Citation: Chuan Li, Yangyang Han, Yanan Zhai, Ke Li, Xingzhong Liu, Zhuan Zhang, Cai Jia, Yongsheng Che. Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.[J]. Chinese Chemical Letters, ;2024, 35(7): 109019. doi: 10.1016/j.cclet.2023.109019 shu

Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.

Chuan Li ^{a, 1} ,
Yangyang Han ^{a, 1} ,
Yanan Zhai ^b ,
Ke Li ^a ,
Xingzhong Liu ^c ,
Zhuan Zhang ^a ,
Cai Jia ^{a, *,} ,
Yongsheng Che ^{a, *,}

a.
NHC Key Laboratory of Biotechnology of Antibiotics, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China
b.
State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology, Beijing 100850, China
c.
Department of Microbiology, College of Life Sciences, Nankai University, Tianjin 300071, China

caijia@imb.cams.cn

ysche@imb.cams.cn

Received Date: 18 July 2023
Revised Date: 27 August 2023
Accepted Date: 30 August 2023
Available Online: 2 September 2023

Figures(7)

Phomaketals A (1) and B (2), two tropolonic meroterpenoids with the unprecedented pentacyclic skeletons, were isolated from the solid-substrate fermentation cultures of a eupC overexpressed mutant strain of the fungus Phoma sp., together with a biogenetically related secondary metabolite pughiinin B (3), and the known one noreupenifeldin B (4). The structures of 1–3 were elucidated primarily by nuclear magnetic resonance (NMR) experiments. The absolute configurations of 1 and 2 were assigned by electronic circular dichroism calculations and the calculated NMR with DP4+ analysis, while that of 3 was established by single-crystal X-ray diffraction analysis using Cu Kα radiation. Biogenetically, phomaketals A (1) and B (2) could be derived from the hypothetical tropolonic sesquiterpene intermediates neosetophomone B (6) and 9-R-neosetophomone B (6′), respectively, via different reactions cascades. Compound 1 showed antiproliferative effect only against the SUPB15 cells, with an 50% inhibitory concentration (IC₅₀) value of 4.85 µmol/L, while the co-isolated known meroterpenoid 4 displayed potent effects against three tumor cell lines, SUPB15, EL4, and H9, showing IC₅₀ values of 0.36–27.08 µmol/L.
- Phoma sp.,
- Tropolonic sesquiterpenes,
- Biosynthetic pathways,
- Hetero-Diels–Alder,
- Cytotoxicity
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