Sorbicillfurans A and B, two novel sorbicillinoid adducts from the fungus Penicillium citrinum SCSIO41402

Jianjiao Wang; Kunlong Li; Xiaowei Luo; Zhaoyuan Wu; Tanwei Gu; Shengrong Liao; Xiuping Lin; Bin Yang; Yonghong Liu; Wei Fang; Xuefeng Zhou

doi:10.1039/C9OB01595G

Sorbicillfurans A and B, two novel sorbicillinoid adducts from the fungus Penicillium citrinum SCSIO41402†

Jianjiao Wang,^ab Kunlong Li,^ab Xiaowei Luo,

^ab Zhaoyuan Wu,^c Tanwei Gu,^d Shengrong Liao,

^a Xiuping Lin,^a Bin Yang,^a Yonghong Liu,

^ab Wei Fang*^c and Xuefeng Zhou

*^ae

Author affiliations

* Corresponding authors

^a CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China
E-mail: xfzhou@scsio.ac.cn

^b University of Chinese Academy of Sciences, Beijing 100049, China

^c Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Sciences, Wuhan 430064, China
E-mail: wei.fang@nberc.com

^d Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China

^e Institution of South China Sea Ecology and Environmental Engineering, Chinese Academy of Sciences, Guangzhou 510301, China

Abstract

Two novel sorbicillinoid adducts containing bicyclo[2.2.2]octane and tetrahydrofuran moieties, named sorbicillfurans A and B (1 and 2), were isolated from the static culture of the marine-derived fungus Penicillium citrinum SCSIO41402. Their structures including absolute configurations were determined by spectroscopic and calculated ECD analyses. Sorbicillfurans A and B (1 and 2) are the first examples of sorbicillinoids possessing a tetrahydrofuran unit. In the proposed biosynthetic pathway, sorbicillfuran B (2), harboring a rare and complex polycyclic framework, is probably formed by two Diels–Alder reactions. Both isolates were evaluated for the cytotoxicity against six human cancer cell lines, only sorbicillfuran B (2) showed weak cytotoxicity against HL-60 cells with an IC₅₀ value of 9.6 μM.

Organic & Biomolecular Chemistry

Sorbicillfurans A and B, two novel sorbicillinoid adducts from the fungus Penicillium citrinum SCSIO41402†

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Sorbicillfurans A and B, two novel sorbicillinoid adducts from the fungus Penicillium citrinum SCSIO41402

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