title: Bacaryolanes A-C, Rare Bacterial Caryolanes from a Mangrove Endophyte.
abstract: 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.
authors.affiliation: Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI) , Beutenbergstraße 11a, 07745 Jena, Germany.
authors.forename: Ling
authors.initials: L
authors.lastname: Ding
authors.affiliation: Institute for Inorganic and Analytical Chemistry, Friedrich Schiller University , Humboldtstraße 8, 07743 Jena, Germany.
authors.forename: Helmar
authors.initials: H
authors.lastname: Goerls
authors.affiliation: Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI) , Beutenbergstraße 11a, 07745 Jena, Germany.
authors.forename: Katharina
authors.initials: K
authors.lastname: Dornblut
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, Peking University , Beijing, People's Republic of China.
authors.forename: Wenhan
authors.initials: W
authors.lastname: Lin
authors.affiliation: Oncotest GmbH , Am Flughafen 12-14, 79108 Freiburg, Germany.
authors.forename: Armin
authors.initials: A
authors.lastname: Maier
authors.affiliation: Oncotest GmbH , Am Flughafen 12-14, 79108 Freiburg, Germany.
authors.forename: Heinz-Herbert
authors.initials: HH
authors.lastname: Fiebig
authors.affiliation: Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI) , Beutenbergstraße 11a, 07745 Jena, Germany.|Friedrich Schiller University , 07737 Jena, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Hertweck
mesh_terms: D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry; D060026:Endophytes / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018547:Plant Stems / Q000737:chemistry; D043982:Rhizophoraceae / Q000382:microbiology*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification*; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D004365:Drugs, Chinese Herbal; D012717:Sesquiterpenes; C000607241:bacaryolane A; C000607242:bacaryolane B; C000607244:bacaryolane C