ABSTRACT
A new 28-norolean-12,17-diene triterpene lantigdienone (1) oxidised at C-11 and C-22 has been isolated from the aerial parts of Lantana camara, along with two known compounds, camarinin (2) and camangeloyl acid (3). The structure of compound 1 was elucidated as 3,25-epoxy-3alpha-hydroxy-22beta-[beta,betadimethylacryloyloxy]-11-oxo-28-norolean-12,17-diene, with the help of spectral studies.
Subject(s)
Lantana/chemistry , Plant Components, Aerial/chemistry , Plant Extracts/isolation & purification , Triterpenes/isolation & purification , Flavonoids/isolation & purification , Glucosides/isolation & purification , Molecular Structure , Pakistan , Plant Extracts/chemistry , Spectrophotometry, Ultraviolet , Triterpenes/chemistryABSTRACT
Two new pentacyclic triterpenoids, namely lantanoic acid (1) and camaranoic acid (2), and six known compounds such as lantic acid, camarinic acid, camangeloyl acid, camarinin, oleanonic acid, and ursonic acid were isolated from the aerial parts of Lantana camara LINN. Structures of the new constituents were elucidated by chemical transformation and spectral studies including 1D ((1)H- and (13)C-NMR) and 2D ((1)H-(1)H correlation spectroscopy (COSY), nuclear Overhauser effect spectroscopy (NOESY), (1)H-(1)H total correlation spectroscopy (TOCSY), J-resolved, (1)H-detected heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond connectivity (HMBC)) NMR spectroscopy.
Subject(s)
Lantana/chemistry , Triterpenes/chemistry , Chromatography, Thin Layer , Magnetic Resonance Spectroscopy , Methylation , Solvents , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Triterpenes/isolation & purificationABSTRACT
Two new olean-12-ene triterpenoids, camarolic acid (1) and lantrigloylic acid (2), have been isolated from the aerial parts of Lantana camara, along with ten known triterpenes, namely, camaric acid, lantanolic acid, lantanilic acid, pomolic acid, camarinic acid, lantoic acid, camarin, lantacin, camarinin, and ursolic acid. The new compounds have been characterized as 3,25-epoxy-3alpha-hydroxy-22beta-{[(S)-3-hydroxy-2-methylidenebutanoyl]oxy}olean-12-en-28-oic acid (1) and 3,25-epoxy-3alpha-hydroxy-22beta-[(3-methylbut-2-enoyl)oxy]olea-9(11),12-dien-28-oic acid (2) through spectroscopic studies and a chemical transformation. Seven of the constituents, namely pomolic acid, lantanolic acid, lantoic acid, camarin, lantacin, camarinin, and ursolic acid, were tested for nematicidal activity against root-knot nematode Meloidogyne incognita. Pomolic acid, lantanolic acid, and lantoic acid showed 100% mortality at 1 mg/ml concentration after 24 h, while camarin, lantacin, camarinin, and ursolic acid exhibited 100% mortality at this concentration after 48 h. These results are comparable to those obtained with the conventional nematicide furadan (100% mortality at 1 mg/ml concentration after 24 h).