Gomisins

Two classes of a-hydroxylated lignans have been enantioselectively prepared a) wikstromol (3) [10, 38] and related natural products [39] and b) gomisin A (1) and congeners [40, 41]. In both cases, chiral, non-racemic ita-conic acid derivatives have been synthesized as key compounds for the preparation of -benzyl-y-butyrolactones (either by resolution (g [32]) or by asymmetric hydrogenation (h [25])). 

Fujihashi T, Hara H, Sakata T, Mori K, Higuchi H, Tanaka A, Kaji H, Kaji A (1995) Anti-Human Immunodeficiency Virus (HIV) Activities of Halogenated Gomisin J Derivatives, New Nonnucleoside Inhibitors of HIV Type 1 Reverse Transcriptase. Antimicrob Agents Chemother 39 2000... 

Tanaka M, Mukaiyama C et al (2002) Synthesis of optically pure gomisi lignans the total synthesis of (+)-schizandrin, (+)-gomisin A, and (+)-isoschizandrin in naturally occurring forms. J Org Chem 60 4339 -352... 

Further examples of oxidative arylic coupling within this family of lignan precursors include the preparation of (+)-schizandrin (169) and (+)-gomisin A (170) (Figure 5), as published by Tanaka and co-workers. In this instance, the key Ar-Ar coupling step with 194 was realized using either ruthenium tetrakis(trifluoroacetate) or iron perchlorate (Scheme 47) [124, 131-133]. As pointed out by the authors, this result was noteworthy as this simple... 

The hepatoprotective efficacy of Schizandra chinensis is based on its lignoids Gomisines A, C, N, Wuweizisu C and Schisanthesin D. (302) A rapid decrease in transaminases was verified in chronic viral hepatitis (189 patients). (308) Hepatoprotective and anticarcinogenic effects were demonstrated in experimental studies. (301, 303-307)... 

Kiso, Y., Tohkin, M., Hikino, H., Dreya, Y., Tagnchi, H. Mechanism of antihepatotoxic activity of Wuweizisu C and Gomisin Al. Planta... 

Maeda, S., Takeda, S., I> yamoto, Y., Aburada, M., Harada, M. Effects of Gomisin A on liver functions in hepatotoxic chemicals-treated rats. Jpn. J. Pharmacol. 1985 38 347-353... 

Miyamoto, K., Wakusawa, S., Nomura, M., Sanae, F., Sakai, R., Sudo, K., Ohtaki, Y., Takeda, S., Fujii, Y. Effects of Gomisin A on hepato-carcinogenesis by 3 -methyl-4-dimethylaminoazobenzene in rats. Japan... 

The earliest work on the isolation and structure elucidation was performed by Kochetkov and co-workers (154,155). Particularly noteworthy have been the continuing efforts of Ikeya and Taguchi and their co-workers on the isolation, structure elucidation and absolute configuration determination of the schizandrins and gomisins beginning in 1979 (156). Application of a wide range of techniques (UV,... 

Carragenin-induced paw edema and 12-0-tetradecanoylphorbol 13-acetate (TPA)-induced edema have been used as experimental models of acute inflammation. Gomisin A (49), gomisin J (140), and wuweizisu C (141) inhibited inflammation induced by TPA in mice [44], Diphyllin acetyl apioside (142) and diphyllin apioside (tuberculatin) (143) also showed an anti-inflammatory effect with IDjg values of 0.27 and 1.23 pM/ ear, respectively, in rabbit [98]. 

K Miyamoto, K Hiramatsu, Y Ohtani, M Kanitani, M Nomura, M Aburada. Effects of gomisin A on the promotor action and serum bile acid concentration in hepatocarcino-genesis induced by 3 -methyl-4-dimethy aminoazobenzene. Biol Pharm Bull 18 1443-1445, 1994. 

Y Ohtani, M nomura, T Hida, K Miyamoto, M Kanitani, T Aizawa, M Aburada. Inhibition by gomisin A, a lignan compound, of hepatocarcinogenesis by 3 -methyl-4-dimethylaminoazobenzene in rat. Biol Pharm Bull 17 808-814,1994. 

K Miyamoto. Gomisin A, a lignan component of Schizandra fruits, inhibits develope-ment of preneoplastic lesions in rat liver by 3 -methyl-4- dimethylamino-azobenzene. Cancer Letters 1994. 

K Miyamoto, S Wakusawa, M Nomura, F Sanae, R Sakai, K Sudo, Y Ohtani, S Takeda, Y Fujii. Effect of gomisin A on hepatocarcinogenesis by 3 -methyM- dimethylamino-azobenzene in rats. Japan J Pharmacol 57 71-77, 1991. 

KYasukawa, Y Ikeya, H Mitsuhashi, M Iwasaki, M Aburada, S Nakagawa, M Takeuchi, M Takido. Gomisin A inhibits tumor promotion by 12-0-tetra-decanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin. Oncology 49 68-71, 1992. 

Y Kiso, M Tohkin, H Hikino, Y Bceya, H Taguchi. Mechanism of antihepatotoxic activity of wnweizisn C and gomisin A. Planta Medica 331-334, 1985. 

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