Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Phytochemistry. 2024 Jul;223:114139. doi: 10.1016/j.phytochem.2024.114139.
Epub  2024 May 13.

Structurally diverse isoquinoline alkaloids from the barks of Alangium 
salviifolium (L. f.) Wangerin and their cytotoxicity.

Wei YM(1), Zhang X(1), Cen FL(1), Du YY(1), Liu YL(1), Han QY(1), Yu ZX(2), Chen 
GY(3).

Author information:
(1)Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of 
Education, Hainan Normal University, Haikou, Hainan, 571158, China; Key 
Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of 
Chemistry and Chemical Engineering, Hainan Normal University, Haikou, Hainan, 
571158, China.
(2)Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of 
Education, Hainan Normal University, Haikou, Hainan, 571158, China; Key 
Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of 
Chemistry and Chemical Engineering, Hainan Normal University, Haikou, Hainan, 
571158, China. Electronic address: yzhx712@hainnu.edu.cn.
(3)Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of 
Education, Hainan Normal University, Haikou, Hainan, 571158, China; Key 
Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of 
Chemistry and Chemical Engineering, Hainan Normal University, Haikou, Hainan, 
571158, China. Electronic address: cgy@hainnu.edu.cn.

Eleven undescribed isoquinoline alkaloids (1-8, 14, 15, and 24), along with 19 
analogues (9-13, 16-23, and 25-30) were isolated from the barks of Alangium 
salviifolium. The structures of the undescribed compounds were elucidated 
through the analysis of their HR-ESI-MS, 1D and 2D NMR, IR, UV, and X-ray 
diffraction. The absolute configuration of 8 was established via the ECD 
calculation. Notably, compounds 1/2 and 3/4 were two pairs of C-14 epimers. The 
isolated alkaloids were evaluated for their cytotoxicity against various cancer 
cell lines, including SGC-7901, HeLa, K562, A549, BEL-7402, HepG2, and B16, 
β-carboline-benzoquinolizidine (14-22) and cepheline-type (24-28) alkaloids 
exhibited remarkable cytotoxicity, with IC50 values ranging from 0.01 to 
48.12 μM. Remarkably, compounds 17 and 21 demonstrated greater cytotoxicity than 
the positive control doxorubicin hydrochloride. Furthermore, a significant 
proportion of these bioactive alkaloids possess a C-1' epimer configuration. The 
exploration of their structure-activity relationship holds promise for directing 
future investigations into alkaloids derived from Alangium, potentially leading 
to novel insights and therapeutic advancements.

Copyright © 2024 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2024.114139
PMID: 38750707 [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. Nat Prod Res. 2021 Aug;35(16):2784-2788. doi: 10.1080/14786419.2019.1666386. 
Epub 2019 Sep 23.

Alkaloids and sesquiterpenes from roots and leaves of Lycium europaeum L. 
(Solanaceae) with antioxidant and anti-acetylcholinesterase activities.

Bendjedou H(1), Barboni L(2), Maggi F(3), Bennaceur M(1)(4), Benamar H(1)(5).

Author information:
(1)Department of Biology, University of Oran1, Oran, Algeria.
(2)School of Science and Technology, University of Camerino, Camerino, Italy.
(3)School of Pharmacy, University of Camerino, Camerino, Italy.
(4)Laboratory of Research in Arid Areas, Algiers, Algeria.
(5)Department of Biology, University of Mostaganem Abdelhamid Ibn Badis, 
Mostaganem, Algeria.

Lycium europaeum L. is a spiny shrub of the Solanaceae family, known in Algeria 
as 'Awsaj' and used as food and herbal remedy. The phytochemical investigation 
of the alkaloid extract of roots and leaves led to the isolation and 
characterisation of one alkaloid (harmine (3)) and four sesquiterpenes (C-1' 
epimer of 
(2 R,5S,10R)-2-(1',2'-dihydroxy-1'-methylethyl)-6,10-dimethylspiro[4,5]dec-6-en-8-one 
(1), C-1' epimer of 
2-(1',2'-di-hydroxy-1'-methylethyl)-6,10-dimethylspiro[4,5]dec-6,9-dien-8-one 
(2), (+)-dehydrovomifoliol (4), vomifoliol (5)). Their structures were 
elucidated using NMR and MS spectroscopic data. The isolated compounds were 
characterised for the first time from the genus Lycium. All isolated compounds 
have shown antioxidant and acetylcholinesterase (AChE) inhibitory activities in 
the bioautography assays. The ethanolic and alkaloid extracts of roots and 
leaves were also tested, and, particularly, the alkaloid extracts were the most 
active ones as antioxidant and AChE inhibitors.

DOI: 10.1080/14786419.2019.1666386
PMID: 31542954 [Indexed for MEDLINE]


3. Sci Rep. 2019 Jul 8;9(1):9812. doi: 10.1038/s41598-019-46336-z.

An Unusually Broad Series of Seven Cyclombandakamines, Bridged Dimeric 
Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus 
ealaensis.

Tshitenge DT(1)(2), Bruhn T(3), Feineis D(1), Mudogo V(4), Kaiser M(5)(6), Brun 
R(5)(6), Bringmann G(7).

Author information:
(1)Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074, 
Würzburg, Germany.
(2)Faculty of Pharmaceutical Sciences, University of Kinshasa, B.P. 212, 
Kinshasa XI, Democratic Republic of the Congo.
(3)Federal Institute for Risk Assessment, Max-Dohrn-Straße 8-10, D-10589, 
Berlin, Germany.
(4)Faculty of Sciences, University of Kinshasa, B.P. 202, Kinshasa XI, 
Democratic Republic of the Congo.
(5)Swiss Tropical and Public Health Institute, Socinstrasse 57, CH-4002, Basel, 
Switzerland.
(6)University of Basel, Petersplatz 1, CH-4003, Basel, Switzerland.
(7)Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074, 
Würzburg, Germany. bringman@chemie.uni-wuerzburg.de.

A series of seven unusual dimeric naphthylisoquinoline alkaloids was isolated 
from the leaves of the tropical liana Ancistrocladus ealaensis J. Léonard, named 
cyclombandakamine A (1), 1-epi-cyclombandakamine A (2), and cyclombandakamines 
A3-7 (3-7). These alkaloids have a chemically thrilling structural array 
consisting of a twisted dihydrofuran-cyclohexenone-isochromene system. The 
1'″-epimer of 4, cyclombandakamine A1 (8), had previously been discovered in an 
unidentified Ancistrocladus species related to A. ealaensis. Both lianas produce 
the potential parent precursor, mbandakamine A (9), but only A. ealaensis 
synthesizes the corresponding cyclized form, along with a broad series of 
slightly modified analogs. The challenging isolation required, besides 
multi-dimensional chromatography, the use of a pentafluorophenyl stationary 
phase. Featuring up to six stereocenters and two types of chiral axes, their 
structures were elucidated by means of 1D and 2D NMR, HRESIMS, in combination 
with oxidative chemical degradation experiments as well as chiroptical 
(electronic circular dichroism spectroscopy) and quantum chemical calculations. 
Compared to the 'open-chain' parent compound 9, these dimers displayed rather 
moderate antiplasmodial activities.

DOI: 10.1038/s41598-019-46336-z
PMCID: PMC6614417
PMID: 31285489 [Indexed for MEDLINE]

Conflict of interest statement: The authors declare no competing interests.


4. Yakugaku Zasshi. 2011;131(7):1141-7. doi: 10.1248/yakushi.131.1141.

[Isomeric analysis of synthetic cannabinoids detected as designer drugs].

[Article in Japanese]

Uchiyama N(1), Kikura-Hanajiri R, Shoda T, Fukuhara K, Goda Y.

Author information:
(1)National Institute of Health Sciences, Tokyo, Japan.

Recently, many psychotropic herbal products, named such as "Spice", were 
distributed worldwide via the Internet. In our previous study, several synthetic 
cannabinoids were identified as adulterants in herbal products being available 
in Japan due to their expected narcotic effects. Among those, two derivatives of 
Δ(9)-tetrahydrocannabinol (Δ(9)-THC), which is major psychotropic cannabinoid of 
marijuana, cannabicyclohexanol (CCH, 
3-[2-hydroxy-4-(2-methylnonan-2-yl)phenyl]cyclohexan-1-ol) and CP-47,497 
(3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-ol), have been 
controlled as designated substances (Shitei-Yakubutsu) under the Pharmaceutical 
Affairs Law since November 2009. CCH was detected together with its trans-form 
(1-epimer) in many herbal products, and CCH and CP-47,497 have two chiral 
centers in the structures. However, the pharmaceutical activities of the isomers 
of CCH have not been reported. This study presents chiral separations of CCH, 
its trans-form and CP-47,497 in the products using LC-circular dichroism (CD) 
and LC-MS analyses. The enantiomeric pairs of CCH, its trans-form and CP-47,497 
were separated, respectively. Subsequently, the analyses of the herbal products 
showed that CCH and its trans-form existed as mixtures of enantiomers and the 
relative ratios of CCH and the trans-form enantiomers ranged from 42/58% to 
53/47% and from 33/67% to 52/48%, respectively.

DOI: 10.1248/yakushi.131.1141
PMID: 21720146 [Indexed for MEDLINE]


5. Org Lett. 2009 Jun 18;11(12):2583-6. doi: 10.1021/ol9008987.

Efficient synthesis of (+)-MK7607 and its C-1 epimer via the stereoselective 
transposition of a tertiary allylic alcohol.

Lim C(1), Baek DJ, Kim D, Youn SW, Kim S.

Author information:
(1)College of Pharmacy, Seoul National University, Seoul 151-742, Korea.

These studies provide an efficient and stereoselective synthetic route to 
(+)-MK7607 and its C-1 epimer from a common intermediate in high overall yields. 
The synthetic methodologies mainly rely on the stereospecific 1,3-allylic 
transposition of the hindered tertiary alcohol group through a 
palladium-catalyzed allylic rearrangement as well as a PBr(3)-mediated 
allylic-transposed bromination.

DOI: 10.1021/ol9008987
PMID: 19514793 [Indexed for MEDLINE]