Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Phytochemistry. 2022 Nov;203:113384. doi: 10.1016/j.phytochem.2022.113384.
Epub  2022 Aug 23.

Vobasine, vincamine, voaphylline, tacaman, and iboga alkaloids from 
Tabernaemontana corymbosa.

Sim DS(1), Tang SY(1), Low YY(1), Lim SH(2), Kam TS(3).

Author information:
(1)Department of Chemistry, Faculty of Science, Universiti Malaya, Kuala Lumpur, 
50603, Malaysia.
(2)Department of Chemistry, Faculty of Science, Universiti Malaya, Kuala Lumpur, 
50603, Malaysia. Electronic address: shlim80@um.edu.my.
(3)Department of Chemistry, Faculty of Science, Universiti Malaya, Kuala Lumpur, 
50603, Malaysia. Electronic address: tskam@um.edu.my.

Thirteen indole alkaloids comprising six vobasine/sarpagine, one vincamine, two 
voaphylline, two tacaman, one iboga, and one corynantheine alkaloid, were 
isolated from the leaf extract of Tabernaemontana corymbosa (sample from 
Taiping, Perak, Malaysia). The structures of these alkaloids were determined 
based on analysis of the spectroscopic data (NMR and MS), and in the case of 
vincarudine, the absolute configuration was established by ECD and X-ray 
diffraction analysis. Vobasidine E represents the first vobasine-type alkaloid 
characterized by a contracted ring C and loss of the ethylidene/ethyl side 
chain. A possible biogenetic pathway from a perivine precursor, which was also 
present in the leaf extract, is presented. Differences in the new alkaloid 
content between the present and previous sample of the same plant (occurring in 
a different location) are discussed.

Copyright © 2022 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2022.113384
PMID: 36007666 [Indexed for MEDLINE]

Conflict of interest statement: Declaration of competing interest The authors 
declare that they have no known competing financial interests or personal 
relationships that could have appeared to influence the work reported in this 
paper.


2. Molecules. 2019 May 24;24(10):2002. doi: 10.3390/molecules24102002.

Exploring African Medicinal Plants for Potential Anti-Diabetic Compounds with 
the DIA-DB Inverse Virtual Screening Web Server.

Pereira ASP(1), den Haan H(2), Peña-García J(3), Moreno MM(4), Pérez-Sánchez 
H(5), Apostolides Z(6).

Author information:
(1)Department of Biochemistry, Genetics and Microbiology, University of 
Pretoria, Pretoria, Hillcrest 0083, South Africa. aspdpereira@gmail.com.
(2)Structural Bioinformatics and High Performance Computing Research Group 
(BIO-HPC), Universidad Católica de Murcia 30107, Spain. hden@alu.ucam.edu.
(3)Structural Bioinformatics and High Performance Computing Research Group 
(BIO-HPC), Universidad Católica de Murcia 30107, Spain. Jorge.dlpg@gmail.com.
(4)Structural Bioinformatics and High Performance Computing Research Group 
(BIO-HPC), Universidad Católica de Murcia 30107, Spain. memoreno@ucam.edu.
(5)Structural Bioinformatics and High Performance Computing Research Group 
(BIO-HPC), Universidad Católica de Murcia 30107, Spain. hperez@ucam.edu.
(6)Department of Biochemistry, Genetics and Microbiology, University of 
Pretoria, Pretoria, Hillcrest 0083, South Africa. zeno.apostolides@up.ac.za.

Medicinal plants containing complex mixtures of several compounds with various 
potential beneficial biological effects are attractive treatment interventions 
for a complex multi-faceted disease like diabetes. In this study, compounds 
identified from African medicinal plants were evaluated for their potential 
anti-diabetic activity. A total of 867 compounds identified from over 300 
medicinal plants were screened in silico with the DIA-DB web server 
(http://bio-hpc.eu/software/dia-db/) against 17 known anti-diabetic drug 
targets. Four hundred and thirty compounds were identified as potential 
inhibitors, with 184 plants being identified as the sources of these compounds. 
The plants Argemone ochroleuca, Clivia miniata, Crinum bulbispermum, Danais 
fragans, Dioscorea dregeana, Dodonaea angustifolia, Eucomis autumnalis, Gnidia 
kraussiana, Melianthus comosus, Mondia whitei, Pelargonium sidoides, Typha 
capensis, Vinca minor, Voacanga Africana, and Xysmalobium undulatum were 
identified as new sources rich in compounds with a potential anti-diabetic 
activity. The major targets identified for the natural compounds were aldose 
reductase, hydroxysteroid 11-beta dehydrogenase 1, dipeptidyl peptidase 4, and 
peroxisome proliferator-activated receptor delta. More than 30% of the compounds 
had five or more potential targets. A hierarchical clustering analysis coupled 
with a maximum common substructure analysis revealed the importance of the 
flavonoid backbone for predicting potential activity against aldose reductase 
and hydroxysteroid 11-beta dehydrogenase 1. Filtering with physiochemical and 
the absorption, distribution, metabolism, excretion and toxicity (ADMET) 
descriptors identified 28 compounds with favorable ADMET properties. The six 
compounds-crotofoline A, erythraline, henningsiine, nauclefidine, vinburnine, 
and voaphylline-were identified as novel potential multi-targeted anti-diabetic 
compounds, with favorable ADMET properties for further drug development.

DOI: 10.3390/molecules24102002
PMCID: PMC6571761
PMID: 31137754 [Indexed for MEDLINE]

Conflict of interest statement: The authors declare no conflict of interest.


3. Phytochemistry. 2015 Dec;120:46-52. doi: 10.1016/j.phytochem.2014.12.025. Epub
 2015 Feb 13.

Cytotoxic indole alkaloids from Tabernaemontana officinalis.

Zhang BJ(1), Teng XF(2), Bao MF(3), Zhong XH(1), Ni L(1), Cai XH(4).

Author information:
(1)State Key Laboratory of Phytochemistry and Plant Resources in West China, 
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, 
People's Republic of China; University of Chinese Academy of Sciences, Beijing 
100049, People's Republic of China.
(2)School of Traditional Chinese Medicine, Guangdong Pharmaceutical University, 
Guangzhou 510006, People's Republic of China.
(3)State Key Laboratory of Phytochemistry and Plant Resources in West China, 
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, 
People's Republic of China.
(4)State Key Laboratory of Phytochemistry and Plant Resources in West China, 
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, 
People's Republic of China. Electronic address: xhcai@mail.kib.ac.cn.

Continued interest in cytotoxic alkaloids resulted in the isolation of 37 
alkaloids including 29 known monoterpenoid indole alkaloids from the aerial 
parts of Tabernaemontana officinalis. Of the remaining 8 alkaloids, six were 
bisindole alkaloids named taberdivarines A-F (1-6) and the two were monomers 
named taberdivarines G and H (7-8). Alkaloids 1 and 2 are voaphylline-vobasinyl 
type bisindole alkaloids, a structural type previously unknown, while 3-6 
exhibited cytotoxicity against three human cancer cell lines HeLa, MCF-7, and 
SW480 with IC50 values ranging from 1.42 to 11.35 μM.

Copyright © 2014 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2014.12.025
PMID: 25687604 [Indexed for MEDLINE]


4. Bioinformation. 2014 Mar 19;10(3):152-6. doi: 10.6026/97320630010152. 
eCollection 2014.

Virtual Screening of compounds from Tabernaemontana divaricata for potential 
anti-bacterial activity.

Gogoi RR(1), Gogoi D(2), Bezbaruah RL(2).

Author information:
(1)Centre for Bioinformatics Studies, Dibrugarh University, Dibrugarh, Assam.
(2)DBT-Bioinformatics Infrastructure Facility, Biotechnology Division, 
CSIR-North East Institute of Science and Technology, Jorhat, Assam.

Virtual Screening and Molecular Docking analysis for Tabernaemontana divaricata 
derived 66 Law Molecular Weight Compounds (LMW) was conducted and to identified 
and predicted novel molecules as a inhibitor of Streptococcus pneumonia. The 
investigation has revealed several compounds with optimum binding towards 
Penicillin-binding proteins, Sialidases, Aspartate betasemialdehide 
dehydrogenase cell membrane protein of Streptococcus pneumonia. Docking results 
were computed in term of binding energy, ligand efficiency and number of 
hydrogen bonding. Apparicine (-5.14), 5-Hydroxyvoaphylline (-4.78), Voacangine 
(-4.7), 19-Hydroxycoronaridine (-4.44) and Coronaridine (-4.72) are identified 
as most suitable to bind with N-acetylglucosamine-1- phosphate uridyltransferase 
receptor. Ervaticine (-6.33), Ibogamine (-6.15), Methylvoaphylline (-5.74) and 
Coronaridine hydroxyindolenine (-5.32) has showed novel binding against the 
penicillin-binding proteins. Ervaticine (-6.42), 5-oxo-11-hydroxy voaphylline 
(-6.18), Conolobine B (-6.02) has found optimum binding against the active site 
of NanB sialidase of Streptococcus pneumonia. The compounds 3S-Cyanocoronaridine 
(-6.71), 19-Epivoacristine (-5.48) and Ervaticine(-5.45) interacting with 
aspartate beta-semialdehide and found suitable with least docking score.

DOI: 10.6026/97320630010152
PMCID: PMC3974242
PMID: 24748755


5. Phytochemistry. 2012 Nov;83:116-24. doi: 10.1016/j.phytochem.2012.06.013. Epub
 2012 Jul 18.

Alkaloids from Melodinus yunnanensis.

Cai XH(1), Li Y, Liu YP, Li XN, Bao MF, Luo XD.

Author information:
(1)State Key Laboratory of Phytochemistry and Plant Resources in West China, 
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China. 
xhcai@mail.kib.ac.cn

Ten monoterpenoid indole alkaloids, namely meloyine, 19S-methoxytubotaiwine 
N₄-oxide, 16,19-epoxy-Δ¹⁴-vincanol, 14β-hydroxymeloyunine, meloyunine, 
Δ¹⁴-vincamenine N₄-oxide, 16β,21β-epoxy-vincadine, 14β,15β-20S-quebrachamine, 
3-oxo-voaphylline, 2α,7α-dihydroxy-dihydrovoaphylline, and 32 known alkaloids 
were isolated from leaves and twigs of Melodinus yunnanensis. Their structures 
were elucidated based on 1- and 2-D NMR, FTIR, UV, and MS spectroscopic data. 
Meloyine I showed weak cytotoxic activity against four human cancer cell lines: 
MCF-7 breast cancer, SMMC-7721 hepatocellular carcinoma, HL-60 myeloid leukemia, 
and A-549 lung cancer.

Copyright © 2012 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2012.06.013
PMID: 22818523 [Indexed for MEDLINE]