6415-59-4 Usage
Description
SEDANOLIDE, a natural phthalide isolated from the seed oil of the Umbelliferae family, is a bioactive compound with potential health benefits. It possesses the ability to induce the expression of glutathione S-transferase, an enzyme that plays a crucial role in detoxification processes, and has been shown to reduce chemical-induced carcinogenesis in mice.
Uses
Used in Pharmaceutical Applications:
SEDANOLIDE is used as a therapeutic agent for its potential cancer-preventive properties. It functions by inducing the expression of glutathione S-transferase, which aids in the detoxification of harmful substances and reduces the risk of chemical-induced carcinogenesis in mice.
Used in Anticancer Research:
In the field of cancer research, SEDANOLIDE is utilized as a compound of interest for its ability to potentially reduce the incidence of cancer. Its mechanism of action involves the induction of glutathione S-transferase, which may contribute to the prevention of carcinogenesis and the overall management of cancer risk.
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].
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.
Check Digit Verification of cas no
The CAS Registry Mumber 6415-59-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,4,1 and 5 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 6415-59:
(6*6)+(5*4)+(4*1)+(3*5)+(2*5)+(1*9)=94
94 % 10 = 4
So 6415-59-4 is a valid CAS Registry Number.
InChI:InChI=1/C22H16ClN3OS2/c1-13-6-2-3-7-15(13)20(27)26-22(28)25-18-12-14(10-11-16(18)23)21-24-17-8-4-5-9-19(17)29-21/h2-12H,1H3,(H2,25,26,27,28)
6415-59-4Relevant articles and documents
Total syntheses of (±)-cis- and (±)-trans-neocnidilides
Mahadevegowda, Surendra H.,Khan, Faiz Ahmed
supporting information, p. 4400 - 4403 (2014/07/22)
Total syntheses of two antimicrobial natural products (±)-cis- neocnidilide and (±)-trans-neocnidilide starting from a readily preparable cyclohexa[b]-fused 5-oxabicyclo[2.1.1]hexane derivative are presented. The diastereomeric tetrahydrofuran tricarboxylate epimers obtained from a BF3·OEt2 promoted Grob-type fragmentation of the oxa-bicycle derivative were converted into title natural products by employing pyridinium dichromate/acetic anhydride mediated bis-oxidative cleavage reaction.
Pentacovalent Oxaphosphorane Chemistry in Organic Synthesis. 2. Total Syntheses of (+/-)-trans- and (+/-)-cis-Neocnidilides
McClure, Cynthia K.,Jung, Kang-Yeoun
, p. 2326 - 2332 (2007/10/02)
Both (+/-)-trans- and (+/-)-cis-neocnidilides (1 and 2) have been synthesized via the route illustrated in Scheme III.The condensation of the 1,2λ5-oxaphospholene 5b with valeraldehyde produced the highly substituted phosphonates 12s and 12a, which were transformed via an intramolecular Wadsworth-Horner-Emmons olefination reaction to the title compounds.
