Three new abietane-type diterpenoids: ent-abieta-8,11,13-trien-16-ol (1), ent-abieta-8,11,13-trien-11,16-diol (2) and 11,12-dihydroxy-7-oxo-ent-abieta-8,11,13-trien-16-oic acid methyl ester (3), in addition to three known triterpenoids: euphol (4), 24,25-epoxycycloartanol (5) and β-sitosterol O-β-D-glucoside (6) were isolated from the chloroform extract of the roots of Euphorbia guyoniana. Structures of the isolated compounds were established on the basis of spectroscopic analyses, including 1D and 2D homo and heteronuclear NMR experiments and ESIMS, and comparison with literature data.
OzendaP. (1991) Flore et végétation du Sahara, 3rd Edition. CNRS, Paris, France.
2.
QuezelP., SantaS. (1963) Nouvelle flore de l'Algérie et des régions désertiques méridionales, Vol. 1–2. CNRS, Paris, France.
3.
BellakhdarJ. (1997) La Pharmacopée Marocaine Traditionnelle, Ibis Press, Paris, France.
4.
SinglaA.K., PathakK. (1990) Phytoconstituents of Euphorbia species. Fitoterapia, 61, 483–516.
5.
AhmadW., NazirM., KhanS.A. (1988) The chemical composition of various Euphorbia species for industrial applications. Part II. Neutral lipids of Euphorbia cauducifolia. Pakistan Journal of Scientific and Industrial Research, 31, 85–89.
6.
DuarteN., GyémántN., AbreuP.M., MolnárJ., FerreiraM.J.U. (2006) New macrocyclic lathyrane diterpenes, from Euphorbia lagascae, as inhibitors of multidrug resistance of tumour cells. Planta Medica, 72, 162–168.
7.
YanS.S., LiY., WangY., ShenS.S., GuY., WangH.B., QinG.W., YuQ. (2008) 17–Acetoxyjolkinolide B irreversibly inhibits I-kappaB kinase and induces apoptosis of tumor cells. Molecular Cancer Therapeutics, 7, 1523–1532.
8.
VasasA., SulyokE., MartinsA., RedeiD., ForgoP., KeleZ., ZupkoI., MolnarJ., PinkeG., HohmannJ. (2012) Cyclomyrsinane and premyrsinane diterpenes from Euphorbia falcata modulate resistance of cancer cells to doxorubicin. Tetrahedron, 68, 1280–1285.
9.
ShiQ.W., SuX.H., KiyotaH. (2008) Chemical and pharmacological research of the plants in genus Euphorbia. Chemical Reviews, 108, 4295–4327.
10.
BoudiarT., HichemL., KhalfallahA., KaboucheA., KaboucheZ., BrouardI., BermejoJ., BruneauC. (2010) A new alkaloid and flavonoids from the aerial parts of Euphorbia guyoniana. Natural Product Communications, 5, 35–37.
11.
HabaH., LavaudC., MarcourtL., LongC., HarkatH., BenkhaledM. (2009) Ent-abietane diterpenoids from Euphorbia guyoniana Boiss. & Reut. Biochemical Systematics and Ecology, 35, 504–508.
12.
HabaH., LavaudC., HarkatH., Alabdul MagidA., MarcourtL., BenkhaledM. (2007) Diterpenoids and triterpenoids from Euphorbia guyoniana. Phytochemistry, 68, 1255–1260.
13.
AhmedA.A., GherrafN., El-BassuonyA.A., RhouatiS., GadM.H., OhtaS., HirataT. (2006) Guyonianin A and B, two polyester diterpenes from Algerian Euphorbia guyoniana. Natural Product Communications, 1, 273–279.
14.
HegazyM-EF, MohamedA.H., AokiN., IkeuchiT., OhtaE., OhtaS. (2010) Bioactive jatrophane diterpenes from Euphorbia guyoniana. Phytochemistry, 71, 249–253
15.
De Pascual TeresaJ., UronesJ.G., MarcosI.S., BasabeP., CuadradoM.J.S., MoroR.F. (1987) Triterpenes from Euphorbia broteri. Phytochemistry, 26, 1767–1776.
16.
VoutquenneL., LavaudC., MassiotG., SevenetT., HadiH.A. (1999) Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus. Phytochemistry, 50, 63–69.
17.
UlubelenA., TopcuG., TanN. (1992) Rearranged abietane diterpenes from Salvia candidissima. Phytochemistry, 31, 3637–3638.
18.
Hueso-RodriguezJ.A., JimenoM.L., RodriguezB., SavonaG., BrunoM. (1983) Abietane diterpenoids from the root of Salvia phlomoides. Phytochemistry, 22, 2005–2009.
19.
UlubelenA., TopcuG., SonmezU., ChoudharyM.I., Atta-Ur-Rahman. (1995) Abietane diterpenes from Salvia napifolia. Phytochemistry, 40, 861–864.
20.
MatsumotoT., ImaiS., YoshinariT., TsurutaK. (1987) The synthesis of ar-abietatrien-12,16-oxide and its C-15 epimer. Bulletin of the Chemical Society of Japan, 60, 2401–2407.
21.
TanakaR., OhtsuH., MatsunagaS. (1997) Abietane diterpene acids and other constituents from the leaves of Larix kaempferi. Phytochemistry, 46, 1051–1057.
22.
Amaro-LuisJ.M., HerreraJ.R., LuisJ.G. (1998) Abietane diterpenoids from Salvia chinopeplica. Phytochemistry, 47, 895–897.
23.
KolakU., AriS., BirmanH., HasançebiS., UlubelenA. (2001) Cardioactive diterpenoids from the roots of Salvia amplexicaulis. Planta Medica, 67, 761–762.
MatsumotoT., TeraoH., ImaiS. (1991) Conversion of (+)-8,11,13-abietatriene into (15R)-16-hydroxyferruginol and its (15S)- epimer. Bulletin of the Chemical Society of Japan, 64, 2855–2856.
26.
TopcuG., UlubelenA. (1996) Abietane and rearranged abietane diterpenes from Salvia montbretii. Journal of Natural Products, 59, 734–737.
27.
FrontanaB., CardenasJ., Rodriguez-HahnL. (1994) Diterpenoids from Salvia coulteri. Phytochemistry, 36, 739–741.
28.
LalA.R., CambieR.C., RutledgeP.S., WoodgateP.D. (1990) Ent-pimarane and ent-abietane diterpenes from Euphorbia fidjiana. Phytochemistry, 29, 2239–2246.
29.
SattiN.K., SuriK.A., SuriO.P., SkibickiP., DaniewskitW.M. (1994) A highly oxygenated phenanthrofuran skeleton diterpene from Euphorbia acaulis. Phytochemistry, 35, 1061–1062.
30.
SutthivaiyakitS., ThapsutM., PrachayasittikulV. (2000) Constituents and bioactivity of the tubers of Euphorbia sessiliflora. Phytochemistry, 53, 947–950.
31.
ValenteC., PedroM., DuarteA., NascimentoM.S.J., AbreuP.M., FerreiraM-JU. (2004) Bioactive diterpenoids, a new jatrophane and two ent-abietanes, and other constituents from Euphorbia pubescens. Journal of Natural Products, 67, 902–904.