Abstract
A new characteristic steroidal glycoside possessing a hydroxyl group at C-23, inunigroside A (1), was isolated from the withered berries of Solanum nigrum L. On the basis of spectroscopic analysis, the structure of 1 was characterized as (5α,22S,23S,25R)-3β,23-dihydroxyspirostane 3-O-β-lycotetraoside. Next, a major steroidal sapogenol, (22R, 25S)-3β,15α-dihydroxy-spirost-5-ene (3), was obtained from the acid hydrolysate of the methanolic extract of the aerial parts of Solanum jasminoides L. A new bisdesmoside, 3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl (22R,25S)-3β,15α-dihydroxyspirost-5-ene 15-O-α-l-rhamnopyranoside (4), named jasminoside A, was isolated from the methanolic extract of S. jasminoides.
References
Saijo R, Murakami K, Nohara T, Tomimatsu T, Sato A, Matsuoka K (1982) Studies on the constituents of the immature berries of Solanum nigrum L. Yakugaku Zasshi 102:300–305
Nohara T, Ikeda T, Fujiwara Y, Matsushita S, Noguchi E, Yoshimitsu H, Ono M (2007) Physiological functions of solanaceous and tomato steroidal glycosides. J Nat Med 61:1–13
Noguchi E, Fujiwara Y, Matsushita S, Ikeda T, Ono M, Nohara T (2006) Metabolism of tomato steroidal glycosides in human. Chem Pharm Bull 54:1312–1314
Nohara T (2010) Efficacy of tomato-saponin, esculeoside A. J Tradit Med 27:217–224
Nohara T, Ono M, Ikeda T, Fujiwara Y, El-Aasr M (2010) The tomato saponin, esculeoside A. J Nat Prod 73:1734–1741
Yoshida K, Yahara S, Saijo R, Murakami K, Tomimatsu T, Nohara T (1887) Changes caused by included enzymes in the constituents of Solanum nigrum berries. Chem Pharm Bull 35:1645–1648
Ito S, Takahama H, Kawaguchi T, Tanaka S, Iwaki MJ (2002) Post-transcriptional silencing of the tomatinase gene in Fusarium oxysporum f. sp lycopersici. Phytopathology 150:474–480
Matsushita S, Yanai Y, Fusyuku A, Ikeda T, Ono M, Nohara T (2007) Distinction of absolute configuration at C-23 of C-23-hydroxyspirostane and C-23-hydroxy-spirosolane glycosides. Chem Pharm Bull 55:1079–1081
Freire R, Gonzalez AG, Suarez E (1970) New sources of steroid sapogenins––VIII: Sceptrumgenin and isoplexigenin A, B, C and D from Isoplexis sceptrum. Tetrahedron 26:3233–3244
Matsushita S, Yoshizaki M, Fujiwara Y, Ikeda T, Ono M, Okawara T, Nohara T (2005) Facile conversion of 23-hydroxyspirosolane into pregnane. Tetrahedron Lett 46:3549–3551
Soule S, Guenter C, Vazquez A, Argandona V, Moyna P, Ferreira F (2000) An aphid repellent glycoside from Solanum laxum. Phytochemistry 55:217–222
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ohno, M., Murakami, K., El-Aasr, M. et al. New spirostanol glycosides from Solanum nigrum and S. jasminoides . J Nat Med 66, 658–663 (2012). https://doi.org/10.1007/s11418-012-0637-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-012-0637-z