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Phytochemistry ; 138: 170-177, 2017 Jun.
Article in English | MEDLINE | ID: mdl-28284566

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.


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