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Isosteviol

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-I3011

  • Specification : 98%

  • CAS number : 27975-19-5

  • Formula : C20H30O3

  • Molecular Weight : 318.45

  • PUBCHEM ID : 99514

  • Volume : 25mg

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Catalogue Number

BF-I3011

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

318.45

Appearance

White crystalline powder

Botanical Source

Stevia rebaudiana

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC12CCC3C4(CCCC(C4CCC3(C1)CC2=O)(C)C(=O)O)C

Synonyms

16-oxo-ent-beyeran-19-oic acid/iso-Steviol/ent-16-oxobeyeran-19-oic acid/16-oxobeyeran-19-oic acid/16-Oxobeyeran-18-oic acid/ent-16-ketobeyeran-19-oic acid

IUPAC Name

(1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

Density

1.2±0.1 g/cm3

Solubility

Methanol; Chloroform

Flash Point

243.5±23.3 °C

Boiling Point

455.6±38.0 °C at 760 mmHg

Melting Point

228.0 to 232.0 °C

InChl

InChI=1S/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)

InChl Key

KFVUFODCZDRVSS-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:27975-19-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30769819

Abstract

Steviosides, rebaudiosides and their analogues constitute a major class of naturally occurring biologically active diterpene compounds. The wide spectrum of pharmacological activity of this group of compounds has developed an interest among medicinal chemists to synthesize, purify, and analyze more selective and potent isosteviol derivatives. It has potential biological applications and improves the field of medicinal chemistry by designing novel drugs with the ability to cope against resistance developing diseases. The outstanding advancement in the design and synthesis of isosteviol and its derivative has proved its effectiveness and importance in the field of medicinal chemical research. The present review is an effort to integrate recently developed novel drugs syntheses from isosteviol and potentially active pharmacological importance of the isosteviol derivatives covering the recent advance

KEYWORDS

antitumor; diterpenoids; isosteviol; natural products; stevioside.

Title

Bioactivity Profile of the Diterpene Isosteviol and Its Derivatives

Author

Asad Ullah 1 , Sidra Munir 2 , Yahia Mabkhot 3 , Syed Lal Badshah 4

Publish date

2019 Feb 14

PMID

30046042

Abstract

NC-8 (ent-16-oxobeyeran-19-N-methylureido) is an isosteviol-derived analogue with multiple biological effects, including anti-inflammation and anti-bacterial activities and inhibition of HBV viral surface antigen gene expression. In this study, we explored the effects of NC-8 on the formation of osteoclasts from RAW 264.7 cells. We found that NC-8 exerts the novel effect of inhibiting osteoclast-like cell formation. Our experiments showed that RANKL-induced ERK, p38, and JNK phosphorylation were inhibited by NC-8. An ovariectomy-induced osteoporosis animal model was used to examine the protective effects of oral treatment with NC-8. Serum analysis was used to examine markers of osteoblasts, osteoclasts, and renal and hepatic function in rats. Micro CT scanning and histological analysis were used to measure bone loss in ovariectomized rats. Oral administration of NC-8 effectively decreased excess bone resorption and significantly antagonized trabecular bone loss in ovariectomized rats. Serum analysis of C-terminal telopeptide of type-I collagen, an osteoclast marker, also showed that NC-8 administration inhibited excess bone resorption. Furthermore, serum analysis showed that renal and liver function were not affected by these doses of NC-8 during long-term treatment. Our results demonstrate that NC-8 inhibits osteoclast differentiation and effectively ameliorates ovariectomy-induced osteoporosis.

KEYWORDS

antitumor; diterpenoids; isosteviol; natural products; stevioside.

Title

Isosteviol Derivative Inhibits Osteoclast Differentiation and Ameliorates Ovariectomy-Induced Osteoporosis

Author

Huey-En Tzeng 1 2 3 , Po-Hao Huang 4 5 , Chun-Hao Tsai 6 , Gregory J Tsay 4 5 , Yi-Ju Lee 7 , Tsurng-Juhn Huang 8 , Tzu-Hung Lin 9 , Ying-Ming Chiu 10 11 , Yi-Ying Wu 12 13 14

Publish date

2018 Jul 25

PMID

30880146

Abstract

Isosteviol is a lead compound whose cardioprotective property has been partly explained by its regulation of ion channels and interference with signalling pathways in the metabolism of some fatty acids. This study determined the metabolic stability of isosteviol in human liver microsomes and H9c2 cell line, and the identity of its metabolites in human and rat liver fractions. Isosteviol was largely unmetabolized in H9c2 cells and in NADPH-only supplemented human liver fractions, suggesting a very limited contribution of phase I biotransformation to its hepatic clearance. The in vitro half-life of isosteviol in UDPGA-only supplemented medium was observed to be 24.9 min with an estimated intrinsic clearance of 0.349 mL/min/kg in man. Analysis by LC-MS/MS and Q-tof showed that isosteviol is mainly metabolised to its acyl-β-D-glucuronide in humans and rats. Mono-hydroxy-isosteviol and dihydroisosteviol were also identified. Rat liver fraction, however, generated dihydroxy-isosteviol in addition to two mono-hydroxy derivatives. Further studies confirmed that dihydroisosteviol is subsequently biotransformed to its acyl-β-D-glucuronide in man and rat. These findings suggest that future studies of the efficacy and toxicity of isosteviol might have to consider xenobiotics that alter the glucuronidation pathways significantly in man.

KEYWORDS

Cardiac hypertrophy; Drug metabolism; Glucuronidation; Inflammation; Isosteviol.

Title

In Vitro Metabolic Stability and Biotransformation of Isosteviol in Human and Rat Liver Fractions

Author

Ayorinde Adehin 1 , Keai Sinn Tan 2 , Zhiqiang Lu 3 , Qing Cheng 4 , Wen Tan 5

Publish date

2019 Jun


Description :

Isosteviol is a derivative of stevioside, a constituent of Stevia rebaudiana, which is commonly used as a noncaloric sugar substitute in Japan and Brazil.Target:Isosteviol dose-dependently relaxed the vasopressin (10-8 M)-induced vasoconstriction in isolated aortic rings with or without endothelium. However, in the presence of potassium chloride (3×10-2 M), the vasodilator effect of isosteviol on arterial strips disappeared. Only the inhibitors specific for the ATP-sensitive potassium (KATP) channel or small conductance calcium-activated potassium (SKCa) channel inhibited the vasodilator effect of isosteviol in isolated aortic rings contracted with 10-8 M vasopressin [1]. The attenuation by isosteviol of the vasopressin- and phenylephrine-induced increase in [Ca (2+)]i was inhibited by glibenclamide, apamin and 4-aminopyridine but not by charybdotoxin. Furthermore, the inhibitory action of isosteviol on [Ca (2+)]i was blocked when A7r5 cells co-treated with glibenclamide and apamin in conjunction with 4-aminopyridine were present [2]. Isosteviol (1-100 micromol/l) inhibits angiotensin-II-induced DNA synthesis and endothelin-1 secretion. Measurements of 2'7'-dichlorofluorescin diacetate, a redox-sensitive fluorescent dye, showed an isosteviol-mediated inhibition of intracellular reactive oxygen species generated by the effects of angiotensin II [3].