Simiarenol

CAS# 1615-94-7

Simiarenol

2D Structure

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Simiarenol

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Chemical Properties of Simiarenol

Cas No. 1615-94-7 SDF Download SDF
PubChem ID 12442794 Appearance Cryst.
Formula C30H50O M.Wt 426.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3R,3aR,5aR,5bS,9S,11aS,11bR,13aS,13bR)-3a,5a,8,8,11b,13a-hexamethyl-3-propan-2-yl-1,2,3,4,5,5b,6,9,10,11,11a,12,13,13b-tetradecahydrocyclopenta[a]chrysen-9-ol
SMILES CC(C)C1CCC2C1(CCC3(C2(CCC4(C3CC=C5C4CCC(C5(C)C)O)C)C)C)C
Standard InChIKey XVXPXUMUGATHPD-JMJRLLIOSA-N
Standard InChI InChI=1S/C30H50O/c1-19(2)20-9-12-23-27(20,5)15-17-30(8)24-13-10-21-22(11-14-25(31)26(21,3)4)28(24,6)16-18-29(23,30)7/h10,19-20,22-25,31H,9,11-18H2,1-8H3/t20-,22-,23-,24+,25+,27-,28+,29+,30-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Simiarenol

The root of Rhododendron dauricum L.

Biological Activity of Simiarenol

Description1. Simiarenol may have in vitro leishmanicidal activity against Leishmania donovani promastigotes.
TargetsAntifection

Simiarenol Dilution Calculator

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Preparing Stock Solutions of Simiarenol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3436 mL 11.7178 mL 23.4357 mL 46.8713 mL 58.5892 mL
5 mM 0.4687 mL 2.3436 mL 4.6871 mL 9.3743 mL 11.7178 mL
10 mM 0.2344 mL 1.1718 mL 2.3436 mL 4.6871 mL 5.8589 mL
50 mM 0.0469 mL 0.2344 mL 0.4687 mL 0.9374 mL 1.1718 mL
100 mM 0.0234 mL 0.1172 mL 0.2344 mL 0.4687 mL 0.5859 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Simiarenol

Antiproliferative constituents of the roots of Conyza canadensis.[Pubmed:21294076]

Planta Med. 2011 Jul;77(11):1183-8.

Bioassay-guided fractionation of the N-hexane and CHCl(3) phases of the methanol extract of the roots of Conyza canadensis (L.) Cronquist led to the isolation of two new dihydropyranones named conyzapyranone A (1) and B (2), and the known 4 Z,8 Z-matricaria- gamma-lactone (3), 4 E,8 Z-matricaria- gamma-lactone (4), 9,12,13-trihydroxy-10(E)-octadecenoic acid (5), epifriedelanol (6), friedeline (7), taraxerol (8), Simiarenol (9), spinasterol (10), stigmasterol, beta-sitosterol, and apigenin. The structures were determined by means of ESIMS and 1D and 2D NMR spectroscopy, including (1)H-(1)H COSY, NOESY, HSQC, and HMBC experiments. The isolated compounds were evaluated for their antiproliferative activities and were demonstrated to exert considerable cell growth-inhibitory activity against human cervix adenocarcinoma (HeLa), skin carcinoma (A431), and breast adenocarcinoma (MCF-7) cells. Some of the active components, including 2, 4, and 10, proved to be substantially more potent against these cell lines than against noncancerous human foetal fibroblasts (MRC-5) and can therefore be considered selective antiproliferative natural products.

3 beta-hydroxy-28-P-coumaroyloxy-lup-20(29)-en-27-oic acid from Caraipa densifolia.[Pubmed:6854336]

J Nat Prod. 1983 Jan;46(1):118-22.

Caraipa densifolia Mart. (Clusiaceae) has afforded the new lupene derivative 3 beta-hydroxy-28-p-coumarolyoxy-lup-20(29)-en-27-oic acid (8), whose structure was deduced by chemical correlation with betulin (6). Simiarenol (1), taraxerone (2), friedelin (3), lupeol (4), betulinic acid (5), betulin (6), and beta-sitosterol-beta-D-glucoside (7) were also isolated in this study.

[Chemical constituents from Imperata cylindrica].[Pubmed:23189737]

Zhongguo Zhong Yao Za Zhi. 2012 Aug;37(15):2296-300.

Chemical investigation of Imperata cylindrica led to the isolation of thirteen compounds using various chromatographic techniques. The structure of these compounds were identified as: three phenylpropanoids, 1-(3,4,5-trimethoxyphenyl)-1,2,3-propanetriol ( 1 ), 1-O-p-coumaroylglycerol (2), 4-methoxy-5-methyl coumarin-7-O-beta-D-glucopyranoside (3); four organic acids, 4-hydroxybenzene carboxylic acid(4), 3,4-dihydroxybenzoic acid (5), vanillic acid (6), 3, 4-dihydroxybutyric acid (7); one phenolic compound, salicin (8); and five triterpenes, namely, arundoin (9), cylindrin (10), fernenol (11), Simiarenol (12), glutinone (13) by their physicochemical properties and spectral data analysis. Among them, compounds 1-8 were isolated from the genus Imperata for the first time.

Biologically-guided isolation of leishmanicidal secondary metabolites from Euphorbia peplus L.[Pubmed:28344474]

Saudi Pharm J. 2017 Feb;25(2):236-240.

Leishmaniasis is a worldwide health problem, highly endemic in developing countries. Moreover, the severe side effects and the reported drug resistance make it an urgent need to search for effective drugs that can replace or supplement those currently used. In a research program designed to investigate the antileishmanial activity of plants collected from the Egyptian flora, twenty extracts from fifteen plants growing in Egypt have been investigated for in vitro leishmanicidal activity against Leishmania donovani promastigotes. Among the tested extracts, the methanol extract of Euphorbia peplus aerial parts exhibited a significant antileishmanial activity as it produced 100% inhibition of growth with activity similar to amphotericin B. The total extract was subjected to liquid-liquid fractionation using solvents of different polarities, followed by testing the antileishmanial activity of the successive fractions. Phytochemical exploration of the active n-hexane fraction (which produced 75% inhibition of growth) led to isolation of four compounds: Simiarenol (1), 1-hexacosanol (2), beta-sitosterol (3), and beta-sitosterol-3-O-glucoside (4) from the biologically active sub-fractions. Structure elucidation was aided by 1D and 2D NMR techniques. In conclusion, E. peplus plant has many non-polar secondary metabolites that can be used as drug leads for treatment of leishmaniasis.

Phytochemical constituents of Artemisia stolonifera.[Pubmed:11534763]

Arch Pharm Res. 2001 Aug;24(4):312-5.

Repeated column chromatographic separation of the CH2Cl2 extract of Artemisia stolonifera (Asteraceae) led to the isolation of a triterpene (I), a sesquiterpene (II), two aromatic compounds (III and IV) and a benzoquinone (V). Their structures were determined by spectroscopic means to be Simiarenol (I), (1S,7S)-1beta-hydroxygermacra-4(15),5,10(14)-triene (II), 3'-methoxy-4'-hydroxy-trans-cinnamaldehyde (III), vanillin (IV) and 2,6-dimethoxy-1,4-benzoquinone (V), respectively. Among these products, compound V showed significant cytotoxicity against five human tumor cell lines in vitro, A549 (non small cell lung adenocarcinoma), SK-OV-3 (ovarian), SK-MEL-2 (skin melanoma), XF498 (CNS) and HCT15 (colon) with ED50 values ranging from 1.33-4.22 microg/ml.

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