Bacaryolanes A–C, Rare Bacterial Caryolanes from a Mangrove Endophyte

详细信息    查看全文

• 作者：Ling Ding ; Helmar Goerls ; Katharina Dornblut ; Wenhan Lin ; Armin Maier ; Heinz-Herbert Fiebig ; Christian Hertweck
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：December 24, 2015
• 年：2015
• 卷：78
• 期：12
• 页码：2963-2967
• 全文大小：329K
• ISSN：1520-6025

文摘

Caryolanes are known as typical plant-derived sesquiterpenes. Here we describe the isolation and full structure elucidation of three caryolanes, bacaryolane A–C (1–3), that are produced by a bacterial endophyte (Streptomyces sp. JMRC:ST027706) of the mangrove plant Bruguiera gymnorrhiza. By 2D NMR, analysis of the first X-ray crystallographic data of a caryolane (bacaryolane C), CD spectroscopy, and comparison with data for plant-derived caryolanes, we rigorously established the absolute configuration of the bacaryolanes and related compounds from bacteria. Bacterial caryolanes appear as the mirror images of typical plant caryolanes. Apparently plant and bacteria harbor stereodivergent biosynthetic pathways, which may be used as metabolic signatures. The discovery of plant-like volatile terpenes in endophytes not only is an important addition to the bacterial terpenome but may also point to complex molecular interactions in the plant–microbe association.