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Related CAS#:
27975-19-5 1080018-94-5
216150-83-3 23963-60-2

27975-19-5

27975-19-5 structure
27975-19-5 structure
  • Name: Isosteviol
  • Chemical Name: Isosteviol
  • CAS Number: 27975-19-5
  • Molecular Formula: C20H30O3
  • Molecular Weight: 318.450
  • Catalog: Biochemical Chinese herbal medicine ingredients
  • Create Date: 2018-06-03 08:00:00
  • Modify Date: 2024-01-02 17:11:45
  • 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].
Name Isosteviol
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
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].
Related Catalog
References

[1]. Wong KL, et al. Isosteviol acts on potassium channels to relax isolated aortic strips of Wistar rat. Life Sci. 2004 Mar 26;74(19):2379-87.

[2]. Wong KL, et al. Isosteviol as a potassium channel opener to lower intracellular calcium concentrations in cultured aortic smooth muscle cells. Planta Med. 2004 Feb;70(2):108-12.

[3]. Wong KL, et al. Antiproliferative effect of isosteviol on angiotensin-II-treated rat aortic smooth muscle cells. Pharmacology. 2006;76(4):163-9.
Density 1.2±0.1 g/cm3
Boiling Point 455.6±38.0 °C at 760 mmHg
Melting Point 228.0 to 232.0 °C
Molecular Formula C20H30O3
Molecular Weight 318.450
Flash Point 243.5±23.3 °C
Exact Mass 318.219482
PSA 54.37000
LogP 4.13
Vapour Pressure 0.0±2.4 mmHg at 25°C
Index of Refraction 1.551
Storage condition -20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RC5532500
CHEMICAL NAME :
17-Norkauran-18-oic acid, 13-methyl-16-oxo-, (4-alpha,8-beta,13-beta)-
CAS REGISTRY NUMBER :
27975-19-5
LAST UPDATED :
199703
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C20-H30-O3
MOLECULAR WEIGHT :
318.50

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3160 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
671 mg/kg
TOXIC EFFECTS :
Vascular - regional or general arteriolar or venous dilation Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
503 mg/kg
TOXIC EFFECTS :
Vascular - regional or general arteriolar or venous dilation Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5060 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1070 mg/kg
TOXIC EFFECTS :
Vascular - regional or general arteriolar or venous dilation Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
612 mg/kg
TOXIC EFFECTS :
Vascular - regional or general arteriolar or venous dilation Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 8,33,1994
RIDADR NONH for all modes of transport
57817-89-7 structure

57817-89-7

~10%

27975-19-5 structure

27975-19-5
Literature: Ukiya, Motohiko; Sawada, Shingo; Kikuchi, Takashi; Kushi, Yasunori; Fukatsu, Makoto; Akihisa, Toshihiro Chemistry and Biodiversity, 2013 , vol. 10, # 2 p. 177 - 188
1347574-22-4 structure

1347574-22-4

~%

27975-19-5 structure

27975-19-5
Literature: Chaturvedula, Venkata Sai Prakash; Upreti, Mani; Prakash, Indra Molecules, 2011 , vol. 16, # 5 p. 3552 - 3562
29584-19-8 structure

29584-19-8

~%

27975-19-5 structure

27975-19-5
Literature: Mosettig; Nes Journal of Organic Chemistry, 1955 , vol. 20, p. 884,895 Full Text Show Details Bridel; Lavieille Journal de Pharmacie et de Chimie, 1931 , vol. <8> 14, p. 321,325, 369, 372 Bulletin de la Societe de Chimie Biologique, 1931 , vol. 13, p. 781,785, 790
7664-93-9 structure

7664-93-9
29584-19-8 structure

29584-19-8

~%

27975-19-5 structure

27975-19-5
Literature: Bridel; Lavieille Journal de Pharmacie et de Chimie, 1931 , vol. <8> 14, p. 321,325, 369, 372 Bulletin de la Societe de Chimie Biologique, 1931 , vol. 13, p. 781,785, 790
50-99-7 structure

50-99-7
7664-93-9 structure

7664-93-9
57817-89-7 structure

57817-89-7

~%

27975-19-5 structure

27975-19-5
Literature: Bridel; Lavieille Journal de Pharmacie et de Chimie, 1931 , vol. <8> 14, p. 99,100 Bulletin de la Societe de Chimie Biologique, 1931 , vol. 13, p. 636,645, 656

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