4.7 Article

Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22

期刊

JOURNAL OF NATURAL PRODUCTS
卷 79, 期 8, 页码 2022-2031

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.6b00327

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资金

  1. Hi-Tech R&D Program of China [2011AA10A202]
  2. National Basic Research Program of China [2013CB127805]
  3. Special Fund for Agro-Scientific Research in the Public Interest of China [201203037]
  4. Chinese Universities Scientific Fund [2016QC047, 2014RC020]
  5. Project of Science and Technology of Hunan Tobacco Industry Co. Ltd [KY2012YC0001]

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Six new dibenzo-alpha-pyrones, rhizopycnolides A (1) and B (2) and rhizopycnins A-D (3-6), together with eight known congeners (7-14), were isolated from the endophytic fungus Rhizopycnis vagum Nitaf22 obtained from Nicotiana tabacum. The structures of the new compounds were unambiguously elucidated using NMR, HRESIMS, TDDFT ECD calculation, and X-ray crystallography data. Rhizopycnolides A (1) and B (2) feature an uncommon gamma-butyrolactone-fused dibenzo-alpha-pyrone tetracyclic skeleton (6/6/6/5), while rhizopycnin B (4) was the first amino group containing dibenzo-alpha-pyrone. Rhizopycnolides A (1) and B (2) are proposed to be biosynthesized from polyketide and tricarboxylic acid cycle pathways. The isolated compounds were tested for their antibacterial, antifungal, and cytotoxic activities. Among them, rhizopycnolide A (1), rhizopycnins C (5) and D (6), TMC-264 (8), penicilliumolide D (11), and alternariol (12) were active against the tested pathogenic bacteria Agrobacterium tumefaciens, Bacillus subtilis, Pseudomonas lachrymans, Raistonia solanacearum, Staphylococcus hemolyticus, and Xanthomonas vesicatoria with MIC values in the range 25-100 mu g/mL. Rhizopycnin D (6) and TMC-264 (8) strongly inhibited the spore germination of Magnaporthe oryzae with IC50 values of 9.9 and 12.0 mu g/mL, respectively. TMC-264 (8) showed potent cytotoxicity against five human cancer cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780) with IC50 values of 3.2-7.8 mu M.

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