Journal article
Bacaryolanes A-C, Rare Bacterial Caryolanes from a Mangrove Endophyte
Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI) , Beutenbergstraße 11a, 07745 Jena, Germany.1
Institute for Inorganic and Analytical Chemistry, Friedrich Schiller University , Humboldtstraße 8, 07743 Jena, Germany.2
State Key Laboratory of Natural and Biomimetic Drugs, Peking University , Beijing, People's Republic of China.3
Oncotest GmbH , Am Flughafen 12-14, 79108 Freiburg, Germany.4
Friedrich Schiller University , 07737 Jena, Germany.5
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.
Language: | English |
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Publisher: | American Chemical Society (ACS) |
Year: | 2015 |
Pages: | 2963-2967 |
ISSN: | 15206025 and 01633864 |
Types: | Journal article |
DOI: | 10.1021/acs.jnatprod.5b00674 |
Crystallography, X-Ray Drug Screening Assays, Antitumor Drugs, Chinese Herbal Endophytes Microbial Sensitivity Tests Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Plant Stems Rhizophoraceae Sesquiterpenes Streptomyces bacaryolane A bacaryolane B bacaryolane C