Expanstines A–D: four unusual isoprenoid epoxycyclohexenones generated by Penicillium expansum YJ-15 fermentation and photopromotion. Issue 23 (17th October 2019)

• Record Type: Journal Article
• Authors: Wang, Jia-Peng; Shu, Yan; Liu, Shi-Xi; Hu, Jun-Tao; Sun, Cheng-Tong; Zhou, Hao; Gan, Dong; Cai, Xue-Yun; Pu, Wei; Cai, Le; Ding, Zhong-Tao
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 23(2019)
• Page Start: 3839
• Page End: 3846
• Publication Date: 2019-10-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c9qo01076a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Expanstines A–D from P. expansum YJ-15 were derived under UV and visible light from 4′-oxomacrophoin A (5 ) and its acetate (6 ), which plausibly underwent a rare intramolecular photoene reaction and a [2 + 2] Paternò–Büchi photoaddition respectively. Abstract : Two new isoprenoid epoxycyclohexenones, expanstines A–B (1–2 ), and two novel isoprenoid epoxycyclohexenones, expanstines C–D (3–4 ), featuring an unusual oxetane ring were isolated from Penicillium expansum YJ-15. Their structures were initially investigated in detail by NMR spectroscopy, HRESIMS, XRD and ECD experiments. Expanstines A–D were derived under UV and visible light from 5 and 6, which plausibly underwent a rare intramolecular photoene reaction and a [2 + 2] Paternò–Büchi photoaddition respectively. Both 3 and 4 exhibited potent antibacterial activities against B. subtilis, with an MIC of 0.25 μg mL −1 .