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Pseudoprotodioscin

$178

  • Brand : BIOFRON

  • Catalogue Number : BF-P4014

  • Specification : 98%(HPLC)

  • CAS number : 102115-79-7

  • Formula : C51H82O21

  • Molecular Weight : 1031.18

  • PUBCHEM ID : 51346147

  • Volume : 25mg

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Catalogue Number

BF-P4014

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

1031.18

Appearance

White crystal

Botanical Source

Dioscorea nipponica

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(C(C(C(O1)OC2C(OC(C(C2O)OC3C(C(C(C(O3)C)O)O)O)OC4CCC5(C6CCC7(C(C6CC=C5C4)CC8C7C(=C(O8)CCC(C)COC9C(C(C(C(O9)CO)O)O)O)C)C)C)CO)O)O)O

Synonyms

PSEUDOPROTOTRIBESTIN/β-D-Glucopyranoside, (25R)-3-[[O-6-deoxy-α-L-mannopyranosyl-(1->2)-O-[6-deoxy-α-L-mannopyranosyl-(1->4)]-β-D-glucopyranosyl]oxy]furosta-5,20(22)-dien-27-yl/(3β,25R)-26-(β-D-Glucopyranosyloxy)furosta-5,20(22)-dien-3-yl 6-deoxy-α-L-mannopyranosyl-(1->;2)-[6-deoxy-α-L-mannopyranosyl-(1->;4)]-β-D-glucopyranoside/pseudo-Protodioscin/PROTODIOSCIN,PSEUDO/β-D-Glucopyranoside, (25R)-26-(β-D-glucopyranosyloxy)furosta-5,20(22)-dien-3-yl O-6-deoxy-α-L-mannopyranosyl-(1->2)-O-[6-deoxy-α-L-mannopyranosyl-(1->4)]-/(25R)-26-(β-D-Glucopyranosyloxy)furosta-5,20(22)-dien-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[6-deoxy-α-L-mannopyranosyl-(1->4)]-β-D-glucopyranoside/Pseduoprotodioscin/(25R)-3-{[6-Deoxy-α-L-mannopyranosyl-(1->2)-[6-deoxy-α-L-mannopyranosyl-(1->4)]-β-D-glucopyranosyl]oxy}furosta-5,20(22)-dien-27-yl β-D-glucopyranoside/β-D-Glucopyranoside, (3β,25R)-26-(β-D-glucopyranosyloxy)furosta-5,20(22)-dien-3-yl O-6-deoxy-α-L-mannopyranosyl-(1->2)-O-[6-deoxy-α-L-mannopyranosyl-(1->4)]-/Pseudoprotodioscin

IUPAC Name

(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(1S,2S,4S,8S,9S,12S,13R)-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-6,18-dien-16-yl]oxy]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Density

1.45 g/cm3

Solubility

Methanol; Water

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C51H82O21/c1-20(19-64-46-40(60)39(59)36(56)31(17-52)69-46)7-10-29-21(2)33-30(68-29)16-28-26-9-8-24-15-25(11-13-50(24,5)27(26)12-14-51(28,33)6)67-49-45(72-48-42(62)38(58)35(55)23(4)66-48)43(63)44(32(18-53)70-49)71-47-41(61)37(57)34(54)22(3)65-47/h8,20,22-23,25-28,30-49,52-63H,7,9-19H2,1-6H3/t20-,22+,23+,25?,26-,27+,28+,30+,31-,32-,33+,34+,35+,36-,37-,38-,39+,40-,41-,42-,43+,44-,45-,46-,47+,48+,49-,50+,51+/m1/s1

InChl Key

MDCUMTGKKLOMCW-MQDUZHDNSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:102115-79-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

15254856

Abstract

Microbial transformation of the furostanol saponin pseudoprotodioscin ( 1) using Aspergillus fumigatus resulted in the isolation of two new steroidal metabolites, 3- O-[bis- alpha- L-rhamnopyranosyl-(1–>2 and 1–>4)- beta- D-glucopyranosyl]-22 R,25 R-spirost-5-ene-3 beta,20 alpha-diol ( 2) and 3- O-[bis- alpha- L-rhamnopyranosyl-(1–>2 and 1–>4)- beta- D-glucopyranosyl]-25 R-furost-5-ene-3 beta,22 alpha,26-triol ( 3), in addition to the previously reported steroidal saponins: dioscin ( 4) and progenin II ( 5). The structure elucidation of these metabolites was based primarily on 1D and 2D NMR analyses. Metabolites 2 – 5 showed significant cytotoxicity against cancer cell lines A375, L929, and HeLa with IC (50) values ranging from 1.18 microM to 17.88 microM.

Title

Microbial Metabolism of Pseudoprotodioscin

Author

Mei Dong 1 , Xizhi Feng, Ben-Xiang Wang, Takashi Ikejima, Li-Jun Wu

Publish date

2004 Jul

PMID

31669721

Abstract

The extract of Dioscorea zingiberensis C.H. Wright rhizomes is found to be effective in the therapy of cardiovascular disease. Steroidal saponins make substantial contribution. Previous study has proposed that methylprotodioscin (MP) may promote cholesterol efflux by increasing ABCA1 expression. But the other main saponins ingredients are not referred to. The aim of the present work was to reveal the effect and mechanism of protodioscin (PD), MP and pseudoprotodioscin (PPD) on the synthesis-related gene expression of cholesterol and triglycerides. MTT assay apoptosis assay with annexin AV-APC and 7-AAD double staining were performed. MicroRNA assay and qRT-PCR were used to analyze the gene expression which regulates synthesis of cholesterol and triglycerides. Western blot was to demonstrate the levels of target proteins. Cholesterol efflux assay was executed to study the stimulative effect of saponins on cholesterol efflux. In Hep G2 cells, PPD increased ABCA1 protein and mRNA levels, and promoted the effluxion of ApoA-1-mediated cholesterol. The underlying mechanisms involved that PPD inhibited SREBP1c and SREBP2 transcription by decreasing microRNA 33a/b levels. This procedure reciprocally led to the increase of ABCA1 levels. In THP-1 macrophages, PPD showed the similar effect, which reduced HMGCR, FAS and ACC mRNA levels and promoted low density lipoprotein receptor by decreasing the PCSK9 levels. These studies demonstrated that PPD is a potential agent for cholesterol efflux, SREBPs and microRNA 33a/b inhibition, which related to the gene expression for the synthesis of cholesterol and triglycerides.

KEYWORDS

Dioscorea zingiberensis C.H. Wright; Low density lipoprotein; Pseudoprotodioscin; SREBPs; microRNA 33a/b.

Title

Pseudoprotodioscin Inhibits SREBPs and microRNA 33a/b Levels and Reduces the Gene Expression Regarding the Synthesis of Cholesterol and Triglycerides

Author

Yanan Gai 1 , Yingshuo Li 1 , Zenglai Xu 2 , Jian Chen 3

Publish date

2019 Nov

PMID

26012509

Abstract

An original and sensitive ultraperformance liquid chromatography-tandem mass spectrometric (UPLC-MS/MS) method for the determination of pseudoprotodioscin (PPD) in rat plasma was developed and validated. Digitoxin was applied as an internal standard. Plasma samples were processed by acetonitrile-mediated plasma protein precipitation and chromatographed using a step gradient program on a C18 column (2.1×50mm i.d., 1.7μm). The mobile phase was comprised of acetonitrile and 0.1mmolL(-1) aqueous lithium acetate mixed with 0.03% formic acid at the flow rate of 0.2mLmin(-1). Multiple reaction monitoring (MRM) transitions were performed for detection and lithium adduct ions were employed with a significant improvement of the response of the analytes in electrospray positive ionization mode. The concentration range of calibration curve was linear over the range 2-5000ngmL(-1). The intra- and inter-day precisions were all less than 11.5% and accuracies were within the range of 94.1-103.5%, and the analytes exhibited no severe matrix effect. The validated method was successfully applied in the pharmacokinetics of PPD after intragastric (50mgkg(-1)) and intravenous (4mgkg(-1)) administration in rats. PPD showed rapid excretion and with bioavailability of simply about 5.7% in rats.

KEYWORDS

Method validation; Pharmacokinetics; Pseudoprotodioscin; Rat plasma; UPLC-MS/MS.

Title

Determination of Pseudoprotodioscin in Rat Plasma by UPLC-MS/MS: Assay Development and Application to Pharmacokinetic Study

Author

Min Liao 1 , Xiao Chen 1 , Jiefeng Chen 1 , Mengping Liu 1 , Junyi Wang 1 , Zuanguang Chen 1 , Zhiyong Xie 1 , Meicun Yao 2

Publish date

2016 Jul 15


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