| Identification | More | [Name]
SEDANOLIDE | [CAS]
6415-59-4 | [Synonyms]
1(3H)-ISOBENZOFURANONE
3-BUTYL-3A,4,5,6-TETRAHYDRO-1(3H)-ISOBENZOFURANON
3-BUTYL-3A,4,5,6-TETRAHYDRO-1(3H)-ISOBENZOFURANONE
3-BUTYL-3ALPHA,4,5,6-TETRAHYDRO-1(3H)-ISOBENZOFURANONE
SEDANOLIDE
SEDANOLIDE FROM CELERY SEEDS OIL
fromceleryseedsoil
neocnidilide
(3S)-3aβ,4,5,6-Tetrahydro-3β-butylisobenzofuran-1(3H)-one
(3S)-3β-Butyl-1,3,3aβ,4,5,6-hexahydroisobenzofuran-1-one
trans-Sedanolide
cis-Sedanolide | [Molecular Formula]
C12H18O2 | [MDL Number]
MFCD00171327 | [Molecular Weight]
194.27 | [MOL File]
6415-59-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
30～31℃ | [Boiling point ]
342.0±11.0 °C(Predicted) | [density ]
1.03 | [storage temp. ]
Store at -20°C, protect from light | [solubility ]
insoluble in H2O; ≥52.8 mg/mL in EtOH; ≥6.65 mg/mL in DMSO | [form ]
White to off-white solid. | [color ]
White to off-white | [Odor]
at 100.00 %. herbal celery | [Odor Type]
herbal | [LogP]
2.756 (est) | [CAS DataBase Reference]
6415-59-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It comes from the rhizome of Ligusticum chuanxiong Hort. | [Uses]
Sedanolide is a natural phthalide isolates from seed oil of Umbelliferae family. It induces the expression of glutathione S-transferase and reduces chemical induced carcinogenesis in mice. | [Definition]
ChEBI: Sedanolide is a member of 2-benzofurans. | [Biological Activity]
sedanolide is a natural compound produced in edible umbelliferous plants, such as celery seed oil [1].in hepg2 and caco-2 cells, treatment with sedanolide (7-500 μm) for 24h showed no effect on cell viability. in hepg2 cells cultured in sedanolide-free medium, sedanolide (500 μm) treatment for 72h decreased cell viability. pretreatment with sedanolide (100 μm) for 24 h and exposement to either h2o2 or tbooh did not exhibit statistically significant difference in viability from controls. in hepg2 following 24-h incubation with 500 μm sedanolide, a significant increase in dna strand breaks was observed. sedanolide did not modulate h2o2- and tbooh-induced dna damage. sedanolide was relatively nontoxic to cells in culture [1]. sedanolide (sn) possesses antioxidant effects. in human liver cancer (j5) cells, treatment with sedanolide suppressed j5 cell viability by inducing autophagy. sedanolide decreased protein expression levels of phosphoinositide 3-kinase (pi3k)-i, mammalian target of rapamycin (mtor) and akt and increased pi3k-iii, lc3-ii and beclin-1 protein levels. sedanolide increased the cytosolic phosphorylation of inhibitor of kappa b (iκb) and nuclear p65 and the dna-binding activity of nf-κb. sedanolide induced j5 cell autophagy by regulating pi3k, p53 and nf-κb autophagy-associated signaling pathways in j5 cells [2]. sedanolide (100 μg/ml) inhibited cyclooxygenases-1 and -2 at 250 pg/ml and blocked topoisomerase-i and-ii activity [3]. | [in vivo]
Sedanolide increases the activity of glutathione-S-transferase (GST) in the liver, small intestinal mucosa, and forestomach of A/J mice[1]. | [References]
[1] woods j a, jewell c, o'brien n m. sedanolide, a natural phthalide from celery seed oil: effect on hydrogen peroxide and tert-butyl hydroperoxide-induced toxicity in hepg2 and caco-2 human cell lines[j]. in vitro & molecular toxicology: a journal of basic and applied research, 2001, 14(3): 233-240.
[2] hsieh s l, chen c t, wang j j, et al. sedanolide induces autophagy through the pi3k, p53 and nf-κb signaling pathways in human liver cancer cells[j]. international journal of oncology, 2015, 47(6): 2240-2246
[3] momin r a, nair m g. antioxidant, cyclooxygenase and topoisomerase inhibitory compounds from apium graveolens linn. seeds[j]. phytomedicine, 2002, 9(4): 312-318. |
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