A NEW NEO-CLERODANE DITERPENOID FROM TEUCRIUM POLIUM LINN.

Teucrium polium L. is a member of the Lamiaceae family and is represented in the Flora of Syria by two variety: Teucrium polium var. angusti folium and Teucrium polium var. mollissimum. Teucrium polium is a wild-growing flowering plant, found abundantly in Syria, and it is used traditional medicine for it’s diuretic, antipyretic, antispasmodic, tonic, anti-inflammatory, antihypertensive, anorexic, analgesic, antibacterial and antidiabetic effects. Several reports have demonstrated a wide range of beneficial biological and pharmacological activities of the phenylethanoid, phenylpropanoid, and flavonoid components, while the furano neo-clerodane diterpenoids present in germander have been implicated in the in-vivo hepatotoxicity of this botanical. Phytochemical studies of this plant have been carried out. Aerial parts of the plant were extracted with petroleum ether at room temperature, and then extract with methanol in Soxhlet, and finally extract with aqueous methanol at room temperature successively. Fractionation of the methanol extract by column chromatography and purification by crystallization yielded three known flavonoids Cirsimartin 2, Cirsiliol 3, and Apigenin 4. The aqueous methanolic extract yielded one new neo-clerodane type diterpenoid, Syrapolin I 1 (3,12- diacetoxy – 4α,18α ; 15,16- diepoxy – 6 – oxo – neo – cleroda – 13 (16), 14- diene -7α, 20β- dihydroxy-19- hemiacetal). The structure of compounds was proposed based on spectroscopic methods IR, MS, and 1-D (¹H, ¹³C, and DEPT) and 2-D (COSY, HETCOR, HMBC) NMR experiment, and comparison with closely related compounds.