A new diarylheptanoid glycoside from the stem bark of Alnus hirsuta and protective effects of diarylheptanoid derivatives in human HepG2 cells.
To search for secondary metabolites of Alnus hirsuta (Betulaceae), various chromatographic separations of the ethyl acetate soluble fraction of the stem bark of A. hirsuta led to the isolation of a new diarylheptanoid glycoside, (3R)-1,7-bis-(4-dihydroxyphenyl)-3-heptanol 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranoside (13) and twelve diarylheptanoid derivatives, namely, oregonin (1), rubranoside A (2), hirsutanonol 5-O-beta-D-glucopyranoside (3), rubranoside B (4), rubranoside C (5), hirsutanonol (6), hirsutenone (7), (5S)-O-methylhirsutanonol (8), platyphylloside (9), platyphyllonol 5-O-beta-D-xylopyranoside (10), aceroside VII (11) and platyphyllenone (12). Isolates were assessed for their hepatoprotective effects against tert-butylhydroperoxide (t-BHP)-induced toxicity in HepG2 cells. Of these isolates, compounds 1-8 showed significant hepatoprotective effects on t-BHP-induced damage to HepG2 cells, with 8 exhibiting the greatest protective effect (50.7 + or - 3.7% at a concentration of 10 microM).
Park
Daae
D
Department of Pharmaceutical Science, College of Pharmacy, Kyung Hee University, 1 Hoegi-Dong, Seoul 130-701, Korea.
Kim
Hyoung Ja
HJ
Jung
Seo Yun
SY
Yook
Chang-Soo
CS
Jin
Changbae
C
Lee
Yong Sup
YS
D029661:Alnus / Q000737:chemistry* / Q000378:metabolism; D002470:Cell Survival / Q000187:drug effects; D019610:Cytoprotection; D036381:Diarylheptanoids / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*; D056945:Hep G2 Cells; D022781:Hepatocytes / Q000166:cytology / Q000187:drug effects*; D006801:Humans; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D020122:tert-Butylhydroperoxide / Q000009:adverse effects
D036381:Diarylheptanoids; D006027:Glycosides; D020122:tert-Butylhydroperoxide