Insight into Antioxidant and Photoprotective Properties of Natural Compounds from Marine Fungus SCIE SCOPUS

Cited 12 time in WEB OF SCIENCE Cited 13 time in Scopus
Title
Insight into Antioxidant and Photoprotective Properties of Natural Compounds from Marine Fungus
Author(s)
Duy Quang Dao; Thi Thu Trang Phan; Thi Le Anh Nguyen; Phan Thi Hoai Trinh; Thi Thanh Van Tran; Lee, Jong Seok; Shin, Hee Jae; Choi, Byeoung-Kyu
KIOST Author(s)
Lee, Jong Seok(이종석)Shin, Hee Jae(신희재)
Alternative Author(s)
이종석; 신희재; 최병규
Publication Year
2020-03
Abstract
This computational and experimental work aims to elucidate physicochemical and photophysical natures of free radical scavenging and ultraviolet radiation (UVR) filtering activities of five terpenoids available in the extract of marine fungus. The antioxidant activities of ochraceopone F (C1), aspertetranone D (C2), cycloechinulin (C3), wasabidienone E (C4), and mactanamide (C5) are evaluated by using density functional theory (DFT) at the M05-2X/6-311++G(d,p) level of theory in the gas phase, water, and pentyl ethanoate (PEA). Double antioxidant mechanisms allowing the second (H+/e(-)) donation such as double hydrogen atom transfer (dHAT), double single electron transfer-proton transfer (dSET-PT), and double sequential proton loss-electron transfer (dSPL-ET) are considered. Reaction enthalpies (Delta H-t(0)), standard Gibbs free energies (Delta(r)G(0)) and potential energy surfaces of reactions toward HOO center dot radical are then established to evaluate the hydrogen transfer (HT) and radical adduct formation (RAF) mechanisms. The computational results are supported by DPPH center dot and ABTS(center dot+) antioxidant essays. Results show that all compounds C1-C5 are able to scavenge two free radicals via dHAT, dSET-PT, and dSPL-ET mechanisms. Among the compounds, C3 and C4 represent the most potential antioxidants, especially via HAT and RAF mechanisms in all the reaction media. Their rate constants for both HAT and RAF reactions are remarkably higher than that of Trolox and ascorbic acid. The kinetic calculations on activation Gibbs free energies (Delta G(double dagger)) and rate constants (k(TST)) based on conventional transition state theory (TST) reveal that HAT and RAF processes are in competition in solvents. Photophysical processes occurring during UVR exposure are investigated using the time dependent density functional theory (TD-DFT) combined with UV-vis experiments. The obtained results highlight the promising activities of C1-C5 in UVR absorption in the ranges of UVA and UVB. Among them, C3 and C4 also show better UV absorption properties with the easiest excitations (band gaps equal to 4.06 and 3.65 eV). This study suggests the natural candidates possibly used in organic sunscreen.
ISSN
1549-9596
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/38713
DOI
10.1021/acs.jcim.9b00964
Bibliographic Citation
JOURNAL OF CHEMICAL INFORMATION AND MODELING, v.60, no.3, pp.1329 - 1351, 2020
Publisher
AMER CHEMICAL SOC
Type
Article
Language
English
Document Type
Article
Publisher
AMER CHEMICAL SOC
Files in This Item:
There are no files associated with this item.

qrcode

Items in ScienceWatch@KIOST are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse