Steroidal Saponins Isolated from an Australian Yam Dioscorea sp.
Victoria L. Challinor A , David M. Smith A and James J. De Voss A BA School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.
B Corresponding author. Email: j.devoss@uq.edu.au
Australian Journal of Chemistry 64(5) 545-549 https://doi.org/10.1071/CH11056
Submitted: 31 January 2011 Accepted: 5 March 2011 Published: 30 May 2011
Abstract
Phytochemical characterization of the rhizome of an Australian species of Dioscorea, acquired as Dioscorea transversa R Br. but botanically identified as Dioscorea sp., led to the isolation of two steroidal saponins. The major constituent 1β-hydroxyprotogracillin (1) was previously unknown while the minor one was identified as protogracillin (2). The structure and stereochemistry of 1 were elucidated using a combination of MS studies, 1D and 2D NMR experiments and chemical degradation.
References
[1] L. R. Caddick, P. Wilkin, P. J. Rudall, T. A. J. Hedderson, M. W. Chase, Taxon 2002, 51, 103.| Crossref | GoogleScholarGoogle Scholar |
[2] P. Wilkin, P. Schols, M. W. Chase, K. Chayamarit, C. A. Furness, S. Huysmans, F. Rakotonasolo, E. Smets, C. Thapyai, Syst. Bot. 2005, 30, 736.
| Crossref | GoogleScholarGoogle Scholar |
[3] Australian Plant Name Index IBIS database, Centre for Australian National Biodiversity Research. Australian Government: Canberra. Available online at: http://www.cpbr.gov.au/cgi-bin/apni [accessed 2 January 2011].
[4] R. Asiedu, A. Sartie, Food Sec. 2010, 2, 305.
| Crossref | GoogleScholarGoogle Scholar |
[5] B. van Wyk, M. Wink, Medicinal Plants of the World 2004 (Briza Publications: Pretoria).
[6] M. Sautour, A. C. Mitaine-Offer, M. A. Lacaille-Dubois, J. Nat. Med. 2007, 61, 91.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXkt1WlsLg%3D&md5=807d9adca908342ced3b9d7c55c00df9CAS |
[7] S. G. Sparg, M. E. Light, J. van Staden, J. Ethnopharmacol. 2004, 94, 219.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmvFWktrc%3D&md5=184a7af4282b1200b0fdcf4556ebca1dCAS | 15325725PubMed |
[8] P. K. Agrawal, Steroids 2005, 70, 715.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXmtFSntrY%3D&md5=9007ee084c7feb2c26d6f9f4ec435349CAS | 15923015PubMed |
[9] This assumes that the steroidal nucleus of the aglycone has the absolute configuration reported for all other naturally occurring steroids and in particular for the co-occurring and structurally related protogracillin 2.
[10] E. Fattorusso, M. Iorizzi, V. Lanzotti, O. Taglialatela-Scafati, J. Agric. Food Chem. 2002, 50, 5686.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmtlGksrc%3D&md5=0d339c3b958d3ca619a040b9b8103dd1CAS | 12236699PubMed |
[11] G. Corea, E. Fattorusso, V. Lanzotti, J. Nat. Prod. 2003, 66, 1405.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXotVGht7c%3D&md5=31c13ec8950b9b344af1cc0bf0ffc556CAS | 14640509PubMed |
[12] G. Corea, E. Fattorusso, V. Lanzotti, R. Capasso, A. A. Izzo, J. Agric. Food Chem. 2005, 53, 935.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXkvVOisw%3D%3D&md5=279ce74023f6a4d2eb8388c939f80607CAS | 15713001PubMed |
[13] I. Dini, G. C. Tenore, E. Trimarco, A. Dini, Food Chem. 2005, 93, 205.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXkt1alsrk%3D&md5=6781157fa29af2d1213529a4f407a272CAS |
[14] W. A. König, I. Benecke, H. Bretting, Angew. Chem. Int. Ed. Engl. 1981, 20, 693.
| Crossref | GoogleScholarGoogle Scholar |
[15] T. Kawasaki, T. Komori, K. Miyahara, T. Nohara, I. Hosokawa, K. Mihashi, Chem. Pharm. Bull. 1974, 22, 2164.
| 1:CAS:528:DyaE2MXjtFCrsw%3D%3D&md5=825b20a2dbe97de5b6fb285105eb32f9CAS |
[16] K. Inoue, S. Kobayashi, H. Noguchi, U. Sankawa, Y. Ebizuka, Nat. Med. 1995, 49, 336.
| 1:CAS:528:DyaK2MXhtVSlsLzJ&md5=5558d15ded9db180c69fd80f63ad22dbCAS |
[17] R. Aquino, I. Behar, F. De Simone, M. D’Agostino, C. Pizza, J. Nat. Prod. 1986, 49, 1096.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXhvFaksbw%3D&md5=9e45c145be76dd69afb255667a366672CAS |
[18] A. Perrone, T. Muzashvili, A. Napolitano, A. Skhirtladze, E. Kemertelidze, C. Pizza, S. Piacente, Phytochemistry 2009, 70, 2078.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFSht7bI&md5=d74cb6e34a592f0b2d03e1cac244290cCAS | 19772977PubMed |
[19] L. Yuan, T. F. Ji, A. G. Wang, J. B. Yang, Y. L. Su, Chin. Chem. Lett. 2008, 19, 461.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmtlaqu7Y%3D&md5=bd173fa8c7f62f3b38dbecde8a0fb79fCAS |