title: Chemical constituents from aerial parts of Caryopteris incana and cytoprotective effects in human HepG2 cells.
abstract: An ethyl acetate fraction of the aerial parts of Caryopteris incana (Verbenaceae) showed potent cytoprotective effects against damage to HepG2 cells induced by tert-butylhydroperoxide (t-BHP). To search for hepatoprotective components of C. incana, various chromatographic separations of the ethyl acetate soluble fraction of C. incana led to isolation of three phenylpropanoid glycosides, 6‴-O-feruloylincanoside D, 6‴-O-sinapoylincanoside D and caryopteroside, and two iridoid glycosides, incanides A and B, together with 17 known compounds. Structures of these compounds were determined by spectroscopic analyses. The absolute stereochemistry of the caryopteroside was established with the help of circular dichroism data and in comparison with literature data. All isolated substances were determined for their cytoprotective effects against t-BHP-induced toxicity in HepG2 cells. Among the tested compounds, 6'-O-caffeoylacteoside exhibited the most potent cytoprotective activity with an IC50 value of 0.8±0.1 μM against t-BHP-induced toxicity. Structure-activity relationships of the assay results indicated an important role of the catechol moiety in phenylpropanoid, iridoid and flavonoid derivatives in eliciting cytoprotective effects.
authors.affiliation: Molecular Recognition Research Center, Future Convergence Research Division, Korea Institute of Science and Technology, Hwarangno 14 gil 5, Seoul 136-791, Republic of Korea; Department of Pharmacy, College of Pharmacy, Kyung Hee University, 1 Hoegi-Dong, Seoul 130-701, Republic of Korea.
authors.forename: Sunmi
authors.initials: S
authors.lastname: Park
authors.affiliation: Molecular Recognition Research Center, Future Convergence Research Division, Korea Institute of Science and Technology, Hwarangno 14 gil 5, Seoul 136-791, Republic of Korea; Research Institute for Basic Sciences and Department of Chemistry, College of Sciences, Kyung Hee University, Seoul 130-701, Republic of Korea.
authors.forename: Min Jeong
authors.initials: MJ
authors.lastname: Son
authors.affiliation: Department of Pharmacy, College of Pharmacy, Kyung Hee University, 1 Hoegi-Dong, Seoul 130-701, Republic of Korea.
authors.forename: Chang-Soo
authors.initials: CS
authors.lastname: Yook
authors.affiliation: Molecular Recognition Research Center, Future Convergence Research Division, Korea Institute of Science and Technology, Hwarangno 14 gil 5, Seoul 136-791, Republic of Korea.
authors.forename: Changbae
authors.initials: C
authors.lastname: Jin
authors.affiliation: Department of Pharmacy, College of Pharmacy, Kyung Hee University, 1 Hoegi-Dong, Seoul 130-701, Republic of Korea.
authors.forename: Yong Sup
authors.initials: YS
authors.lastname: Lee
authors.affiliation: Molecular Recognition Research Center, Future Convergence Research Division, Korea Institute of Science and Technology, Hwarangno 14 gil 5, Seoul 136-791, Republic of Korea. Electronic address: khj@kist.re.kr.
authors.forename: Hyoung Ja
authors.initials: HJ
authors.lastname: Kim
mesh_terms: D019610:Cytoprotection; D056945:Hep G2 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D020011:Protective Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D029648:Verbenaceae / Q000737:chemistry*; D020122:tert-Butylhydroperoxide / Q000633:toxicity
chemical_list: D010936:Plant Extracts; D020011:Protective Agents; D020122:tert-Butylhydroperoxide
keywords: Caryopteris incana (Thunb.) Miq.; Cytoprotection; HepG2 cell; Iridoids; Phenylpropanoids; Verbenaceae; tert-Butylhydroperoxide (t-BHP)