CATECHIN AND AFZELECHIN FROM THE LEAVES OF ARTOCARPUS CHAMPEDEN SPRENG

• Main Author: Yulvianti ( NIM : 20505006), Meri
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/6456
• Institution: Institut Teknologi Bandung

Abstract: <br /> <br /> <br /> <br /> <br /> Numerous secondary metabolites, with different basic skeleton of flavonoid, have been isolated from Artocarpus champeden Spreng. Most of them shows potent activity towards murine leukemia cell lines P388 and also as antimalaria. More than 25 secondary metabolites have been isolated from all parts of the plant, leaves, root trunk, root bark, tree bark, and heartwood of Artocarpus champeden Spreng. Previous experiment has reveal the fact that the basic skeleton of the compound found in the leaves of Artocarpus champeden is different with those found in the other parts of the species. Further investigation of secondary metabolites in the leaves will complete the information of the distribution of the flavonoid secondary metabolites found in Artocarpus champeden Spreng. Fraction ethyl acetate of Artocarpus champeden Spreng leaves extract gave 2 compounds with the same basic skeleton, flavan-3-ol. Further interpretation of the spectra yields in this experiment has identified these two compounds as catechin and afzelechin, the difference lies on the number of oxygenated substituen in B ring of this basic skeleton. Catechin bears two hidroxy at C-3 and C-4, while afzelechin only bears one hydroxy at C-4 in B-ring. Those two compounds also identified having trans configuration. Catechin, as yellowish white powder, having melting point 185-187 C and optical rotation D -0,5, while afzelechin, also as yellowish white powder, having melting point 243 to 245 C and optical rotation D +0,7. The optical rotation of these compounds indicated that these two compounds are rasemic. Thus, the catechin from this experiment is a mixture of (+) (2R,3S) catechin and (-) (2S,3R) catechin, and the afzelechin also as a mixture of (2R,3S) afzelechin dan (-) (2S,3R) afzelechin. The rasemic of (+) catechin and (-) catechin are rarely occur in nature and their presence seems to be induced by enzymatic action. The presence of these rasemic has been reported from the roots of Centaurea maculosa and the seed of Paullinia cupana var. Sorbilis. Catechin and afzelechin together in one species has been reported in A.fretessi and A.reticulatus.