Anti-Complement Activity of Norlignans and Terpenes from the Stem Bark ofStyrax japonica

Abstract

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.

Styraxoside A Isolated from the Stem Bark of <i>Styrax japonica</i> Inhibits Lipopolysaccharide-Induced Expression of Inducible Nitric Oxide Synthase and Cyclooxygenase-2 in RAW 264.7 Cells by Suppressing Nuclear Factor-kappa B Activation

“…Although it has been previously reported that certain triterpenoids and lignans isolated from S. japonica extract have pharmacological effects, i.e., anti-complementary, 32) antioxidative 34,35) and matrix metalloprotease (MMP)-1 inhibitory effects, 36,37) its anti-inflammatory effects and the mechanisms involved have not been addressed.…”

“…et ZUCC were used. 32) These compounds isolated were determined by HPLC to be Ͼ97% pure. Dulbecco's modified Eagle's minimum essential medium (DMEM), fetal bovine serum (FBS), penicillin, and streptomycin were obtained from Life Technologies Inc. (Grand Island, NY, U.S.A.).…”

“…17,18) Active NF-kB exists mainly as a heterodimer that consists of subunits of the Rel family p50 and p65, which is normally sequestered in the cytosol as an inactive complex by binding to inhibitors of kB (IkBs) in unstimulated cells. 19) The mechanism of NF-kB activation involves the phosphorylation of IkBs at two critical serine residues (Ser 32 and Ser…”

“…[26][27][28][29] Jegosaponins from fresh fruits display antisweet activity, 25) and egonol from seeds has attracted the attention of synthetic organic chemists, due to its activity against human leukemic HL-60 cells. 30,31) Although styraxoside B, egonol, masutakeside, and styraxlignolide A have been reported to play a role in the enhancement of anti-complement activity, 32) no report has been issued on its anti-inflammatory activity or mode of action. Therefore, we evaluated and compared the effects of various terpenes and lignans ( Fig.…”

Effects of egonol that isolated from seeds of Styrax officinalis (L.) on lipid peroxidation and antioxidant defense system in human erythrocytes

“…Moreover, egonol has been shown to inhibit the hemolytic activity of the complement system, which could be beneficial in the therapy of inflammatory diseases 24 . However, investigation of its antioxidant properties is quite incomplete.…”