Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Antibiotics (Basel). 2022 Jan 17;11(1):121. doi: 10.3390/antibiotics11010121.

A New Antimicrobial Phenylpropanol from the Leaves of Tabernaemontana 
inconspicua Stapf. (Apocynaceae) Inhibits Pathogenic Gram-Negative Bacteria.

Ngah L(1), Tsopgni WDT(1), Nyobe JCN(2), Tcho AT(3), Langat MK(4), Ndom JC(1), 
Mas-Claret E(4), Sadgrove NJ(4), Waffo AFK(1), Phumthum M(4)(5).

Author information:
(1)Faculty of Sciences, Department of Chemistry, University of Douala, Douala 
P.O. Box 24157, Cameroon.
(2)Laboratory of Quality Control for Food, Pharmaceutical and Cosmetic Products, 
Department of Thermal Engineering and Energy, University Institute of 
Technology, University of Douala, Douala P.O. Box 8698, Cameroon.
(3)Department of Chemistry, Faculty of Sciences, University of Buea, Buea P.O. 
Box 63, Cameroon.
(4)Royal Botanic Gardens, Kew, Kew Green, Richmond, Surrey TW9 3AE, UK.
(5)Department of Pharmaceutical Botany, Faculty of Pharmacy, Mahidol University, 
Bangkok 10400, Thailand.

A chemical investigation of the leaves of Tabernaemontana inconspicua Stapf. led 
to the isolation of a new phenylpropanol derivative, namely irisdichototin G 
(1), together with nine known compounds, including one polyol derivative, 
dambonitol (2); three alkaloids, 10-hydroxycoronaridine (3), voacristine (4) and 
vobasine (5); two triterpenes lupeol (6), betulinic acid (7) and three sterols, 
sitosterol (8), sitosterol-3-O-β-D-glucopyranoside (9) and stigmasterol (10). 
The structure of the new compound, as well as those of the known ones, was 
established by means of spectroscopic methods: NMR analysis (1H and 13C NMR, 
1H-1H-COSY, HSQC, HMBC and NOESY), high-resolution mass spectrometry (HR-ESI-MS) 
and comparisons with previously reported data. Among the known compounds, 
compound 2 was firstly reported from the family Apocynaceae. Compounds 1-5 were 
tested for their antimicrobial effects against three Gram-negative organisms 
associated with human wound and systemic infections, namely Haemophilus 
influenzae 9435337A, Klebsiella pneumoniae 17102005 and Pseudomonas aeruginosa 
2137659B. Compounds 1, 3, and 5 showed significant antimicrobial effects with 
minimum inhibitory concentrations (MIC) of 62.5 μg/mL, 62.5 μg/mL and 7.81 
μg/mL, respectively, against Haemophilus influenzae, whereas compounds 1 and 5 
showed significant antimicrobial effects, with a MIC value of 31.25 μg/mL 
against Pseudomonas aeruginosa. In addition, compound 3 showed significant 
antimicrobial activity, with a MIC value of 31.25 μg/mL against Klebsiella 
pneumoniae.

DOI: 10.3390/antibiotics11010121
PMCID: PMC8773313
PMID: 35052998

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


2. Nat Prod Res. 2022 Mar;36(5):1365-1369. doi: 10.1080/14786419.2021.1871906.
Epub  2021 Jan 18.

Antileishmanial and cytotoxic activity of secondary metabolites from 
Taberneamontana ventricosa and two aloe species.

Andima M(1)(2), Ndakala A(1), Derese S(1), Biswajyoti S(3), Hussain A(3), Yang 
LJ(4), Akoth OE(1), Coghi P(5), Pal C(3), Heydenreich M(6), Wong VK(4), Yenesew 
A(1).

Author information:
(1)Department of Chemistry, University of Nairobi, Nairobi, Kenya.
(2)Department of Chemistry, Busitema University, Tororo, Uganda.
(3)Cellular Immunology and Experimental Therapeutics Laboratory, Department of 
Zoology, West Bengal State University, Parganas, West Bengal, India.
(4)State Key Laboratory of Quality Research in Chinese Medicine, Macau 
University of Science and Technology, Macau, China.
(5)School of Pharmacy, Macau University of Science and Technology, Taipa, Macau, 
China.
(6)Institut für Chemie, Universität Potsdam, Potsdam, Germany.

In this study, the antileishmanial and cytotoxic activities of secondary 
metabolites isolated from Tabernaemontana ventricosa Hochst. ex A. DC., Aloe 
tororoana Reynolds, and Aloe schweinfurthii var. labworana Reynolds were 
investigated. Overall, nineteen known compounds were isolated from the three 
plant species. The compounds were characterized based on their spectroscopic 
data. Voacristine and aloenin were the most active compounds against 
promastigotes of antimony-sensitive Leishmania donovani (IC50 11 ± 5.2 μM and 
26 ± 6.5 µM, respectively) with low toxicity against RAW264.7, murine 
monocyte/macrophage-like cells. The in silico docking evaluation and in vitro NO 
generation assay also substantially support the antileishmanial effects of these 
compounds. In a cytotoxicity assay against cancer and normal cell lines, ursolic 
acid highly inhibited proliferation of lung cancer cells, A549 (IC50 
6.61 ± 0.7 μM) while voacristine was moderately active against human liver 
cancer cells, HepG2 (IC50 23.0 ± 0.0 μM). All other compounds were inactive 
against the test parasites and cell lines. [Formula: see text].

DOI: 10.1080/14786419.2021.1871906
PMID: 33459049 [Indexed for MEDLINE]


3. Molecules. 2020 Dec 25;26(1):70. doi: 10.3390/molecules26010070.

Alkaloids with Anti-Onchocercal Activity from Voacanga africana Stapf 
(Apocynaceae): Identification and Molecular Modeling.

Babiaka SB(1)(2), Simoben CV(3), Abuga KO(4), Mbah JA(1), Karpoormath R(5), 
Ongarora D(4), Mugo H(4), Monya E(6), Cho-Ngwa F(6), Sippl W(3), Loveridge 
EJ(7), Ntie-Kang F(1)(3)(8).

Author information:
(1)Department of Chemistry, Faculty of Science, University of Buea, P.O. Box 63, 
Buea CM-00237, Cameroon.
(2)AgroEco Health Platform, International Institute of Tropical Agriculture, 
Cotonou, Abomey-Calavi BEN-00229, Benin.
(3)Institute for Pharmacy, Martin-Luther-Universität Halle-Wittenberg, 
Kurt-Mothes-Str. 3, 06120 Halle, Germany.
(4)Department of Pharmaceutical Chemistry, School of Pharmacy, University of 
Nairobi, Nairobi P.O. Box 19676-00202, Kenya.
(5)Department of Pharmaceutical Chemistry, School of Chemistry, University of 
KwaZulu-Natal, Durban 4001, South Africa.
(6)ANDI Centre of Excellence for Onchocerciasis Drug Research, Biotechnology 
Unit, Faculty of Science, University of Buea, P.O. Box 63, Buea CM-00237, 
Cameroon.
(7)Department of Chemistry, Swansea University, Singleton Park, Swansea SA2 8PP, 
UK.
(8)Institute of Botany, Technical University of Dresden, 01217 Dresden, Germany.

A new iboga-vobasine-type isomeric bisindole alkaloid named voacamine A (1), 
along with eight known compounds-voacangine (2), voacristine (3), coronaridine 
(4), tabernanthine (5), iboxygaine (6), voacamine (7), voacorine (8) and 
conoduramine (9)-were isolated from the stem bark of Voacangaafricana. The 
structures of the compounds were determined by comprehensive spectroscopic 
analyses. Compounds 1, 2, 3, 4, 6, 7 and 8 were found to inhibit the motility of 
both the microfilariae (Mf) and adult male worms of Onchocerca ochengi, in a 
dose-dependent manner, but were only moderately active on the adult female worms 
upon biochemical assessment at 30 μM drug concentrations. The IC50 values of the 
isolates are 2.49-5.49 µM for microfilariae and 3.45-17.87 µM for adult males. 
Homology modeling was used to generate a 3D model of the O. ochengi thioredoxin 
reductase target and docking simulation, followed by molecular dynamics and 
binding free energy calculations attempted to offer an explanation of the 
anti-onchocercal structure-activity relationship (SAR) of the isolated 
compounds. These alkaloids are new potential leads for the development of 
antifilarial drugs. The results of this study validate the traditional use of V. 
africana in the treatment of human onchocerciasis.

DOI: 10.3390/molecules26010070
PMCID: PMC7795662
PMID: 33375687 [Indexed for MEDLINE]

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


4. Zhongguo Zhong Yao Za Zhi. 2018 Apr;43(7):1471-1475. doi: 
10.19540/j.cnki.cjcmm.20180115.007.

[Studies on alkaloids from Ervatamia pandacaqui].

[Article in Chinese]

Zhang QH(1)(2), Ding Y(1)(2), Bai WX(1)(2), Zhang J(1)(2), Zhang XQ(1)(2), Ye 
WC(1)(2).

Author information:
(1)Institute of Traditional Chinese Medicine & Natural Products, College of 
Pharmacy, Ji'nan University, Guangzhou 510632, China.
(2)Guangdong Technology Research Center for Advanced Chinese Medicine, College 
of Pharmacy, Ji'nan University, Guangzhou 510632, China.

To inverstigate the alkaloids from the twigs and leaves of Ervatamia pandacaqui, 
eleven known alkaloids were isolated by silica gel, Sephadex LH-20, and ODS 
column chromatography, as well as RP-HPLC. Their structures were elucidated by 
UV, IR, MS, and NMR spectral data as coronaridine (1), 3-oxocoronaridine (2), 
19S-heyneanine (3), 19R-heyneanine (4), voacangine (5), 3-oxovoacangine (6), 
voacristine (7), 19-epi-voacristine (8), iso-voacangine (9), coronaridine 
7-hydroxyindolenine (10), and voacangine 7-hydroxyindolenine (11). Compounds 
1-11 were isolated from E. pandacaqui for the first time.

Copyright© by the Chinese Pharmaceutical Association.

DOI: 10.19540/j.cnki.cjcmm.20180115.007
PMID: 29728039 [Indexed for MEDLINE]

Conflict of interest statement: The authors of this article and the planning 
committee members and staff have no relevant financial relationships with 
commercial interests to disclose.


5. Org Lett. 2018 May 4;20(9):2702-2706. doi: 10.1021/acs.orglett.8b00913. Epub 
2018 Apr 20.

Antibacterial Indole Alkaloids with Complex Heterocycles from Voacanga africana.

Ding CF(1)(2), Ma HX(3), Yang J(1), Qin XJ(1), Njateng GSS(4), Yu HF(1)(2), Wei 
X(1)(2), Liu YP(1), Huang WY(3), Yang ZF(3), Wang XH(3), Luo XD(1)(3).

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.
(2)Graduate University of the Chinese Academy of Sciences , Beijing 100049 , 
People's Republic of China.
(3)State Key Laboratory of Respiratory Disease , Guangzhou Medical University , 
Guangzhou 510120 , People's Republic of China.
(4)Department of Biochemistry, Faculty of Science , University of Dschang , P.O. 
Box 67, Dschang , Cameroon.

Voacafricines A and B, two unique monoterpenoid indole alkaloids each bearing 
five fused heterocycles, were obtained from the fruits of Voacanga africana. 
Their structures were elucidated by extensive spectroscopic methods and 
computational studies. A plausible biogenetic pathway was proposed from a common 
precursor, 19- epi-voacristine. Both compounds exhibited potent activity against 
Staphylococcus aureus and Salmonella typhi, and their activities were superior 
to those of the well-known antibacterial drugs berberine and fibrauretine.

DOI: 10.1021/acs.orglett.8b00913
PMID: 29676579 [Indexed for MEDLINE]