Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Nat Prod Res. 2022 Feb;36(4):942-951. doi: 10.1080/14786419.2020.1855160. Epub
 2020 Dec 12.

New bioactive monoterpene indole alkaloid from Rinorea yaundensis Engl.

Khatoon B(1), Zikr Ur Rehman S(1), Yousuf S(1), Lateef M(2), Essombo MFA(3), 
Kamdem Waffo AF(3), Ali MS(1).

Author information:
(1)H.E.J Research Institute of Chemistry, International Center for Chemical and 
Biological Sciences, University of Karachi, Karachi, Pakistan.
(2)Multi-Disciplinary Research Lab, Bahria University Medical and Dental 
College, Karachi, Pakistan.
(3)Faculty of Science, Department of Chemistry, University of Cameroon, Douala, 
Douala.

Extraction of the aerial part of Rinorea yaundensis has led to the isolation of 
a new monoterpene indole alkaloid (1) along with 10 known compounds (2-11) for 
the first time from this plant. Their structures were determined by HRMS and NMR 
spectroscopic analyses as yaundentine hydrochloride (1), Nb-oxide of 
iso-reserpiline (2), iso-reserpiline (3), iso-carapanaubine (4), lichenxanthone 
(5), stigmastane-3,6-dione (6), methyl β-orcinol carboxylate (7), 
β-sitosterol-3-O-β-D-glucoside (8), betulinic acid (9), ursolic acid (10) and 
benzoic acid (11) while the stereochemistry and absolute configuration of 1 was 
confirmed by single crystal x-ray crystallography and circular dichroism CD 
spectrum. Yaundentine hydrochloride (1) exhibited pronounced antioxidant, urease 
and lipoxygenase inhibitory activities with IC50 values of 35.6 ± 0.23, 
20.3 ± 0.58 and 29.6 ± 0.77 µM, respectively. Compound 1 also showed good 
antimicrobial activity against some Gram positive and negative bacteria.

DOI: 10.1080/14786419.2020.1855160
PMID: 33307809 [Indexed for MEDLINE]


2. J Parasit Dis. 2019 Mar;43(1):103-112. doi: 10.1007/s12639-018-1064-1. Epub
2018  Dec 1.

In-vitro and in silico efficacy of isolated alkaloid compounds from Rauvolfia 
tetraphylla L. against bovine filarial parasite Setaria cervi: a drug discovery 
approach.

Behera DR(1), Bhatnagar S(1).

Author information:
(1)Regional Plant Resource Centre, Nayapalli, Bhubaneswar, Odisha 751015 India.

Bioassay guided isolation from the leaves of Rauvolfia tetraphylla L. resulted 
in the isolation and characterization of three compounds of alkaloid in nature 
namely, Curan-17-oic acid (F1); 18, 19-Secoyohimban (F2) and Reserpiline (F3). 
Macrofilaricidal activity of three compounds was tested against bovine filarial 
parasite Setaria cervi using in vitro assays and supported by in silico docking 
analysis on glutathione-S-transferase (GST) enzyme of Wuchereria bancrofti. All 
the molecules inhibited GST enzyme to some extent 35.78%, 78.22% and 64.21% 
respectively. Results were supported by molecular docking studies, which showed 
docking scores for compound F1 (- 5.14), compound F2 (- 7.19) and compound F3 
(- 7.2) on GST enzyme. Thus, in conclusion the in vitro and in silico studies 
indicated that isolated compounds are promising, inexpensive and widely 
available natural leads, which can be designed and developed into the 
macrofilaricidal drugs.

DOI: 10.1007/s12639-018-1064-1
PMCID: PMC6423205
PMID: 30956453

Conflict of interest statement: Compliance with ethical standardsNo potential 
conflict of interest was reported by the authors.


3. Phytochemistry. 2019 Mar;159:20-29. doi: 10.1016/j.phytochem.2018.11.009. Epub
 2018 Dec 17.

UPLC and ESI-MS analysis of metabolites of Rauvolfia tetraphylla L. and their 
spatial localization using desorption electrospray ionization (DESI) mass 
spectrometric imaging.

Mohana Kumara P(1), Uma Shaanker R(2), Pradeep T(3).

Author information:
(1)DST Unit of Nanoscience and Thematic Unit of Excellence, Department of 
Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India; Center 
for Ayurveda Biology and Holistic Nutrition, The University of 
Trans-Disciplinary Health Sciences and Technology (TDU), Bengaluru, 560064, 
India. Electronic address: monapatelpgatti@gmail.com.
(2)School of Ecology and Conservation, Department of Crop Physiology, University 
of Agricultural Sciences, GKVK, Bengaluru, 560065, India.
(3)DST Unit of Nanoscience and Thematic Unit of Excellence, Department of 
Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India. 
Electronic address: pradeep@iitm.ac.in.

Rauvolfia tetraphylla L. (family Apocynaceae), often referred to as the wild 
snakeroot plant, is an important medicinal plant and produces a number of indole 
alkaloids in its seeds and roots. The plant is often used as a substitute for 
Ravuolfia serpentine (L.) Benth. ex Kurz known commonly as the Indian snakeroot 
plant or sarphagandha in the preparation of Ayurvedic formulations for a range 
of diseases including hypertension. In this study, we examine the spatial 
localization of the various indole alkaloids in developing fruits and plants of 
R. tetraphylla using desorption electrospray ionization mass spectrometry 
imaging (DESI-MSI). A semi-quantitative analysis of the various indole alkaloids 
was performed using UPLC-ESI/MS. DESI-MS images showed that the distribution of 
ajmalcine, yohimbine, demethyl serpentine and mitoridine are largely localized 
in the fruit coat while that for ajmaline is restricted to mesocarp of the 
fruit. At a whole plant level, the ESI-MS intensities of many of the ions were 
highest in the roots and lesser in the shoot region. Within the root tissue, 
except sarpagine and ajmalcine, all other indole alkaloids occurred in the 
epidermal and cortex tissues. In leaves, only serpentine, ajmalcine, reserpiline 
and yohimbine were present. Serpentine was restricted to the petiolar region of 
leaves. Principal component analysis based on the presence of the indole 
alkaloids, clearly separated the four tissues (stem, leaves, root and fruits) 
into distinct clusters. In summary, the DESI-MSI results indicated a clear 
tissue localization of the various indole alkaloids, in fruits, leaves and roots 
of R. tetraphylla. While it is not clear of how such localization is attained, 
we discuss the possible pathways of indole alkaloid biosynthesis and 
translocation during fruit and seedling development in R. tetraphylla. We also 
briefly discuss the functional significance of the spatial patterns in 
distribution of metabolites.

Copyright © 2018 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2018.11.009
PMID: 30562679 [Indexed for MEDLINE]


4. Chem Biol Drug Des. 2015 Dec;86(6):1471-81. doi: 10.1111/cbdd.12613. Epub 2015
 Aug 21.

Synergy Potential of Indole Alkaloids and Its Derivative against Drug-resistant 
Escherichia coli.

Dwivedi GR(1)(2), Gupta S(3), Maurya A(3), Tripathi S(1), Sharma A(1), Darokar 
MP(1), Srivastava SK(3).

Author information:
(1)Biotechnology Division, Central Institute of Medicinal and Aromatic Plants 
(CSIR-CIMAP), P.O.- CIMAP, Lucknow, 226015, India.
(2)School of Environmental Sciences, Babasaheb Bhimrao Ambedkar Central 
University, Vidya Vihar, Rae Bareli Road, Lucknow, 226025, India.
(3)Medicinal Chemistry Department, Central Institute of Medicinal and Aromatic 
Plants (CSIR-CIMAP), P.O.- CIMAP, Lucknow, 226015, India.

Antibacterial and synergy potential of naturally occurring indole alkaloids 
(IA): 10-methoxy tetrahydroalstonine (1), isoreserpiline (2), 10 and 11 
demethoxyreserpiline (3), reserpiline (4), serpentine (5), ajmaline (6), 
ajmalicine (7), yohimbine (8), and α-yohimbine (9) was evaluated using 
microbroth dilution assay. Further, α-yohimbine (9) was chemically transformed 
into six semisynthetic derivatives (9A-9F), and their antibacterial and synergy 
potential in combination with nalidixic acid (NAL) against E. coli strains 
CA8000 and DH5α were also evaluated. The IA 1, 2, 4, 5, 9 and the derivative 9F 
showed eightfold reduction in the MIC of NAL against the DH5α and four- to 
eightfold reduction against CA8000. These alkaloids also reduced MIC of another 
antibiotic, tetracycline up to 8folds, against the MDREC-KG4, a 
multidrug-resistant clinical isolate of E. coli. Mode of action study of these 
alkaloids showed efflux pumps inhibitory potential, which was supported by their 
in silico binding affinity and downregulation of efflux pump genes. These 
results may be of great help in the development of cost-effective antibacterial 
combinations for treating patients infected with multidrug-resistant 
Gram-negative infections.

© 2015 John Wiley & Sons A/S.

DOI: 10.1111/cbdd.12613
PMID: 26132412 [Indexed for MEDLINE]


5. Biomed Res Int. 2014;2014:798742. doi: 10.1155/2014/798742. Epub 2014 Jun 19.

Drug design of cyclin-dependent kinase 2 inhibitor for melanoma from traditional 
Chinese medicine.

Tang HC(1), Chen CY(2).

Author information:
(1)Department of Biomedical Informatics, Asia University, Taichung 41354, 
Taiwan.
(2)Department of Biomedical Informatics, Asia University, Taichung 41354, Taiwan 
; Department of Medicine, China Medical University, Taichung 40402, Taiwan ; 
Research Center for Chinese Medicine & Acupuncture, China Medical University, 
Taichung 40402, Taiwan ; Human Genetic Center, Department of Medical Research, 
China Medical University Hospital, Taichung 40447, Taiwan.

One has found an important cell cycle controller. This guard can decide the cell 
cycle toward proliferation or quiescence. Cyclin-dependent kinase 2 (CDK2) is a 
unique target among the CDK family in melanoma therapy. We attempted to find out 
TCM compounds from TCM Database@Taiwan that have the ability to inhibit the 
activity of CDK2 by systems biology. We selected Tetrahydropalmatine, 
Reserpiline, and (+)-Corydaline as the candidates by docking and screening 
results for further survey. We utilized support vector machine (SVM), multiple 
linear regression (MLR) models and Bayesian network for validation of predicted 
activity. By overall analysis of docking results, predicted activity, and 
molecular dynamics (MD) simulation, we could conclude that Tetrahydropalmatine, 
Reserpiline, and (+)-Corydaline had better binding affinity than the control. 
All of them had the ability to inhibit the activity of CDK2 and might have the 
opportunity to be applied in melanoma therapy.

DOI: 10.1155/2014/798742
PMCID: PMC4090515
PMID: 25045703 [Indexed for MEDLINE]