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 its
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 flavonoide 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 flvonoides 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 on the basis of 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.