Four new crotofolane-type diterpenoids, crotocarasin (A-D) (1–4), together with the known crotofolin E, were isolated from a dichloromethane extract of the stems of Croton caracasanus Pittier. The structures of the new compounds were determined by spectroscopic methods, and the structure of 3 was further confirmed by single-crystal X-ray data analyses.
RiinaR., van EeB., WiedenhoeftA.C., CardozoA., BerryP.B. (2010) Sectional rearrangement of arborescent clades of Croton (Euphorbiaceae) in South America: evolution of arillate seeds and a new species Croton domatifer. Taxon, 59, 1147–1160.
YangX-D, ChenW., ZhaoJ-F, YangL-J, ZhangH-B, LiL. (2009) Ent-kaurane diterpenes and phenolic compounds from Croton kongensis (Euphorbiaceae). Biochemical Systematic and Ecology, 37, 23–240.
6.
MulhollandD.A., LangatM.K., CrouchN.R., ColeyH.M., MutambiE.M., NuzillardJ.M. (2010) Cembranolides from the stem bark of the southern African medicinal plant, Croton gratissimus (Euphorbiaceae). Phytochemistry, 71, 1381–1386.
7.
KawakamiS., MatsunamiK., OtsukaH., ShinzatoT., TakedaY., KawahataM., YamaguchiK. (2010) A crotofolane-type diterpenoid and a rearranged nor-crotofolane-type diterpenoid with a new skeleton from the stems of Croton cascarilloides. Tetrahedron Letters, 51, 4320–4322.
8.
ChanW.R., PrinceE.C., ManchandP.S., SpringerJ.P., ClardyJ. (1975) The structure of Crotofolin A, a diterpene with a new skeleton. Journal of the American Chemical Society, 97, 4437–4439.
9.
BurkeB.A., ChanW.R., PascoeK.O., BlountJ.F., ManchandP.S. (1979) The structure of Crotofolin E, a novel tryciclic diterpene from Croton corylifolius. Tetrahedron Letters, 36, 3345–3348.
10.
JogiaM.K., AndersenR.J., PárkaniL., ClardyJ., DublinH.T., SinclairA.R.E. (1989) Crotofolane diterpenoids from the African shrub Croton dichogamus Pax. Journal of Organic Chemistry, 54, 1654–1657.
11.
KawakamiS., ToyodaH., HarinantenainaL., MatsunamiK., OtsukaH., ShinzatoT., TakedaY., KawahataM., YamaguchiK. (2013) Eight new diterpenoids and two new nor-diterpenoids from the stems of Croton cascarilloides. Chemical & Pharmaceutical Bulletin, 61, 411–418.
12.
SuárezA.I., BlancoZ., Delle MonacheF., CompagnoneR.S. (2004) Three new glutarimide alkaloids from Croton cuneatus. Natural Products Research, 18, 421–426.
13.
SuárezA.I., ChávezK., Delle MonacheF., VásquezL., DelannoyD.M., OrsiniG., CompagnoneR.S. (2008) New 3,4-Seco-ent-kaurenes from Croton caracasana flowers. Natural Product Communications, 3, 319–322.
14.
SuárezA.I., BlancoZ., CompagnoneR.S., Salazar-BookamanM.M., ZapataV., AlvaradoC. (2006) Anti-inflammatory activity of Croton cuneatus aqueous extract. Journal of Ethnopharmacology, 105, 99–101.
15.
MoralesA., AlvarezA., ArveloF., SuárezA.I., CompagnoneR.S., Galindo-CastroI. (2011) The natural diterpene ent-16β-17α-dihydroxykaurane down-regulates Bcl-2 by disruption of the Ap-2α/Rb transcription activating complex and induces E2F1 up-regulation in MCF-7 cells. Apoptosis, 16, 1245–1252.
16.
MosmannT. (1983) Rapid colorimetric assay for celular growth and survival. Application to proliferation and cytotoxicity assays. Journal of Immunology Methods, 65, 55–63.
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