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Sanggenon C

$480

  • Brand : BIOFRON

  • Catalogue Number : AV-H19069

  • Specification : 98%

  • CAS number : 80651-76-9

  • Formula : C40H36O12

  • Molecular Weight : 708.71

  • PUBCHEM ID : 442458

  • Volume : 20mg

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Catalogue Number

AV-H19069

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

708.71

Appearance

Yellow crystalline powder

Botanical Source

Morus alba L. /Morus cathayana

Structure Type

Flavonoids

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(C5=C(C=C4O)OC6(C7=C(C=C(C=C7)O)OC6(C5=O)O)CC=C(C)C)O

Synonyms

2-[(1S,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/sanggenon D/Sanggenon C/2-[(1S,5S,6R)-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/11H-Benzofuro[3,2-b][1]benzopyran-11-one, 2-[(1S,5S,6R)-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)-/11H-Benzofuro[3,2-b][1]benzopyran-11-one, 2-[(1S,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)-sanggennon D/Sanggenone C/sanggenone D

IUPAC Name

2-[(1S,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

312.7±27.8 °C

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

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-QAHMVTMMSA-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#:80651-76-9) 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

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

PMID

30217005

Abstract

Sanggenon C (SC), which is a natural flavonoid found in the stem bark of Cortex Mori, has been discovered to have the antioxidant, anti-inflammatory, and antitumor properties. However, its effect in osteoporosis has not yet been reported. In this research, the effect of SC on the proliferation of MC3T3-E1 cells was evaluated by using the MTT assay. Alkaline phosphatase (ALP) activity and the mRNA expression of Runx2, Collagen I, OPG, and RANKL were examined. TRAP-positive cell counting and bone resorption pits were adopted to observe the effect of SC on the formation and function of osteoclasts. Next, the mRNA level of TRAP, CTSK, NFATc1, and TRAF6 of osteoclasts were measured by real-time qPCR. In addition, the anti-osteoporosis activity of SC in vivo was evaluated in the zebrafish model. Our study indicated that SC exhibited a significant stimulatory effect on MC3T3-E1 cell proliferation at 1 to 10 μM and caused an increase in ALP activity at 0.3 to 10 μM. It could upregulate the expression of Runx2, Collagen I, and increases the OPG/RANKL ratio. Furthermore, SC was found to inhibit the formation and function of osteoclasts, which is demonstrated by a lower number of TRAP-positive multinuclear cells and a fewer area of bone resorption pits compared to the control group. TRAP, CTSK, and NFATc1 were downregulated in 0.3 to 10 μM SC treated groups. In addition, 3 to 10 μM SC also inhibited the expression of TRAF6 mRNA. When prednisone-induced zebrafish was treated with 0.3, 1, 3, and 10 μM SC, higher mineralization of vertebrate column was discovered in a dose-dependent pattern, which suggests that SC could reverse the bone loss of zebrafish caused by prednisone. In summary, these findings indicated that SC has the potential to prevent or treat osteoporosis.

KEYWORDS

Sanggenon C; osteoblast; osteoclast; osteoporosis; zebrafish

Title

Sanggenon C Stimulates Osteoblastic Proliferation and Differentiation, Inhibits Osteoclastic Resorption, and Ameliorates Prednisone-Induced Osteoporosis in Zebrafish Model.

Author

Wang H1, Feng T2, Guo D3, Zhang M4, Chen L5, Zhou Y6,7.

Publish date

2018 Sep 13;

PMID

30032067

Abstract

Pancreatic lipase (PL), a key enzyme responsible for the hydrolysis of triacylglycerides in the gastrointestinal tract, has been identified as the therapeutic target for the regulation of lipid absorption. In the present study, six major constituents from a famous Chinese herbal medicine Cortex Mori Radicis (also named sangbaipi in Chinese), have been collected and their inhibitory effects on PL have been carefully investigated and well characterized by a fluorescence-based assay. The results clearly demonstrated that all tested bioactive constituents from Cortex Mori Radicis including sanggenone C (SC), sanggenone D (SD), kuwanon C (KC), kuwanon G (KG), morin and morusin displayed strong to moderate inhibitory effects towards PL with the IC50 values ranging from 0.77?μM to 20.56?μM. Further investigations on inhibition kinetics demonstrated that SC, SD, KC and KG functioned as potent and mixed inhibitors against PL-mediated 4-MU oleate hydrolysis, with the Ki values less than 5.0?μM. Furthermore, molecular docking simulations demonstrated that SD (the most potent PL inhibitor from Cortex Mori Radicis) could create strong interaction with Ser152 (the key amino acid in the catalytic triad) of PL via hydrogen bonding. All these findings provided a new powerful evidence for explaining the hypolipidemic effect of Cortex Mori Radicis, also suggested that some abundant natural compounds in this herbal medicine could be served as lead compounds for the development of new PL inhibitors.

Copyright ? 2018 Elsevier Inc. All rights reserved.

KEYWORDS

Cortex Mori Radicis; Inhibitory effects; Pancreatic lipase; Sanggenone C; Sanggenone D

Title

Natural constituents from Cortex Mori Radicis as new pancreatic lipase inhibitors

Author

Hou XD1, Ge GB2, Weng ZM3, Dai ZR4, Leng YH1, Ding LL3, Jin LL1, Yu Y3, Cao YF5, Hou J6.

Publish date

2018 Oct;