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Xanthyletin

$855

  • Brand : BIOFRON

  • Catalogue Number : AV-C10655

  • Specification : 98%

  • CAS number : 553-19-5

  • Formula : C14H12O3

  • Molecular Weight : 228.24

  • PUBCHEM ID : 65188

  • Volume : 5mg

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Catalogue Number

AV-C10655

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

228.24

Appearance

Powder

Botanical Source

Structure Type

Coumarins

Category

Standards;Natural Pytochemical;API

SMILES

CC1(C=CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)C

Synonyms

8,8-dimethyl-2H,3H-pyrano[3,2-g]chromen-2-one/Xanthyletine/8,8-Dimethyl-8H-pyrano[3,2-g]chromen-2-on/xanthylelin/Xanthyletin/8,8-dimethylpyrano[3,2-g]chromen-2(8H)-one/8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one

IUPAC Name

2,2-dimethylpyrano[3,2-g]chromen-8-one

Applications

Xanthyletin is a coumarin isolated from Citrus, with anti-tumor and anti-bacterial activities. Xanthyletin also inhibits symbiotic fungus cultivated by leaf-cutting ants[1].

Density

1.222g/cm3

Solubility

K. pneumoniae ST2501; P. insidiosum; P. stutzeri ST1302; Synchrotron radiation-based Fourier-transform infrared (FTIR) microspectroscopy; Xanthyletin

Flash Point

161.9ºC

Boiling Point

384.6ºC at 760mmHg

Melting Point

InChl

InChI=1S/C14H12O3/c1-14(2)6-5-10-7-9-3-4-13(15)16-11(9)8-12(10)17-14/h3-8H,1-2H3

InChl Key

QOTBQNVNUBKJMS-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:553-19-5) 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

30991991

Abstract

BACKGROUND:
Pythium insidiosum is a member of the oomycetes class of aquatic fungus-like microorganisms. It can infect humans and animals through skin wounds and the eyes, causing pythiosis, an infectious disease with high morbidity and mortality rates. Antifungal agents are ineffective as pythiosis treatments because ergosterol, the target site of most antifungal agents, is not found in the P. insidiosum cytoplasmic membrane. The best choice for treatment is surgical removal of the infected organ. While natural plant products or secretory substances from bacterial flora have exhibited in vitro anti-P. insidiosum activity, their mechanism of action remains unknown. Therefore, this study hypothesized that the mechanism of action could be related to changes in P. insidiosum biochemical composition (such as lipid, carbohydrate, protein or nucleic acid) following exposure to the inhibitory substances. The biochemical composition of P. insidiosum was investigated by Synchrotron radiation-based Fourier-transform infrared (FTIR) microspectroscopy.

RESULTS:
Fraction No.6 from the crude extract of P. stutzeri ST1302, fraction No.1 from the crude extract of K. pneumoniae ST2501 and xanthyletin were used as anti-P. insidiosum substances, with MFCs at 3.125, 1.57-1.91, 0.003 mg/ml, respectively. The synchrotron FTIR results show that the deconvoluted peak distributions in the amide I, amide II, and mixed regions were significantly different between the treatment and control groups.

CONCLUSIONS:
Xanthyletin and the secondary metabolites from P. stutzeri ST1302 and K. pneumoniae ST2501 exerted anti-P. insidiosum activity that clearly changed the proteins in P. insidiosum. Further study, including proteomics analysis and in vivo susceptibility testing, should be undertaken to develop a better understanding of the mechanism of anti-P. insidiosum activity.

KEYWORDS

K. pneumoniae ST2501; P. insidiosum; P. stutzeri ST1302; Synchrotron radiation-based Fourier-transform infrared (FTIR) microspectroscopy; Xanthyletin

Title

Analysis of xanthyletin and secondary metabolites from Pseudomonas stutzeri ST1302 and Klebsiella pneumoniae ST2501 against Pythium insidiosum.

Author

Wittayapipath K1, Laolit S1, Yenjai C2, Chio-Srichan S3, Pakarasang M1, Tavichakorntrakool R1, Prariyachatigul C4.

Publish date

2019 Apr 16

PMID

19296958

Abstract

Xanthyletin, an inhibitor of symbiotic fungus (Leucoagaricus gongylophorus) of leaf-cutting ant (Atta sexdens rubropilosa), as well as suberosin, seselin and xanthoxyletin were isolated from Citrus sinensis grafted on Citrus limonia. A two-phase solvent system composed of hexane/ethanol/acetonitrile/water (10:8:1:1, v/v) was used for the high-speed counter-current chromatographic isolation of xanthyletin with high yield and over 99% purity as determined by liquid and gas chromatography with mass spectrometry detection. Identifications were performed by UV spectra, IR spectra, (1)H NMR and (13)C NMR.

Title

Isolation of xanthyletin, an inhibitor of ants' symbiotic fungus, by high-speed counter-current chromatography.

Author

Cazal Cde M1, Domingues Vde C, Batalh?o JR, Bueno OC, Filho ER, da Silva MF, Vieira PC, Fernandes JB.

Publish date

2009 May 8

PMID

32161276

Abstract

Pythiosis is a harmful disease caused by Pythium insidiosum, an aquatic oomycete. Therapeutic protocols based on antifungal drugs are often ineffective because the cytoplasmic membrane of P. insidiosum does not contain ergosterol. Therefore, the treatment of pythiosis is still challenging, particularly making use of natural products and secondary metabolites from bacteria. In this study, xanthyletin and substances obtained from Pseudomonas stutzeri ST1302 and Klebsiella pneumoniae ST2501 exhibited anti-P. insidiosum activity and, moreover, xanthyletin was non-toxic against human cell lines. The hyphae of P. insidiosum treated with these three substances exhibited lysis holes on a rough surface and release of anamorphic material. Therefore, xanthyletin could be considered a promising alternative agent for treating cutaneous pythiosis in the near future.

Title

Evaluation of antifungal effect and toxicity of xanthyletin and two bacterial metabolites against Thai isolates of Pythium insidiosum.

Author

Wittayapipath K1, Yenjai C2, Prariyachatigul C3, Hamal P4.

Publish date

2020 Mar 11