Citation
Mohamad Ali, Nor Azah
(2004)
Chemical Constituents and Biological Activites of Selected Cinnamomum Species (Lauraceace) and Melicope Cf. Hookeri T.G. Hartley (Rutaceae.
Doctoral thesis, Universiti Putra Malaysia.
Abstract
The essential oils of nine Cinnamomum species (C, sintoc, C. pubescens, C.
impressiscostaturn, C. subavenium, C, microphyllum, C. scortechinii, C.
rhyncophyllum, C. aureofulvum and C. verum) were investigated by means of gas
chromatography (GC) and combination of gas chromatography/mass spectrometer
(GUMS). The chemical components of the essential oils (leaf, stem bark and twig
oils) were identified by co-chromatography with authentic samples on three columns
of different polarity, comparison with Kovats retention indices, capillary GUMS
and proton NMR on selected isolated components. The essential oils were made up
of one, two or all three of the following class of compounds; monoterpenes and
sesquiterpenoids, phenylpropanoids and benzyl esters. Some of the chemical
components observed in the oils are (E)-methyl cinnamate, safrole, benzyl benzoate,
linalool, terpinen-4-01 and camphor which are commercially important chemicals in
the flavour and pharmaceutical industries. The distribution and occurrences of be used as a chemotaxonomic marker for species identification.
Cinnamomum species (C. impressicostatum, C. pubescens, C. microphyllum) and
Melicope cf. hookeri were selected for a study of their chemical constituents and
biological properties. All of these species have not been reported previously on their
chemical constituents. Phytochemical analysis of the bark and stem parts of C.
impressicostatum yielded safrole (IS), (@-methyl cinnamate (17), (apiperonylprop-
2-enal (1 16), cinnamic acid (1 17) and P-sitosterol (1 18). Similar
analysis on the bark of C. pubescens also afforded safrole (IS), (@-methyl
cinnamate (17), (E)-piperonylprop-2-enal (1 16) and P-sitosterol (1 18) as well as (E)-
piperonylprop-2-en01 (119). Antimicrobial test using the disc diffusion method
showed that the chloroform and the hexane extract of the two species contained
almost solely (8-methyl cinnamate, which were active against fungus. The presence
of (Q- piperonyl-2-enal (1 16) and (Q-piperonylprop-2-en01 (1 19) were reported for
the first time from the genus Cinnamomum.
Phytochemical investigation on the stem and bark of Cinnamomum microphyllum
resulted in the isolation of a coumarin; scoparone (120), benzyl benzoate (4), Psitosterol
(118) and mixtures of pinoresinol-type lignans; pinoresinol (121),
syringaresinol (37) and medioresinol (122). The lignan mixture was found to
possess significant antioxidant activity against three antioxidant a autooxidation of linoleic acid, xanthinelxanthine oxidase superoxide scavenging
assay and DPPH radical scavenging activity.
Phytochemical investigation on the leaves and bark of Melicope cf. hookeri T.G.
Hartley resulted in the isolation of three flavonoids, two coumarins and sterols. The
three flavonoids; ayanin (57), ombuin (123) and kumatakenin (124) together with Psitosterol
(1 18) were isolated from the leaves. The bark extract afforded ayanin (57),
P-sitosterol (lls), urnbelliferone (102) and scopoletin (125). Crude extracts of M. cf.
hookeri were screened for antimicrobial activity, antioxidant activity and TPAinduced
ear oedema assay. The extracts failed to show significant antimicrobial or
antioxidant activity. However, the leaf ethyl acetate extract showed strong antiinflammatory
activity with the chloroform extract (95%) and methanol extract (92%)
showing the highest inhibitions as compared to the petroleum ether extract (70%).
The presence of flavonoid compounds in the species probably contribute to the antiinflammatory
activity of the plant extracts
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