PHYTOCHEMISTRY AND ANTIBACTERIAL PROPERTIES OF SECONDARY METABOLITES FROM INDONESIAN FABACEAE

Cassia and Tephrosia are two tropical genera belong to Fabaceae (Leguminosae) family. This family is widely distributed around the world. In Indonesia, this plants are known as “Polong-polongan”. Indonesian people have used the plants for building materials, household, traditional medicines, n...

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Main Author: ADIMURTI KUSUMANINGTYAS ( NIM : 30511004 ), VALENTINA
Format: Dissertations
Language:Indonesia
Online Access:https://digilib.itb.ac.id/gdl/view/24608
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Institution: Institut Teknologi Bandung
Language: Indonesia
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Summary:Cassia and Tephrosia are two tropical genera belong to Fabaceae (Leguminosae) family. This family is widely distributed around the world. In Indonesia, this plants are known as “Polong-polongan”. Indonesian people have used the plants for building materials, household, traditional medicines, nitrogen-fixing species, and soil reclamation. Phytochemical investigation on these two genus are relatively still limited. The main secondary metabolites found in these genera include flavonoids, isoflavonoids, rotenoids, stilbenoids and polyketides. While Cassia species is a rich source of anthraquinone derivatives, stilbenoids and flavonoids, the genus Tephrosia is notably the plants that produce flavonoids and isoflavonoids, including rotenoids.By considering the relatively large number of the Fabaceae growing in Indonesia, therefore in this research a phytochemical study of three species of two genus has been conducted, namely Cassia grandis, C. alata, and Tephrosia vogelii. The objectives of this study are to isolate the secondary metabolites of the three species, and to elucidate their chemical structures by using modern spectroscopic techniques, as well as to evaluate their antibacterial properties against four bacteria.Plant materials include the heartwoods of C. grandis collected from Cikaret, Bogor, West Java, while the leaves and heartwoods of C. alata were obtained from Jambi, West Sumatera, and the seedpods of T. vogelii were obtained from Cisarua, Cimahi, West Java. The isolation of the secondary metabolites involved extraction by a maceration technique at room temperature, followed by fractionation and purification steps using various chromatographic techniques, such as vacuum liquid chromatography, column chromatography, and radial chromatography. The molecular structures of the isolated compounds were determined based on spectroscopic data, including 1D and 2D NMR, and mass spectra. The antibacterial activity of the isolated compounds was evaluated against four pathogenic bacteria (Staphylococcus aureus ATCC 25923, Bacillus substilis, Escherichia coli ATCC 25922 and Salmonella typhi).Fourteen compounds, including a new compound, have been succesfully isolated from C. grandis, C. alata and T. vogelii. The new compound, i.e. tephrovogelinon (1), was isolated from T. vogelii. Along with the new compound six known compounds were also obtained from T. vogelii, namely tephrosin (2), dehydrodeguelin (3), obovatachalcone (4), isolonchocarpin (5), obovatin (6), pongachin (7), and seven known compounds were isolated from C. grandis, namely piceatannol (8), resveratrol (9), compound mixture (1 : 1) of rhapontigenin (10) and aromadendrin (11), and compound mixture (1 : 1) of rhapontigenin (10) and luteolin (12), as well as two compounds from C. alata i.e. kaempferol (13) and emodin (14).The new compound (1) gives an important contribution on the phytochemistry of Tephrosia. In particular, compound 1, is the first time a quinone derivatives tobe isolated in Tephrosia and also is the first time a modified isoflavone to be found in the nature. Compound 1 will certainly be important to the phytochemistry of the genus. The presence of compounds 8 in the Cassia also the first time. It is interesting to note that compounds 8-9, and 13-14, which were isolated from C. grandis and C. alata, respectively, can become markers compounds to some Cassia plants, and therefore they have significance to their chemotaxonomical relationships.The antibacterial properties of the isolated pure compounds were evaluated against S. aureus, B. substilis, E. coli and S. typhi. These compounds showed various antibacterial properties. Four of them, namely compounds 1, 2, 7, and 13, exhibited potent antibacterial activities against all bacteria (S. aureus, B. substilis, E. coli and S. typhi) with their MIC values were 25-50 (rumus). Compounds 5 and 6 also exhibited promising selective antibacterial activities against S. typhi with their MIC values 50 (rumus), while compounds 9 and 14 exhibited potent against B. substilis with their MIC values were 25 (rumus) and against E. coli with MIC values were 50 (rumus). Compounds 3, 4 and 8 were not a potential as antibacterial (MIC values were &#8805; 100 (rumus)).As a conclusion, the phytochemical studies on C. grandis, C. alata and T. vogelii (Fabaceae) led to the isolation of one new compound, together with thirteen known compounds, that gives an important contribution to the phytochemistry of Fabaceae. The eleven isolated compounds also exhibited potential or promising selective antibacterial activities. <br />