Validamycin A
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| Category | Agricultural |
| Catalog number | BBF-03433 |
| CAS | 37248-47-8 |
| Molecular Weight | 497.49 |
| Molecular Formula | C20H35NO13 |
| Purity | >95% by HPLC |
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Description
The major analogue of a family of cyclitol disaccharides isolated from streptomyces hygroscopicus var. Limoneus. It is a potent antifungal agent used to control fungi in crop production and acts as a potent inhibitor of trehalase, an important enzyme in carbohydrate storage and ultilisation in fungi.
Specification
| Synonyms | jinggangmycin; Antibiotic T 7545A |
| Storage | Store at-20°C |
| IUPAC Name | [(1S,2S,3R,4R,5R)-2,3-dihydroxy-5-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]azanium |
| Canonical SMILES | C1C(C(C(C(C1[NH2+]C2C=C(C(C(C2O)O)O)CO)O)O)OC3C(C(C(C(O3)CO)O)O)O)CO |
| InChI | InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/p+1/t7-,8+,9+,10-,11-,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1 |
| InChI Key | JARYYMUOCXVXNK-CSLFJTBJSA-O |
| Source | Streptomyces sp. |
Properties
| Appearance | White Amorphous Powder |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 813.66°C at 760 mmHg |
| Melting Point | 130-135°C |
| Density | 1.70 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. |
Reference Reading
1.Potential role and therapeutic interests of myo-inositol in metabolic diseases.
Croze ML1, Soulage CO. Biochimie. 2013 Oct;95(10):1811-27. doi: 10.1016/j.biochi.2013.05.011. Epub 2013 Jun 10.
Several inositol isomers and in particular myo-inositol (MI) and D-chiro-inositol (DCI), were shown to possess insulin-mimetic properties and to be efficient in lowering post-prandial blood glucose. In addition, abnormalities in inositol metabolism are associated with insulin resistance and with long term microvascular complications of diabetes, supporting a role of inositol or its derivatives in glucose metabolism. The aim of this review is to focus on the potential benefits of a dietary supplement of myo-inositol, by far the most common inositol isomer in foodstuffs, in human disorders associated with insulin resistance (polycystic ovary syndrome, gestational diabetes mellitus or metabolic syndrome) or in prevention or treatment of some diabetic complications (neuropathy, nephropathy, cataract). The relevance of such a nutritional strategy will be discussed for each context on the basis of the clinical and/or animal studies. The dietary sources of myo-inositol and its metabolism from its dietary uptake to its renal excretion will be also covered in this review.
2.Updates on the myo-inositol plus D-chiro-inositol combined therapy in polycystic ovary syndrome.
Unfer V1, Porcaro G. Expert Rev Clin Pharmacol. 2014 Sep;7(5):623-31. doi: 10.1586/17512433.2014.925795. Epub 2014 Jun 5.
Polycystic ovary syndrome (PCOS) is one of the most common endocrine disorders affecting women of reproductive age. It is characterized by chronic anovulation, hyperandrogenism, and insulin resistance. It is the main cause of infertility due to the menstrual dysfunction and metabolic disorders. Women with PCOS also have an increased cardiovascular risk because of dyslipidemia and insulin resistance. So far, we have a lot of information about the etiology of PCOS, and many steps forward have been made about the diagnosis of this syndrome, but there is still no certainty about the therapy. Myo-inositol (MI) and D-chiro-inositol, two inositol stereoisomers, have been proven to be effective in PCOS treatment. However, only MI has been shown to have beneficial effects on reproductive function, whereas the administration of MI/D-chiro-inositol, in the physiological plasma ratio (i.e., 40:1) ensures better clinical results, such as the reduction of insulin resistance, androgens' blood levels, cardiovascular risk and regularization of menstrual cycle with spontaneous ovulation.
3.Toxicological evaluation of the natural products and some semisynthetic derivatives of Heterotheca inuloides Cass (Asteraceae).
Rodríguez-Chávez JL1, Coballase-Urrutia E2, Sicilia-Argumedo G3, Ramírez-Apan T1, Delgado G4. J Ethnopharmacol. 2015 Dec 4;175:256-65. doi: 10.1016/j.jep.2015.08.055. Epub 2015 Sep 5.
ETHNOPHARMACOLOGICAL RELEVANCE: Heterotheca ineuloides Cass (Asteraceae), popularly known as árnica mexicana, is widely used in Mexican traditional medicine to treat bruises, dermatological problems, rheumatic pains, and other disorders as cancer. The major constituents in H. inuloides are cadinane type sesquiterpenes, flavonoids and phytosterols. Compounds with a cadinane skeleton have been proved to possess cytotoxic activity against human-tumor cell lines and brine shrimp, and display toxic effects in different animal species. Although this plant has been widely used, there is little available information on the safety and toxicity especially of pure compounds.
4.Quantification of myo-inositol, 1,5-anhydro- D-sorbitol, and D-chiro-inositol using high-performance liquid chromatography with electrochemical detection in very small volume clinical samples.
Schimpf KJ1, Meek CC2, Leff RD2, Phelps DL3, Schmitz DJ1, Cordle CT1. Biomed Chromatogr. 2015 Nov;29(11):1629-36. doi: 10.1002/bmc.3470. Epub 2015 May 26.
Inositol is a six-carbon sugar alcohol and is one of nine biologically significant isomers of hexahydroxycyclohexane. Myo-inositol is the primary biologically active form and is present in higher concentrations in the fetus and newborn than in adults. It is currently being examined for the prevention of retinopathy of prematurity in newborn preterm infants. A robust method for quantifying myo-inositol (MI), D-chiro-inositol (DCI) and 1,5-anhydro- D-sorbitol (ADS) in very small-volume (25 μL) urine, blood serum and/or plasma samples was developed. Using a multiple-column, multiple mobile phase liquid chromatographic system with electrochemical detection, the method was validated with respect to (a) selectivity, (b) accuracy/recovery, (c) precision/reproducibility, (d) sensitivity, (e) stability and (f) ruggedness. The standard curve was linear and ranged from 0.5 to 30 mg/L for each of the three analytes. Above-mentioned performance measures were within acceptable limits described in the Food and Drug Administration's Guidance for Industry: Bioanalytical Method Validation.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
