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Ptaquiloside

$896

  • Brand : BIOFRON

  • Catalogue Number : BN-O1323

  • Specification : 98%(HPLC)

  • CAS number : 87625-62-5

  • Formula : C20H30O8

  • Molecular Weight : 398.4

  • PUBCHEM ID : 13962857

  • Volume : 5mg

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Catalogue Number

BN-O1323

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

398.4

Appearance

Botanical Source

Structure Type

Category

SMILES

CC1CC2(C=C(C3(CC3)C(C2C1=O)(C)O)C)OC4C(C(C(C(O4)CO)O)O)O

Synonyms

(2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one

IUPAC Name

(2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one

Density

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

InChl

InChl Key

GPHSJPVUEZFIDE-YVPLJZHISA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:87625-62-5) 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

31226154

Abstract

Ptaquiloside is a natural toxin present in bracken ferns (Pteridium sp.). Cattle ingesting bracken may develop bladder tumours and excrete genotoxins in meat and milk. However, the fate of ptaquiloside in cattle and the link between ptaquiloside and cattle carcinogenesis is unresolved. Here, we present the toxicokinetic profile of ptaquiloside in plasma and urine after intravenous administration of ptaquiloside and after oral administration of bracken. Administered intravenously ptaquiloside, revealed a volume of distribution of 1.3 L kg-1 with a mean residence-time of 4 hours. A large fraction of ptaquiloside was converted to non-toxic pterosin B in the blood stream. Both ptaquiloside and pterosin B were excreted in urine (up to 41% of the dose). Oral administration of ptaquiloside via bracken extract or dried ferns did not result in observations of ptaquiloside in body fluids, indicating deglycosolidation in the rumen. Pterosin B was detected in both plasma and urine after oral administration. Hence, transport of carcinogenic ptaquiloside metabolites over the rumen membrane is indicated. Pterosin B recovered from urine counted for 7% of the dose given intravenously. Heifers exposed to bracken for 7 days (2 mg ptaquiloside kg-1) developed preneoplastic lesions in the urinary bladder most likely caused by genotoxic ptaquiloside metabolites.

Title

Fate of ptaquiloside-A bracken fern toxin-In cattle.

Author

Aranha PCDR1, Rasmussen LH2, Wolf-Jackel GA1, Jensen HME1, Hansen HCB3, Friis C1.

Publish date

2019 Jun 21

PMID

27128893

Abstract

Ptaquiloside, along with other natural phytotoxins, is receiving increased attention from scientists and land use managers. There is an urgent need to increase empirical evidence to understand the scale of phytotoxin mobilisation and potential to enter into the environment. In this study the risk of ptaquiloside to drinking water was assessed by quantifying ptaquiloside in the receiving waters at three drinking water abstraction sites across Ireland and in bracken fronds surrounding the abstraction sites. We also investigated the impact of different management regimes (spraying, cutting and rolling) on ptaquiloside concentrations at plot-scale in six locations in Northern Ireland, UK. Ptaquiloside concentrations were determined using recent advances in the use of LC-MS for the detection and quantification of ptaquiloside. The results indicate that ptaquiloside is present in bracken stands surrounding drinking water abstractions in Ireland, and ptaquiloside concentrations were also observed in the receiving waters. Furthermore, spraying was found to be the most effective bracken management regime observed in terms of reducing ptaquiloside load. Increased awareness is vital on the implications of managing land with extensive bracken stands.

KEYWORDS

Ireland; bracken; drinking water; land management; phytochemicals; ptaquiloside

Title

Ptaquiloside in Irish Bracken Ferns and Receiving Waters, with Implications for Land Managers.

Author

O'Driscoll C1,2, Ramwell C3, Harhen B4, Morrison L5, Clauson-Kaas F6, Hansen HC7, Campbell G8, Sheahan J9, Misstear B10, Xiao L11.

Publish date

2016 Apr 26

PMID

27640346

Abstract

Bracken is a fern with worldwide distribution. Exposure to bracken toxins such as ptaquiloside is hypothesized to increase the risk of papillomavirus-related cancers of the upper digestive tract. Ptaquiloside is thought to be an immunosupressor, thus allowing for the development of viral lesions. We have used a human papillomavirus type 16-transgenic (K14-HPV16) mouse model to study the effects of ptaquiloside on tumour-infiltrating CD8+ T lymphocytes, which are critical players in anti-tumour immunity. HPV16+/- mice received ptaquiloside (0.5 mg/mouse/week) for 10 weeks. These were then euthanized at 30 weeks of age, along with age-matched untreated controls. Skin samples were enzymatically digested and CD8+ T cells analysed for CD107a and CD44 surface expression. Ptaquiloside-exposed HPV16+/- mice showed a significantly decreased percentage (P < 0.05) of CD8+CD107a+ and CD8+CD44 + T cells when compared with untreated HPV16+/- animals. Histologically, 100% of ptaquilosidetreated mice showed diffuse epidermal dysplasia, compared with 50% of the untreated mice. These findings suggest that ptaquiloside exerts an immunosuppressive role by decreasing CD8+ T cell activation and degranulation in HPV-induced lesions. Given the key role of CD8+ T lymphocytes against HPV-induced lesions, this effect is likely to contribute for viral persistence, tumour progression and increased aggressiveness in patients with HPV-related malignancies. Copyright © 2016 Elsevier Ltd. All rights reserved.

KEYWORDS

Bracken; CD8(+) T cells; Cancer; Human papillomavirus; Ptaquiloside

Title

Ptaquiloside from bracken (Pteridium spp.) inhibits tumour-infiltrating CD8+ T cells in HPV-16 transgenic mice.

Author

Santos C1, Ferreirinha P2, Sousa H3, Ribeiro J4, Bastos MM5, Neto T6, Oliveira PA7, Medeiros R8, Vilanova M2, Gil da Costa RM9.

Publish date

2016 Nov


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