Bacaryolanes A-C, Rare Bacterial Caryolanes from a Mangrove Endophyte
| Autor: | Christian Hertweck, Armin Maier, Heinz-Herbert Fiebig, Katharina Dornblut, Helmar Goerls, Wenhan Lin, Ling Ding |
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| Rok vydání: | 2015 |
| Předmět: |
Molecular Conformation
Pharmaceutical Science Microbial Sensitivity Tests Bruguiera Crystallography X-Ray Endophyte Streptomyces Analytical Chemistry Terpene Drug Discovery Botany Endophytes Nuclear Magnetic Resonance Biomolecular Pharmacology biology Molecular Structure Plant Stems fungi Organic Chemistry Absolute configuration food and beverages Rhizophoraceae biology.organism_classification Complementary and alternative medicine Molecular Medicine Mangrove Drug Screening Assays Antitumor Sesquiterpenes Bacteria Drugs Chinese Herbal |
| Zdroj: | Journal of natural products. 78(12) |
| ISSN: | 1520-6025 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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