Polyporolide, a new acetogenin from the mycelial culture of a Polyporus fungus

Abstract

A new acetogenin, polyporolide (1), was isolated from the mycelial solid cultures of a Polyporus basidiomycete. Its structure was elucidated as 4-hydroxy-5-(1-hydroxyhexyl)-dihydrofuran-2-one by spectroscopic methods. Its toxicity to brine shrimps was assessed.

Lipid-lowering polyketides from a soft coral-derived fungus Cladosporium sp. TZP29

“…The relative configuration of C-3 and C-4 was deduced as trans according to the coupling constant (6.0 Hz). 22 The modified Mosher's methods was also performed to determine the absolute configuration of 2. 23,24 The positive Dd value of H-12 (+0.07 ppm) and the negative one of H-10 (À0.06 ppm) assigned the absolute configuration of C-11 as R (Fig.…”

A stereoselective synthesis of the reported structure of polyporolide

“…1). 1 Similar relative stereochemistry exists in (+)-mupirocin H 13. However, the chemical shis values of reported 1 for C3, C4 and C5 protons as shown, completely mis-match with that in 13.…”

“…13 C NMR (100 MHz, CDCl 3 ): d 173. 5, 107.8, 79.0, 78.1, 66.6, 60.8, 38.4, 31.9, 29.3, 28.2, 26.3, 25.6, 22.6, 14.2, 14.0 (4R,5S)-4-Hydroxy-5-[(S)-1-hydroxyhexyl]dihydrofuran-2(3H)one (1). The ester 10 (30 mg, 0.104 mmol) was dissolved in methanol (10 mL) and 4 N HCl (2 mL) was added and reuxed for 8 h. The mixture was then cooled to room temperature and quenched with NaHCO 3 and ltered.…”

“…1) from the mycelial solid cultures of Polyporus strain SC0652. 1 They observed this strain to possess antibacterial activity against E. coli. Polyporolide showed weak activity against brine shrimps (Artemia salina) with LC 50 of 424.5 mg mL À1 .…”

“…1. 1 In the course of our synthetic studies directed toward the enantioselective synthesis of pharmacologically active natural products like paraconic acids and butyrolactones, 2 we became interested in synthesis of the newly isolated acetogenin, polyporolide 1.…”