From the stems of Croton micans Sw., five new 3,4-seco-ent-kaurene dimers: micansinoic acid (1), isomicansinoic acid (2), and the dimethyl (3), monomethyl (4) and monoethyl ester (5) of micansinoic acid were isolated. The structures of the new compounds were elucidated by spectroscopic data interpretation, mainly 1D and 2D NMR experiments and MS. These compounds are the first 3,4-seco-ent-kaurene dimers from a Croton species.
RiinaR, Van EeB, WiedenhoeftAC, CardozoA, BerryPE. (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.
2.
AhmatN, SaidIM, LatipJ, DinLB, SyahYM, HakimEH. (2007) New prenylated dihydrostilbenes from Croton laevifolius, Natural Product Communications, 2, 1137–1140.
3.
ArevaloC, LottiC, PiccinelliAL, RussoM, RuizI, RastrelliL. (2009) Magnoflorine and phenolic derivatives from the leaves of Croton xalapensis L. (Euphorbiaceae). Natural Product Communications, 4, 1697–1700.
4.
MehmoodR, MalikA. (2010) Isolation and characterization of crotosparsamide, a new cyclic nonapeptide from Croton sparsiflorus. Natural Product Communications, 5, 1885–1888.
PueblaP, LópezJL, GuerreroM, CarrónR, MartinML, SanRomán L, San FelicianoA. (2003) Neo-clerodane diterpenoids from Croton schiedeanus. Phytochemistry, 62, 551–555.
7.
Palmeira JúniorSF, ConservaLM, Barbosa-FilhoJM. (2006) Clerodane diterpenes from Croton species: distribution and a compilation of their 13C NMR spectral data. Natural Product Communications, 1, 319–344.
YangX-D, ChenW, ZhaoJ-F, YangL-J, ZhangH-B, LiL. (2009) Ent-kaurane diterpenes and phenolic compounds from Croton kongensis (Euphorbiaceae). Biochemical Systematics and Ecology, 37, 23–240.
10.
SetzerWN, StokesSL, BansalA, HaberWA, CaffreyCR, HansellE, McKerrowJH. (2007) Chemical composition and cruzain inhibitory activity of Croton draco bark essential oil from Monteverde, Costa Rica. Natural Product Communications, 2, 685–689.
11.
BayorMT, AyimJSK, MarstonG, PhillipsRM, ShnyderSD, WheelhouseRT, WrightCW. (2008) A cytotoxic diterpenoid from Croton membranaceus, the major constituent of anticancer herbal formulations used in Ghana, Natural Product Communications, 3, 1875–1878.
12.
Van EeBW, BerryPE. (2009). A phylogenetic and taxonomic review of Croton (Euphorbiaceae s.s.) on Jamaica including the description of Croton jamaicensis, a new species of section Eluteria. Systematic Botany, 34, 129–140
13.
SuárezAI, BlancoZ, Delle MonacheF, CompagnoneRS. (2004) Three new glutarimide alkaloids from Croton cuneatus. Natural Products Research, 18, 421–426.
14.
SuárezAI, BlancoZ, CompagnoneRS, Salazar-BookamanMM, ZapataV, AlvaradoC. (2006) Anti-inflammatory activity of Croton cuneatus aqueous extract. Journal of Ethnopharmacology, 105, 99–101.
15.
SuárezAI, ChávezK, Delle MonacheF, VásquezL, DelannoyDM, OrsiniG, CompagnoneRS. (2008) New 3,4-seco-ent-kaurenes from Croton caracasana flowers. Natural Product Communications, 3, 319–322.
16.
SuárezAI, ChavezK, MateuE, MuñozA, SojoF, ArveloF, MijaresM, De SanctisJB. (2009) Cytotoxic activity of seco-entkaurenes from Croton caracasana on human cancer cell lines. Natural Product Communications, 4, 1547–1550.
17.
CompagnoneRS, ChavezK, MateuE, OrsiniG, ArveloF, SuárezAI. (2010) Composition and cytotoxic activity of essential oils from Croton matourensis and Croton micans from Venezuela. Records of Natural Products, 4, 101–108.
18.
WuJ-Z, MorizaneC, IidaA, UedaS-i, ZhuoZ-L, XuM, ZhangM, LiR-M, FujitaT. (1995). Structures of three new diterpenoids, fritillebic acid and fritillebins A and B, from Bulbs of Fritillaria ebeiensis G.D. Yu et G. Q. Ji. Chemical & Pharmaceutical Bulletin, 43, 1448–1453.
19.
TakahashiJA, BoaventuraMAD, de Carvalho BaymaJ, OliveiraAB. (1995) Frutoic acid, a dimeric kaurane from Xylopia frutencens. Phytochemistry, 40, 607–609.
20.
HanQ, LuY, ZhangL, ZhengQ, SunH. (2004) Novel ent-kaurane dimers from Isodon rubencens var. rubescens. Tetrahedron Letters, 45, 2833–2837.
21.
HuangS-H, XiaoW-L, LiL-M, LiS-H, ZhouY, DingL-S, LouL-G, SunH-D. (2006) Bisrubescensins A-C: Three new dimeric-ent-kauranoids isolated from Isodon rubescens Sun. Organic Letters, 8, 1157–1160.
22.
YangY-L, ChangF-R, WuC-C, WangW-Y, WuY-C. (2002) New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa. Journal of Natural Products, 65, 1462–1467.
23.
BracaA, Abdel-RazicAY, MendezJ, MorelliI. (2005) A new kaurane diterpene dimer from Parinari campestris. Fitoterapia, 76, 614–619.
24.
RamosF, TakaishiY, KashiwadaY, OsorioC, DuqueC, AcuñaR, FujimotoY. (2008) Ent-3,4-seco-labdane and ent-labdane diterpenoids from Croton stipuliformis (Euphorbiaceae). Phytochemistry, 69, 2406–2410.
