11-oxo-mogroside V - Moligand™, ≥99% , CAS No.126105-11-1

CAS: 126105-11-1 Cat. No.: O651363 Molecular Weight: 1285.42

GRADE & PURITY Moligand™, ≥99%

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

11-oxo-mogroside V is a natural sweetener that exhibits strong antioxidant activity. It exhibits significant inhibitory effects on reactive oxygen species ( O 2 - , H 2 O 2 and *OH ) with EC 50 of 4.79, 16.52, and 146.17 μg/mL, respectively.

In Vitro

11-oxo-mogroside V shows a higher scavenging effect on O 2 - (concentration at which 50% of chemiluminescence intensity is inhibited [EC 50 ]=4.79 μg/mL) and H 2 O 2 (EC 50 =16.52 μg/mL) than those of mogroside V. 11-oxo-mogroside V exhibits a remarkable inhibitory effect on *OH-induced DNA damage with EC 50 =3.09 μg/mL.11-oxo-mogroside V, a natural sweetener, isolated from the fruits of Momordica grosvenori , exhibits strong inhibitory effect on the primary screening test indicated by the induction of Epstein-Barr virus early antigen (EBV-EA) by a tumor promoter, 12-O-tetradecanoylphorbol-13-acetate (TPA). 11-oxo-mogroside V exhibits strong inhibitory effect on EBV-EA induction (91.2, 50.9 and 21.3% inhibition at 1000, 500 and 100 mol ratio/TPA concentration, respectively). MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

In the group treated with DMBA, TPA and 11-oxo-mogroside V, only 26.6 and 53.3% of mice bore papillomas even at 10 and 15 weeks of promotion, respectively, and only 1.0 3.3 and 4.7 papillomas are formed per mouse at 10, 15 and 20 weeks of promotion. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal administration

Mice Specific pathogen-free female ICR (6 weeks old) and female SENCAR (6 weeks old) mice are use. The animals (female SENCAR, 6 weeks old) are divided into three groups, 15 mice each. The back of each mouse is shaved with surgical clipper, and the mice are topically treated with peroxynitrite (33.1 μg, 390 nmol, 1 mM NaOH) in acetone (0.1 mL) as an initiation treatment. For groups I (control group) II and III, 1 week after initiation with peroxynitrite, mice are promoted by the application with TPA (1 mg, 1.7 nmol) in acetone (0.1 mL) twice a week. For groups II and III, mogroside V and 11-oxo-mogroside V (0.0025%, 2.5 mg/100 mL) in drinking water is given orally, from 1 week before to 1 week after the initiation treatment with peroxynitrite, respectively. The incidence of papillomas is observed weekly for 20 weeks; the percentages of mice bearing papillomas and the average number of papillomas per mouse are recorded. The type of tumors in our experiment is also checked by the pathologist with the histological examination, and the malignant tumors are not observed at 20 weeks of promotion in our experimental system. The tumor incidence is statistically analyzed by Student's t-test in treated mice and controls. aladdin has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:EC50: 4.79 μg/mL (O 2 - ), 16.52 μg/mL (H 2 O 2 ), 146.17 μg/mL (*OH)

Specifications

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

11-oxo-mogroside V is a natural sweetener that exhibits strong antioxidant activity. It exhibits significant inhibitory effects on reactive oxygen species ( O 2 - , H 2 O 2 and *OH ) with EC 50 of 4.79, 16.52, and 146.17 μg/mL, respectively.

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 528754842
• Canonical Smiles: CC(CCC(C(C)(C)O)OC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)OC3C(C(C(C(O3)CO)O)O)O)C4CCC5(C4(CC(=O)C6(C5CC=C7C6CCC(C7(C)C)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)C)C
• IUPAC Name: (3S,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-hydroxy-6-methylheptan-2-yl]-4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• InChIKey: CGGWHBLPUUKEJC-YMWSYRNLSA-N
• INCHI: 1S/C60H100O29/c1-23(9-13-35(57(4,5)79)88-55-50(89-54-49(78)43(72)38(67)29(20-63)84-54)45(74)40(69)31(86-55)22-81-52-47(76)42(71)37(66)28(19-62)83-52)24-15-16-58(6)32-12-10-25-26(60(32,8)33(64)17-59(24,58)7)11-14-34(56(25,2)3)87-53-48(77)44(73)39(68)30(85-53)21-80-51-46(75)41(70)36(65)27(18-61)82-51/h10,23-24,26-32,34-55,61-63,65-79H,9,11-22H2,1-8H3/t23-,24-,26-,27-,28-,29-,30-,31-,32+,34+,35-,36-,37-,38-,39-,40-,41+,42+,43+,44+,45+,46-,47-,48-,49-,50-,51-,52-,53+,54+,55+,58+,59-,60+/m1/s1
• Molecular Weight: 1285.42

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Steroidal glycosides
        • Level5 Steroidal saponins
          • Level6 Cucurbitacin glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Steroidal glycosides
• Intermediate Tree Nodes: Steroidal saponins
• Direct Parent: Cucurbitacin glycosides
• Alternative Parents: Triterpenoids Cucurbitacins Oligosaccharides 11-oxosteroids 14-alpha-methylsteroids Hydroxysteroids Delta-5-steroids Alkyl glycosides O-glycosyl compounds Oxanes Tertiary alcohols Ketones Secondary alcohols Oxacyclic compounds Polyols Acetals Hydrocarbon derivatives Primary alcohols Organic oxides
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Cucurbitacin glycoside skeleton - Cucurbitacin skeleton - Triterpenoid - 25-hydroxysteroid - Oligosaccharide - 14-alpha-methylsteroid - 11-oxosteroid - Oxosteroid - Delta-5-steroid - Fatty acyl glycoside - Alkyl glycoside - O-glycosyl compound - Glycosyl compound - Fatty acyl - Oxane - Tertiary alcohol - Secondary alcohol - Ketone - Polyol - Organoheterocyclic compound - Oxacycle - Acetal - Primary alcohol - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Organooxygen compound - Alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (77.80 mM; Need ultrasonic)
• Sensitivity: light sensitive
• Molecular Weight: 1285.400 g/mol
• XLogP3: -4.000
• Hydrogen Bond Donor Count: 18
• Hydrogen Bond Acceptor Count: 29
• Rotatable Bond Count: 20
• Exact Mass: 1284.64 Da
• Monoisotopic Mass: 1284.64 Da
• Topological Polar Surface Area: 474.000 Ų
• Heavy Atom Count: 89
• Formal Charge: 0
• Complexity: 2410.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 34
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1