Pestarhamnoses A–C, Rhamnosylated Phenol Derivatives from the Soft Coral-Derived Fungus Pestalotiopsis sp.

Marine natural products

“…273 These mixed polyketide-cyclopeptide metabolites (PKS-NRPS hybrids) possessed a unique, symmetric spiro [oxazinane-piperazinedione] skeleton and the racemate and each enantiomer exhibited Enterovirus 71 (EV71) activity but 434 was more selective and more potent. 273 The 277 The pestarhamnoses were obtained through cultivation on a modied medium which contained equal concentrations of sodium chloride and potassium bromide in an expectation of producing brominated analogues of the previously isolated pestalachlorides. 278,279 Interestingly, no brominated analogues were detected but pestalachlorides C and D 279 were isolated along with pestarhamnoses A-C 442-444.…”

“…278,279 Interestingly, no brominated analogues were detected but pestalachlorides C and D 279 were isolated along with pestarhamnoses A-C 442-444. 277 Other fungal genera to yield new metabolites included Phaeosphaeria pretrichodermamide A 300 and the related trichodermamide A 301 when grown on a freshwater medium, chlorinated derivatives trichodermamide B 301 and DC1149B 302 506 when cultured in natural seawater and a new iodinated derivative 507 (ref. 303) when cultured in a freshwater medium supplemented with sodium iodide.…”

Isolation, resolution and biological evaluation of pestalachlorides E and F containing both point and axial chirality

“…5 Marine-derived microorganisms have proved to be a rich and important source of drug candidates. 1,6 Dichlorinated benzophenones (diphenylmethanes) represent a rare family of marine natural products that only six in the class have been reported to date, including pestalone, 7 desmethyl pestalone, 8 and pestalachlorides A-D. 9,10 As part of a continuing program to evaluate bioactive marine natural products as potential drug leads from marine invertebrate derived microorganisms, [11][12][13][14] further chemical investigation 15,16 of laboratory cultures of the Pestalotiopsis fungus (ZJ-2009-7-6) resulted in the isolation of two new chlorinated enantiomeric diphenylmethanes, (AE)-pestalachlorides E (1) and F (2) (Fig. 1).…”