Antifungal Steroid Saponins from Dioscorea cayenensis

 

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Abstract

From the rhizomes of Dioscorea cayenensis Lam.-Holl (Dioscoreaceae), the new 26-O-β-D-glucopyranosyl-22-methoxy-3β,26-dihydroxy-25(R)-furost-5-en-3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (1) was isolated together with the known dioscin (2) and diosgenin 3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (3). Their structures were established on the basis of spectral data. Compound 2 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs of 12.5, 12.5 and 25 µg/mL, respectively) whereas 3 showed weak activity and 1 was inactive.

References

• 1 Hu K, Dong A, Yao X, Kobayashi H, Iwasaki S. Antineoplasic agents; I. Three spirostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca .  Planta Med. 1996;  62 573-5
  PubMedGoogle Scholar
• 2 Hu K, Dong A, Yao X, Kobayashi H, Iwasaki S. Antineoplasic agents; II. Four furostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca .  Planta Med. 1997;  63 161-5
  PubMedGoogle Scholar
• 3 Dong M, Feng X Z, Wu L J, Wang B X, Ikejima T. Two new steroidal saponins from the rhizomes of Dioscorea panthaica and their cytotoxic activity.  Planta Med. 2001;  67 853-7
  Article in Thieme ConnectPubMedGoogle Scholar
• 4 Liu H W, Hu K, Zhao Q C, Cui C B, Kobayashi H, Yao X S. Bioactive saponins from Dioscorea futschauensis .  Pharmazie. 2002;  57 570-2
  PubMedGoogle Scholar
• 5 Agbor-Egbe T, Treche S. Evaluation of the chemical composition of Cameroonian yam germplasm.  J Food Comp Anal. 1995;  8 274-83
  CrossrefPubMedGoogle Scholar
• 6 Brutus T C, Pierce-Noel A V. Les plantes et les légumes d'Haiti qui guérissent. Imprimerie de l'Etat Port-au-Prince, Haiti; 1960
  Google Scholar
• 7 Altschul S VR. Drugs and Foods from Little Known Plants (Harvard Herbarium). Cambridge, MA; Harvard Univ. Press 1973
  Google Scholar
• 8 Lin R C, Hanquet B, Lacaille-Dubois M A. Aferoside A, a steroidal saponin from Costus afer .  Phytochemistry. 1996;  3 665-8
  PubMedGoogle Scholar
• 9 Lin R C, Lacaille-Dubois M A, Hanquet B, Correia M, Chauffert B. New diosgenin glycosides from Costus afer .  J Nat Prod. 1997;  60 1165-9
  CrossrefPubMedGoogle Scholar
• 10 Pereira Da Silva B P, Bernardo R R, Parente J P. A furostanol glycoside from rhizomes of Costus spicatus .  Phytochemistry. 1999;  51 931-5
  CrossrefPubMedGoogle Scholar
• 11 Agrawal P K, Jain D C, Pathak A K. NMR spectroscopy of steroidal sapogenins and steroidal saponins: an update.  Mag Reson Chem. 1995;  33 923-53
  PubMedGoogle Scholar
• 12 Ju Y, Jia Z J. Steroidal saponins from the rhizomes of Smilax menispermoidea .  Phytochemistry. 1992;  4 1349-51
  PubMedGoogle Scholar
• 13 Buckingham J B. Dictionary of Natural Products on CD-ROM, Version 10 : 2. Chapman and Hall, CRC Press London, UK; 2002
  Google Scholar
• 14 Matsuda H, Pongpiriyadacha Y, Morikawa T, Kishi A, Kataoka S, Yoshikawa M. Protective effects of steroid saponins from Paris polyphylla var. yunnanensis on ethanol - or indomethacin-induced gastric mucosal lesions in rats: structural requirement for activity and mode of action.  Bioorg Med Chem Lett. 2003;  13 1101-6
  CrossrefPubMedGoogle Scholar
• 15 Takechi M, Tanaka Y. Structure-activity relationships of the saponin α hederin.  Phytochemistry. 1990;  2 451-2
  PubMedGoogle Scholar
• 16 Takechi M, Tanaka Y. Structure-activity relationships of synthetic diosgenyl monoglycosides.  Phytochemistry. 1991;  8 2557-8
  PubMedGoogle Scholar
• 17 Haddad M, Miyamoto T, Laurens V, Lacaille-Dubois M A. Two new biologically active triterpenoidal saponins acylated with salicylic acid from Albizia adianthifolia .  J Nat Prod. 2003;  66 372-7
  CrossrefPubMedGoogle Scholar
• 18 Quiroga E N, Sampietro A R, Vattuone M A. Screening antifungal activities of selected medicinal plants.  J Ethnopharmacol. 2001;  74 89-96
  CrossrefPubMedGoogle Scholar
• 19 Favel A, Steinmetz M D, Regli P, Vidal-Ollivier E, Elias R, Balansard G. In vitro antifungal activity of triterpenoid saponins.  Planta Med. 1994;  60 50-3
  Article in Thieme ConnectPubMedGoogle Scholar

Prof. Marie-Aleth Lacaille-Dubois

Laboratoire de Pharmacognosie

Unité UMIB, EA 3660

Faculté de Pharmacie

Université de Bourgogne

7, Bd. Jeanne d'Arc

BP 87900

21079 Dijon Cedex

France

Fax: +33-3-80-39-33-00

Email: malacd@u-bourgogne.fr