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MedKoo Cat#: 525360 | Name: Nomilin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nomilin is an inducer of phase II detoxifying enzymes, showing anti-proliferative active on cultured human breast cancer cells.

Chemical Structure

Nomilin
Nomilin
CAS#1063-77-0

Theoretical Analysis

MedKoo Cat#: 525360

Name: Nomilin

CAS#: 1063-77-0

Chemical Formula: C28H34O9

Exact Mass: 514.2203

Molecular Weight: 514.57

Elemental Analysis: C, 65.36; H, 6.66; O, 27.98

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
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Synonym
Nomilin
IUPAC/Chemical Name
1-(Acetyloxy)-1,2-dihydroobacunoic acid e-lactone
InChi Key
KPDOJFFZKAUIOE-WNGDLQANSA-N
InChi Code
InChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3/t16-,17+,19+,21+,22-,25+,26-,27+,28-/m1/s1
SMILES Code
C[C@@]([C@H](C(C)(C)O1)C2)([C@@H](OC(C)=O)CC1=O)[C@@H]3[C@@]([C@]([C@H]4C(O[C@H]5C6=COC=C6)=O)(O4)[C@@]5(C)CC3)(C)C2=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Nomilin is an inducer of phase II detoxifying enzymes.
In vitro activity:
Administration of nomilin significantly reduced the serum level of VEGF, a proangiogenic factor and increased the antiangiogenic factors IL-2 and TIMP-1. In vitro studies using rat aortic ring assay showed that administration of nomilin at non-toxic concentrations significantly inhibited microvessel sprouting. Studies using human umbilical vein endothelial cells clearly demonstrated that administration of nomilin significantly retarded endothelial cell proliferation, migration, invasion and tube formation. Reference: Eur J Pharmacol. 2011 Oct 15;668(3):450-8. https://pubmed.ncbi.nlm.nih.gov/21839074/
In vivo activity:
NOM (nomilin) improved infarct area, brain edema and neurological deficits in an experimental stroke rat model via middle cerebral artery occlusion (MCAO). Furthermore, NOM attenuated blood-brain barrier (BBB) disruption in MCAO rats, which might be associated with alleviating the loss of tight junction proteins, including ZO-1 and occludin-5. Further results revealed that NOM treatment effectively mitigated oxidative stress and facilitated the expressions of Nrf2 and NQO1, which might confirm that the loss of tight junction proteins in the microvasculature was likely mediated by oxidative stress. In conclusion, this study provided evidence that the protective effects of NOM in cerebral ischemia-reperfusion rats were related to the Nrf2/NQO1 pathway. Reference: Food Funct. 2019 Sep 1;10(9):5323-5332. https://pubmed.ncbi.nlm.nih.gov/31389456/
Solvent mg/mL mM
Solubility
DMF 30.0 58.30
DMSO 76.7 148.99
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 514.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Kimira Y, Taniuchi Y, Nakatani S, Sekiguchi Y, Kim HJ, Shimizu J, Ebata M, Wada M, Matsumoto A, Mano H. Citrus limonoid nomilin inhibits osteoclastogenesis in vitro by suppression of NFATc1 and MAPK signaling pathways. Phytomedicine. 2015 Nov 15;22(12):1120-4. doi: 10.1016/j.phymed.2015.08.013. Epub 2015 Sep 25. PMID: 26547535. 2. Pratheeshkumar P, Kuttan G. Nomilin inhibits tumor-specific angiogenesis by downregulating VEGF, NO and proinflammatory cytokine profile and also by inhibiting the activation of MMP-2 and MMP-9. Eur J Pharmacol. 2011 Oct 15;668(3):450-8. doi: 10.1016/j.ejphar.2011.07.029. Epub 2011 Aug 5. PMID: 21839074. 3. Xue XH, Xue JX, Hu W, Shi FL, Yang Y. Nomilin targets the Keap1-Nrf2 signalling and ameliorates the development of osteoarthritis. J Cell Mol Med. 2020 Aug;24(15):8579-8588. doi: 10.1111/jcmm.15484. Epub 2020 Jun 21. PMID: 32564468; PMCID: PMC7412705. 4. Shi YS, Zhang Y, Liu B, Li CB, Wu J, Li Y. Nomilin protects against cerebral ischemia-reperfusion induced neurological deficits and blood-brain barrier disruption via the Nrf2 pathway. Food Funct. 2019 Sep 1;10(9):5323-5332. doi: 10.1039/c9fo01481k. Epub 2019 Aug 7. PMID: 31389456.
In vitro protocol:
1. Kimira Y, Taniuchi Y, Nakatani S, Sekiguchi Y, Kim HJ, Shimizu J, Ebata M, Wada M, Matsumoto A, Mano H. Citrus limonoid nomilin inhibits osteoclastogenesis in vitro by suppression of NFATc1 and MAPK signaling pathways. Phytomedicine. 2015 Nov 15;22(12):1120-4. doi: 10.1016/j.phymed.2015.08.013. Epub 2015 Sep 25. PMID: 26547535. 2. Pratheeshkumar P, Kuttan G. Nomilin inhibits tumor-specific angiogenesis by downregulating VEGF, NO and proinflammatory cytokine profile and also by inhibiting the activation of MMP-2 and MMP-9. Eur J Pharmacol. 2011 Oct 15;668(3):450-8. doi: 10.1016/j.ejphar.2011.07.029. Epub 2011 Aug 5. PMID: 21839074.
In vivo protocol:
1. Xue XH, Xue JX, Hu W, Shi FL, Yang Y. Nomilin targets the Keap1-Nrf2 signalling and ameliorates the development of osteoarthritis. J Cell Mol Med. 2020 Aug;24(15):8579-8588. doi: 10.1111/jcmm.15484. Epub 2020 Jun 21. PMID: 32564468; PMCID: PMC7412705. 2. Shi YS, Zhang Y, Liu B, Li CB, Wu J, Li Y. Nomilin protects against cerebral ischemia-reperfusion induced neurological deficits and blood-brain barrier disruption via the Nrf2 pathway. Food Funct. 2019 Sep 1;10(9):5323-5332. doi: 10.1039/c9fo01481k. Epub 2019 Aug 7. PMID: 31389456.
1: Ronningen I, Miller M, Xia Y, Peterson DG. Identification and validation of sensory-active compounds from data-driven research: A flavoromics approach. J Agric Food Chem. 2017 May 19. doi: 10.1021/acs.jafc.7b00093. [Epub ahead of print] PubMed PMID: 28525713. 2: Bai J, Baldwin EA, McCollum G, Plotto A, Manthey JA, Widmer WW, Luzio G, Cameron R. Changes in Volatile and Non-Volatile Flavor Chemicals of "Valencia" Orange Juice over the Harvest Seasons. Foods. 2016 Jan 4;5(1). pii: E4. doi: 10.3390/foods5010004. PubMed PMID: 28231099; PubMed Central PMCID: PMC5224568. 3: Avula B, Sagi S, Wang YH, Wang M, Gafner S, Manthey JA, Khan IA. Liquid Chromatography-Electrospray Ionization Mass Spectrometry Analysis of Limonoids and Flavonoids in Seeds of Grapefruits, Other Citrus Species, and Dietary Supplements. Planta Med. 2016 Jul;82(11-12):1058-69. doi: 10.1055/s-0042-107598. Epub 2016 May 25. PubMed PMID: 27224266. 4: Hijaz F, Manthey JA, Van der Merwe D, Killiny N. Nucleotides, micro- and macro-nutrients, limonoids, flavonoids, and hydroxycinnamates composition in the phloem sap of sweet orange. Plant Signal Behav. 2016 Jun 2;11(6):e1183084. doi: 10.1080/15592324.2016.1183084. PubMed PMID: 27171979; PubMed Central PMCID: PMC4976783. 5: Wang F, Yu X, Liu X, Shen W, Zhu S, Zhao X. Temporal and spatial variations on accumulation of nomilin and limonin in the pummelos. Plant Physiol Biochem. 2016 Sep;106:23-9. doi: 10.1016/j.plaphy.2016.04.039. Epub 2016 Apr 23. PubMed PMID: 27135815. 6: Wang S, Tu H, Wan J, Chen W, Liu X, Luo J, Xu J, Zhang H. Spatio-temporal distribution and natural variation of metabolites in citrus fruits. Food Chem. 2016 May 15;199:8-17. doi: 10.1016/j.foodchem.2015.11.113. Epub 2015 Nov 26. PubMed PMID: 26775938. 7: Raithore S, Bai J, Plotto A, Manthey J, Irey M, Baldwin E. Electronic Tongue Response to Chemicals in Orange Juice that Change Concentration in Relation to Harvest Maturity and Citrus Greening or Huanglongbing (HLB) Disease. Sensors (Basel). 2015 Dec 2;15(12):30062-75. doi: 10.3390/s151229787. PubMed PMID: 26633411; PubMed Central PMCID: PMC4721708. 8: Kimira Y, Taniuchi Y, Nakatani S, Sekiguchi Y, Kim HJ, Shimizu J, Ebata M, Wada M, Matsumoto A, Mano H. Citrus limonoid nomilin inhibits osteoclastogenesis in vitro by suppression of NFATc1 and MAPK signaling pathways. Phytomedicine. 2015 Nov 15;22(12):1120-4. doi: 10.1016/j.phymed.2015.08.013. Epub 2015 Sep 25. PubMed PMID: 26547535. 9: Cai Y, Zhang S, Wang Q, Sun H, Zhou M, Hu S, Xiang Z. A Rapid, Selective and Sensitive UPLC-MS/MS Method for Quantification of Nomilin in Rat Plasma and Its Application in a Pharmacokinetic Study. Planta Med. 2016 Feb;82(3):224-9. doi: 10.1055/s-0035-1558157. Epub 2015 Nov 6. PubMed PMID: 26544116. 10: Raithore S, Dea S, McCollum G, Manthey JA, Bai J, Leclair C, Hijaz F, Narciso JA, Baldwin EA, Plotto A. Development of delayed bitterness and effect of harvest date in stored juice from two complex citrus hybrids. J Sci Food Agric. 2016 Jan 30;96(2):422-9. doi: 10.1002/jsfa.7105. Epub 2015 Feb 27. PubMed PMID: 25615579. 11: Zhao P, Duan L, Guo L, Dou LL, Dong X, Zhou P, Li P, Liu EH. Chemical and biological comparison of the fruit extracts of Citrus wilsonii Tanaka and Citrus medica L. Food Chem. 2015 Apr 15;173:54-60. doi: 10.1016/j.foodchem.2014.10.010. Epub 2014 Oct 13. PubMed PMID: 25465994. 12: Xiang Y, Cao J, Luo F, Wang D, Chen W, Li X, Sun C, Chen K. Simultaneous purification of limonin, nomilin and isoobacunoic acid from pomelo fruit (Citrus grandis) segment membrane. J Food Sci. 2014 Oct;79(10):C1956-63. doi: 10.1111/1750-3841.12581. Epub 2014 Sep 11. PubMed PMID: 25212475. 13: Liu C, Yan F, Gao H, He M, Wang Z, Cheng Y, Deng X, Xu J. Features of citrus terpenoid production as revealed by carotenoid, limonoid and aroma profiles of two pummelos (Citrus maxima) with different flesh color. J Sci Food Agric. 2015 Jan;95(1):111-9. doi: 10.1002/jsfa.6689. Epub 2014 Apr 29. PubMed PMID: 24723118. 14: Kim SY, Shin KS. Evaluation of Physiological Activities of the Citron (Citrus junos Sieb. ex TANAKA) Seed Extracts. Prev Nutr Food Sci. 2013 Sep;18(3):196-202. doi: 10.3746/pnf.2013.18.3.196. PubMed PMID: 24471132; PubMed Central PMCID: PMC3892494. 15: Zeng R, Fu J, Wu LB, Huang LF. [Analysis on component difference in Citrus reticulata before and after being processed with salt by UPLC-Q-TOF/MS]. Zhongguo Zhong Yao Za Zhi. 2013 Jul;38(14):2318-20. Chinese. PubMed PMID: 24199563. 16: Li S, Wang Z, Ding F, Sun D, Ma Z, Cheng Y, Xu J. Content changes of bitter compounds in 'Guoqing No.1' Satsuma mandarin (Citrus unshiu Marc.) during fruit development of consecutive 3 seasons. Food Chem. 2014 Feb 15;145:963-9. doi: 10.1016/j.foodchem.2013.09.040. Epub 2013 Sep 14. PubMed PMID: 24128570. 17: Bilal H, Akram W, Ali-Hassan S. Larvicidal Activity of Citrus Limonoids against Aedes albopictus Larvae. J Arthropod Borne Dis. 2012 Dec;6(2):104-11. Epub 2012 Dec 31. PubMed PMID: 23378967; PubMed Central PMCID: PMC3547300. 18: Sato R. Nomilin as an anti-obesity and anti-hyperglycemic agent. Vitam Horm. 2013;91:425-39. doi: 10.1016/B978-0-12-407766-9.00018-3. Review. PubMed PMID: 23374727. 19: Kim J, Jayaprakasha GK, Patil BS. Limonoids and their anti-proliferative and anti-aromatase properties in human breast cancer cells. Food Funct. 2013 Feb;4(2):258-65. doi: 10.1039/c2fo30209h. PubMed PMID: 23117440. 20: Chaudhary P, Jayaprakasha GK, Porat R, Patil BS. Degreening and postharvest storage influences 'Star Ruby' grapefruit (Citrus paradisi Macf.) bioactive compounds. Food Chem. 2012 Dec 1;135(3):1667-75. doi: 10.1016/j.foodchem.2012.05.095. Epub 2012 May 30. PubMed PMID: 22953908.