Sains Malaysiana 33(2): 83-88 (2004) Sains Fizis dan Gunaan /
Physical and Applied Sciences
Pengasingan dan Kajian Struktur Andrografolid daripada
Andrographis paniculata Nees
(Separation and Structural Study of Andrographolide from
Andrographis paniculata Nees)
Wan Zuraida Wan Mohd Zain. Nik Loris Yusoff.
Jalifah Latip & Bohari M. Yamin
Pusat Pengajian Sains Kimia dan Teknologi Makanan
Fakulti Sains dan Teknologi
43600 UKM Bangi, Selangor D.E. Malaysia
ABSTRAK
Andrografolid telah dipisahkan daripada herba Andrographis paniculata Nees dengan kaedah kromatografi turus dan dihablur semula daripada metanol. Analisis spektroskopi RMN 1H dan 13C, 1M, UL, KGSJ bersetuju dengan laporan terdahulu. Hablur produk mempunyai sistem monoklinik dengan kumpulan ruang P21, a=6.541(1), b=8.003(1), c=I7.962(2)Å dan β =97.39(1)°. Fragmen bisikloheksana berkonformasi kerusi dengan kumpulan metil dan CH2OH mengisi kedudukan paksi. Kumpulan OH serta C2-lakton berada di kedudukan khatulistiwa. Panjang dan sudut ikatan adalah normal. Terdapat dua ikatan intrahidrogen O-H .... O dan satu C-H .. O. Molekul distabilkan oleh dua ikatan interhidrogen O-H ……O dan C-H .… O membentuk rangkaian polimer tak terhingga selari dengan paksi- b.
ABSTRACT
Andrographolide was separated from Andrographis paniculata Nees by using column chromatography and recrystallized from methanol. 1H and 13C NMR, IR, UV spectroscopic and GCMS data were in agreement with the previous report. The crystallined product has a monoclinic system with space group P21, a=6.541(1), b=8.003(1), c=17.962(2) Å and β=97.39(1)19o. The bicyclohexane fragments have a chair conformation with the methyl and the methylene hydroxyl groups occupying the axial position, while the OH and the C2-lactone are in the equatorial positions. The bond lengths and the angles are in the normal ranges. There are two intramolecular interactions of the type O-H … O and C-H …. O in the molecule. The molecule is stabilized by two interhydrogen bonds O-H … O and C-H … O to form polymeric chains parallel to b-axis.
RUJUKAN/REFERENCES
Allen, F.H., Kennard, O. Watson, D.G. Brammer, L., Orpen, A.G. & Taylor, R., 1987. Tables of Bond Lengths determined by X-ray and Neutron Difrraction. Part I. Bond Lengths in Organic Compounds. J. Chem. Soc. Perkin Trans. 2: SI-SI9.
Anon, 1978. A Barefoot Doctor's Manual Revised and enlarged Ed. The Revolution Health Committee of Huan Province, Routledge and Kegan Paul, Ltd. ms 23.
Du, Q., Jerz, G., & Winterhalterz P., 2003. Separation of andrographolide and neoandrographolide from the leaves of Andrographis paniculata using high-speed counter -current chromatography. Journal of Chromatography A, 984: 147-151.
Fujita, T., Fujitani, R., Takeda, Y., Takaishi,Y., Yamada,T., Kido, M. & Miura, I., 1984. On the Diterpenoid of Andrographis paniculata: X-Ray Crystallographic Analysis of Andrographolide and Structure Determination of New Minor Diterpenoids. J. Chem. Pharm. Bull, 32(6): 2117-2125.
|