BIOMAT Database Logo BIOMAT Database Logo

Triterpenoids from Eugenia grandis: structure elucidation by NMR spectroscopy. 2007

Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Department of Chemistry, National University of Singapore, Science Drive 3, 117543 Singapore.

A new pentacyclic triterpenoid, 2alpha,3beta-dihydroxylup-12-en-28-oic acid (1) and a rarely encountered pentacyclic triterpenoid, 3beta-hydroxylup-12-en-28-oic acid (2), together with five known compounds, friedelin (3), 3beta-friedelinol (4), betulinic acid (5), oleanolic acid (6) and beta-sitosterol (7) were isolated from the chloroform extract of stem bark of Eugenia grandis (Syn: Syzygium grande). The structure and stereochemistry of the new compound (1) and the rarely encountered compound (2) were established by 1D and 2D NMR spectroscopic techniques. All the above isolated compounds from this plant are reported for the first time.

UI MeSH Term Description Entries
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009828 Oleanolic Acid A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. Oleanol,Hederins,Oleanane Triterpenes,Triterpenes, Oleanane
D011522 Protons Stable elementary particles having the smallest known positive charge, found in the nuclei of all elements. The proton mass is less than that of a neutron. A proton is the nucleus of the light hydrogen atom, i.e., the hydrogen ion. Hydrogen Ions,Hydrogen Ion,Ion, Hydrogen,Ions, Hydrogen,Proton
D012015 Reference Standards A basis of value established for the measure of quantity, weight, extent or quality, e.g. weight standards, standard solutions, methods, techniques, and procedures used in diagnosis and therapy. Standard Preparations,Standards, Reference,Preparations, Standard,Standardization,Standards,Preparation, Standard,Reference Standard,Standard Preparation,Standard, Reference
D003903 Deuterium The stable isotope of hydrogen. It has one neutron and one proton in the nucleus. Deuterons,Hydrogen-2,Hydrogen 2
D000094062 Betulinic Acid A lupane-type triterpene derivative of betulin which was originally isolated from BETULA or birch tree. It has anti-inflammatory, anti-HIV and antineoplastic activities. 3-Epi-betulinic Acid,3-Hydroxy-lup-20(29)-en-28-oic Acid,3-Hydroxylup-20(29)-en-28-oic Acid,Betulic Acid,3 Epi betulinic Acid
D012680 Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed) Specificity,Sensitivity,Specificity and Sensitivity
D012855 Sitosterols A family of sterols commonly found in plants and plant oils. Alpha-, beta-, and gamma-isomers have been characterized.
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

Related Publications

Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Structure Elucidation of Antibiotics by Nmr Spectroscopy.
January 2017, Methods in molecular biology (Clifton, N.J.),
Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Structure elucidation by NMR spectroscopy of a new acetylated saponin from Centratherum anthelminticum.
December 2004, Carbohydrate research,
Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Structure elucidation of a pyrazolo[3,4]pyran derivative by NMR spectroscopy.
May 2007, Molecules (Basel, Switzerland),
Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Structure elucidation of glycoprotein glycans and of polysaccharides by NMR spectroscopy.
January 2000, Journal of biotechnology,
Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Structure elucidation of procyanidin oligomers by low-temperature 1H NMR spectroscopy.
January 2011, Journal of agricultural and food chemistry,
Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Structure elucidation of novel degradation products of thiocolchicoside by NMR spectroscopy.
April 2019, Journal of pharmaceutical and biomedical analysis,
Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Structure elucidation and NMR assignments of two new triterpenoids from the stems of Paragonia pyramidata (Bignoniaceae).
April 2011, Magnetic resonance in chemistry : MRC,
Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Structure elucidation of an acetylated saponin of Blighia welwitschii by NMR spectroscopy.
October 1994, Carbohydrate research,
Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
RDC-enhanced NMR spectroscopy in structure elucidation of sucro-neolambertellin.
January 2008, Angewandte Chemie (International ed. in English),
Karuppiah Pillai Manoharan, and Fan Jing Song, and Tan Kwong Huat Benny, and Daiwen Yang
Protein structure elucidation from NMR proton densities.
May 2002, Proceedings of the National Academy of Sciences of the United States of America,
Copied contents to your clipboard!