Triterpenoidal Saponins: Bioactive Secondary Metabolites from Zygophyllum coccineum

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
• 2 El-Hadidi M N. Flora des Iranischen Hochgebirges und der umrahmenden Gebirge, Vol. 98. Graz; Akademische Druck- und Verlagsanstalt 1972: 28
• 3 Saber A H, El-Moghazy A M. Zygophyllum coccineum. V. The chemistry of the leaf and stem.  J Pharm Sci. 1960;  1 135
• 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
• 5 Gibbons S, Oriowo M A. Antihypertensive effect of an aqueous extract of Zygophyllum coccineum L. in rats.  Phytother Res. 2001;  15 452-455
• 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
• 7 Ahmed V U, Uddin G S, Ali M S. Saponins from Zygophyllum probinquum.  Phytochemistry. 1993;  33 453-455
• 8 Attia A A. Triterpenoidal saponins from the aerial parts of Zygophyllum coccineum and Zygophyllum fabago.  Pharmazie. 1999;  54 931-934
• 9 Ahmed V U, Uddin G S. A triterpenoid saponin from Zygophyllum propinquum.  Phytochemistry. 1992;  31 1051-1054
• 10 Ahmad V U, Uddin G S, Bano S. Saponins from Zygophyllum propinquum.  J Nat Prod. 1990;  53 1193-1197
• 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
• 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
• 13 Harput Ü S, Saracoğlu Ï, Ogihara Y. Methoxyflavonoids from Pinaropappus roseus.  Turk J Chem. 2004;  28 761-766
• 14 Wedge D E, Kuhajek J M. A microbioassay for fungicide discovery.  SAAS Bull Biochem Biotechnol. 1998;  11 1-7
• 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
• 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