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Steviolbioside

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-S4002

  • Specification : 98%(HPLC)

  • CAS number : 41093-60-1

  • Formula : C32H50O13

  • Molecular Weight : 642.734

  • PUBCHEM ID : 16401639

  • Volume : 25mg

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Catalogue Number

BF-S4002

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

642.734

Appearance

White crystalline powder

Botanical Source

Stevia rebaudiana (stevia)

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)(C)C(=O)O

Synonyms

steviobioside/13-{[2-O-(β-D-Glucopyranosyl)-β-D-glucopyranosyl]oxy}kaur-16-en-18-oic acid/Steviolbioside

IUPAC Name

(1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

Applications

Antituberculosis activity of glycosides from Stevia rebaudiana and hybrid compounds of steviolbioside and pyridinecarboxylic acid hydrazides PUMID/DOI:DOI: 10.1007/s10600-011-9779-6 Chemistry of Natural Compounds, 2011, 46(6):902-5. Stevioside and Steviolbioside, glycosides from Stevia rebaudiana Bertoni, in addition to hybrid compounds synthesized from Steviolbioside and the antituberculosis drug isoniazid and its isomer nicotinic acid hydrazide exhibited moderate antituberculosis activity against M. tuberculosis strain H37RV in vitro (MIC = 7.5, 3.75, 5, and 10 μg/mL, respectively). Soyasaponin I, III, and Soyasapogenol B Inhibit Proliferation and Modulate PKC Expression in Caco-2 Human Colon Cancer Cells. PUMID/DOI:DOI: 10.5539/jfr.v2n4p81 J. Food Res., 2013, 2(4):81-7. Group B saponins, the predominant form of saponins in heat-treated soy products, have been shown to possess hypocholesterolemic, antimutagenic, and anticarcinogenic properties. Previous studies have evaluated crude mixtures of soyasaponins, but studies evaluating a single purified soyasaponin as an anticarcinogenic agent are limited. The goal of this study is to examine the effects of purified soyasaponins I and III as well as their aglycone form, Soyasapogenol B, as anticarcinogenic agents on the human colon adenocarcinoma cell line (Caco-2). Experiments were conducted to examine the effects of purified soyasaponins on cell proliferation, Protein Kinase C (PKC) activity, and cell morphology in Caco-2 cell cultures. Treatment of cells with soyasaponins I and III at concentrations of 0.3-0.9 mg/ml significantly reduced viable cell numbers after 48 and 72 hours of exposure by 8.6-65.3% (p < 0.05). Soyasapogenol B at a concentration of 0.15 mg/ml significantly reduced viable cell numbers after 24 hours by 62.4% (p < 0.05). Cell morphology changes demonstrated that as concentrations and lipophilicity of soyasaponins increased, cell membranes became rougher and more irregular. Treatment of cells for 72 hours significantly reduced the amount of PKC activity by 9-40% (p < 0.05). Results indicate that purified soyasaponins I, III and Soyasapogenol B can suppress Caco-2 colon cancer cell proliferation. These findings suggest that purified group B soyasaponins and their final metabolite Soyasapogenol B may be a colon-cancer suppressive component of soy that warrants further examination as a potential nutraceutical or functional food.

Density

1.5±0.1 g/cm3

Solubility

DMSO

Flash Point

267.6±27.8 °C

Boiling Point

847.3±65.0 °C at 760 mmHg

Melting Point

190ºC (methanol )

InChl

InChI=1S/C32H50O13/c1-15-11-31-9-5-18-29(2,7-4-8-30(18,3)28(40)41)19(31)6-10-32(15,14-31)45-27-25(23(38)21(36)17(13-34)43-27)44-26-24(39)22(37)20(35)16(12-33)42-26/h16-27,33-39H,1,4-14H2,2-3H3,(H,40,41)/t16-,17-,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31+,32-/m1/s1

InChl Key

OMHUCGDTACNQEX-QEBBIIKSSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:41093-60-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

27513814

Abstract

Steviol glycosides are a family of compounds found in Stevia rebaudiana Bertoni that are responsible for sweetness capacity. The antihyperglycemic effect of the two major steviol glycosides, Rebaudioside A and Stevioside, has been studied and it has been found that despite having the same common structure, only Stevioside exerts an antihyperglycemic effect. Although other steviol derivatives are found in smaller amounts (minor steviol glycosides) in S. rebaudiana, whether or not they possess antihyperglycemic activity has not been evaluated. The aim of this study was to evaluate the antihyperglycemic effect of minor steviol glycosides in normoglycemic and diabetic (streptozotocin/nicotinamide) Wistar rats. Rats were subjected to an intraperitoneal glucose tolerance test (IPGTT) both before and after chronic treatment (28 days). After 6 h of fasting, IPGTT was conducted in pentobarbital-anesthetized rats using 1 g/kg of glucose plus 20 mg/kg of the minor glycoside (Dulcoside A, Rebaudioside B, C, D, or Steviolbioside) or control treatment (distilled water, glibenclamide, or metformin); the blood of the tip of the tail was collected at time 0, 15, 30, 60, and 120 min.; and blood glucose was measured, and its net area under the curve (AUCnet) was calculated. After 28-day chronic oral administration, IPGTT was again performed. Differences were considered significant at P < .05 by one-way ANOVA. Acute intraperitoneal or chronic oral administration of 20 mg/kg of minor steviol glycosides had no antihyperglycemic effect in normoglycemic or induced-diabetic Wistar rats. Considering the dose tested, it is unlikely that these glycosides have an effect on glucose in diabetic or normoglycemic humans.

KEYWORDS

Stevia rebaudiana; antihyperglycemic; dulcoside; rebaudioside; steviol glycosides; steviolbioside

Title

Evaluation of the Antihyperglycemic Effect of Minor Steviol Glycosides in Normoglycemic and Induced-Diabetic Wistar Rats.

Author

Aranda-Gonzalez I1,2, Moguel-OrdoNez Y3, Chel-Guerrero L2, Segura-Campos M2, Betancur-Ancona D2.

Publish date

2016 Sep

PMID

26593477

Abstract

A β-galactosidase from Kluyveromyces lactis was found to specifically catalyze hydrolysis of the glycosyl ester linkage of stevioside to yield steviolbioside, a rare sweetener that also exists in Stevia rebaudiana leaves. In a packed bed reactor, a reaction coupling separation was realized and a production yield of steviolbioside reached 90% in 6 h. The hydrolysis product steviolbioside presented higher cytoxicity on human normal cells (hepatocytes cell L02 and intestinal epithelial cell T84) than stevioside did. Comparing to the typical chemotherapy agent, 5-fluorouracil (5-FU), steviolbioside presents much lower cytotoxicity on all assayed human normal cells; it presented notable inhibition on human hepatocarcinoma cell Hep3B, human breast cancer cell MDA-MB-231 and human pancreatic cancer cell BxPC-3. The remarkable inhibition on MDA-MB-231 cells makes steviolbioside a potential remedy for human breast cancer, when steviolbioside is served as a natural sweetener.

Copyright © 2015 Elsevier Ltd. All rights reserved.

KEYWORDS

Anti-cancer; Hydrolysis; Reaction coupling separation; Steviolbioside; Stevioside; β-Galactosidase

Title

Production of a bioactive sweetener steviolbioside via specific hydrolyzing ester linkage of stevioside with a β-galactosidase

Author

Chen JM1, Ding L1, Sui XC1, Xia YM2, Wan HD1, Lu T1.

Publish date

2016 Apr 1

PMID

26003514

Abstract

The hydrolysis of the steviol glycosides rebaudioside (Reb) A and E, as well as steviolbioside (a metabolic intermediate) to steviol was evaluated in vitro using human fecal homogenates from healthy Caucasian and Asian donors. Incubation of each of the Rebs in both groups resulted in a rapid hydrolysis to steviol. Metabolism of 0.2mg/mL sample was complete within 24h, with the majority occurring within the first 16 h. There were no clear differences in the rate or extent of metabolism of Reb E relative to the comparative control Reb A. The hydrolysis of samples containing 2.0mg/mL of steviol glycosides Reb A and Reb E tended to take slightly longer than 0.2mg/mL samples. Herein, we report for the first time that there were no apparent gender or ethnicity differences in the rate of metabolism of any of the Rebs, regardless of the concentrations tested. Steviolbioside, an intermediate in the hydrolysis of Reb E to steviol was also found to be rapidly degraded to steviol. These results demonstrate Reb E is metabolized to steviol in the same manner as Reb A. These data support the use of toxicology data available on steviol, and on steviol glycosides metabolized to steviol (i.e., Reb A) to underpin the safety of Reb E.

Copyright © 2015 Elsevier Inc. All rights reserved.

KEYWORDS

Human; In vitro metabolism; Purified stevia leaf extract; Rebaudiosides; Stevia extract; Stevia leaf extract; Steviol

Title

In vitro metabolism of rebaudioside E under anaerobic conditions: Comparison with rebaudioside A.

Author

Purkayastha S1, Bhusari S2, Pugh G Jr2, Teng X3, Kwok D3, Tarka SM4.

Publish date

2015 Aug;