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

Ling Ding, Helmar Goerls, Katharina Dornblut, Wenhan Lin, Armin Maier, Heinz-Herbert Fiebig, Christian Hertweck

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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.
Original languageEnglish
JournalJournal of Natural Products
Issue number12
Pages (from-to)2963-2967
Number of pages5
Publication statusPublished - 2015
Externally publishedYes

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