Issue 23, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
01 Sep 2019
Accepted
08 Oct 2019
First published
12 Oct 2019

Org. Chem. Front., 2019,6, 3839-3846

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, 6, 3839 DOI: 10.1039/C9QO01076A

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