Nematicidal epipolysulfanyldioxopiperazines from Gliocladium roseum.
Five new verticillin-type epipolysulfanyldioxopiperazines, gliocladine A (1), B (2), C (3), D (4), and E (5), were isolated from wheat solid-substrate fermentation of Gliocladium roseum 1A, along with four known compounds, verticillin A (6), 11'-deoxyverticillin A (7), Sch52900 (8), and Sch52901 (9). Their structures were elucidated by extensive 1D and 2D NMR studies, MS, and chemical transformations. In vitro immersion tests showed that all nine compounds exhibited antinematodal activity against Caenorhabditis elegans and Panagrellus redivivus. The monomeric epipolysulfanydioxopiperazines (3-5), with the indole moiety, were found to be less active than the dimeric compounds (1, 2, 6-8).
Dong
Jin-Yan
JY
Key Laboratory for Conservation and Utilization of Bioresources, Yunnan University, Kunming, Yunnan 650091, People's Republic of China.
He
Hong-Ping
HP
Shen
Yue-Mao
YM
Zhang
Ke-Qin
KQ
D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017173:Caenorhabditis elegans / Q000187:drug effects*; D002681:China; D020462:Gliocladium / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000969:Antinematodal Agents; D007211:Indoles; D010879:Piperazines; C009654:verticillins