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Sambutoxin

$1,248

  • Brand : BIOFRON

  • Catalogue Number : BN-O1009

  • Specification : 99%(HPLC)

  • CAS number : 160047-56-3

  • Formula : C28H39NO4

  • Molecular Weight : 453.61

  • PUBCHEM ID : 54724817

  • Volume : 5mg

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Catalogue Number

BN-O1009

Analysis Method

HPLC,NMR,MS

Specification

99%(HPLC)

Storage

-20℃

Molecular Weight

453.61

Appearance

Powder

Botanical Source

This product is isolated and purified from the rotted potato tubers

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCC(C)CC(C)C=C(C)C1C(CCC(O1)C2=C(C(=CN(C2=O)C)C3=CC=C(C=C3)O)O)C

Synonyms

3-{(2S,5R,6R)-6-[(2E,4R,6S)-4,6-Dimethyl-2-octen-2-yl]-5-methyltetrahydro-2H-pyran-2-yl}-2-hydroxy-5-(4-hydroxyphenyl)-1-methyl-4(1H)-pyridinone/2(1H)-Pyridinone, 4-hydroxy-5-(4-hydroxyphenyl)-1-methyl-3-[(2S,5R,6R)-tetrahydro-5-methyl-6-[(1E,3R,5S)-1,3,5-trimethyl-1-hepten-1-yl]-2H-pyran-2-yl]-/4(1H)-Pyridinone, 2-hydroxy-5-(4-hydroxyphenyl)-1-methyl-3-[(2S,5R,6R)-tetrahydro-5-methyl-6-[(1E,3R,5S)-1,3,5-trimethyl-1-hepten-1-yl]-2H-pyran-2-yl]-/3-{(2S,5R,6R)-6-[(2E,4R,6S)-4,6-Dimethyl-2-octen-2-yl]-5-methyltetrahydro-2H-pyran-2-yl}-4-hydroxy-5-(4-hydroxyphenyl)-1-methyl-2(1H)-pyridinone/Sambutoxin

IUPAC Name

3-[(2S,5R,6R)-6-[(E,4R,6S)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl]-4-hydroxy-5-(4-hydroxyphenyl)-1-methylpyridin-2-one

Density

1.1±0.1 g/cm3

Solubility

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

Flash Point

311.5±30.1 °C

Boiling Point

591.4±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C28H39NO4/c1-7-17(2)14-18(3)15-20(5)27-19(4)8-13-24(33-27)25-26(31)23(16-29(6)28(25)32)21-9-11-22(30)12-10-21/h9-12,15-19,24,27,30-31H,7-8,13-14H2,1-6H3/b20-15+/t17-,18+,19+,24-,27+/m0/s1

InChl Key

FVYDVAOTXPELMH-SPRAOHHPSA-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#:160047-56-3) 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

30223653

Abstract

Sambutoxin, a representative derivative of 4-hydroxy-2-pyridone, was isolated from Hericium alpestre for the first time in this study. The possible correlation between the sambutoxin-induced suppression of tumor growth and its influence on cell-cycle arrest and apoptosis was investigated. The effects of sambutoxin on reactive oxygen species (ROS) production, DNA damage, mitochondrial transmembrane potential, cell apoptosis, and the expression of related proteins were evaluated. An in vitro cell viability study demonstrated that sambutoxin could inhibit the proliferation of various cancer cells. Treatment with sambutoxin induced the production of ROS, which caused DNA damage. Furthermore, the subsequent sambutoxin-induced activation of ATM and Chk2 resulted in G2/M arrest, accompanied by decreased expression of cdc25C, cdc2, and cyclin B1. Sambutoxin induced apoptosis by activating the mitochondrial apoptosis pathway through an increased Bax/Bcl-2 ratio, loss of mitochondrial membrane potential (ΔΨm), cytochrome (Cyt) c release, caspase-9 and caspase-3 activation, and poly(ADP-ribose) polymerase (PARP) degradation. The ROS elevation induced the sustained phosphorylation of c-Jun N-terminal kinase (JNK), while SP600125, a JNK inhibitor, nearly completely reversed sambutoxin-induced apoptosis. Accordingly, an in vivo study showed that sambutoxin exhibited potential antitumor activity in a BALB/c nude mouse xenograft model without significant systemic toxicity. Moreover, the expression changes in proteins related to the G2/M phase, DNA damage, and apoptosis in vivo were consistent with those in vitro. Importantly, sambutoxin has remarkable antiproliferative effects and is a promising anticarcinogen candidate for cancer treatment.

KEYWORDS

DNA damage; JNK; ROS; cell proliferation and apoptosis; cell-cycle arrest; sambutoxin.

Title

Discovery and Characterization of 4-Hydroxy-2-pyridone Derivative Sambutoxin as a Potent and Promising Anticancer Drug Candidate: Activity and Molecular Mechanism

Author

Lu-Ning Li, Lei Wang, Yan-Na Cheng, Zhan-Qi Cao, Xin-Ke Zhang, Xiu-Li Guo

Publish date

2018 Nov 5.

PMID

7811078

Abstract

Ninety-nine isolates of Fusarium species were obtained from rotted potato tubers from various parts of Korea. Of these isolates, 80 were identified as Fusarium oxysporum, F. solani, or F. sambucinum. The isolates of these species were grown on autoclaved wheat grains and examined for toxicity in a rat-feeding test. A total of 8 of 57 F. oxysporum isolates, 3 of 14 F. solani isolates, and 5 of 9 F. sambucinum isolates caused the death of the rats. Of the 16 toxic isolates, 1 isolate of F. oxysporum produced a substantial amount of moniliformin, which could account for its toxicity. None of the other 15 isolates produced trichothecenes, moniliformin, fusarochromanone, fumonisin B1, or wortmannin. F. sambucinum PZF-4 produced an unknown toxin in wheat culture. This new toxin, given the trivial name sambutoxin, caused toxic effects in rats, including body weight loss, feed refusal, hemorrhage in the stomach and intestines, and, finally, death when rats were fed diets supplemented with 0.05 and 0.1% sambutoxin. The toxin was also toxic to chicken embryos, and the 50% lethal concentration was 29.6 micrograms per egg. Sambutoxin formed as white crystals that turned purple when combined with reagents such as sulfuric acid and p-anisaldehyde. It exhibited a green color immediately after treatment with potassium ferricyanide-ferric chloride. Its UV spectrum had absorption maxima at 213, 233, and 254 nm, and its infrared spectrum showed an amide group at 1,650 and 1,560 cm-1 and a hydroxy group at 3,185 cm-1. Mass spectrometry showed that the molecular weight of the toxin was 453 and the molecular formula was C28H39NO4.(ABSTRACT TRUNCATED AT 250 WORDS)

Title

Sambutoxin, a New Mycotoxin Produced by Toxic Fusarium Isolates Obtained From Rotted Potato Tubers

Author

J C Kim 1, Y W Lee

Publish date

1994 Dec;

PMID

21419624

Abstract

Biomimetic-type reactions of the tricyclic pyridone alkaloid, (-)-fusoxypyridone [(-)-4,6′-anhydrooxysporidinone] (1), recently encountered in an endophytic strain of Fusarium oxysporum, and (-)-oxysporidinone (2) afforded (-)-sambutoxin (3) and an analogue of 1, identified as (-)-1′(6′)-dehydro-4,6′-anhydrooxysporidinone (4), thus confirming the structure previously proposed for 1 and suggesting that 1-3 bear the same relative stereochemistry. Oxidation of 4 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) yielded a hitherto unknown sambutoxin analogue, (-)-4,2′-anhydrosambutoxin (5).

Copyright © 2011 Elsevier Ltd. All rights reserved.

Title

Biomimetic Conversion of (-)-Fusoxypyridone and (-)-Oxysporidinone to (-)-Sambutoxin: Further Evidence for the Structure of the Tricyclic Pyridone Alkaloid, (-)-Fusoxypyridone

Author

E M Kithsiri Wijeratne 1, A A Leslie Gunatilaka

Publish date

2011 Apr 15


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