Flavonoids, Coumarins and Triterpenes from the Aerial Parts of Cnidoscolus texanus

Abstract

Phytochemical investigation on Cnidoscolus texanus led to the isolation of 26 compounds, which included 15 flavonoids (1 - 15), three coumarins (16 - 18), three coumaric acid derivatives (19 - 21), four triterpenoids (22 - 25), and one phytosterol (26). Among them, aromadendrin 7-O-(4′′-O-p-E-coumaroyl-β-glucopyranoside) (1), aromadendrin 7-O-(3′′,6′′-di-O-p-E-coumaroyl-β-glucopyranoside) (2), and naringenin 7-O-(4′′-O-p-Z-coumaroyl-β-glucopyranoside) (3) are new compounds. Their structures were determined by spectroscopic and chemical methods. All flavonoids were found to be inactive against DNA topoisomerase I.

Key words

Cnidoscolus texanus - Euphorbiaceae - flavonoids - topoisomerase I - coumarins - triterpenoids

References

• 1 Kolterman D A, Breckon G J. Chemotaxonomic studies in Cnidoscolus (Euphorbiaceae). I. Flavonol glycosides of the C. tubulosus complex.  Syst Bot. 1982;  7 178-85.
• 2 Delgado G, Hernández J. Yolanda M, Aguilar MI. Pentacyclic triterpenes from Cnidoscolus multilobus .  Planta Med. 1994;  60 389-90.
• 3 Tull D. Edible and useful plants of Texas and the southwest: a practical guide. Austin; University of Texas Press 1999.
• 4 Bhattacharyya J, Barros C B. Triterpenoids of Cnidosculus urens .  Phytochemistry. 1985;  23 274-6.
• 5 Escalante-Erosa F, Ortegón-Campos I, Parra-Tabla V, Pena-Rodríguez L M. Chemical composition of the epicuticular wax of Cnidoscolus aconitifolius .  Rev Soc Quím Méx. 2004;  48 24-5.
• 6 Brum B L, Honda N K, Hess S C, Cavalheiro A J, Monache F D. Acyl lupeols from Cnidoscolus vitifolius .  Phytochemistry. 1998;  49 1127-8.
• 7 Kuti J O, Konuru H B. Antioxidant capacity and phenolic content in leaf extracts of tree spinach (Cnidoscolus spp.)  J Agric Food Chem. 2004;  52 117-21.
• 8 Ohta T, Endo Y, Nozoe S. Faveloxide, a new isoprenoid derivative from the Brazilian plant, Cnidoscolus phyllacanthus .  Heterocycles. 1994;  38 55-6.
• 9 Lookadoo S E, Pollard A J. Chemical contents of stinging trichomes of Cnidoscolus texanus .  J Chem Ecol. 1991;  17 1561-73.
• 10 Rouse S H, Bienfang R. A note on the phytochemical study of the root of Cnidoscolus texanus (Muell. Arg.) Small.  J Am Pharm Assoc Am Pharm Assoc (Baltim). 1954;  43 699-700.
• 11 Zhang Z, Li S, Zhang S. Six new triterpenoid saponins from the root and stem bark of Cephalanthus occidentalis .  Planta Med. 2005;  71 355-61.
• 12 Zhang Z, Li S, Zhang S, Gorenstein D. Triterpenoid saponins from the fruits of Aesculus pavia .  Phytochemistry. 2006;  67 784-94.
• 13 Webb M R, Ebeler S E. A gel electrophoresis assay for the simultaneous determination of topoisomerase I inhibition and DNA intercalation.  Anal Biochem. 2003;  321 22-30.
• 14 Li Y, Zhao Y, Fan Y, Wang X, Cai L. Flavonoids from Speranskia tuber .  J Chin Pharm Sci. 1997;  6 70-4.
• 15 Rahman W, Ishratullah K, Wagner H, Seligmann O, Chari V M, österdahl B G. Prunin-6′′-O-p-coumarate, a new acylated flavanone glycoside from Anacardium occidentale .  Phytochemistry. 1987;  17 1064-5.
• 16 Mohan L J, Kumari G NK, Rao N SP. Flavonoid glycosides from Anisomeles ovata .  J Nat Prod. 1985;  48 150-1.
• 17 Singh K N, Pandey V B, Banerjee S, Bohlmann F, Keinan E. Novel acyl flavone glycosides from Echinops echinatus .  Chem Ind London. 1986;  22 713-4.
• 18 Rao L JM, Kumari G NK, Rao N SP. Anisofolin-A, a new acylated flavone glucoside from Anisomeles ovata R. Br.  Heterocycles. 1982;  19 1655-61.
• 19 Rao L JM, Kumari G NK, Rao N SP. Two further acylated flavone glucosides from Anisomeles ovata .  Phytochemistry. 1983;  22 1058-60.
• 20 Sakushima A, Nishibe S, Hisada S. A new flavonol glycoside from Cerbera manghas .  Phytochemistry. 1980;  19 712-3.
• 21 Woo W S, Choi J S, Kang S S. A flavonol glucoside from Typha latifolia .  Phytochemistry. 1983;  22 2881-2.
• 22 Yoshitama K, Oyamada T, Yahara S. Flavonoids in the leaves of Trillium undulatum .  J Plant Res. 1997;  110 379-81.
• 23 Gamez E JC, Luyengi L, Lee S K, Zhu L F, Zhou B N, Fong H H. et al . Antioxidant flavonoid glycosides from Daphniphyllum calycinum .  J Nat Prod. 1998;  61 706-8.
• 24 Hasan A, Ahmed I, Jay M, Voirin B. Flavonoid glycosides and an anthraquinone from Rumex chalepensis .  Phytochemistry. 1995;  39 1211-3.
• 25 Murray R DH, Mendez J, Brown S A. The natural coumarins: occurrence, chemistry and biochemistry. New York; John Wiley & Sons 1982.
• 26 Gaffield W. Circular dichroism, optical rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides.  Tetrahedron. 1970;  26 4093-108.
• 27 Zhao J, Pawar R S, Ali Z, Khan I A. Phytochemical investigation of Turnera diffusa .  J Nat Prod. 2007;  70 289-92.
• 28 Constantinou A, Mehta R, Runyan C, Ral K, Vaughan A, Moon R. Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships.  J Nat Prod. 1995;  58 217-25.
• 29 Boege F, Straub T, Kehr A, Boesenberg C, Christiansen K, Andersen A. et al . Selected novel flavones inhibit the DNA binding or the DNA religation step of eukaryotic topoisomerase I.  J Biol Chem. 1996;  271 2262-70.