The roots of Stevia nepetifolia afforded the new longipinene derivative (4R,5S,7S,8S,9S,10R,11R,2'S,2″S)-(+)-7,8-di-(α-methylbutyryloxy)-9-hydroxylongipin-2-en-1-one (1), together with the known 7-angeloyloxy-8-(α-methylbutyryloxy)-9-hydroxylongipin-2-en-1-one (2), 7,8-diangeloyloxy-9-hydroxylongipin-2-en-1-one (3), valeranone, 2,3-epoxybisabol-10-en-1-one, γ-cadinene and α-cadinol. The new substance was fully characterized by 1D- and 2D- NMR spectroscopy, molecular modelling, and by partial synthesis using (S)-(+)-α-methylbutyric acid.
Cerda-García-RojasCM, Pereda-MirandaR. (2002) The phytochemistry of Stevia: a general survey. In: KinghornAD (Eds.), Stevia: the genus Stevia; Medicinal and Aromatic Plants Industrial Profiles, Vol. 19, Chapter 5. Taylor & Francis, London, pp. 86–118.
2.
KinghornAD, SoejartoDD, NanayakkaraNPD, CompadreCM, MakapugayHC, Hovanec-BrownJM, MedonPJ, KamathSK. (1984) A phytochemical screening procedure for sweet ent-kaurene glycosides in the genus Stevia.Journal of Natural Products, 47, 439–444.
3.
HernándezLR, CatalánCAN, Joseph-NathanP. (1998) The chemistry of the genus Stevia (Asteraceae). Revista de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales, 22, 229–279.
4.
BohlmannF, SuwitaA, NatuAA, CzersonH, SuwitaA. (1977) Über weitere α-longipinen-derivate aus Compositen. Chemische Berichte, 110, 3572–3581.
5.
AmaroJM, AdrianM, CerdaCM, Joseph-NathanP. (1988) Longipinene derivatives from Stevia lucida and S.triflora. Phytochemistry, 27, 1409–1412.
Sánchez-ArreolaE, Cerda-García-RojasCM, RománLU, HernándezJD, Joseph-NathanP. (2000) Longipinane derivatives from Stevia connata.Journal of Natural Products, 63, 12–15.
8.
Torres-ValenciaJM, Meléndez-RodríguezM, álvarez-GarcíaR, Cerda-García-RojasCM, Joseph-NathanP. (2004) DFT and NMR parameterized conformation of valeranone. Magnetic Resonance in Chemistry, 42, 898–902.
9.
BohlmannF, ZderoC, SchöneweissS. (1976) Über die Inhaltsstoffe aus Stevia-Arten. Chemische Berichte, 109, 3366–3370.
10.
MotlO, RomanukM, HeroutV. (1966) Terpenes. CLXXVIII. Composition of the oil from Amorpha fruticosa fruits; structure of (-)-γ-amorphene. Collection of Czechoslovak Chemical Communications, 31, 2025–2033.
11.
Borg-KarlsonA.-K, NorinT, TalvitieA. (1981) Configuration and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol. Tetrahedron, 37, 425–430.
12.
KiemPV, MinhCV, HuongHT, NamNH, LeeJJ, KimYH. (2004) Pentacyclic triterpenoids from Mallotus apelta.Archives of Pharmacal Research, 27, 1109–1113.
13.
RajbhandariA, RobertsMF. (1984) Flavonoids of Stevia nepetifolia.Journal of Natural Products, 47, 559–560.
14.
Cerda-García-RojasCM, Guerra-RamírezD, Román-MarínLU, Hernández-HernándezJD, Joseph-NathanP. (2006) DFT molecular modeling and NMR conformational analysis of a new longipinenetriolone diester. Journal of Molecular Structure, 789, 37–42.
15.
RománLU, del RíoRE, HernándezJD, CerdaCM, CervantesD, CastañedaR, Joseph-NathanP. (1985) Structural and stereochemical studies of naturally occurring longipinene derivatives. Journal of Organic Chemistry, 50, 3965–3972.
16.
álvarez-GarcíaR, Torres-ValenciaJM, RománLU, HernándezJD, Cerda-García-RojasCM, Joseph-NathanP. (2005) Absolute configuration of the α-methylbutyryl residue in longipinene derivatives from Stevia pilosa.Phytochemistry, 66, 639–642.
17.
ChangG, GuidaWC, StillWC. (1989) An internal coordinate Monte Carlo method for searching conformational space. Journal of the American Chemical Society, 111, 4379–4386.
