Photodamage attenuation effect by a tetraprenyltoluquinol chromane meroterpenoid isolated from Sargassum muticum

E M Balboa; Y-X Li; B-N Ahn; S-H Eom; H Domínguez; C Jiménez; J Rodríguez

doi:10.1016/j.jphotobiol.2015.03.026

Photodamage attenuation effect by a tetraprenyltoluquinol chromane meroterpenoid isolated from Sargassum muticum

J Photochem Photobiol B. 2015 Jul:148:51-58. doi: 10.1016/j.jphotobiol.2015.03.026. Epub 2015 Apr 4.

Authors

E M Balboa¹, Y-X Li², B-N Ahn³, S-H Eom⁴, H Domínguez⁵, C Jiménez⁶, J Rodríguez⁷

Affiliations

¹ Department of Chemical Engineering, Faculty of Science, Campus Ourense, University of Vigo, Spain; CITI-University of Vigo, Parque Tecnolóxico de Galicia, Ourense, Spain. Electronic address: elenamba@uvigo.es.
² Department of Chemistry, Pukyong National University, Busan 608-737, Republic of Korea; Marine Bioprocess Research Center, Pukyong National University, Busan 608-737, Republic of Korea. Electronic address: lyxycg@qq.com.
³ Department of Chemistry, Pukyong National University, Busan 608-737, Republic of Korea; Marine Bioprocess Research Center, Pukyong National University, Busan 608-737, Republic of Korea. Electronic address: icetwig@naver.com.
⁴ Department of Chemistry, Pukyong National University, Busan 608-737, Republic of Korea; Marine Bioprocess Research Center, Pukyong National University, Busan 608-737, Republic of Korea. Electronic address: dalgoo52@gmail.com.
⁵ Department of Chemical Engineering, Faculty of Science, Campus Ourense, University of Vigo, Spain; CITI-University of Vigo, Parque Tecnolóxico de Galicia, Ourense, Spain. Electronic address: herminia@uvigo.es.
⁶ Centro de Investigacións Científicas Avanzadas (CICA), Departamento Química Fundamental, Facultade de Ciencias, Universidade da Coruña, A Coruña E-15071, Spain. Electronic address: carlos.jimenez@udc.es.
⁷ Centro de Investigacións Científicas Avanzadas (CICA), Departamento Química Fundamental, Facultade de Ciencias, Universidade da Coruña, A Coruña E-15071, Spain. Electronic address: jaime.rodriguez@udc.es.

PMID: 25874662
DOI: 10.1016/j.jphotobiol.2015.03.026

Abstract

A tetraprenyltoluquinol meroterpenoid with a chromane moiety, obtained as an epimeric mixture at C3, was isolated for the first time from the dichloromethane fraction of a methanolic extract from the brown alga Sargassum muticum. The structure has been established by means of spectral methods including NMR spectroscopy and MS and comparison with reported data. The compound showed photodamage attenuation on irradiated cells with UVA light, presented protection against intracellular ROS generation in a degree comparable to retinoic acid (9.1-20.6%) and did not display toxicity against human dermal fibroblast cells.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antioxidants / chemistry
Cell Line
Cell Survival / drug effects
Cell Survival / radiation effects
Chromans / chemistry
Humans
Magnetic Resonance Spectroscopy
Mass Spectrometry
Microscopy, Electron, Scanning
Molecular Conformation
Protective Agents / chemistry
Protective Agents / isolation & purification
Protective Agents / pharmacology
Reactive Oxygen Species / metabolism
Sargassum / chemistry*
Sargassum / metabolism
Terpenes / chemistry*
Terpenes / isolation & purification
Terpenes / pharmacology
Ultraviolet Rays

Substances

Antioxidants
Chromans
Protective Agents
Reactive Oxygen Species
Terpenes