Cytotoxic Metabolites from the Antarctic Psychrophilic Fungus Oidiodendron truncatum

Abstract

Two new epipolythiodioxopiperazines, named chetracins B and C (1 and 2), and five new diketopiperazines, named chetracin D (4) and oidioperazines A-D (5, 10, 12, and 13), were isolated from the fungus Oidiodendron truncatum GW3-13, along with six known compounds (3, 6, 7, 8, 9, and 11). Their structures were elucidated by extensive NMR, MS, and CD analyses, as well as chemical transformation. An in vitro MTT cytotoxicity assay revealed potent biological activity for 1 in the nanomolar range against a panel of five human cancer lines.

Epidithiodioxopiperazines. occurrence, synthesis and biogenesis

“…84 In 2012, several related metabolites were isolated from Oidiodendron truncatum , including the tetra-, penta- and hexasulfide homologs melinacidin IV, chetracins B and C ( 82 , 83 , and 84 ), and the dethiotetra(methylthio) derivative chetracin D ( 85 ). 85 …”

“…86 Additionally, melinacidin IV and chetracin B ( 82 and 83 ) display nanomolar (3 – 54 nM) activity against five human cancer cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780). 85 …”

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

“…42). 285 Eight new indole alkaloids, melosuavines A (904), B (905), and C (906), an aspidosperma-scandine linkage, bisindole alkaloids melosuavines D (907), E (908), and F (909), possessing an aspidosperma-aspidosperma core, and melosuavines G (910) and H (911), featuring an aspidosperma-venalatonine core, were isolated from the twigs and leaves of Melodinus suaveolens. Compounds 904, 905, 907, 908, and 909 showed low micromolar cytotoxicity against one or more of ve human cancer cell lines (Fig.…”

Cytotoxic indole diketopiperazines from the deep sea-derived fungus Acrostalagmus luteoalbus SCSIO F457

“…[2][3][4]18,20 These metabolites have been found to possess a wide variety of biological activities, especially the significant cytotoxicity. The polysulfide bridge of these compounds contribute more to their activities.…”

“…The molecular formula was determined as C 23 H20 N 4 O 3 S 2 by HRE-SIMS at m/z 465.1087 [M+H] + (calcd for C 23 H 21 N 4 O 3 S 2 , 465.1055), indicating sixteen degrees of unsaturation. Its IR spectrum exhibited bands at 3402, 1676, 1608 and 1462 cm À1, characteristic of an alcohol, an amine, an amide and aromatic ring.…”