- Extraction, Isolation and Characterization of Valuable Worked on Acacia Tortilis
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Acacia tortilis is one of the important species of genus Acacia belonging to family Leguminaceae. Though there is no more study performed on this plant but it plays important role in the countries where it found. These countries include North Africa, Arabian Peninsula and Asian countries. The various part of Acacia tortilis plant say leaves, pods, gum exudates and bark were used as antidiabetic, antidiarrhoeal, antiasthmatic and also had several other medicinal benefits. The present discussion deals with the isolation and characterization of the following compounds from the leaves of Acacia tortilis. Lupan-3-ol, 12,20-diene, Lupan-12, 20-dien 3-one, Friedelin, ?-amyrin, ?- sitosterol, Apigenin, Luteolin, Quercetin, 5,7-dihydroxy-4-p-methyl benzylisoflavone, Vitexin, 2',6'-dihydroxy chalcone-4'-O-glucoside.
- Muhaisen, Hasan M. H.
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p. 6731 - 6747
(2021/11/01)
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- Synthesis and search for 3β,3′β-disteryl ethers after high-temperature treatment of sterol-rich samples
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It has been proven that at increased temperature, sterols can undergo various chemical reactions e.g., oxidation, dehydrogenation, dehydration and polymerisation. The objectives of this study are to prove the existence of dimers and to quantitatively analyse the dimers (3β,3′β-disteryl ethers). Sterol-rich samples were heated at 180 °C, 200 °C and 220 °C for 1 to 5 h. Quantitative analyses of the 3β,3′β-disteryl ethers were conducted using liquid extraction, solid-phase extraction and gas chromatography coupled with mass spectrometry. Additionally, for the analyses, suitable standards were synthetized from native sterols. To identify the mechanism of 3β,3′β-disteryl ether formation at high temperatures, an attempt was made to use the proposed synthesis method. Additionally, due to the association of sterols and sterol derivatives with atherosclerosis, preliminary studies with synthetized 3β,3′β-disteryl ethers on endothelial cells were conducted.
- Bus, Katarzyna,Ofiara, Karol,Sitkowski, Jerzy,Szterk, Arkadiusz,Zmys?owski, Adam
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- Modeling Antibacterial Activity with Machine Learning and Fusion of Chemical Structure Information with Microorganism Metabolic Networks
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Predicting the activity of new chemical compounds over pathogenic microorganisms with different metabolic reaction networks (MRNs) is an important goal due to the different susceptibility to antibiotics. The ChEMBL database contains >160 000 outcomes of preclinical assays of antimicrobial activity for 55 931 compounds with >365 parameters of activity (MIC, IC50, etc.) and >90 bacteria strains of >25 bacterial species. In addition, the Leong and Barabàsi data set includes >40 MRNs of microorganisms. However, there are no models able to predict antibacterial activity for multiple assays considering both drug and MRN structures at the same time. In this work, we combined perturbation theory, machine learning, and information fusion techniques to develop the first PTMLIF model. The best linear model found presented values of specificity = 90.31/90.40 and sensitivity = 88.14/88.07 in training/validation series. We carried out a comparison to nonlinear artificial neural network (ANN) techniques and previous models from the literature. Next, we illustrated the practical use of the model with an experimental case of study. We reported for the first time the isolation and characterization of terpenes from the plant Cissus incisa. The antibacterial activity of the terpenes was experimentally determined. The more active compounds were phytol and α-amyrin, with MIC = 100 μg/mL for Vancomycin-resistant Enterococcus faecium and Acinetobacter baumannii resistant to carbapenems. These compounds are already known from other sources. However, they have been isolated and evaluated for the first time here against several strains of multidrug-resistant bacteria including World Health Organization (WHO) priority pathogens. Last, we used the model to predict the activity of these compounds versus other microorganisms with different MRNs in order to find other potential targets.
- Nocedo-Mena, Deyani,Cornelio, Carlos,Camacho-Corona, María Del Rayo,Garza-González, Elvira,Waksman De Torres, Noemi,Arrasate, Sonia,Sotomayor, Nuria,Lete, Esther,González-Díaz, Humbert
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p. 1109 - 1120
(2019/03/19)
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- Synthesis and biological activity evaluation of novel peroxo-bridged derivatives as potential anti-hepatitis B virus agents
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Previous studies have demonstrated that natural steroid compounds containing a peroxide bridge exhibited potential anti-hepatitis B virus activity. To continue our research, a simple and regioselective methodology, using Eosin Y as a clean photosensitized oxidation catalyst, was developed for the synthesis of a peroxide bridge in steroids. The method that using Eosin Y as the catalyst was exposed to visible light and furbished in high yields, did not involve tedious work-up or purification, and avoided using environmentally hazardous solvents. It can be regarded as a green protocol. Moreover, a series of cholesterol and β-sitosterol derivatives containing a peroxide bridge were synthesized using this method and screened for their anti-HBV activity. Among the compounds synthesized in this research, 5α,8α-cyclicobioxygen-6-vinyl-3-oxo-cholesterone (1f, 3.13 μg ml?1) had the most potent activity with inhibition rates of 77.45% ± 6.01% and 58.73% ± 8.64% on the secretion of HBsAg and HBeAg antigens, respectively, after 8 days. Further acute toxicity test showed that the LD50 value of compound 1f was 362.46 mg kg?1 after an intraperitoneal injection in mice. Moreover, structure-activity relationships of cholesterol and β-sitosterol derivatives were briefly discussed.
- Jia, Menglu,Zhao, Rui,Xu, Bing,Yan, Wenqiang,Chu, Fuhao,Gu, Hongshun,Xie, Tianxin,Xiang, Hongjun,Ren, Jian,Chen, Dagang,Wang, Penglong,Lei, Haimin
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supporting information
p. 148 - 151
(2017/02/05)
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- Phytochemical investigation and characterization of isolated chemical constituents from Kyllinga triceps Rottb.
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Four compounds have been isolated by column chromatography from Kyllinga triceps namely quercetin dihydrate (1), rutin (2), β-sitosterol (3) and stigmasterol (4). Their structures have been elucidated by, FTIR, HR-EIMS, 1H NMR and 13C NMR spectroscopic studies.
- Verma, Nishant,Jha,Ahmad, Shamim,Chaudhary, Sudhir,Ali, Mohammad
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p. 1393 - 1400
(2017/05/02)
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- Practical and facile route to a functional intermediate from stigmasterol for the synthesis of 1α-hydroxyvitamin D5 and related compounds
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As a functional and versatile intermediate for the synthesis of 1α-hydroxyvitamin D5 and related compounds, 1α,2α-epoxy-3β-hydroxystigmasta-5,7-diene was synthesized by a practical and facile 17-step route from stigmasterol in 17% overall yield.
- Takahashi, Michiyasu,Hosokawa, Seiya,Ono, Yuuya,Kubodera, Noboru
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p. 101 - 113
(2017/03/11)
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- COMPOSITION FOR PREVENTING HAIR LOSS AND ACCELERATING HAIR GROWTH
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Disclosed is a composition for prevention of hair loss and promotion of hair growth. The composition includes a compound represented by Formula 1, wherein A is derived from polycyclic compounds, and R is a hydroxyl group, or a saturated or unsaturated straight or branched alkyloxy or acyloxy group having 1 to 20 carbon atoms.
- -
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Paragraph 0017
(2015/10/05)
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- A concise synthesis of β-sitosterol and other phytosterols
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A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of β-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Δ22-23 phytosterols.
- Hang, Jiliang,Dussault, Patrick
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experimental part
p. 879 - 883
(2010/10/19)
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- Sterols as anticancer agents: Synthesis of ring-B oxygenated steroids, cytotoxic profile, and comprehensive SAR analysis
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The cytotoxicity of oxysterols was systematically studied in tumor and normal cells. Synthetic strategies to prepare this library included oxidations at ring B and a new method to yield 6β-hemiphthalates directly from Δ5-steroids. Most oxysterols were cytotoxic and showed selectivity toward cancer cells, LAMA-84 cells (leukemia) being particularly sensitive to 4, 8, 22, and 27 (IC50 5.6 μM). The structural requirements to induce selective toxicity are discussed to shed light on the development of new anticancer drugs.
- Carvalho, Jo?o F. S.,Silva, M. Manuel Cruz,Moreira, Jo?o N.,Sim?es, Sérgio,Sá E Melo, M. Luisa
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supporting information; experimental part
p. 7632 - 7638
(2011/02/21)
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- Cetyl triacontanoate and other constituents from Acacia jacquemontii and Kigelia pinnata
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Leaves of Acacia jacquemontii on chemical investigation afforded a new aliphatic ester - cetyl triacontanoate along with n-triacontanol, n-octacosanol, β-sitosterol and stigmasterol while the heart wood of Kigelia pinnata gave lapachol, dehydro-α-lapachone, tecomaquinone-I, D-sesamin, paulownin, wodeshiol (kigeliol), klgelinone, β-sitosterol and stigmasterol on reinvestigation. The structures of isolated compounds were ascertained using various spectral (IR, 1H, 13C NMR, MS) techniques.
- Singh, Pahup,Khandelwal, Poonam,Sharma, Kuldeep K.,Sharma
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body text
p. 1403 - 1407
(2011/09/20)
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- Convenient synthesis of chlorohydrins from epoxides using zinc oxide: Application to 5,6-epoxysitosterol
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Efficient synthesis of protected and unprotected chlorohydrins has been achieved by ring opening of epoxides with acetyl/benzoyl chloride and TMSCl using a catalytic amount of ZnO as a reusable catalyst. The applicability of ZnO is further extended by performing the cleavage of the natural product 5,6-epoxysitosterol with acetyl chloride.
- Moghaddam, Firouz Matloubi,Saeidian, Hamdollah,Mirjafary, Zohreh,Javan, Marjan Jebeli,Farimani, Mehdi Moridi,Seirafi, Marjan
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scheme or table
p. 157 - 163
(2009/09/30)
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- Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters. Part I. Regioselective hydrogenation of stigmasterol: An easy access to oxyphytosterols
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The synthesis of several oxyphytosterols is described starting from stigmasterol, the key step being the regioselective hydrogenation of the 22-23 double bond of the latter.
- Geoffroy, Philippe,Julien-David, Diane,Marchioni, Eric,Raul, Francis,Aoude-Werner, Dalal,Miesch, Michel
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p. 702 - 707
(2008/09/21)
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- Radermachol and naphthoquinone derivatives from Tecomella undulata: Complete 1H and 13C NMR assignments of radermachol with the aid of computational 13C shift prediction
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Petroleum ether extract of the heartwood of Tecomella undulata affords radermachol, an unusual rare pigment and 2-isopropenylnaphtho[2,3-b]furan-4,9- quinone along with lapachol, tecomaquinone-I, dehydro-α-lapachone, α-lapachone, β-lapachone, cluytyl ferulate, stigmasterol and β-sitosterol. Radermachol and 2-isopropenylnaphtho [2,3-b]furan-4,9-quinone are being reported for the first time from genus Tecomella. Complete assignments of 1H and 13C NMR signals of polyketide, radermachol 1, have been achieved by the 13C NMR chemical shift prediction using ab initio MO and DFT/GIAO methods in addition to 2D-NMR techniques.
- Singh, Pahup,Khandelwal, Poonam,Hara, Noriyuki,Asai, Teigo,Fujimoto, Yoshinori
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experimental part
p. 1865 - 1870
(2009/05/27)
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- Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide
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Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3β-O-acetyl group in the presence of the 6β group in 3β,6β-Di-O-acetyl-5α-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3β,5α,6β-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species.
- Wang, Shao-Min,Zhang, Yan-Bing,Liu, Hong-Min,Yu, Guo-Bin,Wang, Ke-Rang
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- Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives
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β-Sitosterol is the most prevalent plant cholesterol derivative (phytosterol) and can undergo similar oxidation to cholesterol, leading to β-sitosterol oxides. The biological impact of phytosterol oxides has only been evaluated in a phytosterol blend (usually of β-sitosterol, campesterol, stigmasterol and dihydrobrassicasterol). The lack of pure phytosterols, including β-sitosterol, hinders the collection of significant toxicity data on the individual β-sitosterol oxides. An efficient synthetic route to multi-gram quantities of pure β-sitosterol is described here, together with the first syntheses and characterisation of pure β-sitosterol oxides. The Royal Society of Chemistry 2005.
- McCarthy, Florence O.,Chopra, Jay,Ford, Alan,Hogan, Sean A.,Kerry, Joe P.,O'Brien, Nora M.,Ryan, Eileen,Maguire, Anita R.
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p. 3059 - 3065
(2007/10/03)
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- Gram-scale chromatographic purification of β-sitosterol: Synthesis and characterization of β-sitosterol oxides
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An effective purification method for β-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. β-Sitosterol (≥95% purity) was obtained on a gram-scale. Thus, the synthesis of six β-sitosterol oxides, including 7α-hydroxy, 7β-hydroxy, 5,6α-epoxy, 5,6β-epoxy, 7-keto, and 5α,6β-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (~95% purity) were well-documented.
- Zhang, Xin,Geoffroy, Philippe,Miesch, Michel,Julien-David, Diane,Raul, Francis,Aoude-Werner, Dalal,Marchioni, Eric
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p. 886 - 895
(2007/10/03)
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- Synthesis of 1α-Hydroxyvitamin D5 using a modified two wavelength photolysis for vitamin D formation
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1α-Hydroxyvitamin D5 (1) is a promising chemopreventive agent for breast cancer and is being developed as a drug. We report a synthesis for this vitamin D analogue which uses a photochemical method for the B-ring opening, leading to the conjugated triene system. The precursor 7-dehydrositosteryl acetate (4) obtained through a one-pot, five-step procedure, was completely free of the 4,6-diene isomer that usually forms in the 5,7-diene synthesis. The pre-vitamin isomer (11) was generated using a modified two-wavelength photolysis procedure that increases the yield for this step more than 3-fold compared to classically used photolysis. The 1α-hydroxylation step was performed on the 3-triethylsilyl-trans-vitamin D5 (17) obtained via the sulfur dioxide adduct of cis-vitamin D5, in an overall yield of 48%. Photoisomerization and deprotection completed the synthesis.
- Moriarty, Robert M.,Albinescu, Dragos
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p. 7624 - 7628
(2007/10/03)
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- Rapid formation of acetates under microwave irradiation using montmorillonite acid clay catalyst
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The combination of microwave irradiation and montmorillonite [H +] clay catalyst dramatically enhances the rate of formation of acetates of alcohols, phenols and amines when treated with acetic anhydride. A series of acetates have been prepared with significantly low reaction times in very good to excellent yields.
- Mallavadhani, Uppuluri V.,Sahoo, Laxmidhar,Roy, Subhra
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p. 2175 - 2177
(2007/10/03)
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- Microwave enhanced acetylation of alcohols
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Microwave irradiation of alcohols with acetic anhydride in the presence of a catalytic amount of NaOH for a few minutes yielded the corresponding acetylated products in excellent yield.
- Patnam, Ramesh,Chang, Fang-Rong,Kuo, Reen-Yen,Pan, Wen-Bin,Wu, Yang-Chang
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p. 301 - 302
(2007/10/03)
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- Chemical constituents of the roots of Kirganelia reticulata
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Chemical investigation of the roots of Kirganelia reticulata afforded octacosane, tricosyl alcohol, tetracosyl alcohol, sorghumol acetate, friedelin, epifriedelinol, sorghumol, β-sitosterol, kokoonol, stigmasta-5,6-dihydro-22-en-3β-ol and tricin.
- Jain,Nagpal
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p. 776 - 777
(2007/10/03)
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- Synthesis of cytotoxic 6E-hydroximino-4-ene steroids: Structure/activity studies
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In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioctivity than other structural motifs.
- Deive,Rodríguez,Jiménez
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p. 2612 - 2618
(2007/10/03)
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- Synthesis of (24R)-3β-hydroxystigmast-5-en-7-one
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The natural compound (24R)-3β-hydroxystigmast-5-en-7-one has been synthesized from β-sitosterol.
- Kovganko,Kashkan
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p. 433 - 436
(2007/10/03)
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- Uteroactive constituents from Combretum kraussii
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We have established that certain extracts of Combretum kraussii Hochst roots cause contractions in isolated rat uterine tissue, and have purified the most active uterotonic components. The mode of action of the various extracts/components on isolated rat uterus falls into three different categories. The activity of crude extracts from leaves and branches of C .erythrophyllum (Burch.) Sond. and C. kraussii Hochst was also measured. We have identified the following compounds from root extracts: combretastatin, combretastatin A-1 and combretastatin B-1 as well as the corresponding 2-O-β-D-glucosides of the latter two combretastatins, β-sitosterol, ellagic acid and the di- and trimethyl ethers of ellagic acid. This is the first report of the occurrence of combretastatin and ellagic acid derivatives in this Combretum species.
- Brookes, K. Bridget,Doudoukina, Olga V.,Katsoulis, Lynn C.,Veale, D. Joy H.
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p. 127 - 132
(2007/10/03)
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- Isolation and synthesis of the first natural 6-hydroximino 4-en-3-one-steroids from the sponge Cinachyrella spp.
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Two new 6-hydroximino-4-en-3-one steroids: (24R,6E)-24-ethylcholest-6-hydroximino-4-en-3-one (1) and (6E) cholest-6-hydroximino-4-en-3-one (2), accompanied by the known cholest-4-en-3-one were isolated from a mixture of two morphospecies of the sponge Cinachyrella (C. alloclada and C. apion). Use of spectroscopic methods (NMR and MS) was key to establish their structures which were confirmed by synthesis. Described in this report are the first hydroximino steroids derived from a natural source.
- Rodriguez, Jaime,Nunez, Lucia,Peixinho, Solange,Jimenez, Carlos
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p. 1833 - 1836
(2007/10/03)
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- Structures of five hydroxylated sterols from the seeds of Trichosanthes kirilowii maxim
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Five hydroxylated sterols, stigmastane-3β,6α-diol, poriferastane- 3β,6α-diol, stigmast-5-ene-3β,4β-diol, poriferast-5-ene-3β,4β-diol, and poriferasta-5,25-diene-3β,4β-diol, the latter four of which are new naturally occurring compounds, were isolated from the unsaponifiable lipid of the seed extract of Trichosanthes kirilowii MAXIM. The structures were determined by spectral and chemical methods.
- Kimura,Akihisa,Yasukawa,Takido,Tamura
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p. 1813 - 1817
(2007/10/03)
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- Calliphyllin, a New Diterpene from the Leaves of Callicarpa macrophylla
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A new diterpene designated calliphyllin, betulinic acid, 5,4'-dihydroxy-3,7,3'-trimethoxyflavone, 5,4'-dihydroxy-3,7-dimethoxyflavone and β-sitosterol have been isolated from the leaves of Callicarpa macrophylla Vahl. (Verbenaceae).Calliphyllin has been shown to possess 14α-hydroxy-isopimaric acid (1) structure on the basis of nmr and mass spectral and chemical evidence.
- Talapatra, Sunil K.,Polley, Malabika,Talapatra, Bani
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p. 527 - 532
(2007/10/02)
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- Synthesis of Triaromatic Steroid Hydrocarbons Methylated at Position 2, 3 or 6: Molecular Fossils of Yet Unknown Biological Origin.
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C21-29 triaromatic steroid hydrocarbons bearing a methyl group at unusual positions 2, 3 or 6 have been synthesized from pregnenolone, cholesterol or stigmasterol via stera-3,5-dienes.Their occurence in various sedimentary rocks and petroleums suggests the presence of yet unknown biological precursors.
- Lichtfouse, Eric,Albrecht, Pierre
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p. 1731 - 1744
(2007/10/02)
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- Configurations at C-24 of 24-Alkylsterols from Clerodendrum infortunatum Linn.
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The configurations at C-24 of five 24-alkyl-Δ5-sterols isolated from the aerial parts of Clerodendrum infortunatum have been determined with the help of high-resolution 1H NMR spectroscopy.Two major 24-ethylsterols which possess a Δ25-bond (24-ethyl-25-dehydrocholesterol and 24-ethyl-22,25-bisdehydrocholesterol) have been determined to be the 24β-epimers, while the two minor 24-ethylsterols which lack a Δ25-bond (24-ethylcholesterol and 24-ethyl-22-dehydrocholesterol) have been shown to be the 24α-epimers.On the other hand, 24-methylcholesterol, another minor sterol, has been found to be the C-24 epimeric mixture containing predominantly the 24α-epimer.
- Thakur, Swapnadip,Ghosh, Parthasarathi,Akihisa, Toshihiro,Shimizu, Naoto,Tamura, Toshitake,Matsumoto, Taro
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- Triterpenoids from Eucalyptus Perriniana Cultured Cells
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Eight triterpenes were isolated from the methanol extracts of Eucalyptus perriniana cultured cells as their methyl esters.The structures were elucidated by spectral data to be oleanolic acid, ursolic acid, maslinic acid, 2α-hydroxyursolic acid, hederagenin, 23-hydroxyursolic acid, arjunolic acid and asiatic acid.Key word Index - Eucalyptus perriniana; Myrtaceae; plant cell culture; triterpene; arjunolic acid; asiatic acid; hederagenin; 23-hydroxyursolic acid; maslinic acid; 2α-hydroxyursolic acid; oleanolic acid; ursolic acid.
- Furuya, Tsutomu,Orihara, Yutaka,Hayashi, Chisato
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p. 715 - 720
(2007/10/02)
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- SYNTHESIS OF TRITERPENE AND STEROID GLYCOSIDES
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The glycosylation of cholesterol, β-sitosterol, 28-O-acetylbetulin, and betulin with acylated glycosyl halides in the presence of Hg(OAc)2, Hg(CN)2, CdCO3, Ag2O, Ag2CO3, and HgO + HgBr2 usually gives acylated αβ-glycosides accompanied by acetates, ethers, and bromo and unsaturated derivatives of the initial alcohols.The use of Hg(CN)2 gave mainly β anomers (40-87percent), whereas α anomers preponderated when Hg(OAc)2 was the catalyst.When there was a deficiency of hydrogen halide acceptor and in the presence of the acidic catalyst HgBr2*HBr, the β anomer, produced initially, underwent anomerisation.Cholesteryl α-D-glucopyranoside tetra-acetate (48percent) was obtained by anomerisation of the β anomer.
- Uvarova, Nina I.,Atopkina, Lyubov N.,Elyakov, Georgi B.
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