Fitriana et al., ALCHEMY Jurnal Penelitian Kimia, Vol. 17(2), 2021, 219-226
219
Copyright © 2021, ALCHEMY Jurnal Penelitian Kimia, ISSN 1412-4092, e ISSN 2443-4183
A New Limonoid from the Seeds of Chisocheton lasiocarpus (Meliaceae)
Ronauli Fitriana
a
, Nurlelasari Nurlelasari
a
, Darwati Darwati
a
, Desi Harneti
a
, Rani Maharani
a,b
,
Tri Mayanti
a
, Unang Supratman
a,b
a
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, Indonesia
b
Central Laboratory of Universitas Padjadjaran, Jatinangor 45363, Indonesia.
*
Corresponding author: nurlelasari@unpad.ac.id
DOI: 10.20961/alchemy.17.2.44782.219-226
Received 11 October 2020, Accepted 08 June 2021, Published 09 September 2021
Keywords:
limonoids;
chisocheton;
lasiocarpines;
14β,15β-
epoxynimonol.
ABSTRACT. A New Limonoid from the Seeds of Chisocheton lasiocarpus (Meliaceae).
Chisocheton is one of Meliaceae genus, which has about 53 species spreading in subtropical and tropical
regions. One of the species is Chisocheton lasiocarpus. Chisocheton is rich in limonoids that have
various biological activities such as anticancer, antimalarial, anti-inflammatory, antifeedant, antiviral,
neuroprotective, and antimicrobial properties. This study aims to isolate limonoids from the seeds of C.
lasiocarpus, and determine the structures. The dry powder of seeds of C. lasiocarpus (203.75 g) was
macerated with subsequent n-hexane, ethyl acetate, and methanol. Extract of ethyl acetate was separated
and purified using chromatography methods until a new limonoid, lasiocarpines (1) and one known
limonoid, 14β,15β-epoxynimonol (2) were obtained. The purification process was guided by Ehrlich
reagent. The chemical structures were identified by UV, IR,
1
H-NMR,
13
C-NMR, 2D NMR, and mass
spectrometry.
INTRODUCTION
Limonoids are triterpenoid compounds which degrade on their four carbon side chains. This group of
compounds has various biological properties including insecticidal, antibacterial, antimalarial, antiviral,
antifungal, and anticancer activities (Mohamad et al., 2009). This group of compounds is found in the
Meliaceae family, including in the Chisocheton genus (Shilpi et al., 2016). Chisocheton is a genus of the
Meliaceae family which contains approximately 53 species spreading in India, Thailand, Malaysia, and
Indonesia (Nurlelasari et al., 2017). Several limonoids were found in C. siamensis, C. paniculatus, C.
microcarpus, C. ceramicus, C. erythrocarpus, C. cumingianus subsp. balansae, C. macrophyllus, and C.
pentandrus (Shilpi et al., 2016; Nurlelasari et al., 2017 and Supriatno et al., 2018). Limonoid types that have
been isolated from the Chisocheton genus include havanensin (Nurlelasari et al., 2017; Laphookhieo et al.,
2008; Supriatno et al., 2018; Hoai et al., 2018), phragmalin (Najmuldeen et al., 2011; Chong et al., 2012) 30-
nor trijugine (Katja et al., 2016), mexicanolide (Awang et al., 2007), and vokensin (Yang et al., 2009). One of
the Chisocheton species that has not been widely explored for its secondary metabolite content is C.
lasiocarpus. Until now, there are only two phytochemicals of C. lasiocarpus isolated from this plant, namely
stigmast-5 (6) -en-3β-ol (Nurlelasari et al., 2018) and lasiocarpon that showed moderate cytotoxic activity
against MCF-7 breast cancer cell with an IC50 value of 42.5 mM (Hidayat et al., 2018). In this study we
successfully isolated one new limonoid compound from C. lasiocarpus seeds, having unusual side chains and
one known havanensin-type limonoid.
EXPERIMENTAL
In this study we used the seeds of C. lasiocarpus, which were collected in Bogor Botanical Garden, Bogor,
West Java Province, Indonesia.
General experimental procedures
UV (ultraviolet) spectra were measured on a TECAN Infinite M200 pro, with MeOH. The IR spectra
were recorded on a Perkin Elmer spectrum-100 FT-IR (fourier transform infrared) in KBr. Mass spectra were
ALCHEMY Jurnal Penelitian Kimia
Laman resmi: https://jurnal.uns.ac.id/alchemy