Introduction

Plant Callicarpa macrophylla    Vahl. (Family: Verbenaceae) is an important less known  medicinal plant of the lower warm valleys of the Himalaya and  is commonly known as Priyangoo or Daya. It is a perennial, deciduous shrub attaining 2.5mt. in hight. Essential oil obtained from different parts of Priyangoo through steam distillation ,revealed oil content in young leaves and tender stem , panicles and  seeds while no  essential oil content  was observed in the roots. All The parts  are important and are used to cure many diseases. The bark is used to heal cut and wounds. Seeds and roots are used for digestion and leaves are used in rheumatism. The fruits are used for blisters and boils.  Various extract of this plant have shown anti-inflammatory, antifungal and antibacterial activities.^1-4

Material and Method

The fresh leaves of Callicarpa  macrophylla Vahl. (Family: Verbenaceae) was procured from the Central Institute of Medicinal and Aromatic Plants (CIMAP) Lucknow (U.P.) in  Octuber 2009. The plant was identified by a Taxonomist of the center and a specimen was kept for record.

The air dried and coarsely powered leaves (3kg) was sequentialy extracted with petroleum ether (60⁰ -80⁰), chloroform and methanol by the soxhlet apparatus (6 times x 1L. each).The fraction of each extract were mixed together and the excess of solvent was evaporated  under reduced pressure. Out of these extracts only chloroform extract was considered for further examination. A column of silica gel was prepared well stirred with petroleum ether. Than a slarry of chloroform extract (8gm) was made and digested over this column. The column was eluted with different solvents like petroleum ether, benzene, chloroform, ethyl acetate, acetone, methanol and their mixtures of increasing polarity. From the eluent  two compounds could be separated. A compound was obtained by eluting benzene-chloroform (8:2). The compound was further purified by crystallization. The compound was the characterized by m.p., solubility and different spectral studies like IR, NMR( ¹H &¹³C hhhhh).

The compound  crystallized from chloroform as white needles, m.p.- 156⁰C and was characterized as calliterpenone and its monoacetate by comparing spectral data ¹H NMR (CDCl₃) δ 3.64 (2H, H-17), δ 2.31(2H, H-2), δ 1.21 – 1.10 (3H, 3xCH₃ , 18,19,20); ¹³C NMR (CDCl₃) δ 32.9(C-1), δ 33.9(C-2), δ 213.4(C-3), δ 50.7(C-4), δ 49.0(C-5), δ 22.1(C-6), δ 32.0(C-7), δ 31.2(C-8), δ 50.7(C-9), δ 29.4(C-10), δ 20.5(C-11), δ 21.8(C-12), δ 40.6(C-13), δ 32.3(C-14), δ 40.6(C-15), δ 76.8(C-16), δ 72.1(C-17), δ 18.9(C-18), δ 18.9(C-19), δ 20.5(C-20).

Result and Discussion

In the  ¹H  NMR spectrum of the compound (1) a two proton  downfield signal at  δ 3.64 is assignable   to methylene  proton  H-17  to which  a  hydroxyl  group  is attached.  Another  downfield   signal at δ  2.31 was assigned to H-2  proton  next  to carbonyl function. The methyl  proton signals resonates in the rang δ 1.21- δ .10.

The¹³ C NMR   spectrum of the compound clearly indicates twenty  signals which corresponds to its molecular formula C₂₀H₃₂O₃. In its  ¹³C  NMR   spectrum a  downfield signal at 213.4  was clearly indicated  the carbonyl group at  C-3. Another downfield signals at 72.1 and 76.8 were assigned  to C-17 and C-16 to which hydroxy group  is attached. On the basis of  above finding the structure of the compound was characterized as Calliterpenone.

In its acetate (1a) an additional signal for acetyl  proton in its ¹H  NMR appeared at δ 2.09. The rest of the signals are almost same except the signal of methylene proton H-17 which was slightly shifted in downfield region. In the ¹³C  NMR  spectrum of the compound(1a) an additional signals at δ 171.0 was reasonably designated to acetoxy carbon ^5-8.

Acknowledgement

The authors are thankful to the Principal, G.F.College and Head , Department of Chemistry for providing facilities for carrying out this work.

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