Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.1016/j.molstruc.2019.127061Journal NLM ID: 0141747Publisher: Elsevier
Correspondence: Elshamy AI <elshamynrc
yahoo.com>; Son NT <yamantson
gmail.com>
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
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
Structure type: monomer
Location inside paper: Fig. 1, 1
Trivial name: ophiocordylongiiside A
Compound class: glycolipid, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, methanolysis, extraction, optical rotation measurement, EI-MS, column chromatography, cell growth, antioxidant activities, derivatization, flash chromatography, filtration, HR ESI-TOF MS, RP-HPLC-MS
Related record ID(s): 51025
NCBI Taxonomy refs (TaxIDs): 452169
Show glycosyltransferases
There is only one chemically distinct structure:
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Publication DOI: 10.1016/j.molstruc.2019.127061Journal NLM ID: 0141747Publisher: Elsevier
Correspondence: Elshamy AI <elshamynrc
yahoo.com>; Son NT <yamantson
gmail.com>
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
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
Structure type: monomer
Location inside paper: Fig. 1, 2
Compound class: glycoside, steroid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, methanolysis, extraction, optical rotation measurement, EI-MS, column chromatography, cell growth, antioxidant activities, derivatization, flash chromatography, filtration, HR ESI-TOF MS, RP-HPLC-MS
Related record ID(s): 51024
NCBI Taxonomy refs (TaxIDs): 452169
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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