Furan Derivatives and Polyketides from the Fungus Irpex lacteus
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ORIGINAL ARTICLE
Furan Derivatives and Polyketides from the Fungus Irpex lacteus Meng Wang1 · Zheng‑Hui Li1 · Masahiko Isaka2 · Ji‑Kai Liu1 · Tao Feng1 Received: 4 October 2020 / Accepted: 31 October 2020 © The Author(s) 2020
Abstract Eight new furan derivatives, irpexins A‒H (1‒8), two new polyketides, irpexins I and J (9 and 10), together with nine known compounds were isolated from the fermentation of Irpex lacteus. The structures and absolute configurations were elucidated on the basis of extensive spectroscopic methods and Mosher ester reaction. All compounds shows no cytotoxicity to human MCF-7 and Hela cancer cell lines at the concentration of 10 μM. Graphic Abstract OH OHC
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O O
H3CO Ph C
Irpex lacteus
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O C H O 1a MTPA model
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Keywords Irpex lacteus · Furan derivatives · Polyketides
1 Introduction Fungi are important sources of natural products for the discovery of drugs and agricultural chemicals [1‒5], which have attracted great attention from pharmaceutical chemists and pharmacologists. Irpex lacteus is a pathogenic wooddecaying fungus belonging to the family Polyporaceae [6]. Its crude polysaccharide fraction has long been used as a traditional Chinese medicine for the treatment of chronic Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13659-020-00282-w) contains supplementary material, which is available to authorized users. * Tao Feng [email protected] 1
School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, People’s Republic of China
National Center for Genetic Engineering and Biotechnology (BIOTEC), 113 Thailand Science Park, Pathumthani 12120, Thailand
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glomerulonephritis in clinic [7]. Chemists have researched the fermentation products of this fungus and the chemical constituents of fruiting bodies. In 1981, Hayashi et al. isolated three new nematicidal metabolites including two furan derivatives from their lactose liquid medium [8]. Our previous chemical investigations on the liquid fermentation of this fungus reported new carbon skeletons irlactins A–D that featured a 6/6 backbone [9], as well as a series of tremulane sesquiterpenoids [10, 11]. Later, studies on the fruiting bodies reported a series of triterpenes, irpeksins A–E, which inhibit the production of NO by RAW264.7 macrophages induced by LPS, and a new skeletal triterpenoid irpexolidal with a 6/5/6/5/6/5-fused polycyclic skeletal system [12, 13]. Recently, Duan et al. isolated four new bioactive metabolites from the endophytic fungus Irpex lacteus DR10-1, including one tremulane sesquiterpene irpexlacte A and three new furan derivatives irpexlactes B‒D [14]. In the current study, eight new furan derivatives, irpexins A‒H (1‒8), two new polyketides, irpexins I and J (9 and 10), together with nine known compounds were obtained from cultures of I. lacteus
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in rice medium. Their structures have been established by extensive spectroscopic methods, as
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