A new longipinene diester from Stevia monardifolia Kunth

Natural Product Communications

Volumn 4, Issue 6, 2009, Pages 757-762

  Rojas Pérez, Rodrigo E ^a   Cedillo Portugal, Ernestina ^b   Joseph Nathan, Pedro ^c   Burgueño Tapia, Eleuterio ^a  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^b UNIVERSIDAD AUTÓNOMA CHAPINGO   (Mexico)

^c DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

Absolute configuration; Longipinene; NMR; Stevia monardifolia; Vibrational circular dichroism

Indexed keywords

7BETA ANGELOYLOXY 8ALPHA ISOVALEROYLOXYLONGIPIN 2 EN 1 ONE; 7BETA,8ALPHA DIACETYLOXYLONGIPIN 2 EN 1 ONE; 7BETA,8ALPHA DIANGELOYLOXYLONGIPIN 2 EN 1 ONE; 7BETA,8ALPHA DIANGELOYLOXYLONGIPINAN 1 ONE; 7BETA,8ALPHA DIHYDROXYLONGIPIN 2 EN 1 ONE; ESTER DERIVATIVE; UNCLASSIFIED DRUG; LONGIPINENE; SESQUITERPENE;

ALKALINITY; ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DRUG ISOLATION; DRUG STRUCTURE; ENANTIOMER; HYDROLYSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEVIA; STEVIA MONARDIFOLIA; X RAY DIFFRACTION; CHEMICAL STRUCTURE; CHEMISTRY;

MODELS, MOLECULAR; MOLECULAR STRUCTURE; SESQUITERPENES; STEVIA;

EID: 69849100052     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0900400603     Document Type: Article

References (22)

1. Cerda-García-Rojas CM, Pereda R. (2002) The phytochemistry of Stevia: a general survey. In Stevia: the genus Stevia; Medicinal and aromatic plants industrial profiles. Vol. 19, Chapter 5, Kinghorn, AD. (Eds). Taylor & Francis, London pp. 86-118.
2. Hernández LR, Catalán CAN, Joseph-Nathan P. (1998) The chemistry of the genus Stevia (Asteraceae). Revista de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales, 22, 229-279.
3. (a) Bohlmann F, Suwita A, Natu AA, Czerson H, Suwita A. (1977) Über weitere α-Longipinen-Derivate aus Compositen. Chemische Berichte, 110, 3572-3581;
4. (b) Bohlmann F, Zdero C. (1985) Stevisalicinon, ein neuer Diterpentyp, sowie weitere Inhaltsstoffe aus Stevia-arten. Liebigs Annalen der Chemie, 1764-1783;
5. (c) Sánchez-Arreola E, Cerda-García-Rojas CM, Joseph-Nathan P, Román LU, Hernández JD. (1995) Longipinene derivatives from Stevia serrata. Phytochemistry, 39, 853-857.
6. Román LU, del Río RE, Hernández JD, Cerda-García-Rojas CM, Castañeda R, Joseph-Nathan P. (1985) Structural and stereochemistry studies of naturally occurring longipinene derivatives. Journal of Organic Chemistry, 50, 3965-3972.
7. Joseph-Nathan P, Cerda-García-Rojas CM, del Río RE, Román LU, Hernández JD. (1986) Conformation and absolute configuration of naturally occurring longipinene derivatives. Journal of Natural Products, 49, 1053-1060.
8. (a) Burgueño-Tapia E, Joseph-Nathan P. (2008) Absolute configuration of eremophilanoids by vibrational circular dichroism. Phytochemistry, 69, 2261-2256;
9. (b) Cerda-García-Rojas CM, Catalán CAN, Muro AC, Joseph-Nathan P. (2008) Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia. Journal of Natural Products, 71, 967-971.
10. Roman LU, Loeza-Coria M, Hernández JD, Cerda-García-Rojas CM, Sánchez-Arreola E, Joseph-Nathan P. (1993) Preparation of a new longipinane derivative from Stevia serrata. Journal of Natural Products, 56, 1148-1152. (Pubitemid 23222215)
11. Nafie LA. (2008) Vibrational circular dichroism: a new tool for the solution-state determination of the structure and absolute configuration of chiral natural product molecules. Natural Product Communications, 3, 451-466.
12. (a) Perdew JP. (1986) Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Physical Reviews B, 33, 8822-8824;
13. (b) Godbout N, Salahud DR, Andzelm J, Wimmer E. (1992) Optimization of Gaussian-type-basis sets for local spin functional calculations. Part 1. Boron through neon, optimization technique and validation. Canadian Journal of Chemistry, 70, 560-571;
14. (c) Andzelm J, Wimmer EJ. (1992) Density functional Gaussian-type-orbital approach to molecular geometries, vibrations, and reaction energies. Journal of Chemical Physics, 96, 1280-1303.
15. Romero-Montiel L, Torres-Valencia JM, Álvares-García R, Román LU, Hernández JD, Cerda-García-Rojas CM, Joseph-Nathan P. (2007) Structure and conformation of a new longipinene diester from Stevia nepetifolia. Natural Product Communications, 2, 525-530.
16. Stomberg R, Langer V, Hauteville M. (2002) 1-(2-Hydroxy-4,6-dimethoxy-3- methylphenyl)-3-(4-methoxyphenyl)-2-methyl-1,3-propanedione. Acta Crystallographica, E58, o1116-o1118.
17. Chang G, Guida WC, Still WC. (1989) An internal-coordinate Monte Carlo method for searching conformational space. Journal of the American Chemical Society, 111, 4379-4386.
18. (a) Halgren T. (1996) Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94, Journal of Computational Chemistry, 17, 616-641;
19. (b) Halgren TA. (1996) Merck molecular force field. II. MMFF94 van der Waals and electrostatic parameters for intermolecular interactions. Journal of Computational Chemistry, 17, 587-615;
20. (c) Halgren TA. (1996) Merck molecular force field. III. Molecular geometries and vibrational frequencies for MMFF94. Journal of Computational Chemistry, 17, 553-586;
21. (d) Halgren TA. (1996) Merck molecular force field. V. Extension of MMFF94 using experimental data, additional computational data, and empirical rules. Journal of Computational Chemistry, 17, 490-519.
22. Hehre WJ, Radom L, Schleyer PVR, Pople JA. (1986) Ab initio molecular orbital theory. Wiley, New York.