New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica.
A new furofuran lignan, styraxlignolide B (1), and four new dibenzyl-gamma-butyrolactone lignans, styraxlignolides C-F (2-5), were isolated from the EtOAc-soluble fraction of stem bark of Styrax japonica. Known compounds, taraxerol (6), syringin (7), and (-)-pinoresinol glucoside (8), were also obtained. The structures of styraxligonolides B-F were determined as 2alpha-(4'-hydroxy-3'-methoxyphenyl)-6alpha-(3' ',4' '-methylenedioxyphenyl)-8-oxo-3,7-dioxabicyclo[3.3.0]octane 4'-O-(beta-D-glucopyranoside) (1), (2S,3S)-2alpha-(3' '-hydroxy-4' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (2), (2S,3S)-2alpha-(4' '-hydroxy-3' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (3), (2S,3S)-2alpha-(4' '-hydroxy-3' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4' '-O-(beta-D-glucopyranoside) (4), and (2S,3S)-2alpha-(3' ',4' '-dimethoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (5) by spectroscopic means including 2D NMR. Compounds 1-8 were tested in vitro for antioxidant activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Styraxlignolide C (2), styraxlignolide D (3), styraxlignolide E (4), and (-)-pinoresinol glucoside (8) exhibited weak radical-scavenging activity in the DPPH assay, with IC50 values of 380, 278, 194, and 260 microM, respectively.
Min
Byung-Sun
BS
Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology, 52 Eoeun-dong, Yuseong, Daejeon 305-333, Korea.
Na
Min-Kyun
MK
Oh
Sei-Ryang
SR
Ahn
Kyung-Seop
KS
Jeong
Gil-Saeng
GS
Li
Gao
G
Lee
Sang-Ku
SK
Joung
Hyouk
H
Lee
Hyeong-Kyu
HK
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001713:Biphenyl Compounds; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007723:Korea; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010666:Phenylpropionates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010851:Picrates / Q000494:pharmacology; D024301:Plant Bark / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D032362:Styrax / Q000737:chemistry*
D000975:Antioxidants; D001713:Biphenyl Compounds; D005663:Furans; D005960:Glucosides; D006027:Glycosides; D017705:Lignans; D010666:Phenylpropionates; D010851:Picrates; C431125:pinoresinol glycoside; C496600:styraxlignolide B; D009828:Oleanolic Acid; C005802:taraxerol; C004931:1,1-diphenyl-2-picrylhydrazyl; C028305:syringin; D015107:4-Butyrolactone