Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Nat Prod Res. 2024 Jul 4:1-10. doi: 10.1080/14786419.2024.2372664. Online
ahead  of print.

Maghamesin, a new prenylated flavanone from artocarpus heterophyllus lam. 
(moraceae).

Njindi Kouotou MJ(1), Nsangou MF(1), Kenmogne SB(1), Tcho AT(2), Peyeino JH(1), 
Sikam KG(1), Mandou Michiren VS(1), Happi EN(1), Songue JL(1), Toze FAA(1).

Author information:
(1)Chemistry Laboratory, Department of Chemistry, Faculty of Science, University 
of Douala, Douala, Cameroon.
(2)Department of Chemistry, Faculty of Sciences, University of Buea, Buea, 
Cameroon.

The chemical investigation of the methanol root extract of Artocarpus 
heterophyllus Lam. led to the isolation of a new prenylated flavanone, 
5,7,4'-trihydroxy-3'-(3-methylbuta-1,3-dienyl)-5'-(3-methylbut-2-enyl)flavanone, 
trivially named maghamesin (1), together with nine known compounds, 
5-hydroxy-3',4',5',7-tetramethoxy-8-prenylflavanone (2), cycloheterophyllin (3), 
cyclomorusin (4), isobavachalcone (5), trans-isoferulic acid (6), 
24-methylenecycloartan-3α-ol (7), stigmasterol (8), β-sitosterol (9) and 
β-sitosterol-3-O-β-D-glucopyranoside (10). The structures of the isolates were 
elucidated by extensive spectroscopic and spectrometric analyses (1D and 2D NMR, 
ESI-MS) and by comparison with previously reported data. The absolute 
configuration of 1 was deduced by comparison of its experimental CD with that of 
a reported similar compound. Compounds 1-3 and 6-7 were tested for their 
antibacterial and antifungal activities. Compound 1 displayed a significant 
antibacterial activity against Staphylococcus aureus with MIC value of 
15.625 μg/mL. The others tested compounds showed moderate antibacterial and 
antifungal activities against several microorganisms with MIC values of either 
31.25 or 62.5 μg/mL.

DOI: 10.1080/14786419.2024.2372664
PMID: 38962969


2. Nat Prod Res. 2024 Apr 13:1-8. doi: 10.1080/14786419.2024.2338805. Online
ahead  of print.

Chemical constituents of açai berry pulp (Euterpe oleracea Mart.) by 
LC-UV-BPSU/NMR and LC-UV-SPE/NMR.

Thomasi SS(1), de Benedicto DFC(1), da Conceição Alves T(2), Bellete BS(1), 
Venâncio T(2), de Andrade Mattietto R(3), Ferreira AG(2).

Author information:
(1)Chemistry Department, Federal University of Lavras, Lavras, Brazil.
(2)Chemistry Departament, Federal University of São Carlos, São Carlos, Brazil.
(3)Embrapa Amazônia Oriental, Belém, Brazil.

The techniques LC-UV-BPSU and LC-UV-SPE/NMR were applied for the first time in 
the analysis of açai berry (Euterpe oleracea Mart.) pulp extracts. Those 
techniques allowed the identification of twenty-three metabolites: Valine (1), 
citric acid (2), tachioside (3), isotachioside (4), α-guaiacylglycerol (5), 
syringylglycerol (6), uridine (7), adenosine (8), dimethoxy-1,4-benzoquinone 
(9), koaburaside (10), protocatechuic acid (11), eurycorymboside B (12), 
7',8'-dihydroxy-dihydrodehydroconiferyl alcohol-9-O-β-D-glucopyranoside (13), 
orientin (14), homoorientin (15), dihydrokaempferol-3-glucoside (16), 
isolariciresinol-9'-O-β-D-glucopyranoside (17), 
5'-methoxyisolariciresinol-9'-O-β-D-glucopyranoside (18), cyanidin-3-O-glucoside 
(19), cyandin-3-O-rutenoside (20), 9,12-octadecadienoic acid 
(Z,Z)-2-hydroxy-1-(hydroxymethyl) ethyl ester (21), linolenic acid (22), and 
1,2-di-O-α-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol (23). In this plant, 
compounds 3, 4, 5, 6, 8, 10, 12, 17, 18, 21, and 23 are reported for the first 
time. All the structures were determined through extensive analyses of 1D and 2D 
NMR data, mass spectrometry, and comparison with published data. This 
methodology has proven to be an efficient alternative to the analysis of complex 
extracts containing a large variety of compounds.

DOI: 10.1080/14786419.2024.2338805
PMID: 38613238


3. Chem Biodivers. 2024 Mar;21(3):e202400124. doi: 10.1002/cbdv.202400124. Epub 
2024 Feb 12.

Undescribed Triterpenes from the Leaves of Syzygium myrsinifolium with Their 
α-Glucosidase and α-Amylase Inhibition Activity.

Trang DT(1), Tai BH(1)(2), Hoang NH(1), Cuc NT(1), Bang NA(1), Dung DT(1), Yen 
DTH(1), Huong PTT(1), Dung NV(1), Hang DTT(1), Yen PH(1), Kiem PV(1)(2).

Author information:
(1)Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Cau Giay, Hanoi, 
10072, Vietnam.
(2)Graduate University of Science and Technology, VAST, 18 Hoang Quoc Viet, Cau 
Giay, Hanoi, 10072, Vietnam.

Two undescribed triterpenes, syzyfolium A (1) and syzyfolium B (2), together 
with twelve known compounds, terminolic acid (3), actinidic acid (4), piscidinol 
A (5), threo-dihydroxydehydrodiconiferyl alcohol (6), 
lariciresinol-4-O-β-D-glucoside (7), icariol A2 (8), 
14β,15β-dihydroxyklaineanone (9), garcimangosone D (10), (+)-catechin (11), 
myricetin-3-O-α-L-rhamnopyranoside (12), quercitrin (13), and 3, 4, 
5-trimethoxyphenyl-(6'-O-galloyl)-O-β-D-glucopyranoside (14) were isolated from 
the leaves of Syzygium myrsinifolium. Their chemical structures were determined 
by IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 3 and 4 inhibited 
significantly α-glucosidase with IC50 values of 23.99 and 36.84, respectively, 
and compounds 1 and 2 inhibited significantly α-amylase with IC50 values of 
35.48 and 43.65 μM, respectively.

© 2024 Wiley-VHCA AG, Zurich, Switzerland.

DOI: 10.1002/cbdv.202400124
PMID: 38279623 [Indexed for MEDLINE]


4. Phytochemistry. 2023 Nov;215:113853. doi: 10.1016/j.phytochem.2023.113853.
Epub  2023 Sep 7.

Cytotoxic triterpenoid saponins from the root of Olax subscorpioidea Oliv. 
(Olacaceae).

Adekunle YA(1), Samuel BB(2), Nahar L(3), Fatokun AA(4), Sarker SD(4).

Author information:
(1)Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of 
Ibadan, Nigeria; Centre for Natural Products Discovery, School of Pharmacy and 
Biomolecular Sciences, Faculty of Science, Liverpool John Moores University, 
Byrom Street, L3 3AF, Liverpool, United Kingdom; Department of Pharmaceutical 
and Medicinal Chemistry, College of Pharmacy, Afe Babalola University, 
Ado-Ekiti, Nigeria. Electronic address: yemiadekunle03@yahoo.com.
(2)Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of 
Ibadan, Nigeria. Electronic address: tundebsamuel@gmail.com.
(3)Laboratory of Growth Regulators, Palacký University and Institute of 
Experimental Botany, The Czech Academy of Sciences, Šlechtitelů 27, 78371, 
Olomouc, Czech Republic. Electronic address: nahar@ueb.cas.cz.
(4)Centre for Natural Products Discovery, School of Pharmacy and Biomolecular 
Sciences, Faculty of Science, Liverpool John Moores University, Byrom Street, L3 
3AF, Liverpool, United Kingdom.

Bioactivity-guided phytochemical fractionation of the methanol extract of Olax 
subscorpioidea root has led to the isolation of six triterpenes. Three of these 
compounds are previously undescribed triterpenoid saponins: oleanolic acid 
3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranosyl-(1 → 2)-6-O-methyl-β-D-glucuronopyranoside]-28-O-β-D-glucopyranosyl 
ester (2), oleanolic acid 
3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranoside] 
(3), and oleanolic acid 
3-O-[β-D-glucopyranosyl-(1 → 4)-6-O-methyl-β-D-glucuronopyranoside] ester (5). 
Other reported known compounds include two triterpene glycosides: oleanolic acid 
3-O-[β-D-glucopyranosyl-(1 → 4)-6-O-methyl-β-D-glucuronopyranoside]-28-O-β-D-glucopyranosyl 
ester (1) and oleanolic acid 
3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucuronopyranoside] (4); and a triterpene 
acid, oleanolic acid (6). The structures of these compounds were elucidated by 
spectroscopic means. The isolated compounds were tested against human cervical 
cancer (HeLa), colorectal cancer (Caco-2) and breast cancer (MCF-7) cell lines 
using the in vitro 3-[4,5-dimethylthiazole-2-yl] 3,5-diphenyltetrazolium bromide 
(MTT) assay, with vincristine as positive control. The cytotoxicity assay showed 
that compounds 3 and 5 exhibited significant inhibitory effects on the HeLa cell 
line, with IC50 values of 7.42 ± 0.34 μM and 10.27 ± 1.26 μM; and moderate 
effects on MCF-7 (IC50 values, 36.67 ± 1.23 μM and 43.83 ± 0.65 μM) and Caco-2 
(IC50 values, 35.83 ± 0.55 μM and 39.03 ± 4.38 μM, respectively) cell lines. 
They were also more selectively cytotoxic than vincristine against the cancer 
cell lines, when compared with cytotoxicity against the normal lung cell line 
MRC5.

Copyright © 2023 The Authors. Published by Elsevier Ltd.. All rights reserved.

DOI: 10.1016/j.phytochem.2023.113853
PMID: 37689382 [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.


5. J Pharm Pharmacol. 2023 Apr 17;75(5):693-702. doi: 10.1093/jpp/rgad021.

Piceatannol-3'-O-β-d-glucopyranoside alleviates nephropathy via regulation of 
High mobility group B-1 (HMGB1)/Toll-like receptor 4 (TLR4)/Nuclear factor kappa 
B (NF-κB) signalling pathway.

Du SH(1), Yang MY(1), Gan HL(1), Song ZY(1), Wang MY(1), Li ZY(1), Liu K(2), Qi 
D(3), Fan HY(1).

Author information:
(1)School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug 
Evaluation (Yantai University), Ministry of Education, Collaborative Innovation 
Center of Advanced Drug Delivery System and Biotech Drugs in Universities of 
Shandong, Yantai University, Yantai, PR China.
(2)Shandong Boyuan Biomedical Co., Ltd., Yantai, PR China.
(3)Department of Nephrology, Yu-Huang-Ding Hospital/Qingdao University, Yantai, 
Shandong, PR China.

OBJECTIVES: Nephrotic syndrome (NS) remains a therapeutic challenge for 
nephrologists. Piceatannol-3'-O-β-d-glucopyranoside (PG) is a major active 
ingredient in Quzha. The purpose of the study was to assess the renoprotection 
of PG.
METHODS: In vitro, the podocyte protection of PG was assessed in MPC-5. SD rats 
were injected with adriamycin to induce nephropathy in vivo. The determination 
of biochemical changes and inflammatory cytokines was performed, and 
pathological changes were examined by histopathological examination. 
Immunostaining and western blot analyses were used to analyse expression levels 
of proteins.
KEY FINDINGS: The results showed that PG improved adriamycin-induced podocyte 
injury, attenuated nephropathy, improved hypoalbuminemia and hyperlipidaemia, 
and lowered cytokine levels. The podocyte protection of PG was further verified 
by reduction of desmin and increasing synaptopodin expression. Furthermore, 
treatment with PG down-regulated the expression of HMGB1, TLR4 and NF-κB along 
with its upstream regulator, IKKβ and yet up-regulated IκBα expression by 
western blot analysis.
CONCLUSIONS: Overall, our data showed that PG has a favourable renoprotection in 
experimental nephrosis, apparently by amelioration of podocyte injury. PG might 
mediate these effects via modulation of the HMGB1/TLR4/NF-κB signalling pathway. 
The study first provides a promising leading compound for the treatment of NS.

© The Author(s) 2023. Published by Oxford University Press on behalf of the 
Royal Pharmaceutical Society. All rights reserved. For permissions, please 
e-mail: journals.permissions@oup.com.

DOI: 10.1093/jpp/rgad021
PMID: 36964741 [Indexed for MEDLINE]