In a continuing collaboration in a search for new antiproliferative compounds in Madagascar as part of an International Cooperative Biodiversity Group (ICBG), an ethanol extract of Molinaea retusa Radlk. (Sapindaceae) was investigated on the basis of its moderate antiproliferative activity against the A2780 human ovarian cancer cell line (IC50 16 μg/mL). One new compound, 2″,3″,4″,6′-de-O-acetylcupacinoside (1, IC50 15.4 μM) and two known compounds, cupacinoside (2, IC50 9.5 μM) and 6-de-O-acetylcupacinoside (3, IC50 10.9 μM), were isolated by bioassay-directed fractionation using liquid-liquid partitioning, column chromatography, and HPLC. Compounds 2 and 3 also had moderate antiplasmodial activities, with IC50 values of 4.0 and 6.4 μM, respectively, against Plasmodium falciparum, Dd2 strain. The structures were determined using spectroscopic methods.
Biodiversity Conservation and Drug Discovery in Madagascar, Part 57. For Part 56, see LiuY., HarinantenainaL., BrodieP.J., SlebodnickC., CallmanderM.W., RakotondrajaonaR., RakotobeE., RasamisonV.E., TenDykeK., ShenY., KingstonD.G.I. (2013) Structure elucidation of antiproliferative bisbenzylisoquinoline alkaloids from Anisocycla grandidieri from the Madagascar dry forest. Magnetic Resonance in Chemistry, in press.
2.
MabberleyD.J. (1997) The Plant-book: a Portable Dictionary of the Vascular Plants. 2nd edition, Cambridge, Cambridge University Press.
3.
(a) GachetM.S., KunertO., KaiserM., BrunR., ZehlM., KellerW., MunozR.A., BauerR., SchuehlyW. (2011) Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense. Journal of Natural Products, 74, 559–566;(b) Cao S, Brodie P, Callmander M, Randrianaivo R, Razafitsalama J, Rakotobe E, Rasamison VE, TenDyke K, Shen Y, Suh EM, Kingston DGI. (2009) Antiproliferative triterpenoid saponins of Dodonaea viscosa from the Madagascar dry forest. Journal of Natural Products, 72, 1705–1707; (c) Cavalcanti SBT, Teles HL, Silva DHS, Furlan M, Young MCM, Bolzani VS. (2001) New tetra-acetylated oligosaccharide diterpene from Cupania vernalis. Journal of the Brazilian Chemical Society, 12, 413–416; (d) Fu H, Guo Y, Li W, Dou D, Kang T, Koike K. (2010) A new angeloylated triterpenoid saponin from the husks of Xanthoceras sorbifolia Bunge. Journal of Natural Medicines, 64, 80–84; (e) Ito A, Chai HB, Kardono LB, Setowati FM, Afriastini JJ, Riswan S, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kinghorn AD. (2004) Saponins from the bark of Nephelium maingayi. Journal of Natural Products, 67, 201–205; (f) de Oliveira SQ, de Almeida MTR, Maraslis F, Silva IT, Sincero TCM, Palermo JA, Cabrera GM, Caro MSB, Simőes CMO, Schenkel EP. (2012) Isolation of three new ent-labdane diterpenes from Dodonaea viscosa Jacquin (Sapindaceae): Preliminary evaluation of antiherpes activity. Phytochemistry Letters, 5, 500–505; (g) Tantangmo F, Lenta BN, Ngouela S, Kamdem LM, Weniger B, Tsamo E, Lobstein A, Vonthron-Senecheau C. (2010) New sphingolipids and other constituents of Pancovia laurentii. Helvetica Chimica Acta, 93, 2210–2217; (h) Zhang LB, Ji J, Lei C, Wang HY, Zhao QS, Hou AJ. (2012) Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa. Journal of Natural Products, 75, 699–706.
4.
EberhardB., VoelterW. (1987) Carbon-13 NMR Spectroscopy: High Resolution Methods and Applications in Organic Chemistry and Biochemistry. 3rd edition, Weinheim, FRG, VCH Publishers.
5.
CaoS., BrodieP.J., MillerJ.S., RandrianaivoR., RatovosonF., BirkinshawC., AndriantsiferanaR., RasamisonV.E., KingstonD.G.I. (2007) Antiproliferative xanthones of Terminalia calcicola from the Madagascar rain forest. Journal of Natural Products, 70, 679–681.
6.
LouieK.G., BehrensB.C., KinsellaT.J., HamiltonT.C., GrotzingerK.R., McKoyW.M., WinkerM.A., OzolsR.F. (1985) Radiation survival parameters of antineoplastic drug-sensitive and -resistant human ovarian cancer cell lines and their modification by buthionine sulfoximine. Cancer Research, 45, 2110–2115.
7.
HarinantenainaL., BowmanJ.D., BrodieP.J., SlebodnickC., CallmanderM.W., RakotobeE., RandrianaivoR., RasamisonV.E., GorkaA., RoepeP.D., CasseraM.B., KingstonD.G. (2013) Antiproliferative and antiplasmodial dimeric phloroglucinols from Mallotus oppositifolius from the Madagascar dry forest. Journal of Natural Products, 76, 388–393.