Download PDF
Planta Med 2012; 78(17): 1851-1856
DOI: 10.1055/s-0032-1315391
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Prenylated Flavonoids from the Roots of Desmodium caudatum and Evaluation of Their Antifungal Activity

Hisako Sasaki
1   Graduate School of Pharmaceutical Sciences, University of Tokushima, Tokushima, Japan
,
Yoshiki Kashiwada
1   Graduate School of Pharmaceutical Sciences, University of Tokushima, Tokushima, Japan
,
Hirofumi Shibatav
,
Yoshihisa Takaishi
1   Graduate School of Pharmaceutical Sciences, University of Tokushima, Tokushima, Japan
› Author Affiliations
Further Information

Publication History

received 09 July 2012
revised 29 August 2012

accepted 31 August 2012

Publication Date:
11 October 2012 (online)

    Permissions and Reprints

Abstract

Two new prenylated flavonoids (1, 4) and two new prenylated C-methyl-flavonoids (6, 7), together with four known flavonoids (2, 3, 5, 8), were isolated from the roots of Desmodium caudatum. The structures of the new compounds were elucidated by extensive spectroscopic analyses including 1D-, 2D-NMR and MS. The antifungal activities of five compounds (1, 2, 4, 6, 8) as well as nine flavonoids (9–17) previously isolated from this plant against Aspergillus niger, Penicillium sp., Rhizopus sp., and Trichophyton sp. were evaluated. Compound 6 showed potent antifungal activity against Trichophyton sp. with a minimum inhibitory concentration (MIC) value of 1.95 µg/mL.

Key words

Desmodium caudatum - Fabaceae - prenylated flavonoid - antifungal activity
 

  • References

  • 1 Makino T. Makinoʼs new illustrated flora of Japan. Tokyo: Hokuryu-kan Publishing Co., Ltd.; 1998: 209
    Google Scholar
  • 2 Jiangsu New Medical College. Chinese materia medica. Shanghai: Shanghai Peopleʼs Publishing House; 1977: 1240
    Google Scholar
  • 3 Sasaki H, Kashiwada Y, Shibata H, Takaishi Y. Prenylated flavonoids from Desmodium caudatum and evaluation of their anti-MRSA activity. Phytochemistry 2012; 82: 136-142
    CrossrefPubMedGoogle Scholar
  • 4 Takatori K. Eumycetes inspection manual. Tokyo: Technosystem Co., Ltd.; 2002: 220-419 (in Japanese)
    Google Scholar
  • 5 Saitoh T, Kinoshita T, Shibata S. Flavonols of licorice root. Chem Pharm Bull 1976; 24: 1242-1245
    CrossrefPubMedGoogle Scholar
  • 6 Jia SS, Liu D, Wang HQ, Suo ZX. Isolation and identification of gancaonin p-3′-methylether from the leaves of Glycyrrhiza uralensis Fisch. Acta Pharm Sin 1993; 28: 623-625
    PubMedGoogle Scholar
  • 7 Wu TS. A 2,2-dimethylpyranoflavonol from Citrus nobilis . Phytochemistry 1987; 26: 3094-3095
    CrossrefPubMedGoogle Scholar
  • 8 Ueno A, Ikeya Y, Fukushima S, Noro T, Morinaga K, Kuwano H. Studies on the constituents of Desmodium caudatum DC. Chem Pharm Bull 1978; 26: 2411-2416
    CrossrefPubMedGoogle Scholar
  • 9 Gaffield W. Circular dichroism, optical rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides. Tetrahedron 1970; 26: 4093-4108
    CrossrefPubMedGoogle Scholar
  • 10 Slade D, Ferreira D, Marais JPJ. Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. Phytochemistry 2005; 66: 2177-2215
    CrossrefPubMedGoogle Scholar
  • 11 Sutthivaiyakit S, Thongnak O, Lhinhatrakool T, Yodchun O, Srimark R, Dowtaisong P, Chuankamnerdkarn M. Cytotoxic and antimycobacterial prenylated flavonoids from the roots of Eriosema chinense . J Nat Prod 2009; 72: 1092-1096
    CrossrefPubMedGoogle Scholar