Structure elucidation of a diterpene from Smallanthus sonchifolius by NMR spectroscopy
2011
Alimboyoguen, A.B., Cavite State Univ., Indang 4122 Cavite (Philippines) | Ragasa, C., De La Salle Univ., Manila (Philippines)
Diterpene, a common secondary metabolite, has played an important role in the development of medicinal chemistry. This secondary metabolite is usually present in plants and it has important source and model compound for drug synthesis. Research has also proved that diterpene has tremendous potential to the discovery of new pharmaceutical, nutraceuticals and even agronomicals. In this study, Smallanthus sonchifolius, also known as yacon was investigated for its secondary metabolite chemistry. It was recently introduced in the Philippines and now it is gaining popularity due to its medicinal properties and food value. Studies showed that the oligofructan content of yacon tubers maybe responsible for its potential to treat hyperglycemia, kidney problems and for skin rejuvenation, while the phenolic content of the yacon leaves may be responsible for its anti-pyretic and cytoprotective activity. This investigation aimed to 1) isolate the secondary metabolites from the dichloromethane extracts of the leaves of Smallanthus sonchifolius using chromatographic methods 2) elucidate the structure of the isolate by the application of infrared, 1-dimensional and 2-dimensional Nuclear Magnetic Resonance (NMR) spectroscopy. Results of the study showed that the air-dried leaves of yacon afforded Ent-kaurenoic acid by silica gel chromatography. The structure of this compound was elucidated by infrared and extensive NMR spectroscopic techniques such as sup1H-NMR, sup13C-NMR, COSY, HMBC, HSQC and NOESY. This was the first report on the isolation of ent-kaurenoic acid from Smallanthus sonchifolius. This compound was found to exhibit significant analgesic, anti-inflammatory activities and potential anti-diabetes activity.
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