| Identification | Back Directory | [Name]
Sappanone A | [CAS]
102067-84-5 | [Synonyms]
Sappanone A
(E)-7-hydroxy-3-[(3,4-dihydroxyphenyl)methylene]-chroman-4-one
3-[(3,4-Dihydroxyphenyl)methylene]-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one | [Molecular Formula]
C16H12O5 | [MDL Number]
MFCD21333231 | [MOL File]
102067-84-5.mol | [Molecular Weight]
284.26 |
| Chemical Properties | Back Directory | [Boiling point ]
605.5±55.0 °C(Predicted) | [density ]
1.521±0.06 g/cm3(Predicted) | [solubility ]
DMF: 20 mg/ml; DMSO: 15 mg/ml; Ethanol: 5 mg/ml; PBS (pH 7.2): 0.25 mg/ml | [form ]
A solid | [pka]
7.20±0.20(Predicted) | [color ]
Light yellow to yellow | [InChI]
InChI=1S/C16H12O5/c17-11-2-3-12-15(7-11)21-8-10(16(12)20)5-9-1-4-13(18)14(19)6-9/h1-7,17-19H,8H2 | [InChIKey]
KVYZXXBTJHJISR-UHFFFAOYSA-N | [SMILES]
C1OC2=CC(O)=CC=C2C(=O)C1=CC1=CC=C(O)C(O)=C1 |
| Hazard Information | Back Directory | [Description]
Sappanone A is a homoisoflavonoid with diverse biological activities that has been isolated from the aerial parts of C. pulcherrima, the heartwood of C. sappan, and the stems of H. campechianum.1,2,3,4,5 In vitro, sappanone A inhibits 76.2, 59.2, 37.4, and 35.4% of FGFR1, KDR, c-Met, and c-Kit kinase activity, respectively, when used at a concentration of 10 μM.1 It also inhibits influenza viral neuraminidase (NA) with IC50 values of 0.7, 1.1, and 1 μM for H1N1, H3N2, and H9N2 influenza viral NAs, respectively.2 Sappanone A has antibacterial activity against Gram-positive B. subtilis, B. sphaericus, and S. aureus as well as Gram-negative K. aerogenes and C. violaceum.3 It also inhibits the growth of A. niger and C. albicans fungi. Sapannone A inhibits LPS-induced inflammatory responses in vitro and in vivo, reducing nitric oxide (NO), interleukin-6 (IL-6), and prostaglandin E2 (PGE2; Item No. 14010) production in RAW264.7 cells as well as LPS-induced mortality in mice.4 It also attenuates airway inflammation and mucus hypersecretion via activation of the Nrf2 signaling pathway in a mouse model of ovalbumin-induced asthma.5 | [Uses]
Sappanone A is a natural product flavonoid with some antioxidant properties that can be isolated from C. sappan. | [Biological Activity]
Sappanone A is a homoisoflavanone which exhibits anti-inflammatory effects via modulation of Nrf2 and NF-κB. Sappanone can attenuate allergic airway inflammation in Ovalbumin-induced asthma. | [References]
[1] LI-GEN LIN. Naturally Occurring Homoisoflavonoids Function as Potent Protein Tyrosine Kinase Inhibitors by c-Src-Based High-Throughput Screening[J]. Journal of Medicinal Chemistry, 2008, 51 15: 4419-4429. DOI: 10.1021/jm701501x
[2] HYUNG JAE JEONG. Homoisoflavonoids from Caesalpinia sappan displaying viral neuraminidases inhibition.[J]. Biological & pharmaceutical bulletin, 2012, 35 5: 786-790. DOI: 10.1248/bpb.35.786
[3] BISWANATH DAS. Isolation, synthesis, and bioactivity of homoisoflavonoids from Caesalpinia pulcherrima.[J]. Chemical & pharmaceutical bulletin, 2009, 57 10: 1139-1141. DOI: 10.1248/cpb.57.1139
[4] SUHYUN LEE . Sappanone A exhibits anti-inflammatory effects via modulation of Nrf2 and NF-κB[J]. International immunopharmacology, 2015, 28 1: Pages 328-336. DOI: 10.1016/j.intimp.2015.06.015
[5] XUESHIBOJIE LIU Tiejun W Duo Yu. Sappanone A Attenuates Allergic Airway Inflammation in Ovalbumin-Induced Asthma.[J]. International Archives of Allergy and Immunology, 2016, 170 3: 180-186. DOI: 10.1159/000448331 |
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