Structures and absolute configurations of phomalones from the coral-associated fungus Parengyodontium album sp. SCSIO 40430

  • Org Biomol Chem. 2021 Jul 21;19(27):6030-6037. doi: 10.1039/d1ob00869b.
Lu Wang  1 ,  Yanbing Huang  2 ,  Liping Zhang  3 ,  Zhiwen Liu  3 ,  Wei Liu  3 ,  Huixin Xu  1 ,  Qingbo Zhang  3 ,  Haibo Zhang  3 ,  Yan Yan  4 ,  Zhiyong Liu  5 ,  Tianyu Zhang  5 ,  Wenjun Zhang  4 ,  Changsheng Zhang  6
Affiliations
  • 1. Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China. [email protected] [email protected] and University of Chinese Academy of Sciences, Beijing 100049, China.
  • 2. Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China. [email protected] [email protected] and Guangxi Key Laboratory of Marine Natural Products and Combinatorial Biosynthesis Chemistry, Beibu Gulf Marine Research Center, Guangxi Academy of Sciences, Nanning 530007, China.
  • 3. Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China. [email protected] [email protected] and Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511458, China.
  • 4. Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China. [email protected] [email protected] and University of Chinese Academy of Sciences, Beijing 100049, China and Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511458, China.
  • 5. Tuberculosis Research Laboratory, State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China and Guangdong-Hong Kong-Macao Joint Laboratory of Respiratory Infectious Disease, Guangzhou 510530, China.
  • 6. Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China. [email protected] [email protected] and University of Chinese Academy of Sciences, Beijing 100049, China and Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511458, China and Sanya Institute of Oceanology, SCSIO, Yazhou Scientific Bay, Sanya 572000, China.
PMID: 34190307 DOI: 10.1039/d1ob00869b
Abstract

Coral-associated Microorganisms are likely to play an important role in host defense by the production of antimicrobials. Six new chromanones, namely, phomalichenones H-M (5, 6, and 8-11), and ten known analogues (1-4, 7, and 12-16) were isolated from the coral-associated fungus Parengyodontium album sp. SCSIO 40430. Their structures were elucidated by comprehensive spectroscopic analyses. In addition, the structure of 8 was confirmed by X-ray crystallographic analysis. Resolution using a chiral column showed that each of the compounds 1-8 was an enantiomeric mixture with variable enantiomeric excess (ee) values. Their absolute configurations were determined by a comparison of the experimental and calculated ECD data and by a modified Mosher's method. A plausible biosynthetic scheme was proposed for the production of 1-16. Compounds 2, 3, 13, and 14 were found to be active against Mycobacterium tuberculosis H37Ra with MIC values of 16-64 μg mL-1.

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