Two new 3,4-seco-ent-kaurenes, caracasine (1) and caracasine acid (2), were isolated from non-polar extracts of the flowers of Croton caracasana (Euphorbiaceae), together with six known terpenes, stigmasterol (4), stigmastenone (5), 2,6-dimethylocta-3,7-diene-2, 6-diol (6), spathulenol (7), caryophyllene oxide (8), and aromadendrene (9), and the flavonoid tribuloside (10). The chemical structures were determined by spectroscopic means and chemical correlations. All isolated compounds are being described for the first time for this species.
BerryPE, HippAL, WurdackKJ, VanEE B, RiinaR. (2005) Molecular phylogenetics of the giant genus Croton and tribe Crotoneae (Euphorbiacea sensu stricto) using ITS and trnl-trnf DNA sequence data. American Journal of Botany, 92, 1520–1534.
2.
WebsterGL. (1994) Synopsis of the genera and suprageneric taxa of Euphoprbiaceae. Annals of the Missouri Botanical Garden, 81, 33–144.
3.
SuárezAI, BlancoZ, CompagnoneRS, Salazar-BookamanMM, ZapataV, AlvaradoC. (2006) Anti-inflammatory activity of Croton cuneatus aqueous extract. Journal of Ethnopharmacology, 105, 99–101.
4.
GiangPM, JinHZ, SonPT, LeeJH, HongYS, LeeJJ. (2003) ent-Kaurane diterpenoids from Croton tonkinensis inhibit LPS-induced NF-κ-B activation and NO production. Journal of Natural Products, 66, 1217–1220.
5.
NardiGM, DalBóS, Delle MonacheF, PizzolattiMG, Ribeiro-do-ValleRM. (2006) Antinociceptive effect of Croton celtidifolius Baill. (Euphorbiaceae). Journal of Ethnopharmacology, 107, 73–78.
6.
SuárezAI, SalazarMM, CompagnoneRS, TillettS, Delle MonacheF, DigiulioC, BrugessG. (2003) Antinociceptive and anti-inflammatory effects of Croton malambo aqueous extract. Journal of Ethnopharmacology, 88, 11–14.
7.
SylvestreM, PichetteA, LongtinA, NagauF, LegaultJ. (2006) Essential oil analysis and anticancer activity of leaf essential oil of Croton flavens L. from Guadeloupe. Journal of Ethnopharmacology, 103, 99–102.
8.
TorricoF, CepedaM, GuerreroG, MelendezF, BlancoZ, CanelonDJ, DiazB, CompagnoneRS, SuárezAI. (2007) Hypoglycaemic effect of Croton cuneatus in streptozotocin-induced diabetic rats. Brazilian Journal of Pharmacognosy, 17, 166–169.
9.
SalatinoA, Faria-SalatinoML, NegriG. (2007) Traditional uses, chemistry and pharmacology of Croton species (Euphorbiaceae). Journal of the Brazilian Chemical Society, 18, 11–33.
10.
PueblaP, LòpezJL, GuerreroM, CarrónR, MartínML, San RománL, San FelicianoA. (2003) Neo-clerodane diterpenoids from Croton schiedeanus. Phytochemistry, 62, 551–555.
11.
PalmeiraSFJr, ConservaLM, SilveiraER. (2005) Two clerodane diterpenes and flavonoids from Croton brasilensis. Journal of the Brazilian Chemical Society, 16, 1420–1424.
12.
BlockS, BacelliC, TinantB, Van MeerveltL, RozenbergR, Habib JiwanJL, LlabrèsG, De Pauw-GilletMC, Quetin-LeclercqJ. (2004) Diterpenes from the leaves of Croton zambesicus. Phytochemistry, 65, 1165–1171.
FuentesJC, CastroV, JakupovicJ, MurilloR. (2004) Diterpenos y otros constituyentes de Croton hirtus (Euphorbiaceae). Revista de Biologia Tropical, 52, 269–285.
15.
Palmeira-JuniorSF, AlvesVL, MouraFS, VieiraLFA, ConservaLM, LemosRPL. (2006) Constiyuintes químicos das folhas e caule de Croton sellowii (Euphorbiaceae). Brazilian Journal of Pharmacognosy, 16, 397–402.
16.
SuárezAI, BlancoZ, Delle MonacheF, CompagnoneRS, ArveloF. (2004) Three new glutarimide alkaloids from Croton cuneatus. Natural Products Research, 18, 421–426.
17.
BarbosaPS, AbreuAdaS, BatistaEF, GuilhonGMSP, MüllerAH, ArrudaMSP, SantosLS, ArrudaAC, SeccoRS. (2007) Glutarimide alkaloids and terpenoids from Croton pullei var. glabrior Lanj. Biochemical Systematics and Ecology Doi:10.1016/.BSE.04.006
18.
Araujo-JuniorVT, da SilvaMS, Leitão da-CunhaEV, AgraMdF, da Silva-FilhoRN, Barbosa-FilhoJM, Braz-FilhoR. (2004) Alkaloids and diterpenes from Croton moritibensis. Pharmaceutical Biology, 42, 62–67.
19.
MoralesA, PerezP, MendozaR, CompagnoneRS, SuárezAI, ArveloF, RamirezJL, Galindo-CastroI. (2005) Cytotoxic and proapoptotic activity of ent-16β-17α-dihydroxykaurane on human mammary carcinoma cell line MCF-7. Cancer Letters, 218, 109–116.
20.
SuárezAI, TomassiA, VasquezL, CompagnoneRS. (2006) Essential oil composition of Croton huberi. Journal of Essential Oil Bearing Plants, 100, 75–81.
21.
SuarezAI, ManzanoM, VasquezL, CompagnoneRS. (2005) Essential oil composition of Croton cuneatus and Croton malambo growing in Venezuela. Journal of Flavour and Fragrance, 20, 611–614.
22.
SuárezAI, TapiasE, CompagnoneRS, TillettS, DiazB, CanelónD, BlancoZ. (2005) Chemical constituents from Croton huberi. Revista Facultad de Farmacia, 68, 14–18.
23.
PalazzinoG, FedericoE, RasoanaivoP, GaleffiC, Delle MonacheF. (1997) 3,4-Seco diterpenes of Croton geayi. Gazzetta Chimica Italiana, 127, 311–314.
24.
ForgoP, KöverKE. (2004) Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative. Steroids, 69, 43–50.
25.
BarlaA, BirmanH, KultürsS, ÖksüzS. (2006) Secondary metabolites from Euphorbia helioscopa and their vasodepressor activity. Turkish Journal of Chemistry, 30, 1–8.
26.
SkoldM, BörjeA, HarambasicE, KarlbergAT. (2004) Contact allergens formed on air exposure of linalool. Identification and quantification of primary and secondary oxidation products and the effect on skin sensitization. Chemical Research in Toxicology, 17, 1697–1705.
27.
Aguilar-GuadarramaAB, RiosMY. (2004) Three new sesquiterpenes from Croton arboreus. Journal of Natural Products, 67, 914–917.
28.
KrebsHC, RakotoarimangaJV, HabermehlGG. (2005) Isolation of spathulenol and (-) caryophyllene oxide from Vernonia mollissima Don and 1H and 13C reassignment by two-dimensional NMR spectroscopy. Magnetic Resonance in Chemistry, 28, 124–128.
29.
AtmosukartoI, CastilloU, HessWM, SearsJ, StrobelG. (2005) Isolation and characterization of Muscodor albus I-41.3s, a volatile antibiotic producing fungus. Plant Science, 169, 854–861.
30.
ChariVM, JordanM, WagnerH. (1978) Structure elucidation and synthesis of naturally occurring acyl glycosides. Part 2 Structures of tiliroside, tribuloside and ipomine. Planta Medica, 34, 93–96.