Spiroindimicins A–D: New Bisindole Alkaloids from a Deep-Sea-Derived Actinomycete

• Published in: Organic letters Vol. 14; no. 13; pp. 3364 - 3367
• Main Authors: Zhang, Wenjun, Liu, Zhong, Li, Sumei, Yang, Tingting, Zhang, Qingbo, Ma, Liang, Tian, Xinpeng, Zhang, Haibo, Huang, Caiguo, Zhang, Si, Ju, Jianhua, Shen, Yuemao, Zhang, Changsheng
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.07.2012; Amer Chemical Soc
• Subjects: Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Cell Line, Tumor; Cell Proliferation - drug effects; Chemistry; Chemistry, Organic; Crystallography, X-Ray; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Indole Alkaloids - chemistry; Indole Alkaloids - isolation & purification; Indole Alkaloids - pharmacology; Models, Molecular; Molecular Conformation; Molecular Sequence Data; Physical Sciences; Science & Technology; Stereoisomerism; Streptomyces - chemistry; Structure-Activity Relationship; ANTIBIOTICS; BIOSYNTHETIC GENE-CLUSTER; YEAST MALASSEZIA-FURFUR; MARINE ACTINOMYCETE; NATURAL-PRODUCTS; PITYRIARUBINS; INDOLOCARBAZOLE; INHIBITOR; DERIVATIVES; DISCOVERY
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol301343n

A PCR-based screening approach led to the identification of a deep-sea-derived Streptomyces sp. SCSIO 03032 capable of producing new bisindole alkaloids spiroindimicins A–D (1–4). Structural elucidation of these compounds revealed the presence of unusual [5,6] or [5,5] spiro-ring containing skeletons. Spiroindimicins B–D (2–4) with a [5,5] spiro-ring exhibited moderate cytotoxicities against several cancer cell lines.