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Expanstines A–D: four unusual isoprenoid epoxycyclohexenones generated by Penicillium expansum YJ-15 fermentation and photopromotion

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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.

Graphical abstract: Expanstines A–D: four unusual isoprenoid epoxycyclohexenones generated by Penicillium expansum YJ-15 fermentation and photopromotion

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Publication details

The article was received on 01 Sep 2019, accepted on 08 Oct 2019 and first published on 12 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01076A
Org. Chem. Front., 2019, Advance Article

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    Expanstines A–D: four unusual isoprenoid epoxycyclohexenones generated by Penicillium expansum YJ-15 fermentation and photopromotion

    J. Wang, Y. Shu, S. Liu, J. Hu, C. Sun, H. Zhou, D. Gan, X. Cai, W. Pu, L. Cai and Z. Ding, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01076A

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