Anti-complement activity of norlignans and terpenes from the stem bark of Styrax japonica.
A new norlignan, styraxlignolide A (1), and two new terpenes, styraxosides A (2) and B (3), were isolated from the MeOH-soluble fraction of Styrax japonica Sieb. et Zucc. (Styracaceae) stem bark, together with two known compounds, egonol (4) and masutakeside I (5). The new compounds were determined as 5-(3''-hydroxypropyl)-7-methoxy-2-(3',4'-dimethoxyphenyl)-benzofuran 3''- O-[beta-D-xylopyranoside-(1-->6)-beta- D-glucopyranoside] (1), 3beta,7beta-dihydroxy-4alpha,4beta,8beta,10beta,14alpha-pentamethyl-5alpha-gon-16-en-2-one 3-O-[beta-D-glucopyranoside-(1-->2)-beta-D-glucopyranoside] (2), and 3beta,17beta-dihydroxy-28-norolean-12-en-16-one 3-O-[alpha-L-rhamopyranoside-(1-->2)-beta-D-glucuronopyranoside] (3) by spectroscopic means including 2D-NMR. The five compounds were tested in vitro for anti-complement activity against the complement system. Compounds 1, 3, 4, and 5 displayed inhibitory activity in the anti-complement assay, with IC50 values of 123, 65, 33, and 166 microM, respectively. Compound 1a and camellenodiol (3a), obtained from acid hydrolysis of 1 and 3, respectively, did not affect the hemolytic activity of human serum against sensitized erythrocytes. This shows that a sugar seems to play a role of enhancing significantly anti-complement activity.
Min
Byung-Sun
BS
Korea Research Institute of Bioscience and Biotechnology, Daejeon, Korea.
Oh
Sei-Ryang
SR
Ahn
Kyung-Seop
KS
Kim
Jung-Hee
JH
Lee
Joongku
J
Kim
Doo-Young
DY
Kim
Eun-Hee
EH
Lee
Hyeong-Kyu
HK
D003165:Complement System Proteins / Q000187:drug effects*; D004187:Disaccharides / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D006801:Humans; D020128:Inhibitory Concentration 50; D017705:Lignans / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D009682:Magnetic Resonance Spectroscopy; D008517:Phytotherapy; D024301:Plant Bark; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D032362:Styrax; D013729:Terpenes / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use
D004187:Disaccharides; D017705:Lignans; D010936:Plant Extracts; D013729:Terpenes; C000599169:styraxlignolide A; D003165:Complement System Proteins