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Sanggenon D

$570

  • Brand : BIOFRON

  • Catalogue Number : AV-H19070

  • Specification : 98%

  • CAS number : 81422-93-7

  • Formula : C40H36O12

  • Molecular Weight : 708.7

  • PUBCHEM ID : 442459

  • Volume : 20mg

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Catalogue Number

AV-H19070

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

708.7

Appearance

Yellow crystalline powder

Botanical Source

Morus alba L. /Morus cathayana

Structure Type

Flavonols/Flavanonols

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CC(C(C(C1)C2=C(C=C(C=C2)O)O)C(=O)C3=C(C=C(C=C3)O)O)C4=C(C=C5C(=C4O)C(=O)C6(C(O5)(C7=C(O6)C=C(C=C7)O)CC=C(C)C)O)O

Synonyms

I07-0320/2-[(1R,5S,6R)-6-(2,4-Dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methyl-2-cyclohexen-1-yl]-1,3,8,10a-tetrahydroxy-5a-(3-methyl-2-buten-1-yl)-5a,10a-dihydro-11H-[1]benzofuro[3,2-b]chromen-11-one/2-[(1S,5R,6S)-6-(2,4-Dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methyl-2-cyclohexen-1-yl]-1,3,5a,8-tetrahydroxy-10a-(3-methyl-2-buten-1-yl)-5a,10a-dihydro-11H-[1]benzofuro[3,2-b]chromen-11-one/Sanggenone D/11H-Benzofuro[3,2-b][1]benzopyran-11-one, 2-[(1R,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methyl-2-cyclohexen-1-yl]-5a,10a-dihydro-1,3,8,10a-tetrahydroxy-5a-(3-methyl-2-buten-1-yl)-/11H-Benzofuro[3,2-b][1]benzopyran-11-one, 2-[(1S,5R,6S)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methyl-2-cyclohexen-1-yl]-5a,10a-dihydro-1,3,5a,8-tetrahydroxy-10a-(3-methyl-2-buten-1-yl)-

IUPAC Name

2-[(1R,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8,10a-tetrahydroxy-5a-(3-methylbut-2-enyl)-[1]benzofuro[3,2-b]chromen-11-one

Applications

Sanggenon D is a Diels-Alder-type adduct from Chinese crude drug root bark of Morus cathayana. Sanggenon D possesses antioxidant and inhibits Pancreatic lipase (PL) with the an IC50 of 0.77?μM[1].

Density

1.5±0.1 g/cm3

Solubility

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

Flash Point

312.7±27.8 °C

Boiling Point

999.3±65.0 °C at 760 mmHg

Melting Point

175-185℃

InChl

InChI=1S/C40H36O12/c1-18(2)10-11-39-27-9-6-22(43)16-31(27)52-40(39,50)38(49)35-32(51-39)17-30(46)34(37(35)48)26-13-19(3)12-25(23-7-4-20(41)14-28(23)44)33(26)36(47)24-8-5-21(42)15-29(24)45/h4-10,13-17,25-26,33,41-46,48,50H,11-12H2,1-3H3/t25-,26-,33-,39?,40?/m1/s1

InChl Key

XETHJOZXBVWLLM-ZGXWVFFRSA-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#:81422-93-7) 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

30314378

Abstract

Sanggenons C and D are two Diels-Alder-type adducts from Chinese crude drug Sang-bai-pi. Structurally, both sanggenons construct stereoisomers. In the study, they were comparatively determined using four antioxidant assays, including ferric ion reducing antioxidant power (FRAP) assay, Cu2+-reducing assay, 1,1-diphenyl-2-picryl-hydrazl (DPPH?)-scavenging assay, and 2,2′-azino-bis (3-ethylbenzo-thiazoline-6-sulfonic acid radical (ABTS?+)-scavenging assay. Their Fe2+-binding reactions were explored using UV-Vis spectra. Finally, their cytoprotective effects were evaluated using flow cytometry. In electron transfer (ET)-based FRAP and Cu2+-reducing assays, sanggenon D was found to have lower IC50 values than sanggenon C; however, in multi-pathway-based DPPH?-scavenging and ABTS?+-scavenging assays, sanggenon C possessed lower IC50 values than sanggenon D. UV-Vis spectra suggested that sanggenon C generated a bathochromic-shift (286 nm → 302 nm) and displayed stronger UV absorption than sanggenon D. In flow cytometry, sanggenon C and sanggenon D, respectively, exhibited 31.1% and 42.0% early apoptosis-percentages towards oxidative-stressed mesenchymal stem cells (MSCs). In conclusion, both sanggenons may undergo multiple pathways (e.g., ET and Fe2+-binding) to protect MSCs against oxidative stress. In the mere ET aspect, sanggenon D possesses a higher level than sanggenon C, while in multi-pathway-based radical-scavenging, Fe2+-binding, and cytoprotection aspects, sanggenon C is more active than sanggenon D. These discrepancies can conclusively be attributed to the steric effect.

KEYWORDS

antioxidant, Diels-Alder-type adduct, sanggenon C, sanggenon D, steric effect

Title

Steric Effect of Antioxidant Diels-Alder-Type Adducts: A Comparison of Sanggenon C with Sanggenon D.

Author

Xican Li,1,2,*† Zhenxing Ren,3,4,† Zimei Wu,3,4 Zhen Fu,3,4 Hong Xie,1 Langyu Deng,1 Xiaohua Jiang,5 and Dongfeng Chen3,4,*

Publish date

2018 Oct;

PMID

30314378

Abstract

Sanggenons C and D are two Diels-Alder-type adducts from Chinese crude drug Sang-bai-pi. Structurally, both sanggenons construct stereoisomers. In the study, they were comparatively determined using four antioxidant assays, including ferric ion reducing antioxidant power (FRAP) assay, Cu2+-reducing assay, 1,1-diphenyl-2-picryl-hydrazl (DPPH?)-scavenging assay, and 2,2′-azino-bis (3-ethylbenzo-thiazoline-6-sulfonic acid radical (ABTS??)-scavenging assay. Their Fe2+-binding reactions were explored using UV-Vis spectra. Finally, their cytoprotective effects were evaluated using flow cytometry. In electron transfer (ET)-based FRAP and Cu2+-reducing assays, sanggenon D was found to have lower IC50 values than sanggenon C; however, in multi-pathway-based DPPH?-scavenging and ABTS??-scavenging assays, sanggenon C possessed lower IC50 values than sanggenon D. UV-Vis spectra suggested that sanggenon C generated a bathochromic-shift (286 nm → 302 nm) and displayed stronger UV absorption than sanggenon D. In flow cytometry, sanggenon C and sanggenon D, respectively, exhibited 31.1% and 42.0% early apoptosis-percentages towards oxidative-stressed mesenchymal stem cells (MSCs). In conclusion, both sanggenons may undergo multiple pathways (e.g., ET and Fe2+-binding) to protect MSCs against oxidative stress. In the mere ET aspect, sanggenon D possesses a higher level than sanggenon C, while in multi-pathway-based radical-scavenging, Fe2+-binding, and cytoprotection aspects, sanggenon C is more active than sanggenon D. These discrepancies can conclusively be attributed to the steric effect.

KEYWORDS

Diels-Alder-type adduct; antioxidant; sanggenon C; sanggenon D; steric effect

Title

Steric Effect of Antioxidant Diels-Alder-Type Adducts: A Comparison of Sanggenon C with Sanggenon D.

Author

Li X1,2, Ren Z3,4, Wu Z5,6, Fu Z7,8, Xie H9, Deng L10, Jiang X11, Chen D12,13.

Publish date

2018 Oct 11