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.
Ruijie He  1 ,  Yanjun Zhang  2 ,  Liangdeng Wu  2 ,  Hui Nie  2 ,  Yan Huang  3 ,  Buming Liu  3 ,  Shengping Deng  2 ,  Ruiyun Yang  2 ,  Shuai Huang  2 ,  Zhijie Nong  2 ,  Jun Li  4 ,  Haiyan Chen  5
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.
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