| Identification | Back Directory | [Name]
Sanggenon C | [CAS]
80651-76-9 | [Synonyms]
sanggenone
Sanggenon C
Sanggenone C
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
(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
(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)- | [Molecular Formula]
C40H36O12 | [MDL Number]
MFCD32004761 | [MOL File]
80651-76-9.mol | [Molecular Weight]
708.71 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
6.61±0.60(Predicted) | [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 |
| Hazard Information | Back Directory | [Description]
Sanggenone C is a flavonoid that has been found in mulberry bark and has diverse biological activities.1,2,3,4 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.1 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.2 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.3 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.4 | [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.
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| [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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