Download PDF
Planta Med 2011; 77(5): 488-491
DOI: 10.1055/s-0030-1250463
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Triterpenoidal Saponins: Bioactive Secondary Metabolites from Zygophyllum coccineum

Elham Amin1 , 5 , Seham S. El-Hawary2 , Magda M. Fathy2 , Rabab Mohammed1 , Zulfiqar Ali5 , Nurhayat Tabanca3 , David E. Wedge3 , James J. Becnel4 , Ikhlas A. Khan5
  • 1Faculty of Pharmacy, Beni Suef University, Beni Suef, Egypt
  • 2Faculty of Pharmacy, Cairo University, Cairo, Egypt
  • 3U. S. Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, University of Mississippi, University, MS, USA
  • 4USDA, ARS, Center for Medical, Agricultural, and Veterinary Entomology Gainesville, Gainesville, FL, USA
  • 5National Center for Natural Products Research, University of Mississippi, University, MS, USA
Further Information

Publication History

received July 27, 2010 revised September 27, 2010

accepted September 30, 2010

Publication Date:
26 October 2010 (online)

Also available at
    Permissions and Reprints

Abstract

Phytochemical investigation of the aerial parts of Zygophyllum coccineum L. led to the isolation of nine ursane-type triterpene saponins (1–9), including the new one; zygophylloside S (1), together with a known flavonoid glycoside (10) and a sterol glycoside (11).The isolated compounds were tested for antifungal activity against several important plant pathogens and for insecticidal activity against two important mosquito species. Among the isolated compounds 1, 3, 5, 6, and 9 showed 32–77 % fungal growth inhibition at a concentration of 30 µM against Phomopsis viticola. Compound 9 showed 90 % and 80 % mosquitocidal activity at 3.1 µg/0.5 µL against Aedes aegypti and Culex quinquefasciatus, respectively.

Key words

Zygophyllum coccineum L. - Zygophyllaceae - ursane‐type triterpene glycosides - zygophylloside S - antifungal activity - insecticidal activity

References

  • 1 Sparg S G, Light M E, Staden J V. Biological activities and distribution of plant saponins.  J Ethnopharmacol. 2004;  94 219-243
    CrossrefPubMedSearch in Google Scholar
  • 2 El-Hadidi M N. Flora des Iranischen Hochgebirges und der umrahmenden Gebirge, Vol. 98. Graz; Akademische Druck- und Verlagsanstalt 1972: 28
    Search in Google Scholar
  • 3 Saber A H, El-Moghazy A M. Zygophyllum coccineum. V. The chemistry of the leaf and stem.  J Pharm Sci. 1960;  1 135
    CrossrefPubMedSearch in Google Scholar
  • 4 Eskander E F, Won J H. Hypoglycaemic and hyperinsulinemic effects of some Egyptian herbs used for treatment of diabetes mellitus (Type II) in rats.  Egypt J Pharm Sci. 1995;  36 331-341
    PubMedSearch in Google Scholar
  • 5 Gibbons S, Oriowo M A. Antihypertensive effect of an aqueous extract of Zygophyllum coccineum L. in rats.  Phytother Res. 2001;  15 452-455
    CrossrefPubMedSearch in Google Scholar
  • 6 Poellmann K, Gagel S, Elgamal M H A, Shaker K H, Seifert K. Triterpenoid saponins from the roots of Zygophyllum species.  Phytochemistry. 1997;  44 485-489
    CrossrefPubMedSearch in Google Scholar
  • 7 Ahmed V U, Uddin G S, Ali M S. Saponins from Zygophyllum probinquum.  Phytochemistry. 1993;  33 453-455
    CrossrefPubMedSearch in Google Scholar
  • 8 Attia A A. Triterpenoidal saponins from the aerial parts of Zygophyllum coccineum and Zygophyllum fabago.  Pharmazie. 1999;  54 931-934
    PubMedSearch in Google Scholar
  • 9 Ahmed V U, Uddin G S. A triterpenoid saponin from Zygophyllum propinquum.  Phytochemistry. 1992;  31 1051-1054
    PubMedSearch in Google Scholar
  • 10 Ahmad V U, Uddin G S, Bano S. Saponins from Zygophyllum propinquum.  J Nat Prod. 1990;  53 1193-1197
    CrossrefPubMedSearch in Google Scholar
  • 11 Smati D, Offer A C M, Miyamoto T, Hammiche V, Dubois M A L. Ursane-type triterpene saponins from Zygophyllum geslini.  Helv Chim Acta. 2007;  90 712-719
    CrossrefPubMedSearch in Google Scholar
  • 12 Amin E, El-Hawary S S, Fathy M M, Mohammed R, Ali Z, Khan I A. Zygophylloside S, a new triterpenoid saponin from the aerial parts of Zygophyllum coccineum L.  Planta Med. 2010;  76 P51
    Thieme ConnectPubMedSearch in Google Scholar
  • 13 Harput Ü S, Saracoğlu Ï, Ogihara Y. Methoxyflavonoids from Pinaropappus roseus.  Turk J Chem. 2004;  28 761-766
    PubMedSearch in Google Scholar
  • 14 Wedge D E, Kuhajek J M. A microbioassay for fungicide discovery.  SAAS Bull Biochem Biotechnol. 1998;  11 1-7
    PubMedSearch in Google Scholar
  • 15 Pridgeon J W, Becnel J J, Clark G G, Linthicum K J. A high throughput screening method to identify potential pesticides for mosquito control.  J Med Entomol. 2009;  46 335-341
    CrossrefPubMedSearch in Google Scholar
  • 16 Gerberg E J, Barnard D R, Ward R A. Manual for mosquito rearing and experimental techniques: Bulletin No 5. Mount Laurel; American Mosquito Control Association 1994
    Search in Google Scholar

Ikhlas A. Khan, PhD

Research Institute of Pharmaceutical Sciences and
Department of Pharmacognosy, School of Pharmacy
National Center for Natural Products Research,
The University of Mississippi

University, MS 38677

USA

Phone: +166 29 15 78 21

Fax: +166 29 15 70 62

Email: ikhan@olemiss.edu

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