Cytochalasins from coastal saline soil-derived fungus Aspergillus flavipes RD-13 and their cytotoxicities.

Shuang Miao, Mengshan Liu, Shizhou Qi, Yan Wu, Kunlai Sun, Zhen Zhang, Kongkai Zhu, Guowei Cai, Kaikai Gong

The Journal of antibiotics 2022 Jul

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Chemical investigation of coastal saline soil-derived fungus Aspergillus flavipes RD-13 led to the isolation of two new seco-cytochalasins (1) and (2) along with nine known analogs. Their structures were elucidated by comprehensive spectral analysis, and the absolute configurations of these two new ones were determined through Rh2(OCOCF3)4-induced CD experiment and chemical interconversions. Moreover, the absolute configuration of a known compound named cytochalasins Z18 (3) was also determined for the first time. Structurally, compounds 1, 2 and 3 were the open ring derivatives of compounds 5, 8, and 4, respectively. All compounds were evaluated for their cytotoxic activities on A549, H1299 and H520 cells and 4 exhibited the strongest inhibitory activities towards the above cell lines with IC50 values of 0.15, 0.23 and 0.43 μg/mL, respectively. Preliminary structure-activity relationship analysis suggested the importance of macrocyclic ring in cytochalasins to confer cytotoxicity. © 2022. The Author(s), under exclusive licence to the Japan Antibiotics Research Association.

Citation

Shuang Miao, Mengshan Liu, Shizhou Qi, Yan Wu, Kunlai Sun, Zhen Zhang, Kongkai Zhu, Guowei Cai, Kaikai Gong. Cytochalasins from coastal saline soil-derived fungus Aspergillus flavipes RD-13 and their cytotoxicities. The Journal of antibiotics. 2022 Jul;75(7):410-414