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27975-19-5 Usage

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Isosteviol is a tetracyclic diterpenoid with a beyerane core has drawn attention because it can exhibit antihypertensive activity, reduce blood glucose, suppress cancer cells.

Check Digit Verification of cas no

The CAS Registry Mumber 27975-19-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,7,9,7 and 5 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 27975-19:
(7*2)+(6*7)+(5*9)+(4*7)+(3*5)+(2*1)+(1*9)=155
155 % 10 = 5
So 27975-19-5 is a valid CAS Registry Number.
InChI:InChI=1/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)

27975-19-5 Well-known Company Product Price

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  • (92273)  Isosteviol  analytical standard

  • 27975-19-5

  • 92273-10MG

  • 2,231.19CNY

  • Detail

27975-19-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name ISOSTEVIOL

1.2 Other means of identification

Product number -
Other names ent-16-ketobeyeran-19-oic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:27975-19-5 SDS

27975-19-5Relevant articles and documents

Reaction coupling separation for isosteviol production from stevioside catalyzed by acidic ion-exchange resin

Hu, Xueyi,Zhou, Zhuoyu,Zhang, Zongying,Wang, Xiaoxia,Sui, Xiaochen,Chen, Junming,Xia, Yongmei,Zhang, Jue,Lin, Jianguo

, p. 151 - 159 (2021)

Abstract: Isosteviol, a prodrug used to be obtained via Wagner–Meerwein rearrangement from steviol with low yield and long reaction?time. Herein, an in-situ separation-coupling-reaction is presented to prepare isosteviol from the natural sweetener stevioside. Simply with in-situ water-washing, the product containing 92.98% purity of isosteviol was obtained with a stevioside conversion of 97.23% from a packet bed reactor without further separation. Within the assayed inorganic acid, organic acids and acidic ionic liquids, the acidic ion-exchange resins provided higher product specificity towards isosteviol. Furthermore, comparing to 5-Fluorouracil, the product presented similar and even stronger inhibition on proliferation of the assayed human cancer cells in a time and dose-dependence by causing cell phase arrest. Isosteviol treatment caused G1 arrest on SGC-7901, HCT-8 and HCT-116 cells, S arrest on HepG2, Huh-7 and HepG3B cells, and G2 arrest on MGC-803 cells, respectively. Graphic abstract: Reaction coupling separation for isosteviol production catalyzed by acidic ion-exchange resin.[Figure not available: see fulltext.]

Synthesis, Structure, and Cytotoxic Activities of a Novel Lactam of the Diterpenoid Isosteviol

Liu, Cong-Jun,Li, Jing-Jing,Min, Yu-Tao,Zhang, Ling-Li,Wang, Bao-Yu,Wang, Ya-Hao

, p. 865 - 869 (2020)

A novel compound lactam of 15β-hydroxymethylisosteviol ethyl ester 3 has been synthesized and structurally characterized by IR, NMR, and HR-MS. Its X-ray crystallographic analysis revealed that the nitrogen is attached to C-13 instead of C-15. The reaction mechanism was discussed, and the title compound was further evaluated against HCT-116, HGC-27, and JEKO-1 cells by the MTT assay. The results demonstrated that compound 3 exhibited better cytotoxic activities than its corresponding precursor isosteviol.

Synthesis and anti-hepatitis B virus activity of C4 amide-substituted isosteviol derivatives

Huang, Tsurng-Juhn,Yang, Cheng-Lin,Kuo, Yu-Cheng,Chang, Yi-Chih,Yang, Li-Ming,Chou, Bo-Hon,Lin, Shwu-Jiuan

, p. 720 - 728 (2015)

A series of novel isosteviol derivatives having C4-amide substituents were synthesized in order to test for antiviral effects against the hepatitis B virus (HBV) in vitro. Among them, IN-4 [N-(propylcarbonyl)-4α-amino-19-nor-ent-16-ketobeyeran] (5) exhibited inhibitory activity against secretion of HBsAg and HBeAg as well as inhibition of HBV DNA replication. Therefore, the mechanism of its antiviral activity was further analyzed using HBV-transfected Huh7 cells. Exposure to IN-4 produced minimal inhibitory effects on viral precore/pregenomic RNA expression. However, expression levels of the 2.4/2.1-kb preS/major S RNA of the viral surface gene significantly decreased, along with intracellular levels of HBV DNA. A promoter activity analysis demonstrated that IN-4 significantly inhibited viral X, S, and preS expression levels but not viral core promoter activities. In particular, IN-4 was observed to significantly inhibit HBV gene regulation by disrupting nuclear factor (NF)-κB-associated promoter activity. In addition, the nuclear expression of p65/p50 NF-κB member proteins was attenuated following IN-4 treatment, while cytoplasmic IκBα protein levels were enhanced. Meanwhile, IN-4 was observed to inhibit the binding activity of NF-κB to putative DNA elements. Furthermore, transfection of a p65 expression plasmid into Huh7 cells significantly reversed the inhibitory effect of IN-4 on HBV DNA levels, providing further evidence of the central role of NF-κB in its antiviral mechanism. It is therefore suggested that IN-4 inhibits HBV by interfering with the NF-κB signaling pathway, resulting in downregulation of viral gene expression and DNA replication.

Discovery of lysosome-targeted covalent anticancer agents based on isosteviol skeleton

Liu, Jun,Li, Lin,Li, Xiaobin,Wang, Xin,Zhao, Xiaoyu,Qiao, Yanan,Xu, Yuliang,Sun, Yong,Qian, Lilin,Liu, Zhaopeng,Ji, Aiguo,Lou, Hongxiang

, (2021)

Covalent drugs play corresponding bioactivities by forming covalent bonds with the target, which possess many significant pharmacological advantages including high potency, ligand efficiency, and long-lasting effects. However, development of covalent inhibitors is a challenge due to their presumed indiscriminate reactivity. Here, we report the discovery of series of lysosome-targeting covalent anticancer agents by introducing nitrogenous bases to the modified isosteviol skeleton in order to minimize the toxicity and increase the selectivity. By introducing the electrophilic α, β-unsaturated ketones into the A- and D-rings of isosteviol, the cytotoxicity of the obtained compounds were greatly increased. Further nitrogen-containing modifications to the D-ring led to the discovery of novel molecules that targeted lysosomes, and of which, compound 30 was the most potent and selective antiproliferative one to kill A549 cells in vitro and in vivo. Mechanism investigation revealed that compound 30 was trapped into lysosomes and damaged lysosomes to cause cell death.

Microbial Transformation of Isosteviol and Inhibitory Effects on Epstein-Barr Virus Activation of the Transformation Products

Akihisa, Toshihiro,Hamasaki, Yusuke,Tokuda, Harukuni,Ukiya, Motohiko,Kimura, Yumiko,Nishino, Hoyoku

, p. 407 - 410 (2004)

Microbial transformation of isosteviol (2), a beyerane-type diterpenoid obtained from stevioside (1) by acid hydrolysis, yielded 7β -hydroxyisosteviol (3), 11β-hydroxyisosteviol (5), and 12β -hydroxyisosteviol (6) by the fungus Aspergillus niger, 17-hydroxyisosteviol (7) by the fungus Glomerella cingulata, and 3 and 7-oxoisosteviol (4) by the fungus Mortierella elongate. The five metabolites, 3-7, along with 1 and 2 were evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells as a primary screening test for inhibitors of tumor promoters. All the diterpenes tested showed potent inhibitory effects, with the five metabolites 3-7 exhibiting more potent effects.

The synthesis and crystal structure of (4α,8β,13β,16β) -13-methyl-16,18-diol-17-norkaurane: A simultaneous reduction product of isosteviol

Chen, Junqing,Sun, Min,Cai, Jin,Cao, Meng,Zhou, Wen,Ji, Min

, p. 519 - 522 (2011)

(4α,8β,13β,16β)-13-methyl-16,18-diol-17-norkaurane was synthesized by esterification and reduction of isosteviol, respectively. The structure of the title compound was established by spectral analysis and X-ray diffraction studies. The compound crystallizes in the orthorhombic space group P212121 with unit cell parameters: a = 7.3705 (14) A, b = 13.508 (3) A, c = 20.139 (4) A, V = 2005.1 (7) A3, Z = 4. The conformation of rings A and B is chair, whereas the conformation of ring C is unsymmetrical distorted chair. The stereochemistry of the A/B and B/C ring junctions is trans, while the five-membered ring D adopts an envelope conformation. Springer Science+Business Media, LLC 2010.

Discovery of novel, potent, isosteviol-based antithrombotic agents

Chen, Peng,Zhang, Dianwen,Li, Meng,Wu, Qiong,Lam, Yuko P.Y.,Guo, Yan,Chen, Chen,Bai, Nan,Malhotra, Shipra,Li, Wei,O'Connor, Peter B.,Fu, Hongzheng

, (2019)

Thrombosis is a pathological coagulation process and can lead to many serious thrombotic diseases. Here, we report a novel potent antithrombotic compound (6k) based on isosteviol with anticoagulant and antiplatelet activities. 6k selectively inhibited FXa (Ki = 0.015 μM) against a panel of serine proteases and showed excellent anticoagulant activity (significant prolongation of ex vivo PT and aPTT over the vehicle, p 0.01). 6k also significantly inhibited ADP-induced platelet aggregation in rats relative to the vehicle (p 0.01). Furthermore, 6k exhibited potent ex vivo and in vivo antithrombotic activity in rats relative to the vehicle (p 0.01 and p 0.0001, respectively). Novel structure 6k, with potent antithrombotic activity, is expected to lead a promising approach for the development of antithrombotic agents.

Validation of an HPLC method for direct measurement of steviol equivalents in foods

Bartholomees, Uria,Struyf, Tom,Lauwers, Olivier,Ceunen, Stijn,Geuns, Jan M.C.

, p. 270 - 275 (2016)

Steviol glycosides are intense natural sweeteners used in foods and beverages. Their acceptable daily intake, expressed as steviol equivalents, is set at 0-4 mg/kg body weight. We report the development and validation of a RP-HPLC method with fluorometric detection of derivatized isosteviol, formed by acid hydrolysis of steviol glycosides. Dihydroisosteviol was used as an internal standard. Using this method, the amount of steviol equivalents in commercial steviol glycoside mixtures and different foods can be directly quantified. The method was successfully tested on strawberry jam, low-fat milk, soft drink, yogurt and a commercial mixture of steviol glycosides. Calibration curves were linear between 0.01 and 1.61 mM steviol equivalents, with a quantification limit of 0.2 nmol. The % RSD of intra-day precision varied between 0.4% and 4%, whereas inter-day precision varied between 0.4% and 5%, for high and medium concentrations, and between 3% and 8% for low concentrations. Accuracy of the analysis varied between 99% and 115%.

Synthesis, cytotoxic activity evaluation and HQSAR study of novel isosteviol derivatives as potential anticancer agents

Liu, Cong-Jun,Yu, Shu-Ling,Liu, Yan-Ping,Dai, Xing-Jie,Wu, Ya,Li, Rui-Jun,Tao, Jing-Chao

, p. 26 - 40 (2016)

A series of novel isosteviol derivatives bearing amino alcohol and thiourea fragments have been stereo-selectively synthesized and screened for their in vitro cytotoxic activities against three human cancer cell lines (HCT-116, HGC-27 and JEKO-1). The results demonstrated that these compounds exhibited prominent cytotoxicities. Especially, the compound Iw displayed the most potent anticancer activities against HCT-116 cell with IC50 value of 1.450 μM. On the basis of this bioassay results, these derivatives were further investigated by the hologram quantitative structure-activity relationship (HQSAR) technique. The optimal HQSAR model with q2 Combining double low line 0.663, r2 Combining double low line 0.895, SEE Combining double low line 0.179 was generated using A/B/H/Ch as fragment distinction parameters and 4-7 as fragment size. This model was employed to predict the cytotoxic activities of test set compounds, and the predicted values were in good agreement with the experimental results. The contribution maps derived from the optimal model explained the individual atomic contribution to the total activity of single molecule.

Synthesis, cytotoxic activity, and 2D- and 3D-QSAR studies of 19-carboxyl-modified novel isosteviol derivatives as potential anticancer agents

Liu, Cong-Jun,Zhang, Tao,Yu, Shu-Ling,Dai, Xing-Jie,Wu, Ya,Tao, Jing-Chao

, p. 870 - 887 (2017)

Two series of novel acylthiosemicarbazide and oxadiazole fused-isosteviol derivatives were synthesized based on the 19-carboxyl modification. The target compounds were evaluated for their cytotoxicities against three cancer cell lines (HCT-116, HGC-27, an

Bridel,Lavieille

, (1931)

Synthesis and in vivo screening of isosteviol derivatives as new cardioprotective agents

Zhang, Hanyuan,Liu, Bo,Xu, Geng,Xu, Chao,Ou,Liu, Jiansong,Sun, XiaoOu,Zhao, Yu

, (2021/04/19)

Isosteviol, an ent-beyerane diterpenoid, has been repeatedly reported to possess potent cardioprotective activity. With the aim of discovering new cardioprotective derivatives from isosteviol, 47 compounds, including 40 new ones, were synthesized and eval

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