Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Biochem Biophys Res Commun. 2023 Sep 3;671:80-86. doi: 
10.1016/j.bbrc.2023.05.128. Epub 2023 Jun 2.

Enzymatic biosynthesis of novel 2-(2-phenylethyl)chromone glycosides catalyzed 
by UDP-glycosyltransferase UGT71BD1.

Wang Y(1), Huang W(1), Tian W(1), Mo T(2), Yan Y(3), Cui X(1), Liu X(4).

Author information:
(1)Modern Research Center for Traditional Chinese Medicine, School of Chinese 
Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029, China.
(2)Ningxia Hui Medicine Research Institute, Yinchuan, 750021, People's Republic 
of China.
(3)Shanxi University of Chinese Medicine, Jinzhong, 030619, China.
(4)Modern Research Center for Traditional Chinese Medicine, School of Chinese 
Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029, China. 
Electronic address: liuxiao@bucm.edu.cn.

2-(2-Phenylethyl)chromones (PECs) are the main bioactive components of agarwood 
which showed diverse pharmaceutical activities. Glycosylation is a useful 
structural modification method to improve compounds' druggability. However, PEC 
glycosides were rarely reported in nature which largely limited their further 
medicinal investigations and applications. In this study, the enzymatic 
glycosylation of four naturally separated PECs 1-4 was achieved using a 
promiscuous glycosyltransferase UGT71BD1 identified from Cistanche tubulosa. It 
could accept UDP-Glucose, UDP-N-acetylglucosamine and UDP-xylose as sugar donors 
and conduct the corresponding O-glycosylation of 1-4 with high conversion 
efficiencies. Three O-glucosylated products 1a 
(5-hydroxy-2-(2-phenylethyl)chromone 8-O-β-D-glucopyranoside), 2a 
(8-chloro-2-(2-phenylethyl)chromone 6-O-β-D-glucopyranoside) and 3a 
(2-(2-phenylethyl)chromone 6-O-β-D-glucopyranoside) were prepared and 
structurally elucidated as novel PEC glucosides based on NMR spectroscopic 
analyses. Subsequent pharmaceutical evaluation found that 1a showed remarkably 
improved cytotoxicity against HL-60 cells, whose cell inhibition rate was 19 
times higher than that of its aglycon 1. The IC50 value of 1a was further 
determined to be 13.96 ± 1.10 μM, implying its potential as a promising 
antitumor-leading candidate. To improve the production of 1, docking, simulation 
and site-directed mutagenesis were performed. The important role of P15 in the 
glucosylation of PECs was discovered. Besides, a mutant K288A with a two-fold 
increased yield for 1a production was also afforded. This research reported the 
enzymatic glycosylation of PECs for the first time, and also provide an 
eco-friendly pathway for the alternative production of PEC glycosides for 
leading compounds discovery.

Copyright © 2023 Elsevier Inc. All rights reserved.

DOI: 10.1016/j.bbrc.2023.05.128
PMID: 37300944 [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. Phytochemistry. 2023 Jul;211:113712. doi: 10.1016/j.phytochem.2023.113712.
Epub  2023 May 7.

Seven undescribed compounds from the flower heads of Helianthus annuus L.

Bai J(1), Piao X(2), Wang Y(1), Cheng X(1), Feng M(2), Wang Y(1), Fu R(1), Zhao 
J(1), Yu S(1), Li Z(1), Wang L(3), Huang J(4), Wang J(5).

Author information:
(1)Department of Medicinal Chemistry and Natural Medicine Chemistry, College of 
Pharmacy, Harbin Medical University, Baojian Road 157, Nangang District, Harbin, 
150081, PR China.
(2)Department of Pharmacology (State-Province Key Laboratories of 
Biomedicine-Pharmaceutics of China, Key Laboratory of Cardiovascular Medicine 
Research, Ministry of Education), College of Pharmacy, Harbin Medical 
University, Harbin, 150081, PR China.
(3)Department of Medicinal Chemistry and Natural Medicine Chemistry, College of 
Pharmacy, Harbin Medical University, Baojian Road 157, Nangang District, Harbin, 
150081, PR China. Electronic address: wanglibo66@sina.com.
(4)Department of Medicinal Chemistry and Natural Medicine Chemistry, College of 
Pharmacy, Harbin Medical University, Baojian Road 157, Nangang District, Harbin, 
150081, PR China. Electronic address: 13504051049@163.com.
(5)Department of Medicinal Chemistry and Natural Medicine Chemistry, College of 
Pharmacy, Harbin Medical University, Baojian Road 157, Nangang District, Harbin, 
150081, PR China. Electronic address: 15999290001@163.com.

Seven undescribed compounds, namely, 
4-hydroxy-3-(2'-hydroxy-3'-methyl-1'-butenyl) 
acetophenone-1'-O-β-D-glucopyranoside (1), 
4-hydroxy-3-((Z)-3'-hydroxy-3'-methyl-1'-butenyl) 
acetophenone-8-O-β-D-glucopyranoside (2), 
4,6-hydroxy-3-((Z)-3'-hydroxy-3'-methyl-1'-butenyl) 
acetophenone-8-O-β-D-glucopyranoside (3), 
4-hydroxy-3-((Z)-3'-hydroxy-3'-methyl-1'-butenyl) 
acetophenone-6-O-β-D-glucopyranoside (4), 
2-hydroxymethylimino-3,4-dimethyl-7-hydroxy-6-methyl ketone-2H-chromon (5), 
annuolide A-15-O-β-D-glucopyranoside (6) and heliannuoside A (7), together with 
eighteen known compounds, were obtained from water extract of the flower heads 
of Helianthus annuus L. (Asteraceae). The structures of these compounds were 
elucidated based on spectroscopic analyses. Upon evaluation of the 
anti-inflammatory activity of compounds 1-9, 15-18, 21 and 24-25 by their 
effects on the release of NO in MH-S cells, compound 6 showed significant 
inhibition of NO secretion at 12.5 μM (P < 0.05) and 25 μM (P < 0.01) in a 
dose-dependent manner, and compound 18 showed inhibition of NO secretion at 
25 μM (P < 0.05).

Copyright © 2023. Published by Elsevier Ltd.

DOI: 10.1016/j.phytochem.2023.113712
PMID: 37160194 [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.


3. J Nat Prod. 2022 Dec 23;85(12):2706-2713. doi: 10.1021/acs.jnatprod.2c00406. 
Epub 2022 Dec 13.

Isolation and Structure Elucidation of Compounds from Sesamum alatum and Their 
Antiproliferative Activity against Multiple Myeloma Cells.

Saraux N(1)(2), Cretton S(1)(2), Kilicaslan OS(1)(2), Occioni C(1)(2), Ferro 
A(1)(2), Quirós-Guerrero L(1)(2), Karimou S(3), Christen P(1)(2), Cuendet 
M(1)(2).

Author information:
(1)School of Pharmaceutical Sciences, University of Geneva, 1211 Geneva 4, 
Switzerland.
(2)Institute of Pharmaceutical Sciences of Western Switzerland, University of 
Geneva, 1211 Geneva 4, Switzerland.
(3)Plantasav, B.P. 10308 Niamey, Niger.

The phytochemical investigation of the dichloromethane root extract of Sesamum 
alatum led to the isolation of 18 compounds. Among these, compounds 3-8, defined 
as 9-hydroxy-2,2-dimethyl-2H-benzo[g]chromene-5,10-dione 6-O-β-d-glucopyranoside 
(3), 
(2S,3R)-3,4,7-trihydroxy-2-(3'-methylbut-2'-en-1'-yl)-2,3-dihydro-1H-inden-1-one 
(4), 
(Z)-2-(1',4'-dihydroxy-4'-methylpent-2'-en-1'-ylidene)-4,7-dihydroxy-1H-indene-1,3(2H)-dione 
(5), 
(S)-2,5,8-trihydroxy-3-(2'-hydroxy-3'-methylbut-3'-en-1'-yl)naphthalene-1,4-dione 
(6), 6-hydroxy-3-(3'-methylbut-2'-en-1'-yl)-4-oxo-4H-chromene-5-carboxylic acid 
(7), and (S)-2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)anthracene-9,10-dione (8), 
respectively, have not yet been described. Their structures were elucidated 
based on spectroscopic data analysis, including IR, NMR, HRESIMS and ECD 
measurements. Additional known compounds, namely, hydroxysesamone (1), 
anthrasesamone A (2), 2,6-dimethoxy-1,4-benzoquinone (9), syringic acid (10), 
syringaresinol (11), 2,3-epoxysesamone 8-O-β-d-glucopyranoside (12), 
2,3-diacetylmartinoside (13), 2,3-epoxy-4,5,8-trihydroxy-2-prenyl-1-tetralone 
(14), ursolic acid (15), chlorosesamone (16), 2,3-epoxysesamone (17), and 
2-(4-methyl-3-pentenyl)anthraquinone (18) were isolated. The antiproliferative 
activity of the compounds was tested against the RPMI 8226 multiple myeloma cell 
line. When compounds presented an IC50 value <10 μM, they were tested against 
two other multiple myeloma cell lines, MM.1S and MM.1R. Compound 17 was found to 
be the most potent, with IC50 values of 0.6, 0.7, and 0.9 μM, respectively, for 
the three cell lines.

DOI: 10.1021/acs.jnatprod.2c00406
PMID: 36512676 [Indexed for MEDLINE]


4. Plants (Basel). 2020 Dec 21;9(12):1811. doi: 10.3390/plants9121811.

New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis.

Kim JY(1), Seo YH(2), Lee IH(1), Choi HY(1), Kwon HC(3), Choi JH(1), Lee J(2), 
Jang DS(1).

Author information:
(1)Department of Life and Nanopharmaceutical Sciences, Graduate School, Kyung 
Hee University, Seoul 02447, Korea.
(2)Herbal Medicine Resources Research Center, Korea Institute of Oriental 
Medicine (KIOM), Naju 58245, Korea.
(3)Natural Product Informatics Research Center, Korea Institute of Science and 
Technology (KIST) Gangneung Institute, Gangneung 25451, Korea.

Four new eudesmane-type sesquiterpenoids, 
(1R,5S,6R,7S,9S,10S)-1,6,9-trihydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside 
(1), 
(1R,5S,6S,7R,9S,10S)-1,6,9,11-tetrahydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside 
(3), 
(1R,5S,6R,7S,9S,10R)-9-O-(Z-p-coumaroyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside 
(6), and 
(1R,5S,6R,7S,9S,10R)-9-O-(E-feruloyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside 
(7), were isolated from a 95% EtOH extract of the leaves of Aster koraiensis by 
repeated chromatography. Moreover, three sesquiterpenoids (2, 4, and 5) and two 
caffeoylquinic acids (8 and 9) having previously known chemical structures were 
isolated during the isolation procedure. The four new compounds (1, 3, 6, and 7) 
were elucidated by spectroscopic data (1D- and 2D-NMR, MS, and ECD) 
interpretation and hydrolysis. Moreover, the absolute configurations of 2, 4, 
and 5 were determined for the first time in this study. The compounds isolated 
were tested for their viability on nitric oxide (NO) and prostaglandin E2 (PGE2) 
production on LPS-stimulated RAW 264.7 cells. Among them, only 7 presented weak 
inhibitory effects on both NO and PGE2 production.

DOI: 10.3390/plants9121811
PMCID: PMC7766762
PMID: 33371294

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


5. ACS Omega. 2019 Jul 3;4(7):11621-11630. doi: 10.1021/acsomega.9b01433. 
eCollection 2019 Jul 31.

Rubrofusarin as a Dual Protein Tyrosine Phosphate 1B and Human Monoamine 
Oxidase-A Inhibitor: An in Vitro and in Silico Study.

Paudel P(1), Seong SH(1), Jung HA(2), Choi JS(1).

Author information:
(1)Department of Food and Life Science, Pukyong National University, Busan 
48513, Republic of Korea.
(2)Department of Food Science and Human Nutrition, Chonbuk National University, 
Jeonju 54896, Republic of Korea.

A number of nature-derived biologically active compounds comprise glycosides. In 
some cases, the glycosidic residue is needed for bioactivity; however, in other 
cases, glycosylation just improves some pharmacokinetic/dynamic parameters. The 
patterns of protein tyrosine phosphatase 1B (PTP1B) and human monoamine oxidase 
A (hMAO-A) inhibition by rubrofusarin 6-O-β-d-glucopyranoside (1), rubrofusarin 
6-O-β-d-gentiobioside (2), rubrofusarin triglucoside (3), and cassiaside B2 (4) 
were compared with the aglycone, rubrofusarin, isolated from Cassia obtusifolia 
seeds. Rubrofusarin showed potent inhibition against the PTP1B enzyme (IC50; 
16.95 ± 0.49 μM), and its glycosides reduced activity (IC50; 87.36 ± 1.08 μM for 
1 and >100 μM for 2-4) than did the reference drug, ursolic acid (IC50; 2.29 ± 
0.04 μM). Similarly, in hMAO-A inhibition, rubrofusarin displayed the most 
potent activity with an IC50 value of 5.90 ± 0.99 μM, which was twice better 
than the reference drug, deprenyl HCl (IC50; 10.23 ± 0.82 μM). An enzyme kinetic 
and molecular docking study revealed rubrofusarin to be a mixed-competitive 
inhibitor of both these enzymes. In a western blot analysis, rubrofusarin 
increased glucose uptake significantly and decreased the PTP1B expression in a 
dose-dependent manner in insulin-resistant HepG2 cells, increased the expression 
of phosphorylated protein kinase B (p-Akt) and phosphorylated insulin receptor 
substrate-1 (p-IRS1) (Tyr 895), and decreased the expression of 
glucose-6-phosphatase (G6Pase) and phosphoenol pyruvate carboxykinase (PEPCK), 
key enzymes of gluconeogenesis. Our overall results show that glycosylation 
retards activity; however, it reduces toxicity. Thus, Cassia seed as functional 
food and rubrofusarin as a base can be used for the development of therapeutic 
agents against comorbid diabetes and depression.

DOI: 10.1021/acsomega.9b01433
PMCID: PMC6682096
PMID: 31460269

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