Antiproliferative Cardenolides of an Elaeodendron Sp. from the Madagascar Rain Forest(1)

Overview

Journal J Nat Prod

Date 2007 Jun 6

PMID 17547460

Citations 6

Authors

Shugeng Cao

Peggy J Brodie

James S Miller

Fidy Ratovoson

Martin W Callmander

Sennen Randrianasolo

Etienne Rakotobe

Vincent E Rasamison

Edward M Suh

Karen TenDyke

David G I Kingston

Affiliations

Soon will be listed here.

Abstract

Bioassay-guided fractionation of an ethanol extract obtained from the Madagascar plant Elaeodendron sp. led to the isolation of two new cardenolides, elaeodendrosides T and U (1 and 2). The structures of the new compounds were elucidated using 1D and 2D NMR experiments and mass spectrometry. Compounds 1, 3, 4, and 5 showed significant antiproliferative activity against A2780 human ovarian cancer cells with IC50 values of 0.085, 0.019, 0.19, and 0.10 microM, respectively, while compounds 2 and 6 were less active.

Citing Articles

Oleandrin: A cardiac glycosides with potent cytotoxicity.

Kumar A, De T, Mishra A, Mishra A Pharmacogn Rev. 2013; 7(14):131-9.

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Biodiversity conservation and drug discovery: Can they be combined? The Suriname and Madagascar experiences.

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Antiproliferative cardenolide glycosides of Elaeodendron alluaudianum from the Madagascar Rainforest.

Hou Y, Cao S, Brodie P, Callmander M, Ratovoson F, Randrianaivo R Bioorg Med Chem. 2008; 17(6):2215-8.

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A natural love of natural products.

Kingston D J Org Chem. 2008; 73(11):3975-84.

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Antiproliferative limonoids of a Malleastrum sp. from the Madagascar rainforest.

Murphy B, Brodie P, Slebodnick C, Miller J, Birkinshaw C, Randrianjanaka L J Nat Prod. 2008; 71(3):325-9.

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References

Gil R, Lin L, Chai H, Pezzuto J, Cordell G . Cardenolides from Nierembergia aristata. J Nat Prod. 1995; 58(6):848-56. DOI: 10.1021/np50120a005. View

Kaneda N, Chai H, Pezzuto J, Kinghorn A, Farnsworth N, Tuchinda P . Cytotoxic activity of cardenolides from Beaumontia brevituba stems. Planta Med. 1992; 58(5):429-31. DOI: 10.1055/s-2006-961506. View

Shimada K, Kyuno T, Nambara T, Uchida I . Isolation and characterization of cardiac steroids from seeds of Elaeopendron glaucum Pers. Structures of elaeodendrosides A, D, E, H, I, J and elaeodendrogenin. Chem Pharm Bull (Tokyo). 1982; 30(11):4075-81. DOI: 10.1248/cpb.30.4075. View

Roy M, Chang F, Huang H, Chiang M, Wu Y . Cytotoxic principles from the formosan milkweed, Asclepias curassavica. J Nat Prod. 2005; 68(10):1494-9. DOI: 10.1021/np0501740. View

Cao S, Brodie P, Miller J, Ratovoson F, Birkinshaw C, Randrianasolo S . Guttiferones K and L, antiproliferative compounds of Rheedia calcicola from the Madagascar rain forest. J Nat Prod. 2007; 70(4):686-8. PMC: 2464366. DOI: 10.1021/np070004i. View

Hoffmann J, Cole J . Phytochemical investigation of Adenium obesum Forskal (Apocynaceae): isolation and identification of cytotoxic agents. J Pharm Sci. 1977; 66(9):1336-8. DOI: 10.1002/jps.2600660935. View

Cao S, Norris A, Miller J, Ratovoson F, Razafitsalama J, Andriantsiferana R . Cytotoxic triterpenoid saponins of Albizia gummifera from the Madagascar rain forest. J Nat Prod. 2007; 70(3):361-6. PMC: 2442826. DOI: 10.1021/np060506g. View

Kamano Y, Satoh N, Nakayoshi H, Pettit G, Smith C . Rhinovirus inhibition by bufadienolides. Chem Pharm Bull (Tokyo). 1988; 36(1):326-32. DOI: 10.1248/cpb.36.326. View

Louie K, Behrens B, Kinsella T, Hamilton T, Grotzinger K, McKoy W . Radiation survival parameters of antineoplastic drug-sensitive and -resistant human ovarian cancer cell lines and their modification by buthionine sulfoximine. Cancer Res. 1985; 45(5):2110-5. View

10.

Weeratunga G, Bohlin L, Sandberg F, Kumar V . A muscle-relaxant catechin derivative from Elaeodendron balae (Celastraceae). Acta Pharm Suec. 1984; 21(1):73-6. View

11.

Koike K, Bevelle C, Talapatra S, Cordell G, Farnsworth N . Potential anticancer agents. V. Cardiac glycosides of Asclepias albicans (Asclepiadaceae). Chem Pharm Bull (Tokyo). 1980; 28(2):401-5. DOI: 10.1248/cpb.28.401. View

12.

Ankli A, Heilmann J, Heinrich M, Sticher O . Cytotoxic cardenolides and antibacterial terpenoids from Crossopetalum gaumeri. Phytochemistry. 2000; 54(5):531-7. DOI: 10.1016/s0031-9422(00)00144-8. View

13.

Kitanaka S, Takido M, Mizoue K, Nakaike S . Cytotoxic cardenolides from woods of Euonymus alata. Chem Pharm Bull (Tokyo). 1996; 44(3):615-7. DOI: 10.1248/cpb.44.615. View

14.

Laphookhieo S, Cheenpracha S, Karalai C, Chantrapromma S, Rat-A-Pa Y, Ponglimanont C . Cytotoxic cardenolide glycoside from the seeds of Cerbera odollam. Phytochemistry. 2004; 65(4):507-10. DOI: 10.1016/j.phytochem.2003.10.019. View

15.

Baek N, Lee Y, Park J, Kim S, Ahn B . Euonymoside A: a new cytotoxic cardenolide glycoside from the bark of Euonymus sieboldianus. Planta Med. 1994; 60(1):26-9. DOI: 10.1055/s-2006-959401. View

16.

Cheenpracha S, Karalai C, Rat-A-Pa Y, Ponglimanont C, Chantrapromma K . New cytotoxic cardenolide glycoside from the seeds of Cerbera manghas. Chem Pharm Bull (Tokyo). 2004; 52(8):1023-5. DOI: 10.1248/cpb.52.1023. View

17.

Lhinhatrakool T, Sutthivaiyakit S . 19-Nor- and 18,20-epoxy-cardenolides from the leaves of Calotropis gigantea. J Nat Prod. 2006; 69(8):1249-51. DOI: 10.1021/np060249f. View

18.

Kamel M, Assaf M, Abe Y, Ohtani K, Kasai R, Yamasaki K . Cardiac glycosides from Cryptostegia grandiflora. Phytochemistry. 2001; 58(4):537-42. DOI: 10.1016/s0031-9422(01)00297-7. View

19.

Kiuchi F, Fukao Y, Maruyama T, Obata T, Tanaka M, Sasaki T . Cytotoxic principles of a Bangladeshi crude drug, akond mul (roots of Calotropis gigantea L.). Chem Pharm Bull (Tokyo). 1998; 46(3):528-30. DOI: 10.1248/cpb.46.528. View

20.

Shimada K, Ishii N, Ohishi K, Ro J, Nambara T . Structure-activity relationship of cardiac steroids having a doubly linked sugar and related compounds for the inhibition of Na+,K+-adenosine triphosphatase. J Pharmacobiodyn. 1986; 9(9):755-9. DOI: 10.1248/bpb1978.9.755. View