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.
Dr. Shiyou Li
National Center for Pharmaceutical Crops
Arthur Temple College of Forestry and Agriculture
Stephen F. Austin State University
Nacogdoches
Texas 75965-6109
U.S.A.
Phone: +1-936-468-2071
Fax: +1 936-468-7058
Email: lis@sfasu.edu