CYCLIC DIARYLHEPTANOIDS FROM STEMBARK OF MYRICA JAVANICA (MYRICACEAE)

• Main Author: Pratiwi, Hany
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/75454
• Institution: Institut Teknologi Bandung

Myrica is one of the four genera of plants in the Myricaceae family. This genus is spread almost evenly throughout the world (except in Australia) and is a type of acthinorhizal plant (a plant that has the ability to be symbiotic with the Frankia genus to fix nitrogen). This genus is commonly used as traditional Ayurvedic medicine to treat various ailments, such as coughs, lung infections, and diarrhea. One of the plant of the genus Myrica that grows in Indonesia is Myrica javanica, which has the regional name 'wuru ketek' in the Java region and 'tétékéan' in the Sunda region. In previous research, three compounds that are cyclic diarylheptanoids have been isolated and identified from the stem and twig tissues of M. javanica, namely myricanol, myricanone, and porson, as well as one triterpenoid, namely taraxerol. The cytotoxic bioactivity of these compounds has been tested against murine leukemia cells P-388, and the test results showed low activity. Moreover, two transformation reactions (prenylation and benzylation) have also been carried out on myricanol obtained from M. javanica. However, phytochemicals and bioactivity studies of compounds from Myrica javanica are still limited, so further research is needed. Based on these reasons, the object of this research was to isolate secondary metabolites from stem bark of M. javanica, carry out transformation reactions of the main secondary metabolites, and examine their bioactivity as an antibacterial. As for the isolation stage, M. javanica stem bark powder was extracted by maceration method using acetone to obtain acetone extract. The extract obtained was then fractionated and purified using vacuum liquid chromatography (VLC) and gravity column chromatography (GCC) techniques. The isolated pure compound was then characterized by its structure based on 1D NMR spectroscopy data (1H NMR and 13C NMR). Three pure compounds, namely myricanol, myricanone, and myricananin C, which are cyclic diarylheptanoid, have been isolated and their structures have also been determined. Myricananin C was isolated for the first time from Myrica javanica, but it has been reported from other species in the same genus. The transformation reaction of the main compound, namely myricanol with 2-(2-chloroethoxy)ethanol, has been carried out, and one product was obtained, namely myricanol substituted in the C-5 phenolic group (12.66% yield). Testing the antibacterial bioactivity of the acetone extract of Myrica javanica stem bark showed the presence of an inhibition zone, both for Pseudomonas aeruginosa and Staphylococcus aureus. These results suggest that the acetone extract has antibacterial activity.