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Deacetylasperulosidic acid

$288

  • Brand : BIOFRON

  • Catalogue Number : BD-D1262

  • Specification : 98%(HPLC)

  • CAS number : 14259-55-3

  • Formula : C16H22O11

  • Molecular Weight : 390.383

  • PUBCHEM ID : 12315350

  • Volume : 20MG

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Catalogue Number

BD-D1262

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

390.383

Appearance

White crystalline powder

Botanical Source

Rubia peregrina and Rubia tinctorum

Structure Type

Iridoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=C(C2C(C1O)C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)CO

Synonyms

10-Deacetylasperulosidic acid/desacetyl asperulosidic acid/deacethyl asperulosidic acid/(1S,4aS,5S,7aS)-1-(β-D-Glucopyranosyloxy)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid/10-Desacetylasperulosidic acid/Deacetylasperulosidic acid/Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)-, (1S,4aS,5S,7aS)-

IUPAC Name

(1S,4aS,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

Applications

Deacetylasperulosidic acid (DAA) is a major phytochemical constituent of Morinda citrifolia fruit. Deacetylasperulosidic acidhas antioxidant activity by increasing superoxide dismutase activity. Deacetylasperulosidic acid has anticlastogenic activity, suppressing the induction of chromosome aberrations in hamster ovary cells and mice[1]. Deacetylasperulosidic acid prevents 4-nitroquinoline 1-oxide (4NQO) induced DNA damage in vitro, suppresses IL-2 production along with the activation of natural killer cells[2].

Density

1.7±0.1 g/cm3

Solubility

Methanol; Water

Flash Point

271.7±26.4 °C

Boiling Point

744.1±60.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H22O11/c17-2-5-1-7(19)10-6(14(23)24)4-25-15(9(5)10)27-16-13(22)12(21)11(20)8(3-18)26-16/h1,4,7-13,15-22H,2-3H2,(H,23,24)/t7-,8+,9+,10-,11+,12-,13+,15-,16-/m0/s1

InChl Key

ZVXWFPTVHBWJOU-YYFGDFGFSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:14259-55-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

24371540

Abstract

Deacetylasperulosidic acid (DAA) is a major phytochemical constituent of Morinda citrifolia (noni) fruit. Noni juice has demonstrated antioxidant activity in vivo and in human trials. To evaluate the role of DAA in this antioxidant activity, Wistar rats were fed 0 (control group), 15, 30, or 60 mg/kg body weight per day for 7 days. Afterwards, serum malondialdehyde concentration and superoxide dismutase and glutathione peroxidase activities were measured and compared among groups. A dose-dependent reduction in malondialdehyde was evident as well as a dose-dependent increase in superoxide dismutase activity. DAA ingestion did not influence serum glutathione peroxidase activity. These results suggest that DAA contributes to the antioxidant activity of noni juice by increasing superoxide dismutase activity. The fact that malondialdehyde concentrations declined with increased DAA dose, despite the lack of glutathione peroxidase-inducing activity, suggests that DAA may also increase catalase activity. It has been previously reported that noni juice increases catalase activity in vivo but additional research is required to confirm the effect of DAA on catalase. Even so, the current findings do explain a possible mechanism of action for the antioxidant properties of noni juice that have been observed in human clinical trials.

Title

In Vivo Antioxidant Activity of Deacetylasperulosidic Acid in Noni

Author

De-Lu Ma 1 , Mai Chen 2 , Chen X Su 3 , Brett J West 3

Publish date

2013

PMID

26053360

Abstract

Morinda officinalis is a famous traditional Chinese medicine containing iridoid glycoside compounds, such as monotropein and deacetylasperulosidic acid. The aim of the study was to develop a novel and sensitive liquid chromatography-tandem mass spectrometry (LC/MS/MS) method for the simultaneous determination of the two isomeric iridoid glycosides and then evaluate their pharmacokinetic properties in rats. Selected-reaction monitoring mode was employed for quantification of two analytes in rat plasma. The calibration curves were linear over their respective concentration range with correlation coefficient >0.995 for both analytes. Precision for monotropein and deacetylasperulosidic acid ranged from 2.5 to 11.9% relative standard deviation, and the accuracy of two analytes was -2.0-3.7 and -6.4-10.7% relative error, respectively. This method was successfully applied in pharmacokinetic study after oral administration of M. officinalis extract in rats. The results provided a basis for further research on the bioactivity of M. officinalis.

KEYWORDS

LC/MS/MS; Morinda officinalis; deacetylasperulosidic acid; monotropein; pharmacokinetics.

Title

LC/MS/MS Determination and Pharmacokinetic Study of Iridoid Glycosides Monotropein and Deacetylasperulosidic Acid Isomers in Rat Plasma After Oral Administration of Morinda Officinalis Extract

Author

Chunmin Li 1 , Jian Dong 2 , Jingchang Tian 3 , Zhipeng Deng 4 , Xiujing Song 5

Publish date

2016 Feb

PMID

31434002

Abstract

Ethnobotanical relevance: The interest on herbal health supplements for obesity is increasing globally. Our previous ethnobotanical survey in Tiruvallur district, Tamil Nadu, India indicated the use of Spermacoce hispida L. seeds for the treatment of obesity.
Aim of the study: This study was aimed to validate the traditional claim and to identify the antihyperlipidemic principle in the seeds of Spermacoce hispida using bioassay guided fractionation method.
Methods: Bioassay monitored fractionation of the aqueous extract from Spermacoce hispida seeds was carried out using triton WR 1339 induced hyperlipidemic animals. It yielded deacetylasperulosidic acid (DAA) as the active ingredient. Pharmacokinetic properties of DAA were predicted using DataWarrior and SwissADME tools. In vitro antiobesity and antihyperlipidemic effects of DAA were evaluated in 3T3L1 preadipocytes and HepG2 cells, respectively. The chronic antihyperlipidemic efficacy of DAA was evaluated in high fat diet fed rats.
Results: DAA did not show any mutagenic and tumorigenic properties. It bound with PPARα with comparable ligand efficiency as fenofibrate. The treatment with DAA significantly lowered the proliferation of matured adipocytes, but not preadipocytes. The treatment of steatotic HepG2 cells with DAA significantly decreased the LDH leakage by 43.03% (P < 0.05) at 50 μM concentration. In triton WR 1339 induced hyperlipidemic animals, the treatment with 50 mg/kg dose significantly lowered the TC, TG and LDL-c levels by 40.27, 46.00 and 63.65% respectively. In HFD fed animals, the treatment at 10 mg/kg decreased BMI and AC/TC ratio without altering SRBG. It also improved serum lipid, transaminases and phosphatases levels of HFD fed animals. The treatment lowered adipocyte hypertrophy and steatosis of hepatocytes. Conclusion: This preliminary report supported the traditional use of Spermacoce hispida for the treatment of obesity. Further detailed investigations on the long term safety, efficacy and molecular mode of action of Spermacoce hispida and DAA will throw more light on their usefulness for the management of obesity.

KEYWORDS

Bioassay guided fractionation; Healthcare supplements; Obesity; Siddha.

Title

Antihyperlipidemic Effect of Iridoid Glycoside Deacetylasperulosidic Acid Isolated From the Seeds of Spermacoce Hispida L. - A Traditional Antiobesity Herb

Author

S Esakkimuthu 1 , S Nagulkumar 1 , S Sylvester Darvin 1 , K Buvanesvaragurunathan 1 , T N Sathya 2 , K R Navaneethakrishnan 2 , T S Kumaravel 2 , S S Murugan 2 , Osamu Shirota 3 , K Balakrishna 4 , P Pandikumar 5 , S Ignacimuthu 6

Publish date

2019 Dec 5