ISOLATION AND ANTIBACTERIAL TEST OF SECONDARY METABOLITES FROM LANSIUM DOMESTICUM VAR. LANGSAT SEEDS

• Main Author: AGREEANI SITOHANG (NIM: 20514018), IIN
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/22507
• Institution: Institut Teknologi Bandung

Family Meliaceae or locally known as “Mahony” is a plant family of mostly trees and shrubs distributed in tropical and subtropical countries including Indonesia. Meliaceae consists of 50 genuses and 575 specieses including Lansium. Lansium is one of its genuses with single species named Lansium domesticum Corr. This species distributed in South East Asian countries, China, and North America. This species is classified into three varieties in Indonesia, i.e. “Duku:, “Langsat” and “Kokosan”. L. domesticum var. langsat is a tree with 10-20 metre height, mottled grey and orange bark, odd-pinnate leaves, yellowish peel with bitter seed. Langsat variety has been traditionally used for dysentery,sore eyes, malarial and fevers. There are some bioactivity investigation reports about extract of L. domesticum such as, water extract of leaves and peel reported actively inhibit malarial parasite, Plasmodium falciparum and its peel extract also reported degraded the life cycle of the parasite. In addition, CHCl3 extract of L. domesticum fruits reported has the <br /> <br /> <br /> cytotoxic activity against some cancer cells, such as Murine Melanoma Cells (B16F10), Epidermal Carcinoma (KB) and Human Colon Adenocarcinoma (HT-28). Based on phytochemical studies on L. domesticum reported the presence of two major compounds such as triterpenoids and limonoids. Triterpenoids compound found in every part of this plant, such as peels, twigs, leaves, barks and seeds, while limonoids compound found in seeds. Triterpenoids compound from L. domesticum have skeleton characteristics i.e., onoceranoid, secoonoceranoid, <br /> <br /> <br /> bisecoonoceranoid and cycloartanoid, while limonoids compound found in many type of skeletons i.e., azadirone, andirobin, methyl angolensate, mexicanolide, <br /> <br /> <br /> dukunolide, and kokosanolide. In this current study reported the isolation of seeds of L. domesticum var. langsat using maseration with MeOH. First fractination was done by vacuum liquid chromatography (VLC) using n-hexane and EtOAc as eluents. Next fractination was also done by VLC and purification of secondary metabolites was done by radial chromatography (RC). Structure elucidations were determined by 1D NMR spectroscopy (1H-NMR, 13C-NMR, and NOE) and 2D NMR spectroscopy (HSQC, HMBC and COSY). This isolation resulted three compounds consist of two mexicanolide type limonoids, 6-acetoxymexicanolide and 6-hydroxymexicanolide with one secoonoceranoid type triterpene lansiolic acid. The two of mexicanolide type limonoids were characterized by unit of bicyclo[3.3.1]nonane with addition of hydroxy and acetoxy subtituent in C-6 respectively. The secoonoceranoid type triterpene was characterized by cleavage iv between C-21 and C-22 delivered carboxylic acid and alkene as products of oxidation. All isolated compounds was subjected to antibacterial test against Gram positive and Gram negative bacteria. Triterpenoid compound, lansiolic acid showed potential antibacterial activity against Bacillus subtilis and Shigella dysenteriae with MIC value 3,12 &#956;g/ml. This study reported the isolation and antibacterial activity of L. domesticum var. langsat for the first time. The result of this study revealed that seeds of langsat contain an active triterpenoid compound against S. dysenteriae bacteria known as the cause of dysentery disease. As conclusion, this study delivered two limonoid compounds, 6-acetoxymexicanolide and 6-hydroxymexicanolide with one triterpenoid compound, lansiolic acid from seeds of <br /> <br /> <br /> L. domesticum var. langsat. Triterpenoid compound, lansiolic acid showed potential activity against Bacillus subtilis and Shigella dysenteriae with MIC value 3,12 <br /> &#956;g/ml.