Abstract
Three new hopane saponins, lotoidosides A - C (1 - 3), and four new oleanane saponins, lotoidosides D - G (4 - 7), were isolated from the roots of Glinus lotoides L. (Molluginaceae). Their structures were determined by extensive 1D- and 2D-NMR spectroscopy and ESI-MS analysis. The antiproliferative activity of compounds 1 - 7 was evaluated using three continuous murine and human culture cell lines J774.A1, HEK-293, WEHI-164. Compounds 1 and 3 - 7 showed significant cytotoxicity against the three cancer cell lines with IC50 values ranging from 0.018 to 0.62 μM, while compound 2 exerted a weak activity only against the cell line HEK-293.
Key words
Glinus lotoides
- Molluginaceae - hopane saponins - oleanane saponins - antiproliferative activity
References
-
1 Boules L. Flora of Egypt (Azollaceae-Oxalidaceae). Vol. 1 Al Hadara Publishing Cairo, Egypt; 1999: p 419
-
2 Täckholm V. Student’s Flora of Egypt. 2nd edition Cairo University, Cooperative Printing Company Beirut; 1974: p 888
-
3 Chopra R N, Nayer S L, Chopra I C. Glossary of Indian medicinal plants. CSIR New Delhi, India; 1956: p 168
-
4
Abegaz B, Tecle B.
A new triterpenoid glycoside from Glinus lotoides
.
Phytochemistry.
1980;
19
1553-4
-
5
Chakrabarti P.
The structure and stereochemistry of mollugogenol A.
Tetrahedron.
1969;
25
3301-5
-
6
Choudhury M K, Chakrabarti P.
Stereochemistry of mollugogenol-A, and mollugogenol-E, the triterpenoid sapogenols from Mollugo hirta
.
Phytochemistry.
1976;
15
433-5
-
7
Choudhury M K, Sanyal A K, Chakrabarti P.
Constituent of mollugogenol-D, a new triterpenoid sapogenol from Mollugo hirta
.
Indian J Chem (B).
1976;
14
59-61
-
8
Choudhury M K, Chakrabarti P.
The structure of mollugogenol-F, a new triterpenoid sapogenin from Mollugo hirta
.
Phytochemistry.
1979;
18
1363-5
-
9
Barua A K, Ghosh A, Basu K, Patra A.
Structure and stereochemistry of mollugogenol - G, a new triterpenoid sapogenin from Mollugo hirta
.
J Indian Chem Soc.
1989;
66
64-6
-
10
Barua A K, Chakrabarti S, Basak A, Ghosh A, Chakrabarti P.
A new triterpene glycoside from Mollugo hirta
.
Phytochemistry.
1976;
15
831-2
-
11
Hamed A I, Springuel I, El-Emary N A, Mitome H, Miyaoka H, Yamada Y.
Triterpenoidal saponin glycosides from Glinus lotoides var. dictamnoides
.
Phytochemistry.
1996;
43
183-8
-
12
Hamed A I, El-Emary N A.
Triterpene saponins from Glinus lotoides var. dictamnoides
.
Phytochemistry.
1999;
43
183-8
-
13
Mosman T.
Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxic assay.
J Immunol Methods.
1983;
65
55-63
-
14
Green L M, Reade J L, Ware C F.
Rapid colorimetric assay for cell viability: application to the quantitation of cytotoxic and growth inhibitory lymphokines.
J Immunol Methods.
1984;
70
257-68
-
15
Opipari A WJ, Hu H M, Yabkowitz R, Dixit Y M.
The A20 zinc finger protein protects cell from tumor necrosis factor cytotoxicity.
J Biol Chem.
1992;
267
12 424-7
-
16
Kusumoto H, Maehara Y, Sakaguchi Y, Kohnoe S, Kumashiro R, Sugimachi K.
Modulation of cytotoxic effect of anticancer drugs by dipyridamole in HeLa cells in vitro
.
Anticancer Res.
1990;
10
1643-5
-
17
Arai Y, Hirohara M, Matsuhira M, Toyosaki K, Ageta H.
Fern constituents: triterpenoids isolated from leaflets of Cyathea pirifera
.
Chem Pharm Bull.
1995;
43
1849-52
-
18
Mahato S B, Kundu A P.
13C NMR spectra of pentacyclic triterpenoids - A compilation and some salient features.
Phytochemistry.
1994;
37
1517-75
-
19
Kitagawa I, Yamanaka H, Nakanishi T, Yosoka I.
Saponin and sapogenol. XXII. Structure of spergulatriol, a new bisnorhopane-type genuine sapogenol of isoanhydrospergulatriol, from the root of Mollugo spergula
.
Chem Pharm Bull.
1977;
25
2430-6
-
20
Chaturvedula V SP, Schilling J K, Miller J S, Andriantsiferana R, Rasamison V E, Kingston D GI.
New cytotoxic oleanane saponins from the infructescences of Polyscias amplifolia from the Madagascar rainforest.
Planta Med.
2003;
69
440-4
-
21
Cioffi G, Braca A, Autore G, Morelli I, Pinto A, Venturella F, De Tommasi N.
New cytotoxic saponins from Schefflera fagueti
.
Planta Med.
2003;
69
750-756
-
22
Feng X Z, Dong M, Gao Z J, Xu S X.
Three new triterpenoid saponins from Ixeris sonchifolia and their cytotoxic activity.
Planta Med.
2003;
69
1036-40
-
23
Nagumo A, Takanashi K, Hojo H, Suzuki Y.
Cytotoxicity of bacteriohopane-32-ol against mouse leukemia L1210 and P388 cells in vitro
.
Toxicol Lett.
1991;
58
309-13
Prof. Cosimo Pizza
Dipartimento di Scienze Farmaceutiche
Università di Salerno
Via Ponte Don Melillo
84084 Fisciano
Salerno
Italy
Fax: +39-089-962-828
Email: pizza@unisa.it