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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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 |
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. |
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