Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Molecules. 2021 Sep 26;26(19):5827. doi: 10.3390/molecules26195827.

Isolation, Characterization, Complete Structural Assignment, and Anticancer 
Activities of the Methoxylated Flavonoids from Rhamnus disperma Roots.

Mohammed HA(1)(2), Abd El-Wahab MF(2), Shaheen U(2), Mohammed AEI(2), Abdalla 
AN(3)(4), Ragab EA(2).

Author information:
(1)Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, 
Qassim University, Buraydah 51452, Saudi Arabia.
(2)Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo 
11371, Egypt.
(3)Department of Pharmacology and Toxicology, Faculty of Pharmacy, Umm Al-Qura 
University, Makkah 21955, Saudi Arabia.
(4)Department of Pharmacology and Toxicology, National Center for Research, 
Khartoum 2404, Sudan.

Different chromatographic methods including reversed-phase HPLC led to the 
isolation and purification of three O-methylated flavonoids; 
5,4'-dihydroxy-3,6,7-tri-O-methyl flavone (penduletin) (1), 
5,3'-dihydroxy-3,6,7,4',5'-penta-O-methyl flavone (2), and 
5-hydroxy-3,6,7,3',4',5'-hexa-O-methyl flavone (3) from Rhamnus disperma roots. 
Additionlly, four flavonoid glycosides; kampferol 7-O-α-L-rhamnopyranoside (4), 
isorhamnetin-3-O-β-D-glucopyranoside (5), quercetin 7-O-α-L-rhamnopyranoside 
(6), and kampferol 3, 7-di-O-α-L-rhamnopyranoside (7) along with 
benzyl-O-β-D-glucopyranoside (8) were successfully isolated. Complete structure 
characterization of these compounds was assigned based on NMR spectroscopic 
data, MS analyses, and comparison with the literature. The O-methyl protons and 
carbons of the three O-methylated flavonoids (1-3) were unambiguously assigned 
based on 2D NMR data. The occurrence of compounds 1, 4, 5, and 8 in Rhamnus 
disperma is was reported here for the first time. Compound 3 was acetylated at 
5-OH position to give 5-O-acetyl-3,6,7,3',4',5'-hexa-O-methyl flavone (9). 
Compound 1 exhibited the highest cytotoxic activity against MCF 7, A2780, and 
HT29 cancer cell lines with IC50 values at 2.17 µM, 0.53 µM, and 2.16 µM, 
respectively, and was 2-9 folds more selective against tested cancer cell lines 
compared to the normal human fetal lung fibroblasts (MRC5). It also doubled MCF 
7 apoptotic populations and caused G1 cell cycle arrest. The acetylated compound 
9 exhibited cytotoxic activity against MCF 7 and HT29 cancer cell lines with 
IC50 values at 2.19 µM and 3.18 µM, respectively, and was 6-8 folds more 
cytotoxic to tested cancer cell lines compared to the MRC5 cells.

DOI: 10.3390/molecules26195827
PMCID: PMC8510169
PMID: 34641372 [Indexed for MEDLINE]

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


2. Plants (Basel). 2021 Jun 16;10(6):1224. doi: 10.3390/plants10061224.

Study of the Biologically Active Properties of Medicinal Plant Cotinus 
coggygria.

Sukhikh S(1)(2), Noskova S(1), Pungin A(1), Ivanova S(3)(4), Skrypnik L(1), 
Chupakhin E(1), Babich O(1).

Author information:
(1)Institute of Living Systems, Immanuel Kant Baltic Federal University, A. 
Nevskogo Street 14, 236016 Kaliningrad, Russia.
(2)Department of Bionanotechnology, Kemerovo State University, Krasnaya Street 
6, 650043 Kemerovo, Russia.
(3)Natural Nutraceutical Biotesting Laboratory, Kemerovo State University, 
Krasnaya Street 6, 650043 Kemerovo, Russia.
(4)Department of General Mathematics and Informatics, Kemerovo State University, 
Krasnaya Street, 6, 650043 Kemerovo, Russia.

The results of the studies have shown that to obtain an extract of a complex of 
biologically active substances of Cotinus coggygria, ethyl alcohol (mass 
fraction of alcohol 70%) with a hydromodule of 1:5 should be used, and the 
extraction should be carried out for 60 min at a temperature of 60 °C. The 
investigated plant extracts with the complex of bioactive substances from the 
Cotinus coggygria leaves and flowers are safe from the point of view of the 
content of heavy metals, pesticides, aflatoxin B1, radionuclides, as well as 
pathogenic and opportunistic microorganisms. It has been established that the 
Cotinus coggygria extract contains rutin, hyperoside, ferulic acid, quercetin, 
kaempferol, disulphuretin, sulphurein, sulphurein, gallic acid, methyl gallate, 
pentagalloyl glucose, 3,3',4',5,6,7-hexahydroxyflavonone, 
3,3',4',5,5',7-hexahydroxyflavonone, 3-O-α-L-rhamnofuranoside, 
3,3',4',5,5',7-hexahydroxyflavulium(1+), 7-O-β-D glucopyranoside, and 
3,3',4',7-tetrahydroxyflavonone. The tested extracts have anticancer, 
antigenotoxic, and antimicrobial (against E. coli, S. aureus, P. vulgaris, C. 
albicans, L. mesenteroides) properties. The high antioxidant status of the 
tested extracts was established; the antioxidant activity of the samples was 
145.09 mg AA/g (AA-ascorbic acid).

DOI: 10.3390/plants10061224
PMCID: PMC8235186
PMID: 34208532

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


3. Planta Med. 2021 Oct;87(12-13):989-997. doi: 10.1055/a-1270-7761. Epub 2020
Nov  6.

Studies on Bignoniaceae: Newbouldiosides D - F, Minor Phenylethanoid Glycosides 
from Newbouldia laevis, and New Flavonoids from Markhamia zanzibarica and 
Spathodea campanulata.

Kolodziej H(1).

Author information:
(1)Freie Universität Berlin, Institute of Pharmacy, Pharmaceutical Biology, 
Berlin, Germany.

Continued examination of the stem bark of Newbouldia laevis afforded three minor 
phenylethanoid glycosides, designated as newbouldiosides D - F. Their structures 
were elucidated by spectroscopic methods as β-(3,4-dihydroxyphenyl)ethyl 
5-O-syringoyl-β-D-apiofuranosyloxy-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, 
β-(3,4-dihydroxyphenyl)ethyl 
β-D-apiofuranosyloxy-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, 
and β-(3,4-dihydroxyphenyl)ethyl 
β-D-apiofuranosyloxy-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 2)-6-O-E-sinapoyl-β-D-glucopyranoside, 
respectively. These metabolites are the first members possessing a sinapoyl 
structural element. In addition, the series of naturally occurring flavonoids is 
extended by the identification of 3',4',5,7-tetrahydroxy-5'-methoxyflavanone and 
apigenin-5-O-α-L-rhamnopyranosyl-7-O-β-D-glucopyranoside obtained from leaf 
extracts of Markhamia zanzibarica and 
aromadendrin-7-O-(2″-O-formyl)-β-D-glucopyranoside isolated from Spathodea 
campanulata. The latter compound is the first example of a flavonoid possessing 
a formylated glucosyl moiety.

Thieme. All rights reserved.

DOI: 10.1055/a-1270-7761
PMID: 33157560 [Indexed for MEDLINE]

Conflict of interest statement: The authors declare that they have no conflict 
of interest.


4. Zhongguo Zhong Yao Za Zhi. 2018 Mar;43(5):959-963. doi: 
10.19540/j.cnki.cjcmm.20180104.016.

[Two new compounds from Smilax glaucochina].

[Article in Chinese]

Shu JC(1), Liu M(1), Zhu GH(1), Liu RH(1), Shao F(1), Huang HL(1).

Author information:
(1)Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China.

A new sesquiterpenes named glaucochinarol A (1) and a new phenylpropane 
glycoside named glcacochinaside A (2), together with six known ones, including 
trichothecolone (3), 
β-D-(6-O-trans-feruloyl)fructofuranosyl-α-D-O-glucopyranoisde (4), 
3,4,5-trimethoxyphenyl-β-D-glucopyranoside (5), 
(4R)-p-menth-1-ene-7,8-diol-7-O-β-D-glucopyranoside (6), naringenin (7), and 
emodin-8-O-β-glucoside (8) were isolated from smilax glaucochina warb. Their 
structures were elucidated on the basis of NMR, MS and published data. Compounds 
3-8 were isolated from the species for this first time.

Copyright© by the Chinese Pharmaceutical Association.

DOI: 10.19540/j.cnki.cjcmm.20180104.016
PMID: 29676094 [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. J Food Drug Anal. 2017 Oct;25(4):992-999. doi: 10.1016/j.jfda.2016.10.006.
Epub  2016 Dec 1.

Analysis of bioactive constituents from the leaves of Amorpha fruticosa L.

Cui X(1), Guo J(1), Lai CS(2), Pan MH(2), Ma Z(1), Guo S(1), Liu Q(1), Zhang 
L(1), Ho CT(3), Bai N(1).

Author information:
(1)College of Chemical Engineering, Department of Pharmaceutical Engineering, 
Northwest University, Xi'an, Shaanxi, China.
(2)Institute of Food Science and Technology, National Taiwan University, Taipei, 
Taiwan.
(3)Department of Food Science, Rutgers University, New Brunswick, NJ, USA.

Amorpha fruticosa L. is a Chinese folk medicine and rich in polyphenols. Fifteen 
known compounds were isolated and identified from the leaves of A. fruticosa L. 
They are tephrosin (1), 6a,12a-dehydrodeguelin (2), vitexin (3), 
afrormosin-7-O-β-d-glucopyranoside (4), 2″-O-α-l-rhamnopyranosyl isovitexin (5), 
rutin (6), chrysoeriol (7), 7-O-methylluteolin (8), trans-p-coumaric acid (9), 
2-benzyl-4,6-dihydroxybenzoic acid-4-O-β-d-glucopyranoside (10), formononetin 
(11), quercetin (12), apigenin (13), β-sitosterol (14), and β-daucosterol (15). 
Compounds 3, 4, 5, and 7-9 were isolated from A. fruticosa L. for the first 
time. Cytotoxicity of individual compounds 3-10 and 90% ethanol extract against 
human cancer cell lines HCT116 and HepG2 were reported. The results suggested 
that compounds 7 and 8, and the crude extract exhibited inhibitory effects on 
human cancer cell line HCT116, at concentrations of 100 μg/mL, 5 μg/mL, and 
25 μg/mL at <60% of cell viability rate, respectively. In addition, a valid 
high-performance liquid chromatography diode array detector method was 
established to quantitatively analyze compounds 1-12 in the leaves of A. 
fruticosa L., which was harvested at three different stages of maturity from May 
20 to August 10, 2014. The results demonstrated that contents were greatly 
influenced by the maturity. Total amounts of the analytical constituents 
gradually increased from May 20 to August 10, with the values ranging from 
10.86 mg/g to 18.84 mg/g, whereas bioactive compounds 7 and 8 presented the 
opposite variation trend. The results of this study may provide data for further 
study and comprehensive utilization of A. fruticosa L.

Copyright © 2016. Published by Elsevier B.V.

DOI: 10.1016/j.jfda.2016.10.006
PMCID: PMC9328870
PMID: 28987377 [Indexed for MEDLINE]

Conflict of interest statement: Conflict of interest statement All contributing 
authors declare no conflicts of interest.