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. 2018 Oct 1;16(10):358.
doi: 10.3390/md16100358.

Peniginsengins B⁻E, New Farnesylcyclohexenones from the Deep Sea-Derived Fungus Penicillium sp. YPGA11

Zhongbin Cheng  1   2 , Wei Xu  3 , Lijun Liu  4 , Shumin Li  5 , Wangjun Yuan  6   7 , Zhuhua Luo  8 , Jingjie Zhang  9 , Yongjun Cheng  10 , Qin Li  11   12
Affiliations

Peniginsengins B⁻E, New Farnesylcyclohexenones from the Deep Sea-Derived Fungus Penicillium sp. YPGA11

Zhongbin Cheng et al. Mar Drugs. .

Abstract

Chemical examination of the EtOAc extract of the deep sea-derived fungus Penicillium sp. YPGA11 resulted in the isolation of four new farnesylcyclohexenones, peniginsengins B⁻E (1⁻4), and a known analog peniginsengin A (5). The structures of compounds 1⁻4 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1, 2, and 4 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compounds 1⁻5, characterized by a highly oxygenated 1-methylcyclohexene unit and a (4E,8E)-4,8-dimethyldeca-4,8-dienoic acid side chain, are rarely found in nature. Compounds 2⁻4 exhibited antibacterial activity against Staphylococcus aureus.

Keywords: Penicillium sp.; antibacterial; deep sea-derived fungus; farnesylcyclohexenones.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of compounds 1–5 from Penicillium sp.
Figure 2
Figure 2
Key correlation spectroscopy (COSY), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser effect (NOE) correlations of 1–4.
Figure 3
Figure 3
Experimental and calculated electronic circular dichroism (ECD) spectra of 1.
Figure 4
Figure 4
Experimental and calculated ECD spectra of 2.
Figure 5
Figure 5
Experimental and calculated ECD spectra of 4 and 5.
See this image and copyright information in PMC

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