Sanggenon C
Sanggenon C Basic information
- Product Name:
- Sanggenon C
- Synonyms:
-
- sanggenone
- Sanggenon C
- (5aR,10aS)-2-[6β-(2,4-Dihydroxybenzoyl)-5α-(2,4-dihydroxyphenyl)-3-methyl-2-cyclohexene-1β-yl]-5a,10a-dihydro-1,3,8,10a-tetrahydroxy-5a-(3-methyl-2-butenyl)-11H-benzofuro[3,2-b][1]benzopyran-11-one
- 2-[(1S)-6β-(2,4-Dihydroxybenzoyl)-5α-(2,4-dihydroxyphenyl)-3-methyl-2-cyclohexene-1β-yl]-5a,10a-dihydro-1,3,8,10aβ-tetrahydroxy-5aβ-(3-methyl-2-butenyl)-11H-benzofuro[3,2-b][1]benzopyran-11-one
- Sanggenone C
- (5aR,10aS)-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)-11H-benzofuro[3,2-b][1]benzopyran-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-1,3,8,10a-tetrahydroxy-5a-(3-methyl-2-buten-1-yl)-, (5aR,10aS)-
- (5aR,10aS)-2-((1S,2R,3S)-2-(2,4-Dihydroxybenzoyl)-2',4'-dihydroxy-5-methyl-1,2,3,6-tetrahydro-[1,1'-biphenyl]-3-yl)-1,3,8,10a-tetrahydroxy-5a-(3-methylbut-2-en-1-yl)-5a,10a-dihydro-11H-benzofuro[3,2-b]chromen-11-one
- CAS:
- 80651-76-9
- MF:
- C40H36O12
- MW:
- 708.71
- Product Categories:
-
- phytochemical
- reference standards from Chinese medicinal herbs (TCM).
- standardized herbal extract
- reagent
- standard substance
- chemical reagent
- pharmaceutical intermediate
- Mol File:
- 80651-76-9.mol
Sanggenon C Chemical Properties
- Melting point:
- > 240°C (dec.)
- Boiling point:
- 995.5±65.0 °C(Predicted)
- Density
- 1.512
- storage temp.
- Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- Acetone (Slightly), Methanol (Slightly)
- pka
- 6.61±0.60(Predicted)
- form
- Solid
- color
- Yellow
- InChIKey
- XETHJOZXBVWLLM-HUKCQOFTSA-N
- SMILES
- [C@@]12(C/C=C(/C)\C)C3=CC=C(O)C=C3O[C@]1(O)C(=O)C1=C(O)C([C@@H]3[C@H](C(=O)C4=CC=C(O)C=C4O)[C@@H](C4=CC=C(O)C=C4O)CC(C)=C3)=C(O)C=C1O2
Sanggenon C Usage And Synthesis
Description
Sanggenone C is a flavonoid that has been found in mulberry bark and has diverse biological activities. It inhibits TNF-α- or IL-1β-induced polymorphonuclear leukocyte (PMN) adhesion to human synovial cells (HSCs; IC50s = 27.29 and 54.43 nM, respectively), as well as inhibits NF-κB activation in HSCs. Sanggenone C induces apoptosis and production of reactive oxygen species (ROS) in HT-29 cells when used at concentrations ranging from 10 to 40 μM. It decreases cell viability of HT-29 cells in vitro and reduces tumor growth in an HT-29 mouse xenograft model when administered at a dose of 10 mg/kg. Sanggenone C increases vertebrate column bone mineralization in a zebrafish model of prednisone-induced osteoporosis. It also attenuates cardiac hypertrophy and fibrosis and reduces activation of nuclear factor of activated T cells 2 (NFAT2) in a mouse model of pressure overload-induced cardiac hypertrophy.
Chemical Properties
Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Morus alba bark.
Uses
Sanggenone C is a flavanone isolated from Morus plant that showed cytotoxicity against human oral tumor cell lines (HSC-2 and HSG). Sanggenone C is also an inhibitor of protein tyrosine phosphatase 1B.
Definition
ChEBI: Sanggenon C is a diarylheptanoid.
in vivo
Sanggenon C (10, 20 mg/kg/day; Intraperitoneally; for 3 weeks) improves impaired cardiac function following aortic banding (AB). Sanggenon C protects against cardiac hypertrophy[1].
Sanggenon C (10, 20 mg/kg/day; Intraperitoneally; for 21 days) suppresses the tumor burden in the nude mice bearing tumor xenografts derived from AGS. Sanggenon C downregulates levels of p-ERK expression[2].
| Animal Model: | Male C57/BL6 mice (weight 23.5-27.5 g; age, 8 weeks)[1] |
| Dosage: | 10, 20 mg/kg |
| Administration: | Intraperitoneally; daily; for 3 weeks |
| Result: | Prevented the development of ventricular dysfunction, as evidenced by decreased LV end-diastolic diameter, LV end-systolic diameter, and increased LVFS and LVEF. |
target
NF-kB | NO | NOS | IkB | IKK
IC 50
NF-κB; ERK
References
[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] LI-DONG CHEN. Sanggenon C induces apoptosis of colon cancer cells via inhibition of NO production, iNOS expression and ROS activation of the mitochondrial pathway.[J]. Oncology reports, 2017: 2123-2131. DOI: 10.3892/or.2017.5912
[3] HUIJUAN WANG. Sanggenon C Stimulates Osteoblastic Proliferation and Differentiation, Inhibits Osteoclastic Resorption, and Ameliorates Prednisone-Induced Osteoporosis in Zebrafish Model.[J]. Molecules, 2018. DOI: 10.3390/molecules23092343
[4] LILI XIAO. Sanggenon C protects against pressure overload?induced cardiac hypertrophy via the calcineurin/NFAT2 pathway.[J]. Molecular medicine reports, 2017: 5338-5346. DOI: 10.3892/mmr.2017.7288
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