Title
Eremophilane Sesquiterpenes from a Deep Marine-Derived Fungus, Aspergillussp. SCSIOW2, Cultivated in the Presence of Epigenetic Modifying Agents
Author
Liyan Wang, Mengjie Li, Jianqiang Tang, Xiaofan Li
Year
2016
Journal
Molecules
Abstract
Chemical epigenetic manipulation was applied to a deep marine-derived fungus, Aspergillus sp. SCSIOW2, resulting in significant changes of the secondary metabolites. Three new eremophilane-type sesquiterpenes, dihydrobipolaroxin B (2), dihydrobipolaroxin C (3), and dihydrobipolaroxin D (4), along with one known analogue, dihydrobipolaroxin (1), were isolated from the culture treated with a combination of histone deacetylase inhibitor (suberohydroxamic acid) and DNA methyltransferase inhibitor (5-azacytidine). 1–4 were not produced in the untreated cultures. 2 and 3 might be artificial because 1 could form 2 and 3 spontaneously in water by intracellular acetalization reaction. The absolute configurations of 1 and 2 were assigned based on ECD spectroscopy combined with time-dependent density functional theory calculations. All four compounds exhibited moderate nitric oxide inhibitory activities without cytotoxic effects.
Full Article
Instrument
J-815
Keywords
Circular dichroism, Absolute configuration, Agricultural and environmental, Toxicology