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Polycyclic Macrolactams Generated via Intramolecular Diels–Alder Reactions from an Antarctic Streptomyces Species

Author:
Shen, Jingjing, Fan, Yaqin, Zhu, Guoliang, Chen, Hao, Zhu, Weiming, Fu, Peng
Source:
Organic letters 2019 v.21 no.12 pp. 4816-4820
ISSN:
1523-7052
Subject:
Streptomyces, biochemical pathways, cell lines, chemical structure, cycloaddition reactions, inhibitory concentration 50, neoplasm cells, organic compounds, spectral analysis, Antarctic region
Abstract:
Three new polycyclic macrolactams, cyclamenols B–D (1–3), together with a known macrolactam, cyclamenol A (4), were isolated from the Streptomyces sp. OUCMDZ-4348. Their structures including absolute configurations were determined on the basis of spectroscopic analysis, chemical methods, and ECD calculations. The biosynthetic pathways involving intramolecular Diels–Alder reactions were proposed. Compound 1 exhibited selective inhibition against the gastric carcinoma cell line N87 with an IC₅₀ value of 10.8 μM.
Agid:
6478226