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RESOLUTION OF A RACEMIC ISOLEUCINE MIXTURE BY USING METHYL L-MANDELATE Rani Maharani; Ace Tatang Hidayat; Dadan Sumiarsa; Achmad Zainuddin; Ika Wiani Hidayat
Chimica et Natura Acta Vol 4, No 3 (2016)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (237.517 KB) | DOI: 10.24198/cna.v4.n3.10991

Abstract

A methyl ester of L-mandelic acid was found to be an effective resolving agent for resolution of commercial DL-isoleucine. The resolution was based on Steglich esterification between methyl L-mandelate and Boc-DL-isoleucine. The two resolved isomers were easily separated by using a conventional flash-column chromatography, giving quantitatively good yields. Unfortunately, the methyl L-mandelate was found to be ineffective to resolve four stereoisomers of Fmoc- isoleucine.
Two Limonoids from The Seeds of Chisocheton Macrophyllus and Their Cytotoxic Activity Against Mcf-7 Breast Cancer Cells Intan Rahmayanti; Nurlelasari Nurlelasari; Desi Harneti; Rani Maharani; Darwati Darwati; Yoshihito Shiono; Unang Supratman
Molekul Vol 16, No 2 (2021)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (4976.505 KB) | DOI: 10.20884/1.jm.2021.16.2.708

Abstract

Limonoids (tetranortriterpenoids) are triterpenoid compounds that lose four terminals in their structural framework. These compounds have a wide variety of structures and interesting activities including anti-inflammatory, anti-cancer, anti-tumor and anti-malarial properties. The purpose of this study was to find limonoid compounds from the Indonesian Chisocheton plant, and one of which is Chisocheton macrophyllus. The dried and powdered seeds of C. macrophyllus (4.5 kg) were extracted with methanol and partitioned successively with n-hexane, ethyl acetate and n-butanol. Evaporation of each extract resulted in the crude extracts of n-hexane (346.6 g), ethyl acetate (60.8 g) and n-butanol (14.6 g). The n-hexane fraction was subjected to a silica gel vacuum-liquid chromatography (VLC) column packed with silica gel 60 using gradient of n-hexane, ethyl acetate and methanol (10% stepwise) to afford thirteen fractions (A-M). Fraction F (4.4 g) was subjected to silica gel column chromatography using gradient of n-hexane and ethyl acetate (5% stepwise). Subfraction F5 (1.2 g) was chromatographed on a column of silica gel eluted with n-hexane: CH2Cl2: EtOAc (2:7.5:0.5) to give compound 1 (19.7 mg) and fraction H (1.8 g) was subjected to silica gel column chromatography using gradient of n-hexane and ethyl acetate (5% stepwise) as eluting solvent to give 2 (12.0 mg). Chemical structures of 1 and 2 were elucidated by spectroscopic methods and determined as 6α-acetoxyepoxyazadiradione (1) and Dysobinin(2). Dysobinin (2) showed weak cytotoxic activity against MCF-7 breast cancer cells with an IC50 value of 228.15 μM