The chemical characterization of n-butanol soluble extract of the fungus Ophiocordyceps longiissima NBRC 106965 afforded a new cerebroside, 1-O-(β-D-glucopyranosyl)-(2S,3R,4E,8E)-2-[(2′R)-2′-hydroxyheptadecanoylamino]-9-methylheptadeca-4,8-diene-1,3-diol, trivially named ophiocordylongiiside A (1), in addition to 22E,24R-24-methylcholest-5,22-diene-3-O-β-D-O-glucopyranoside (2). The chemical structure of 1 was established based upon the by modern spectroscopic and chemical techniques. Compound 1 exhibited strong DPPH-free radical scavenging with the IC50 value of 55.72 mg/mL. The biological result can be explained by density functional theoretical (DFT) calculation, in which antioxidant activity is mostly controlled by the O–H bond dissociation enthalpy (BDE) following hydrogen atom transfer (HAT) mechanism. In all studied environments, the lowest BDE values are found in 2′-OH.
Antioxidant, DFT, cerebroside, Ophiocordyceps longiissima
Publication DOI: 10.1016/j.molstruc.2019.127061Journal NLM ID: 0141747Publisher: Elsevier
Correspondence: Elshamy AI
; Son NT
Institutions: aculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Japan, Chemistry of Natural Compounds Chemistry Department, National Research Centre, Giza, Egypt, Department of Bioactive Products, Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam, Medical Mycology Research Center, Chiba University, Japan, Institute for Tropical Technology, Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, methanolysis, extraction, optical rotation measurement, CC, cell growth, antioxidant activities, derivatization, flash chromatography, filtration, HR ESI-TOF MS, RP-HPLC-MS
Found