PHENOLIC DERIVATIVES WITH TERPHENYL GROUP SUBSTITUENT FROM MACARANGA PRUINOSA

• Main Author: ROANISCA (NIM : 20513077), OCCA
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/23614
• Institution: Institut Teknologi Bandung

Macaranga is a large genus in Euphorbiaceae family, locally known as "Mahang-mahangan", and consisting about 300 species. Distribution of Macaranga is widespread from Africa and Madagascar in the west to the tropical regions of Asia. Distribution of Macaranga plants in Indonesia includes Sumatra, Sulawesi, Kalimantan, Java, Halmahera, Bangka, Maluku and Papua. In industry, wood of Macaranga is used as raw material in paper industry and building materials, and the other parts of Macaranga such as roots, leaves, and bark are used as a traditional medicine to cure fever, abdominal pain, and dysentery. Up to now, phytochemical studies of the Macaranga genus had been conducted towards 26 species, 12 of them are from Indonesia. Secondary metabolites found in Macaranga genus include flavonoids, stilbenoid, aryl propanoid, and terpenoids. The uniqueness of secondary metabolites found in Macaranga is the presence of additional substituents which are derived from the terpenil groups such as prenyl (C5), geranyl (C10), farnesyl (C15), and geranil-geranil (C20). Position of the substituents is at C-6 and C-8 in aromatic ring A and at ortho position to the hydroxy group in aromatic ring B. Investigation of the M. pruinosa has been done previously. Secondary metabolites that have been reported from this species which collected from Borneo are flavonoid, and stilbenoid derivatives. They are makapruinosin A - F, nymphaeol C, gliasperin A, and papiriflavonol A. Different secondary metabolite found from leaves of M. pruinosa that grow in South Sumatra namely poilanoat acid (diterpene group) and nymphaeol C. Therefore, this research is done to investigate phytochemical constituent of leaves of M. pruinosa which is obtained from Bangka Belitung Islands. Isolation of secondary metabolites is done through some techniques including maceration in acetone, separation and purification by using various chromatographic techniques, such as vacuum liquid chromatography (VLC) and radial chromatography. Structure determination of isolated compounds were performed by analyzing with 1H-NMR,13C-NMR, 2D NMR, as well as by comparing with literature data. A new stilbene derivative, namely 4-farnesil-3,5,3',4'-tetrahidroksistilben, has been obtained. Other isolated compounds are identified as flavanon derivatives. They are nymphaeol C, nymphaeol B, and 6-farnesil-3',4',5,7-tetrahidroksiflavanon. These compounds are substituted with terphenyl group, known as prenyl (C5), geranyl (C10), and farnesyl (C15). Oxygenation patterns derived on phenolic compounds were obtained following the normal pattern in general flavonoids. Terphenyl group is substituted at the ortho position to the hydroxy group both in ring A and ring B aromatic. Nymphaeol C has also been found in M. pruinosa from Borneo and South Sumatra. While nymphaeol B and compound of 6-farnesil-3', 4', 5,7-tetrahidroksiflavanon have been found in other species of Macaranga. Terpenoid derivatives are not found in Macaranga pruinosa from Bangka Belitung. In conclusion, we here acquired four phenolic derivatives substituted by terphenyl groups from acetone extracts of leaves of M. pruinosa from Bangka Belitung. They are 4-farnesil-3,5,3',4'-tetrahidroksistilben, nymphaeol C, nymphaeol B, and 6-farnesil-3',4',5,7-tetrahidroksiflavanon. The result showed that M.pruinosa can produce different secondary metabolites depend on where they grow.