Chemical constituents and biological activities of scaph/ummacropodum (miq.) beumee and sap/umbaccatum (roxb.) / Laode Muhammad Ramadhan Al Muqarrabun

The stem barks of Scaphium macropodum, known as Kembang Semangkuk Jantung (Malay), and Sapium baccatum, known as Ludai (Malay), have been investigated for their phytochemical and pharmacological properties. Several chromatographic techniques were used to separate the chemical compounds including Vacuum Liquid Chromatography (VLC), Radial Chromatography (Rf') and Column Chromatography (CC). A new sesquiterpene named malayscaphiol (8M4) along with two lupane triterpenes, lupeol (8Ml) and lupenone (8M2) and stigmasterol (SM3), were successfully isolated from the stem bark of S. macropodum, while a new triterp ene, malaytaraxcrate (8B3), along with two oleanane triterpenes, taraxerol (SBl) and taraxerone (882), docosyl trans-isoferulate (8B4) and docosanoic acid-2',3'dihydroxypropyl ester (8B5) were identified from the stem bark of S. baccatum. The structures of the compounds were determined using several spectroscopic methods, i.e. mass spectrometry (MS), UV-Vis, FT-IR, 10 and 2D NMR including HMQC, HMBC, COSY and NOESY. Several isolated compounds were subjected to cytotoxicity and anti-cholinesterase (anti- AChE) assays to identify their biological properties. Six compounds i.e. 8Ml, 8M2, 8M3, 8B2, 8B4 and SB5 were subjected to cytotoxicity assay. All the tested compounds demonstrated weak anti-cancer activity against HT-29 and MDA-MB cell lines, with SMI and 8M2 exhibited the strongest cytotoxicity among the tested compounds against HT-29 and MDA-MB, respectively. Only 8Ml showed toxic effect towards normal cell line (3T3) with ICso of 38.92 ug/ml., For anti-AChE assay, three compounds were tested i.e. SMl, SM2 and SB2. All the tested compounds exhibited insignificant anti-AChE activity at concentration of 1000 ug/ml., The ICso of the tested compounds could not be determined, because there was only one data point available in this test. Their antiAChE activity were significantly lower than the standard tacrine (ICso== 25 ug/ml.)

New indolizidine alkaloids from psychrophilic yeast Glyciozyma antarctica PI12

Two alkaloid compounds: namely 3-(1-aminoethyl)tetrahydro-1H-pyrrolo[1,2-d][1,2,4]oxadiazine-1,4(3H)-dione (1) and tetrahydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,3(4H)-dione (2) was isolated from Glyciozyma antarctica (PI12), a psychrophilic yeast. The isolated compounds were isolated by Radial Chromatography and Thin Layer Chromatography techniques. The chemical structures were elucidated by Ultraviolet-visible, Infrared, Nuclear Magnetic Resonance and Mass Spectroscopy

Tetrahydrothiophene-cucurbit(n)urils and Preliminary Studies on Their Recognition Properties

Substituted cucurbit[n]urils (Q[n]) feature substituent(s) on the convex face of their macrocycle structures. The incorporation of substituents on Q[n] is known to affect the physical and/or chemical properties of the derivatives, e.g. solubility and binding affinity, but also provides a means to functionalising Q[n], which could facilitate further elaboration, an ongoing challenge.Inspired by studies on fully-substituted cyclopentano-Q[n]s, this thesis investigates an alternative 5-membered ring substituent, tetrahydrothiophene (THT) for the synthesis of THTnQ[n] as well as preliminary investigations of their recognition properties and synthetic potential for modification. As a model for the modification of THTnQ[n], we investigated the modification of THT-glycoluril diether (THTGE), the precursor to THTnQ[n], which included oxidation to a sulfoxide followed by Pummerer rearrangement reaction.Modifications of synthetic conditions required for the synthesis of THTnQ[n] where n > 5 were investigated. The effect of using alkali metal ions and guest molecules as templates to achieve this objective is discussed. Also the benefits and limitations of employing methanesulfonic acid as both an alternative solvent and acid catalyst have been explored. Clear evidence is provided for the synthesis of THT5Q[5] and THT6Q[6] in 71% and 17% yield, respectively, with preliminary evidence of THTQ[7]-like product in 12% yield. The chemical recognition properties of THT5Q[5] (for CH4, CH2F2, and CH3Cl gases) and THT6Q[6] (for the hydrochloride salts of 1-cyclopentamine and 1,8-octanediamine) were investigated and compared to classical Q[5 and 6].The surprising finding of THT5Q[5]∙KCl crystalline salt, showing two sets of THT5Q[5] signals in 1H NMR spectrum led to the discovery that a Cl- ion resided in the cavity in solution which is released slowly. The presence of the Cl- ion in the cavity of the solid was established by solid state (SS) 35Cl NMR. This was further supported by the SS 35Cl NMR spectra of Q[5]∙KCl and dioxane@Q[6]∙KCl crystals as comparison. The rates of Cl- release from THT5Q[5] and Q[5] cavity were studied in solution with changes in temperature and in KCl/D2O solutions.Other reactions discussed are the oxidation of THT5Q[5] which gave isomers of the sulfoxide of THT5Q[5] ((SO)5Q[5]) and a synthetic approach to the preparation of partially-substituted THT2Q[6] which resulted in isomers of the THT2Q[6] and also a monosubstituted THTQ[6]

A new sesquiterpenoid from <i>Scaphium macropodum</i> (Miq.) Beumee

<div><p>A new sesquiterpenoid, malayscaphiol (<b>1</b>), and three known compounds, lupeol (<b>2</b>), lupenone (<b>3</b>) and stigmasterol (<b>4</b>), were isolated from the methanolic extract of the stem bark of <i>Scaphium macropodum</i>. The structures of the isolated compounds were determined using several spectroscopic methods, including UV–vis, FT-IR, 1D and 2D NMR, and mass spectrometer. Major isolated compounds were assayed for cytotoxicity and anti-acetylcholinesterase activities. The chemotaxonomy significance of this plant was also discussed.</p></div