Nor-lignans and Steroidal Saponins from Asparagus gobicus

Abstract

From the roots of Asparagus gobicus, four new nor-lignans, 3′-methoxynyasin, iso-agatharesinol, gobicusins A, B and one new steroidal saponin, 3-O-[β-D-xylopyranosyl(1 - 4)-β-D-glucopyranosyl(1 - 2)-β-D-glucopyranosyl]-(25S)-5β-spirostan-3β-ol (11) were isolated, together with twelve known compounds. The structures of the new compounds were established by spectroscopic methods including 2D-NMR techniques (¹H-¹H COSY, HMBC, HMQC) and chemical transformations. Nyasol (5) and 11 exhibited remarkable in vitro cytotoxic activity against cultured HO-8910 (human ovarian carcinoma) and Bel-7402 (human hepatoma) cells with IC₅₀ vales of 30.6 and 29.4 μM, 5.2 and 5.2 μM, respectively.

Key words

Asparagus gobicus - Asparagaceae - nor-lignans - steroidal saponins - cytotoxic activity

References

• 1 Jiangsu New Medical College. A Dictionary of the Traditional Chinese Medicines. Shanghai; Shanghai Science and Technology Press 1985: p 4693
• 2 Jiangsu New Medical College, A Dictionary of the Traditional Chinese Medicines. Shanghai; Shanghai Science and Technology Press 1985: p 318
• 3 Sharma S C, Sati O P, Chand R. Steroidal saponins from Asparagus curillus fruits.  Planta Med. 1983;  47 117-20
• 4 Sharma S C, Thakur N K. Furostanosides from Asparagus filicinus roots.  Phytochemistry. 1994;  36 469-71
• 5 Sati O P, Pant G. Spirostanol glycosides from Asparagus plumosus .  Phytochemistry. 1985;  24 123-6
• 6 Sharma S C, Sati O P, Chand R. Steroidal saponins of Asparagus curillus .  Phytochemistry. 1982;  21 1711-4
• 7 Sharma S C, Sati O P, Chand R. Steroidal saponins of Asparagus adscendens .  Phytochemistry. 1982;  21 2075-8
• 8 Konishi T, Shoji J. Studies on the constitutent of Asparagus radix.  Chem Pharm Bull. 1979;  27 3086-94
• 9 Ding Y, Yang C R. Steroidal saponins from Asparagus filicinus .  Acta Pharmacutica Sinica. 1990;  25 509-14
• 10 Minami E, Taki M, Takaishi S, Iuima Y, Tsutsumi S, Akiyama T. Sterochemistry of cis- and trans-hinokiresinol and their estrogen-like activity.  Chem Pharm Bull. 2000;  48 389-92
• 11 Oketch-Rabah H A, Dossaji S F. Antiprotozoal compound from Asparagus africanus .  J Nat Prod. 1997;  60 1017-22
• 12 Su B N, Zhu Q X, Gao K, Yuan C S, Jia Z J. Lignan and phenylpropanoid glycosides from Lancea tibetica and their antitumor activity.  Planta Med. 1999;  65 558-561
• 13 Marini-Bettolo G B, Nicoletti M, Messana I. Research on African medicinal plants - X. Glucosides of Kypoxis nyasica Bak.  Tetrahedron. 1985;  41 665-70
• 14 Terada K, Honda C, Suwa K, Takeyama S, Oku H, Kamisako W. Acetylenic compounds isolated from cultured cells of Asparagus officinalis .  Chem Pharm Bull. 1995;  43 564-6
• 15 Hatom N AR, Whiting D A. Constituents of Californian redwood. Tetrahedron Letters 1967: 781-5
• 16 Tori K, Seo S, Terui Y, Nishikawa J, Yasuda F. ¹³C NMR spectra of 5β-steroidal sapogenins.  Tetrahedron Letters. 1981;  22 2405-8
• 17 Luo X D, Wu S H, Ma Y B, Wu D G. Chemical constitutents from Dysoxylum hainanense .  Acta Botanica Yunnanica. 2001;  23 368-72
• 18 Enzell C R, Thomas B R. The chemistry of the order Araucariales 5.  Tetrahedron. 1966;  22 2395-02
• 19 Enzell C R, Thomas B R. The chemistry of the order Araucariales.  Acta Chem Scand. 1965;  19 913-9
• 20 Norman J R, Katzenellenbogen E, Dobriner K. The infrared absorption spectra of steroid sapogenins.  J Am Chem Soc. 1953;  75 158-66