Benzofuran glycosides and coumarins from the bark of Streblus indicus (Bur.) Corner

Ruijie He; Yanjun Zhang; Liangdeng Wu; Hui Nie; Yan Huang; Buming Liu; Shengping Deng; Ruiyun Yang; Shuai Huang; Zhijie Nong; Jun Li; Haiyan Chen

doi:10.1016/j.phytochem.2017.01.011

Benzofuran glycosides and coumarins from the bark of Streblus indicus (Bur.) Corner

Phytochemistry. 2017 Jun:138:170-177. doi: 10.1016/j.phytochem.2017.01.011. Epub 2017 Mar 9.

Authors

Ruijie He¹, Yanjun Zhang², Liangdeng Wu², Hui Nie², Yan Huang³, Buming Liu³, Shengping Deng², Ruiyun Yang², Shuai Huang², Zhijie Nong², Jun Li⁴, Haiyan Chen⁵

Affiliations

¹ State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmacy of Guangxi Normal University, Guilin, 541004, PR China; Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guilin, 541006, PR China.
² State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmacy of Guangxi Normal University, Guilin, 541004, PR China.
³ Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, Nanning, 530022, PR China.
⁴ State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmacy of Guangxi Normal University, Guilin, 541004, PR China. Electronic address: [email protected].
⁵ Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, 530004, PR China. Electronic address: [email protected].

PMID: 28284566
DOI: 10.1016/j.phytochem.2017.01.011

Abstract

Two pairs of rare benzofuran glucoside epimers, indicuses A and B and indicuses C and D, three biogenetically related compounds indicuses E-G, and one coumarin indicus H, as well as 11 known compounds, were isolated from the bark of Streblus indicus (Bur.) Corner. The structures of indicuses A-H were elucidated by NMR and MS data, as well as by CD. (S)-Marmesinin exhibited moderate antimicrobial activity in vitro against Bacillus subtilis and Saccharomyces cerevisiae. 7,8-Dihydroxy-3-(3-methyl-2-butenyl) coumarin, umbelliferone, and scopoletin displayed strong cytotoxic activity in vitro against human bladder carcinoma cell line EJ. The structure-activity relationships indicate that hydroxylation at C-7 in the cytotoxic compounds is crucial to their activities.

Keywords: Benzofuran glycoside; Coumarin; Cytotoxicity; Moraccae; Streblus indicus (Bur.) Corner; Streblus lour.

MeSH terms

Anti-Infective Agents / chemistry
Anti-Infective Agents / isolation & purification
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Bacillus subtilis / drug effects
Benzofurans / chemistry*
Benzofurans / isolation & purification
Cell Line, Tumor
Coumarins / chemistry*
Coumarins / isolation & purification
Furans / chemistry
Furans / isolation & purification
Glycosides / chemistry*
Glycosides / isolation & purification
Humans
Microbial Sensitivity Tests
Molecular Structure
Moraceae / chemistry*
Plant Bark / chemistry
Plant Extracts / chemistry
Saccharomyces cerevisiae / drug effects
Scopoletin / chemistry
Scopoletin / isolation & purification
Structure-Activity Relationship
Umbelliferones / chemistry
Umbelliferones / isolation & purification

Substances

Anti-Infective Agents
Antineoplastic Agents, Phytogenic
Benzofurans
Coumarins
Furans
Glycosides
Plant Extracts
Umbelliferones
marmesinin
7-hydroxycoumarin
Scopoletin