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Planta Med 2009; 75(4): 371-374
DOI: 10.1055/s-0028-1112221
Natural Products Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Soyasaponin Bh, a Triterpene Saponin Containing a Unique Hemiacetal-Functional Five-Membered Ring from Glycine max (Soybeans)

Zulfiqar Ali1 , Shabana I. Khan1 , Ikhlas A. Khan1 , 2
  • 1National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, Mississippi, USA
  • 2Department of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, Mississippi, USA
Further Information

Publication History

Received: July 16, 2008 Revised: November 10, 2008

Accepted: November 20, 2008

Publication Date:
15 January 2009 (online)

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Erratum for: Soyasaponin Bh, a Triterpene Saponin Containing a Unique Hemiacetal-Functional Five-Membered Ring from Glycine max (Soybeans)Planta Med 2011; 77(13): 1567-1567
DOI: 10.1055/s-0031-1280145

Abstract

Soybeans (Glycine max L. Merill) and soy-based food products are major dietary sources of saponins. An oleanane triterpenoid saponin, soyasaponin Bh (1) containing a unique five-membered ring with a hemiacetal functionality together with seven known saponins were isolated from soybeans. Their structures were determined by chemical and spectroscopic analyses including HR-ESI-MS, 1D- and 2D-NMR. None of the isolated saponins showed any anti-cell proliferative activity in tumor cell lines. Soysaponin I showed a weak estrogenic effect in the yeast estrogen screen (YES) assay.

Key words

Glycine max - Fabaceae - soybeans - soyasaponin Bh - hemiacetal

References

  • 1 Oakenfull D. Saponins in food – a review.  Food Chem. 1981;  7 19-40
    CrossrefPubMedGoogle Scholar
  • 2 Fenwick D E, Oakenfull D. Saponin content of food plants and some prepared foods.  J Sci Food Agric. 1988;  34 186-91
    PubMedGoogle Scholar
  • 3 Baxter R L, Price K R, Fenwick G R. Sapogenin structure: analysis of the 13C- and 1H-NMR spectra of soyasapogenol B.  J Nat Prod. 1990;  53 298-302
    CrossrefPubMedGoogle Scholar
  • 4 Hu J, Reddy M B, Hendrich S, Murphy P A. Soyasaponin I and sapogenol B have limited absorption by Caco-2 intestinal cells and limited bioavailability in women.  J Nutr. 2004;  134 1867-73
    PubMedGoogle Scholar
  • 5 Kinjo J, Morito K, Tsuchihashi R, Hirosa T, Aomori T, Okawa M. Examination of estrogenic activities of soyasaponin I and related compounds.  Natural Med. 2004;  58 193-7
    PubMedGoogle Scholar
  • 6 Kitagawa I, Wang H K, Taniyama T, Yoshikawa M. Saponin and sapogenol. XLI. Reinvestigation of the structures of soyasapogenols A, B, and E, oleanene-sapogenols from soybean. Structures of soyasaponins I, II, and III.  Chem Pharm Bull. 1988;  36 153-61
    PubMedGoogle Scholar
  • 7 Burrows J C, Price K R, Fenwick G R. Soyasaponin IV an additional monodesmosidic saponin isolated from soyabean.  Pytochemistry. 1987;  26 1214-5
    CrossrefPubMedGoogle Scholar
  • 8 Kitagawa I, Taniyama T, Yoshikawa M. Saponin and sapogenol. XXXIX. Structure of soyasaponin A1, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max Merrill.  Chem Pharm Bull. 1985;  33 1069-76
    PubMedGoogle Scholar
  • 9 Kitagawa I, Saito M, Taniyama T, Yoshikawa M. Saponin and sapogenol. XXXVIII. Structure of soyasaponin A2, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max Merrill.  Chem Pharm Bull. 1985;  33 598-608
    PubMedGoogle Scholar
  • 10 Kitagawa I, Taniyama T, Nagahama Y, Okubo K, Yamauchi F, Yoshikawa M. Saponin and sapogenol. XLII. Structures of acetyl-soyasaponins A1, A2, and A3, astringent partially acetylated bisdesmosides of soyasapogenol A, from American soybean, the seeds of Glycine max Merrill.  Chem Pharm Bull. 1988;  36 2819-28
    PubMedGoogle Scholar
  • 11 Shiraiwa M, Kudo S, Shimoyamada M, Harada K, Okubo K. Composition and structure of ”group A saponin” in soybean seed.  Agric Biol Chem. 1991;  55 315-22
    PubMedGoogle Scholar
  • 12 Arao T, Kinjo J, Nohara T, Isobe R. Leguminous plants. III. Oleanene-type triterpene glycosides from Puerariae Radix. IV. Six new saponins from Pueraria lobata. .  Chem Pharm Bull. 1997;  45 362-6
    PubMedGoogle Scholar
  • 13 Miyao H, Sakai Y, Takeshita T, Kinjo J, Nohara T. Triterpene saponins from Abrus cantoniensis (Leguminosae). I. Isolation and characterization of four new saponins and a new sapogenol.  Chem Pharm Bull. 1996;  44 1222-7
    CrossrefPubMedGoogle Scholar
  • 14 Cui B, Kinjo J, Nohara T. Triterpene glycosides from the bark of Robinia pseudoacacia L. II.  Chem Pharm Bull. 1993;  41 553-6
    PubMedGoogle Scholar
  • 15 Hara S, Okabe H, Mihashi K. Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)thiazolidine-4(R)-carboxylates.  Chem Pharm Bull. 1987;  35 501-6
    CrossrefPubMedGoogle Scholar
  • 16 Mustafa J, Khan S I, Ma G, Walker L A, Khan I A. Synthesis and anticancer activities of fatty acid analogs of podophyllotoxin.  Lipids. 2004;  39 167-72
    CrossrefPubMedGoogle Scholar
  • 17 Tabanca N, Khan S I, Bedir E, Annavarapu S, Willett K, Khan I A. Estrogenic activity of isolated compounds and essential oils of Pimpinella species from Turkey, evaluated using a recombinant yeast screen.  Planta Med. 2004;  70 728-35
    Article in Thieme ConnectPubMedGoogle Scholar
  • 18 Moein M R, Khan S I, Ali Z, Ayatollahi S AM, Kobarfard F, Nasim S. Flavonoids from Iris songarica and their antioxidant and estrogenic activity.  Planta Med. 2008;  74 1492-5
    Article in Thieme ConnectPubMedGoogle Scholar
  • 19 Hosny M, Rosazza J PN. Novel isoflavone, cinnamic acid, and triterpenoid glycosides in soybean molasses.  J Nat Prod. 1999;  62 853-8
    CrossrefPubMedGoogle Scholar

Ikhlas A. Khan

National Center for Natural Products Research

University of Mississippi

University

MS 38677

USA

Phone: +1-662-915-7821

Fax: +1-662-915-7989

Email: ikhan@olemiss.edu

    www.thieme-connect.de/ejournals/toc/plantamedica