ISOLATION AND STRUCTURE DETERMINATION OF SECONDARY METABOLITES FROM THE LEAVES OF Macaranga involucrata (Roxb.) Baill

• Main Author: Ilimu, Edi
• Format: Theses
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/38231
• Institution: Institut Teknologi Bandung

Macaranga is one of the largest genus of the family Euphorbiaceae comprising 300 species with local name “mahang-mahangan”. Macaranga is widespread in the region of Africa and in the west of Madagascar to the tropical regions of Asia, northern Australia and in the Pacific islands. In Indonesia Macaranga spread in several areas: Papua, Maluku, Sulawesi, Kalimantan, Sumatra, Bangka and Java. Macaranga is known to have economic value in society, it used in industry as raw material for paper and also used as building materials. It also known to have various properties in treating several deseases such as fever, headache, abdominal pain, dysentery, and muscle spasms. Phytochemical studies showed the presence of several phenolic compounds such as flavonoids and stilbene derivatives. The phenolic compounds have a unique molecular structure with additional of some substituents such as prenyl (C5), geranyl (C10), farnesyl (C15), and geranylgeranyl (C20). This research has been conducted on the isolation of secondary metabolites from the leaves of M. involucrata by maceration method using acetone, followed by separation and purification by using liquid vacuum chromatography and radial chromatography to obtain pure compounds. Determination of the structure is based on a data analysis of 1D NMR spectrum (1H-NMR dan13C-NMR), 2D NMR (1H-1HCOSY, NOESY, TOCSY, HSQC, and HMBC), and mass spectra (MS). Based on this methodology, a monocyclic diterpene derived from cembrane named poilanoat acid, also two stilbene derivatives named 4-farnesyl-3,5,3'4'- tetrahydroxystilbene and mappain, and also two flavone derivatives 5,7,4'- trihydroxy-3'(3-methylbut-2-enyl)-3-methoxy flavone and macarangin, have been isolated from this plant. From the five compounds isolated from the leaves of M. involucrata, 4-farnesyl-3,5,3',4'-tetrahydroxystilbene known as a novel compound, where as 5,7,4'-trihydroxy-3'(3-methylbut-2-enyl )-3-methoxyflavone a flavone derivative was first found in Macaranga, but has been found before in Dodonaea genus from Sapindaceae family. Poilanoat acid, monocyclic diterpene has previously been found from leaves of M. pruinosa originating from South Sumatra, while mappain has been found from M. mappa and M. makarangin discovered from leaves of M. denticulata and M. vedeliana found in New Caledonia. Based on these results showed that leaf of M. involucrata from Central Buton, Southeast Sulawesi can be used as a source of terpenoid, stilbene, and flavonoid derivatives.