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N1538

Sigma-Aldrich

Nobiletin

≥97%

Synonym(s):

2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 3′,4′,5,6,7,8-Hexamethoxyflavone

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About This Item

Empirical Formula (Hill Notation):
C21H22O8
CAS Number:
Molecular Weight:
402.39
Beilstein:
360887
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.25

Quality Level

Assay

≥97%

form

powder

storage temp.

−20°C

SMILES string

COc1ccc(cc1OC)C2=CC(=O)c3c(OC)c(OC)c(OC)c(OC)c3O2

InChI

1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3

InChI key

MRIAQLRQZPPODS-UHFFFAOYSA-N

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Application


  • Nobiletin as a novel agent to enhance porcine in vitro embryo development and quality: This study explores the potential of nobiletin to improve embryo development and quality in porcine models, providing insights into its applications in reproductive biotechnology and animal science (Cajas YN, Martinez-Serrano CA, 2024 Apr 22) (source).

  • Nobiletin alleviates cisplatin-induced ototoxicity: Research indicates that nobiletin can mitigate the ototoxic effects of cisplatin chemotherapy by activating autophagy and inhibiting ferroptosis, suggesting a new therapeutic avenue for protecting auditory health during cancer treatment (Song W, Lu Z, 2024 Apr 3) (source).

  • Nobiletin targets SREBP1/ACLY to induce autophagy-dependent cell death of gastric cancer cells: This study reveals that nobiletin promotes autophagy-dependent cell death in gastric cancer cells by targeting the SREBP1/ACLY axis within the PI3K/Akt/mTOR signaling pathway, proposing a novel anticancer strategy (Chen M, Sun Q, 2024 Jun) (source).

  • Recent advances in the therapeutic potential of nobiletin against respiratory diseases: A comprehensive review on the therapeutic applications of nobiletin in treating respiratory diseases, emphasizing its anti-inflammatory and antioxidant properties as mechanisms for intervention (Qin Y, Li J, 2024 Jun) (source).

Biochem/physiol Actions

Nobiletin suppresses the expression of matrix metalloproteinases 1, 3 and 9, which participate in the break down of the extracellular matrix during tumor metastasis. Nobiletin is also involved in the increased expression of tissue inhibitor of matrix metalloproteinase 1 further preventing extracellular matrix degradation during tumor invasion. This bioflavonoid is believed to achieve both of these functions by disrupting the signal transduction pathway of Ras-Raf-MEK.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Satoru Horigome et al.
Bioscience, biotechnology, and biochemistry, 78(5), 851-860 (2014-07-19)
The rhizome of Kaempferia parviflora has been used in traditional Thai medicine. In this study, we identified and compared specific compounds from the hexane extract of K. parviflora with those from other Zingiberaceous plants by using gas chromatography-mass spectrometry. We
Salma Malik et al.
Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie, 67(7-8), 427-433 (2015-05-24)
Cisplatin is an effective anti-cancer drug which causes remarkable toxicity to kidney by generating reactive oxygen species and by stimulating inflammatory and apoptotic pathway. Citrus flavonoid, like nobiletin has been reported to possess anti-oxidant, anti-inflammatory and anti-apoptotic properties. Hence, the
Yuan Hao et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 37(1), 306-320 (2015-09-01)
Nobiletin, a citrus flavonoid isolated from tangerines, alters ion transport functions in intestinal epithelia, and has antagonistic effects on eosinophilic airway inflammation of asthmatic rats. The present study examined the effects of nobiletin on basal short-circuit current (I(SC)) in a
Jianchu Chen et al.
BMC pharmacology & toxicology, 15, 59-59 (2014-10-25)
Nobiletin is a non-toxic dietary flavonoid that possesses anti-cancer properties. Nobiletin has been reported to reduce the risk of prostate cancer, but the mechanism is not well understood. In this study, we investigated the effects of nobiletin in prostate cancer
Feng-Quan Tan et al.
BMC plant biology, 15, 89-89 (2015-04-08)
Polyploidy has often been considered to confer plants a better adaptation to environmental stresses. Tetraploid citrus rootstocks are expected to have stronger stress tolerance than diploid. Plenty of doubled diploid citrus plants were exploited from diploid species for citrus rootstock

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