STEROIDAL DERIVATIVES OF PHYSALIS ANGULATA AND THEIR ANTIBACTERIAL ACTIVITY

• Main Author: SURYANINGTIAS (NIM : 20514027), APRILLIYANI
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/21184
• Institution: Institut Teknologi Bandung

Physalis (Solanaceae) is a genus of plants that related to tomatoes and chili <br /> <br /> <br /> peppers and is characterized by a bladder-like bag that covers the fruit. It is the <br /> <br /> <br /> largest genus of the Solanaceae, with 75-90 species of mostly Mexican origin that <br /> <br /> <br /> have now been cultivated and spread into tropical region around the world. One <br /> <br /> <br /> species of the genus, Physalis angulata, is distributed widely in the world. In <br /> <br /> <br /> Indonesia, this plant is known as 'Cecendet (Sundanese)' or 'Ciplukan (Javanese)' <br /> <br /> <br /> and is an herbaceous plant that is used as a medicinal plant for various diseases, <br /> <br /> <br /> such as malaria, asthma, hepatitis, dermatitis, and rheumatism. This plant can be <br /> <br /> <br /> found in various spans, both damp and dry. The fruit is covered by the bag and <br /> <br /> <br /> turn yellow and the bag splits while ripening. The plant’s extracts and pure <br /> <br /> <br /> compounds have been reported to show various activities, such as <br /> <br /> <br /> antimycobacteria, antioxydant, antinociceptive, antiinflamation, antiproliferation, <br /> <br /> <br /> anticancer, cytotoxic, and antiplasmodial. Phytochemically, the Physalis is known <br /> <br /> <br /> as a source of ergostane steroid derivatives with high oxidation rates forming new <br /> <br /> <br /> structures with withanolide carbon skeleton and its modified derivatives. <br /> <br /> <br /> Generally, withanolides are divided based on the lactone group contained in their <br /> <br /> <br /> skeletons, &#948;-lactone or &#947;-lactone. The mayor secondary metabolites from this <br /> <br /> <br /> plant are modified withanolides called physalin, a group with 13,14-seco-16,20- <br /> <br /> <br /> cyclo-steroidal skeleton. In this study, isolation of steroid derivatives from this <br /> <br /> <br /> plant has been conducted and their antibacterial activities have been evaluated. <br /> <br /> <br /> The sample used was its leaves and stems collected from Tawangmangu, Central <br /> <br /> <br /> Java. The isolation steps include extraction, fractionation and purification, with <br /> <br /> <br /> various chromatographic methods. Extraction was performed by maceration using <br /> <br /> <br /> methanol at room temperature. Fractionation was performed using liquid vacuum <br /> <br /> <br /> chromatography with mixture of n-hexane, ethyl acetate, and methanol as gradient <br /> <br /> <br /> eluent while the purification was done using radial chromatography technic with <br /> <br /> <br /> suitable eluent system. The determination of pure compound structures is based <br /> <br /> <br /> on spectra data of NMR 1D (1H and 13C) and 2D (HSQC, COSY, HMBC, <br /> <br /> <br /> NOESY, and TOCSY). Based on the methodology, three pure compounds have <br /> <br /> <br /> been successfully isolated from three different fractions. These three compounds <br /> <br /> <br /> have been identified as physalin D, isophysalin B, and physalin J. Isolation of <br /> <br /> <br /> isophysalin B from this plant was reported for first time, whereas physalin D and <br /> <br /> <br /> physalin J had been reported previously. In this research, a study on the structures <br /> <br /> <br /> of the three compounds that has been conducted yields several suggestions of the <br /> <br /> <br /> previously reported data, including more suitable positioning of isophysalin B carbons’ chemical shifts and completing physalin J carbons’ chemical shifts. The <br /> <br /> <br /> 3D structural study of these compounds produces more comprehensive and <br /> <br /> <br /> appropriate information of the three compounds based on 1D and 2D NMR data. <br /> <br /> <br /> Antibacterial activity assay was performed by agar diffusion method (Kirby- <br /> <br /> <br /> Bauer test) using chloramphenicol as a comparative antibiotic including six Gram <br /> <br /> <br /> -(+) bacteria: Bacillus cereus, Enterococcus faecalis, Kocuria rhizophilla, Listeria <br /> <br /> <br /> monocytogenes, Staphylococcus aureus, and Staphylococcus saprophyticus and <br /> <br /> <br /> five Gram-(-) bacteria: Citrobacter freundii, Enterobacter aerogenes, Escherichia <br /> <br /> <br /> coli, Pseudomonas aeruginosa, and Salmonella enterica. The test results showed <br /> <br /> <br /> that the three compounds are not active as antibacterial even though the extract <br /> <br /> <br /> exhibits inhibition zones with size range from 8 to 12 mm. To conclude, in this <br /> <br /> <br /> study, three withanolide steroid derivative compounds that inactive as antibacteria <br /> <br /> <br /> were successfully isolated.