Beshanzoides A–D, unprecedented cycloheptanone-containing polyketides from Penicillium commune P-4-1, an endophytic fungus of the endangered conifer Abies beshanzuensis

Hao-Wei Chen; Chun-Xiao Jiang; Jiyang Li; Na Li; Yi Zang; Xi-Ying Wu; Wen-Xue Chen; Juan Xiong; Jia Li; Jin-Feng Hu

doi:10.1039/D1RA08377E

Beshanzoides A–D, unprecedented cycloheptanone-containing polyketides from Penicillium commune P-4-1, an endophytic fungus of the endangered conifer Abies beshanzuensis†

Hao-Wei Chen,^ab Chun-Xiao Jiang,^ab Jiyang Li,^a Na Li,^b Yi Zang,^c Xi-Ying Wu,

^ad Wen-Xue Chen,^e Juan Xiong,*^a Jia Li^c and Jin-Feng Hu

*^ab

Author affiliations

* Corresponding authors

^a Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai 201203, PR China
E-mail: jxiong@fudan.edu.cn, jfhu@fudan.edu.cn

^b School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang 318000, PR China
E-mail: jfhu@tzc.edu.cn

^c State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, PR China

^d Shanghai Skin Disease Hospital, School of Medicine, Tongji University, Shanghai 200443, PR China

^e Department of Chemistry, Fudan University, Shanghai 200438, PR China

Abstract

A number of previously undescribed (1–7) and structurally related known (8–17) isobenzofuran-type polyketides were obtained from the fermentation of Penicillium commune P-4-1, an endophytic fungus isolated from the fresh trunk bark of the critically endangered conifer Abies beshanzuensis. Beshanzoides A–D (1–4, resp.) feature a cycloheptanone-containing isobenzofuran ring system hitherto unknown, which might be biosynthesized via two steps of aldol reactions starting from a common co-occurring isobenzofuran-type polyketide as the precursor. The new structures were elucidated by spectroscopic methods, electronic circular dichroism data, and single crystal X-ray diffraction analyses. Beshanzoide E (5) showed antimicrobial activity (MIC: 16 μg mL⁻¹) against Staphylococcus aureus, whereas (±)-strobide A (10) inhibited (MIC: 16 μg mL⁻¹) Candida albicans. Cyclopaldic acid (12) and 3-O-methyl-cyclopaldic acid (13) exhibited inhibitory effects against acetyl-CoA carboxylase 1 (ACC1) with IC₅₀ values of 0.96 and 11.77 μM, respectively. Compound 12 also inhibited (IC₅₀: 7.56 μM) ATP-citrate lyase (ACL).

RSC Advances

Beshanzoides A–D, unprecedented cycloheptanone-containing polyketides from Penicillium commune P-4-1, an endophytic fungus of the endangered conifer Abies beshanzuensis†

Abstract

Article information

Download Citation

Permissions

Beshanzoides A–D, unprecedented cycloheptanone-containing polyketides from Penicillium commune P-4-1, an endophytic fungus of the endangered conifer Abies beshanzuensis

Social activity

Search articles by author

Spotlight

Advertisements