. steyermarkii E. oliviae E. mulungu E. al. 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer
SE
lysistemon et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
(Amer et al. 1991) (Amer et al. 1991) (Amer et al. AR
1991) (Amer et al. 1991) CH
3. Erysopine E. crista galli seeds (Deulofeu and Labriola 1947)
E. abyssinica seeds (Folkers and Koniuszy 1940)
(continued)
3
Table 1. Continued. 4
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) N.
E. variegata bark, leaves, and seeds ( Chawla et al. 1988) M.
E. addisoniae seeds (EtOAc) (Cui et al. 2009) FA
E. chiriquensis E. caribea (Jackson 1985) (Jackson 1985) H
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018) M
4. Erysoline E. melanacantha E. merilliana (Jackson 1985) (Jackson 1985)
Y
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) ET
E. acantbocarpa E. caribea (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 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. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
costaricensis (Amer et al. 1991) (Amer et al. 1991) (Amer et al.
E. folkersii E. melanacantha 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.
formis E. poeppigiana E. coralloides E. goldmanii E. atitlanensis 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer et
E. macrophylla E. tajumulcensis E. guatemalensis E. steyermarkii E. al. 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer
oli- viae E. mulungu flowers (EtOH) E. speciosa flowers 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; 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
9. 11-b-Hydroxyerysotrine (Erythrartine)
10. Erythristemine
11. 11-b-Hydroxyerysodine
12. 11-a-Hydroxyerysodine
13. 11-a-Hydroxyerysotrine
14. 11-a-Hydroxyerythravine
15. 11-b-Hydroxyerysovine
16. 11-b-Methoxyerysodine
17. 11-b-Methoxyerysovine
18. 11-Oxoerysodine
19. 11-Oxyerysovine
20. 11-Oxoerysopine
21. 11-Methoxyerysopine
22. Erysotramidine
23. 8-Oxoerysodine
24. 11-b-Hydroxyerysotramidine
25. 11-b-Methoxyerysotramidine
26. 11-a-Methoxyerysotramidine
27. 10,11-Dehydroerysovine
28. 10,11-Dehydroerysovine
29. Erythraline
Occurrence (Solvent used for extraction) Reference
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)
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)
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)
E. lysistemon seeds and flowers (Jackson 1985; Juma and Majinda 2004)
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)
E. mulungu flowers (70% EtOH) (Flausino et al. 2007; Faggion et al. 2011; Setti-Perdigao
et al. 2013)
E. arborescens E. lysistemon E. senegalensis (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. lysistemon seeds (Jackson 1985)
E. abyssinica seeds (CHCl3) (Mohammed et al. 2012)
E. lysistemon E. abyssinica (Amer et al. 1991)
E. senegalensis E. excelsa E. tabitensis (Synonyms of E. sandwicensin) (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. arborescens E. caffra E. livingstoniana E. abyssinica (Amer et al. 1991) (Amer et al. 1991) (Amer et al.
1991) (Amer et al. 1991)
E. tabitensis (Synonyms of E. sandwicensin) E. arborescens (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
E. livingstoniana
E. tabitensis (Synonyms of E. sandwicensin) E. arborescens (Amer et al. 1991) (Amer et al. 1991)
E. caffra (Amer et al. 1991)
E. arborescens leaves and flowers (MeOH) (Ito et al. 1973c; Wu et al. 2017)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004) NA
E. latissima seeds (Wanjala and Majinda 2000) TU
E. herbacea flowers (MeOH) (Tanaka et al. 2008) RA
E. variegata (Kumar A et al. 2010)
E. tabitensis (Synonyms of E. sandwicensin) (Amer et al. 1991) L
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004; Armwood et al. 2018) PR
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018) O
E. arborescens flowers (MeOH) (Wu et al. 2017) DU
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004; Armwood et al. 2018) CT
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018) RE
(Dyke and Quessy 1981)
(Dyke and Quessy 1981)
SE
E. crista galli leaves, seeds, flowers and bark (MeOH) (Deulofeu and Labriola 1947; Ito et al. 1973a; Chawla A. S., AR
Gupta, et al. 1988; Etoh et al. 2013) CH
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
(continued)
5
Table 1. Continued.
No. Compound Name
30. 11-b-Methoxyerythraline
31. Erythrinine
32. Erythrocarine
33. 11-Oxoerythraline
34. 10-Oxoerythrinine
35. 10,11-Dioxoerythraline
36. 8-Oxoerythrinine
37. 8-Oxoerythraline
6
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) N.
E. variegata seeds and bark (Singh et al. 1981; Chawla et al. 1988) M.
E. chiriquensis (Jackson 1985) FA
E. verna (Synonyms E. mulungu Benth.) (Guaratini et al. 2014) H
E. velutina seeds (MeOH) (Ozawa et al. 2009) M
E. latissima seeds (Wanjala and Majinda 2000)
Y
E. addisoniae seeds (EtOAc) and flowers (MeOH) (Cui et al. 2009; Wu et al. 2017)
E. abyssinica seeds (CHCl3) (Mohammed et al. 2012) ET
E. coralloides E. tajumulcensis E. macrophylla E. guatemalensis E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991) AL
glo- bocalyx E. steyermarkii E. oliviae E. huehuetenangensis E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al.
lanceolate 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer et
E. barqueroana E. folkersii E. stricta E. lysistemon E. zeyheri E. al. 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer
sene- galensis E. excelsa E. latissima E. tabitensis (Synonyms of E. et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
sandwi- censin) E. vespertilio E. burana E. suberosa E. × bidwillii (Amer et al. 1991) (Amer et al. 1991) (Amer et al.
E. caffra 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. vespertilio E. caffra E. lysistemon (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
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. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
varie- gata) E. stricta E. vespertilio E. burana E. macrophylla E. (Amer et al. 1991) (Amer et al. 1991) (Amer et al.
caffra 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer et
al. 1991)
E. caribea (Jackson 1985)
E. zeheri (Amer et al. 1991)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
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)
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
38. 8-Oxo-11-b-methoxyerythraline
39. Crystamidine
40. Erysodine-N-oxide
41. Erysotrine-N-oxide
42. 11-b-Hydroxyerysotrine-N-oxide
(Erythrartine N-oxide)
43. 11-a-Hydroxyerysotrine-N-oxide
44. O-Methylerythrartine-N-oxide
(Erythristemine-N-oxide)
45. Erysovine-N-oxide
46. 11-b-Methoxyerythraline-N-oxide
47. Erythraline N-oxide (Cristanine A)
48. Erythrinine N-oxide
49. Erytharbine
50. 10,11-Dioxoerysotrine
51. 10-Hydroxy-11-oxoerysotrine
52. Erytharborine H
53. 11-b-Methoxy-10-oxoerysotramidine
54. 10,11-Dioxoerysotramidine
55. Erytharborine A
56. Erytharborine B
57. Erysothiovine
58. Erysothiopine
59. Sodium erysovine 15-O-sulfate
60. Erysopine 15-O-sulfate
61. Sodium erysovine-N-oxy-15-O-sulfate
2. Dienoid glycoside alkaloids
62. 11-b-Methoxyglucoerysovine
63. b-Glucoerysodine
Occurrence (Solvent used for extraction) Reference
E. lysistemon seeds (Jackson 1985)
E. crista galli bark and leaves (MeOH) (Ito et al. 1973c; Ozawa et al. 2010)
E. brucei (Amer et al. 1991)
E. velutina seeds (MeOH) (Ozawa et al. 2009)
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)
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)
E. mulungu (Amer et al. 1991)
E. lysistemon flowers (DCM:MeOH) (Juma and Majinda 2004; Armwood et al. 2018)
E. lysistemon flowers (DCM:MeOH) E. × bidwillii (Juma and Majinda 2004) (Amer et al. 1991)
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
E. addisoniae seeds (EtOAc) (Cui et al. 2009)
E. crista galli flowers (MeOH) ( Chawla et al. 1988)
E. suberosa (Chawlaand Kapoor 1995)
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)
E. corallodendron flowers (MeOH) (Zhao et al. 2018)
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)
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)
E. herbacea flowers (MeOH) (Tanaka et al. 2008) NA
E. arborescens flowers (MeOH) (Wu et al. 2017) TU
E. latissima seed flowers (CHCl3:MeOH) (Cornelius et al. 2009) RA
E. latissima seed flowers (CHCl3:MeOH) (Cornelius et al. 2009)
E. arborescens flowers (MeOH) (Wu et al. 2017) L
E. arborescens flowers (MeOH) (Wu et al. 2017) PR
E. glauca E. pallida E. poeppigiana (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991) O
E. glauca (Amer et al. 1991) DU
E. velutina seeds (MeOH) (Ozawa et al. 2011) CT
E. velutina seeds (MeOH) (Ozawa et al. 2011) RE
E. velutina seeds (MeOH) (Ozawa et al. 2011)
SE
E. lysistemon (Amer et al. 1991) AR
E. vespertilio fruits (Iranshahi et al. 2012) CH
E. lysistemon (Amer et al. 1991)
(continued)
7
Table 1. Continued.
No. Compound Name
64. 11-b-Methoxy glucoerysodine
65. Rhamnoerysodine
66. 15-O-b-Glucoerysopine
67. 16-O-b-Glucoerysopine
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
8
Occurrence (Solvent used for extraction) Reference
E. velutina seeds (MeOH) (Ozawa et al. 2009)
E. senegalensis seeds (MeOH) (Wandji et al. 1995) N.
E. latissima seeds (Wanjala and Majinda 2000) M.
E. addisoniae seeds (EtOAc) (Cui et al. 2009) FA
E. lysistemon (Amer et al. 1991) H
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018) M
E. lysistemon (Amer et al. 1991)
Y
E. latissima seeds (Wanjala and Majinda 2000)
E. latissima seeds (Wanjala and Majinda 2000) ET
E. crista galli seeds (MeOH) (Tan et al. 2017) AL
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. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
steyer- markii E. barqueroana E. oliviae E. senegalensis E. excelsa (Amer et al. 1991) (Amer et al. 1991) (Amer et al.
E. living- stoniana E. abyssinica E. falcata E. latissima E. 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer et
tahitensis E. burana al. 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer
E. lysistemon E. variegata E. macrophylla E. melanacantha 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
81. Erythratidinone
82. Erysosalvinone
83. Erysotinone
84. 11-Hydroxyerysotinone
85. Erysoflorinone
86. 3-Demethoxyerythratidinone
87. 10,11-Dioxoerythratine
88. 10,11-Dioxoepierythratidine
89. Erytharborine F
90. 10,11-Dioxoerythratidinone
91. Erytharborine G
92. Erythramine
93. Erythratine
94. Epierythratine
95. 11-Hydroxyerythratine
96. 11-Hydroxyepierythratine
97. Erythratinone
98. 11-Methoxyerythratine
99. Cristanines B
100.8-Oxoerythraline
epoxide
101.Erytharborine E
102.Erysodienone
103.Erythritol
104.Erytharborine C
105.Erytharborine D
4. Lactonic alkaloids
106.a-Erythroidine
Occurrence (Solvent used for extraction) Reference
E. variegata (Kumar A et al. 2010)
E. arborescens flowers (MeOH) (Wu et al. 2017)
E. salviiflora (Amer et al. 1991)
E. addisoniae seeds (EtOAc) (Cui et al. 2009)
E. salviiflora (Millington et al. 1974)
E. macrophylla (Amer et al. 1991)
E. salviiflora E. subumbrans (Amer et al. 1991) (Amer et al. 1991)
E. variegata (Kumar A et al. 2010)
E. subumbrans bark (MeOH) (Rukachaisirikul et al.2008)
E. subumbrans bark (MeOH) (Rukachaisirikul et al.2008)
E. arborescens flowers (MeOH) (Wu et al. 2017)
E. subumbrans bark (MeOH) (Rukachaisirikul et al. 2008)
E. arborescens flowers (MeOH) (Wu et al. 2017)
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)
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. (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991)
folk- ersii E. abyssinica (Amer et al. 1991) (Amer et al. 1991) (Amer et al.
1991) (Amer et al. 1991)
E. subumbrans (Amer et al. 1991)
E. macrophylla E. subumbrans (Amer et al. 1991) (Amer et al. 1991)
E. corallodendron flowers (MeOH) (Zhao et al. 2018) NA
E. subumbrans (Amer et al. 1991) TU
E. glauca E. crista galli E. lithosperma (Synonyms of E. variegata) (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991) RA
E. crista galli flowers (MeOH) ( Chawla et al. 1988)
E. crista galli bark (MeOH) (Ozawa et al. 2010) L
E. poeppigiana wood (DCM) (Tanaka et al. 2001) PR
E. arborescens flowers (MeOH) (Wu et al. 2017) O
E. arborescens flowers (MeOH) (Wu et al. 2017) DU
E. variegata bark ( Chawla et al. 1988) CT
E. variegata (Kumar A et al. 2010) RE
E. arborescens flowers (MeOH) (Wu et al. 2017)
E. arborescens flowers (MeOH) (Wu et al. 2017)
SE
AR
E. poeppigiana stem bark (MeOH) (Djiogue et al. 2014) CH
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. N.
1991) (Amer et al. 1991) M.
E. poeppigiana stem bark (MeOH) (Djiogue et al. 2014)
E. americana (Folkers and Major 1937)
FA
E. coralloides E. oliviae E. berteroana E. standleyana E. chiapasana (Amer et al. 1991) (Amer et al. 1991) (Amer et al. 1991) H
E. globocalyx E. thollonia E. arborescens E. lithosperma (Amer et al. 1991) (Amer et al. 1991) (Amer et al. M
(Synonyms of 1991) (Amer et al. 1991) (Amer et al. 1991) (Amer et Y
E. variegata) al. 1991) ET
E. poeppigiana stem bark (MeOH) and wood (DCM) (Tanaka et al. 2001; Djiogue et al. 2014) 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
123.Hypaphorine methyl ester
124.Abrine
125.N,N-Dimethyltryptophan
methyl ester
126.1H-Indole-3-propanamide
10. Dimeric dienoids alkaloids
127.Erysophorine chloride
128.Erysodinophorine hydroxide
129.Erysopinophorine hydroxide
130.Isoerysopinophorin hydroxide
131.Erythrivarine A
132.Erythrivarine B
11. Dimeric dienoids glycoside alkaloids
133. Erythrivarine C
134. Erythrivarine D
12. Timeric dienoids alkaloids
135. Erythrivarine E
136. Erythrivarine F
137. Erythrivarine G
13. Other Erythrina alkaloids
138. Erythrinarbine
139. Stachydrine
140. Erybidine
141. Isoboldine
142. Reticuline
143. Norreticuline
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)
E. variegata bark, leaves and seeds (Ghosal et al. 1972)
E. caffra stem bark (CHCl3) (El-Masry et al. 2010)
E. variegata bark, leaves and seeds (Ghosal et al. 1972)
E. addisoniae seeds (EtOAc) (Cui et al. 2009)
E. arborescens (Amer et al. 1991)
E. arborescens (Amer et al. 1991)
E. arborescens (Amer et al. 1991)
E. arborescens (Amer et al. 1991)
E. variegata (Zhang BJ et al. 2014)
E. variegata (Zhang BJ et al. 2014)
E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
E. variegata flowers (MeOH) (Zhang B-J et al. 2016)
E. stricta leaves and stems (80% MeOH) E. arborescens stems (Wu et al. 2018) (Dong Lei et al.
1999)
E. variegata leaves and bark (pet. ether) (Singh et al. 1975)
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. ×
E. herbacea
bidwillii E. poeppigiana leaves (Chawla
(Ito Amrik Singh
and Tanaka and Kapoor 1995)
1974)
E. abyssinica E. poeppigiana (Chawla Amrik Singh and Kapoor 1995) (Chawla NA
Amrik Singh and Kapoor 1995) TU
E. variegata leaves (Kumar A et al. 2010) RA
E. corallodendron flowers (MeOH) (Zhao et al. 2018) L
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018) PR
E. corallodendron flowers (MeOH) (Zhao et al. 2018) O
E. stricta leaves and stems (80% MeOH) (Wu et al. 2018)
DU
CT
RE
SE
AR
CH
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 4.6 lg/ml)
Erysovine (2) Cytotoxic against
¼ Jurcat cell lines (IC50 ¼ 24.0 lg/
ml) and enhanced cytotoxicity by the addition (Ozawa et al. 2009)
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)
11- Hep-2 (IC50 ¼ 21.6 lg/ml) cell lines
a-Hydroxyerysotrine (13) Week cytotoxic activity against HL-60, K-562 (Kumar S et al. 2013)
and 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 g/ml) and (Mohammed et al. 2012)
17.6 l Hep-2 (IC50 ¼ 15.9 lg/ml) cell
lines ¼
Cytotoxic against Jurcat cell lines (IC50 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)
Estrogenic activity Hep-2 (IC50 ¼ 18.5 lg/ml) cell lines
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) (Djiogue et al. 2014)
and ERb (0.006 ± 0.010)
Nervous system Erysodine (1) Competitive, reversible antagonist of (-)-nicotine- (Decker et al. 1995)
NA
related activities induced dopamine release from striatal slices and
TU
inhibited (-)-nicotine-induced 86Rb þefflux from
RA
IMR-32 cells L
Competitive antagonist for a4b2 nAChRs (Mansbach et al. 2000) PR
Erythravine (7) Anxiolytic activity by significantly impairing the (Flausino et al. 2007; O
inhibitory avoidance task in the elevated T- Faggion et al. 2011) DU
maze test at a dose of 3 and 10 mg/kg mice CT
Inhibition of CNS nicotinic acetylcholine receptors, (Setti-Perdigao et al. 2013) RE
rine (13) particularly the a4b2 subtype (IC50 ¼ 13 nm) (Flausino et al., 2007) SE
11- Anxiolytic activity by significantly impairing the AR
a-Hydroxyerysot inhibitory avoidance task in the elevated T- CH
maze test at a dose of 3 and 10 mg/kg mice
(continued)

17
Table 2. Continued.
Biological Activity
Dihydro-b-erythroidine
Anti-inflamma-
tory activity
18
Compound Name Compound Number Effect Reference
Low inhibition of CNS nicotinic (Setti-Perdigao et al. 2013)
acetylcho- line receptors N.
11-a-Hydroxyerythravine (14) Anxiolytic activity by significantly impairing the (Flausino et al. 2007; Faggion et al. 2011) M.
inhibitory avoidance task in the elevated T- FA
maze test at a dose of 3 and 10 mg/kg mice H
Inhibition of CNS nicotinic acetylcholine (Setti-Perdigao et al. 2013) M
receptors, Y
particularly the a4b2 subtype (IC50 4 ET
Erythraline (29) nm) Curare-like action in frogs at 8¼mg/kg (Folkers and Koniuszy1940) AL
frog.
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
(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%. (Zhang B-J et al. 2016)
Erythrivarine F (136) Acetylcholinesterase inhibitory activity (IC50
¼ 12.5 lM)
Erythraline (29) Inhibition of LPS-induced NO production (IC50 ¼ (Ozawa et al. 2010)
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 (Zhang B-J et al. 2016)
(IC50
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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