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Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22
- Lai, Daowan, Wang, Ali, Cao, Yuheng, Zhou, Kaiyi, Mao, Ziling, Dong, Xuejiao, Tian, Jin, Xu, Dan, Dai, Jungui, Peng, Yu, Zhou, Ligang, Liu, Yang
- Journal of natural products 2016 v.79 no.8 pp. 2022-2031
- Agrobacterium radiobacter, Bacillus subtilis, Magnaporthe oryzae, Nicotiana tabacum, Pseudomonas, Ralstonia solanacearum, Staphylococcus, X-ray diffraction, Xanthomonas vesicatoria, bacteria, chemical structure, cytotoxicity, endophytes, fungi, humans, inhibitory concentration 50, minimum inhibitory concentration, neoplasms, nuclear magnetic resonance spectroscopy, polyketides, spore germination, tricarboxylic acid cycle
- Six new dibenzo-α-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 γ-butyrolactone-fused dibenzo-α-pyrone tetracyclic skeleton (6/6/6/5), while rhizopycnin B (4) was the first amino group containing dibenzo-α-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, Ralstonia solanacearum, Staphylococcus hemolyticus, and Xanthomonas vesicatoria with MIC values in the range 25–100 μg/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 μg/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 μM.