Terpenes and Flavonoids From Salvia apiana and Their Affinities to Cannabinoid and Opioid Receptors

Hayes, Taylor (2016) Terpenes and Flavonoids From Salvia apiana and Their Affinities to Cannabinoid and Opioid Receptors. Undergraduate thesis, under the direction of Samir A. Ross from Natural Products Center, School of Pharmacy, University of Mississippi.

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Abstract

Salvia apiana (white sage, Lamiacae family) plant is native to southern California and parts of Mexico. Some Native American tribes local to this region consider S. apiana to be sacred and burn the leaves as incense for purification ceremonies. The plant has been used to treat sore throats, coughs, chest colds, upper respiratory infections, and poison oak rashes. Native Americans widely used this plant in traditional Chumash healing. Infusion of the leaves is used as a diaphoretic and diuretic. The aqueous ethanolic extract of S. apiana showed moderate activity towards the CB1 receptor (58.3% displacement). The extract was fractionated on silica gel column chromatography using hexanes-acetone gradient to yield 15 fractions. Further fractionation using column chromatography led to isolation of nine compounds. The structures of the isolated compounds were determined by their 1D, 2D NMR and MS spectral data. They were identified to be four diterpenes: rosmadial, carnosol, 16-hydroxycarnosol, and sageone; two flavonoids: cirsimaritin, and salvigenin; and three triterpenes: oleanolic acid, uvaol, and ursolic acid. All the fractions and isolated compounds were submitted for biological studies for cannabinoid and opioid receptor binding. One diterpene, sageone, was found to be active towards CB1 (72.5% displacement) and CB2 (79.8% displacement) and moderately active towards the mu opioid receptor (54.7% displacement).

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