TRITERPENOID AND LIMONOID DERIVATIVES FROM SEEDS AND FRUIT HULLS OF KECAPI (SANDORICUM KOETJAPE MERR)

The Meliaceae family are well known as producer of limonoid derivatives, triterpenoids. The limonoids of Meliaceae, also known as meliacins, are more complex with very high degree of oxidation and ring rearrangement exhibited in the parent limonoid structure. The limonoids are defined by several...

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Bibliographic Details
Main Author: Banyuning Bumi, Miranti
Format: Theses
Language:Indonesia
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Online Access:https://digilib.itb.ac.id/gdl/view/32320
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Institution: Institut Teknologi Bandung
Language: Indonesia
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Summary:The Meliaceae family are well known as producer of limonoid derivatives, triterpenoids. The limonoids of Meliaceae, also known as meliacins, are more complex with very high degree of oxidation and ring rearrangement exhibited in the parent limonoid structure. The limonoids are defined by several common characteristics: they are tetranortriterpenoid (i.e. they are formed by the loss of four-carbon unit from normal of triterpenoid side chain) and they often contain lactone rings formed by the biological equivalent of the Baeyer-Villiger oxidation reaction (ring A and ring D). The researcher’s interest on meliacin is not only in structural diversity, but also broad range of bioactivity, such as antifeedant, growth-regulating activities, insecticide, antimicrobial (antibacterial and antifungi), antimalarial, antiviral, and cytotoxic. One of Meliaceae family which has known in Indonesia is “Kecapi” or “Sentul” (Sandoricum koetjape Merr, syn. S. indicum Cav., S. nervosum Blume or Melia koetjape Burm.) as economic plant which produces edible fruit. This plant are distributed in tropical and subtropical regions throughout the world, which center of distribution in South-East Asia. Beside its fruit, whole plant have been used as folk medicines as tonic after childbirth and for the treatment of colic and leucorrhea by native people. Previous reports shows the phytochemical studies on parts of S. koetjape Merr, such as: sandoricin (24) and 6-hydroxysandoricin (25) from seeds; 3-oxo-12-oleanen-29- oic acid (6), koetjapic acid (13), katonic acid (4), and sandorinic acid A-C (8-10) from bark; sandrapin A-E (26-30) and sanjecumin A-B (22-23) from leaves. These compounds’s origin from triterpenoid intact-type (oleanane and multiflorane skeleton), limonoid andirobin-type, and limonoid trijugin-type. The phytochemical research which have been done, based on the uniqueness structure of these triterpenoids and limonoid derivatives. In this research, isolation and characterization of secondary metabolites, fruit hulls and seeds of kecapi (S. koetjape Merr) are come from Pandeglang, Banten, Indonesia. The isolation of secondary metabolites involved a number of laboratory works, including fractination and purification of pure compounds using various chromatographic techniques, including vacuum liquid chromatography and radial chromatography. The structures of isolated compounds were determined using spectroscopic data including IR, UV, MS, polarimeter, and NMR [1D-NMR (1H-NMR and 13C NMR) and 2D-NMR (HSQC, HMBC, COSY, and NOESY)]. In this research, six compounds have successfully isolated and characterized, two known triterpenoid acids as bryononic acid (11) and bryonolic acid (12) (triterpenoid intact-type) which have been isolated from same part of plant which come from Singapore and from stem bark which come from Indonesia. Another compounds are four new limonoid derivatives as J.? (31) (limonoid trijugin-type); J.? (32), J.? (33), and M.? (34) (limonoid andirobin-type) which are first time isolated from plant. The isolated limonoids andirobin-type from seeds of kecapi (S. koetjape Merr) have different oxygenated pattern with limonoids andirobin-type from same part on previous report. 32 - 34 have oxygen function group at position C-9 and or C-11, those are different with sandoricin (24) and 6-hydroxysandoricin (25) which have acetoxy function group at position C-12 and C-15. The isolated limonoids trijugin-type from seeds of kecapi (S. koetjape Merr) also have different oxygenated pattern with limonoids trijugin-type (26-30) from leaves of S. koetjape Merr on previous report. Based on analysis of those structures, it can be concluded that seeds of S. koetjape Merr are potential source of limonoids which have different oxygenated pattern with limonoids from another part of this plant.