Obacunone | CAS#751-03-1 | Anti-cancer & Anti-inflammatory

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

MedKoo CAT#: 111014

CAS#: 751-03-1

Description: Obacunone is from bark of the Chinese plant Phellodendron amurense. It exhibits anti-cancer and anti-inflammatory properties. Obacunone also significantly inhibits aromatase activity in an in vitro enzyme assay with an IC50 value of 28.04 μM and is a novel activator of Nrf2.

Chemical Structure

Obacunone

CAS# 751-03-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 111014
Name: Obacunone
CAS#: 751-03-1
Chemical Formula: C26H30O7
Exact Mass: 454.20
Molecular Weight: 454.519
Elemental Analysis: C, 68.71; H, 6.65; O, 24.64

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: AI3-37934; CCRIS 8657; Obacunone

IUPAC/Chemical Name: (1S,3aS,4aR,4bR,6aR,11aR,11bR,13aS)-1-(furan-3-yl)-4b,7,7,11a,13a-pentamethyl-1,6a,7,11a,11b,12,13,13a-octahydrooxepino[4',3':3,4]benzo[1,2-f]oxireno[2,3-d]isochromene-3,5,9(3aH,4bH,6H)-trione

InChi Key: MAYJEFRPIKEYBL-OASIGRBWSA-N

InChi Code: InChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1

SMILES Code: CC1(C)OC(=O)C=C[C@@]2(C)[C@H]1CC(=O)[C@]3(C)[C@@H]2CC[C@@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)c6cocc6

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

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Biological target:	Obacunone, isolated from Citrus fruits, exhibits anti-tumor activity by the induction of apoptosis.
In vitro activity:	MTT assays confirmed that obacunone was strongly inhibited MCF-7 cell proliferation without affecting non-malignant breast cells. Treatment with obacunone increased apoptosis by up-regulating expression of the pro-apoptotic protein Bax and down-regulating the anti-apoptotic protein Bcl2, as well as inducing G1 cell cycle arrest. In addition, obacunone significantly inhibited aromatase activity in an in vitro enzyme assay. Exposure of MCF-7 breast cancer cells to obacunone down-regulated expression of inflammatory molecules including nuclear factor-kappa B (NF-κB) and cyclooxygenase-2 (COX-2). Reference: Biochimie. 2014 Oct;105:36-44. https://pubmed.ncbi.nlm.nih.gov/24927687/
In vivo activity:	Furthermore, in vivo administration of obacunone displayed super therapeutic effects in attenuating ovariectomy-induced bone loss in mice, as indicated by decreases in serum biomarkers of bone turnover, restoring of femur fracture maximum force, and reversing of the worsened bone-related parameters in ovariectomized animals. Taken together, these findings demonstrate that obacunone has pharmacological activities to suppress osteoclast differentiation through modulating the Integrin-FAK-Src pathway, and suggest that obacunone is a therapeutic candidate for the treatment and prevention of bone diseases such as osteoporosis. Reference: Cytokine. 2023 Apr;164:156134. https://pubmed.ncbi.nlm.nih.gov/36804257/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	170.0	374.02

Preparing Stock Solutions

The following data is based on the product molecular weight 454.52 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.

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. Kim J, Jayaprakasha GK, Patil BS. Obacunone exhibits anti-proliferative and anti-aromatase activity in vitro by inhibiting the p38 MAPK signaling pathway in MCF-7 human breast adenocarcinoma cells. Biochimie. 2014 Oct;105:36-44. doi: 10.1016/j.biochi.2014.06.002. Epub 2014 Jun 11. PMID: 24927687. 2. Vikram A, Jayaprakasha GK, Jesudhasan PR, Pillai SD, Patil BS. Obacunone represses Salmonella pathogenicity islands 1 and 2 in an envZ-dependent fashion. Appl Environ Microbiol. 2012 Oct;78(19):7012-22. doi: 10.1128/AEM.01326-12. Epub 2012 Jul 27. PMID: 22843534; PMCID: PMC3457478. 3. Hu H, Wang X, Huang Y, He B, Zhu J, Sun K, Deng C, Guo Y, Hao D, Jian B. Obacunone inhibits RANKL/M-CSF-mediated osteoclastogenesis by suppressing integrin- FAK-Src signaling. Cytokine. 2023 Apr;164:156134. doi: 10.1016/j.cyto.2023.156134. Epub 2023 Feb 15. PMID: 36804257. 4. He J, Zheng L, Li X, Huang F, Hu S, Chen L, Jiang M, Lin X, Jiang H, Zeng Y, Ye T, Lin D, Liu Q, Xu J, Chen K. Obacunone targets macrophage migration inhibitory factor (MIF) to impede osteoclastogenesis and alleviate ovariectomy-induced bone loss. J Adv Res. 2023 Jan 16:S2090-1232(23)00003-6. doi: 10.1016/j.jare.2023.01.003. Epub ahead of print. PMID: 36657717.
In vitro protocol:	1. Kim J, Jayaprakasha GK, Patil BS. Obacunone exhibits anti-proliferative and anti-aromatase activity in vitro by inhibiting the p38 MAPK signaling pathway in MCF-7 human breast adenocarcinoma cells. Biochimie. 2014 Oct;105:36-44. doi: 10.1016/j.biochi.2014.06.002. Epub 2014 Jun 11. PMID: 24927687. 2. Vikram A, Jayaprakasha GK, Jesudhasan PR, Pillai SD, Patil BS. Obacunone represses Salmonella pathogenicity islands 1 and 2 in an envZ-dependent fashion. Appl Environ Microbiol. 2012 Oct;78(19):7012-22. doi: 10.1128/AEM.01326-12. Epub 2012 Jul 27. PMID: 22843534; PMCID: PMC3457478.
In vivo protocol:	1. Hu H, Wang X, Huang Y, He B, Zhu J, Sun K, Deng C, Guo Y, Hao D, Jian B. Obacunone inhibits RANKL/M-CSF-mediated osteoclastogenesis by suppressing integrin- FAK-Src signaling. Cytokine. 2023 Apr;164:156134. doi: 10.1016/j.cyto.2023.156134. Epub 2023 Feb 15. PMID: 36804257. 2. He J, Zheng L, Li X, Huang F, Hu S, Chen L, Jiang M, Lin X, Jiang H, Zeng Y, Ye T, Lin D, Liu Q, Xu J, Chen K. Obacunone targets macrophage migration inhibitory factor (MIF) to impede osteoclastogenesis and alleviate ovariectomy-induced bone loss. J Adv Res. 2023 Jan 16:S2090-1232(23)00003-6. doi: 10.1016/j.jare.2023.01.003. Epub ahead of print. PMID: 36657717.

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1: Melong R, Tamokoue Kengne PC, Dzoyem JP, Fusi AA, Allemann E, Delie F, Bochet CG, Beifuss U, Kapche GDWF. New cytotoxic obacunone-type limonoid and others constituents from the stem bark of Carapa procera DC (Meliaceae). Nat Prod Res. 2021 May 17:1-8. doi: 10.1080/14786419.2021.1927024. Epub ahead of print. PMID: 33993799.

2: Park KR, Kim S, Cho M, Yun HM. Limonoid Triterpene, Obacunone Increases Runt- Related Transcription Factor 2 to Promote Osteoblast Differentiation and Function. Int J Mol Sci. 2021 Mar 2;22(5):2483. doi: 10.3390/ijms22052483. PMID: 33801166; PMCID: PMC7957678.

3: Huang DR, Dai CM, Li SY, Li XF. Obacunone protects retinal pigment epithelium cells from ultra-violet radiation-induced oxidative injury. Aging (Albany NY). 2021 Feb 1;13(8):11010-11025. doi: 10.18632/aging.202437. Epub 2021 Feb 1. PMID: 33535179; PMCID: PMC8109142.

4: Bai Y, Wang W, Wang L, Ma L, Zhai D, Wang F, Shi R, Liu C, Xu Q, Chen G, Lu Z. Obacunone Attenuates Liver Fibrosis with Enhancing Anti-Oxidant Effects of GPx-4 and Inhibition of EMT. Molecules. 2021 Jan 9;26(2):318. doi: 10.3390/molecules26020318. PMID: 33435504; PMCID: PMC7827035.

5: Luo X, Yu Z, Yue B, Ren J, Zhang J, Mani S, Wang Z, Dou W. Obacunone reduces inflammatory signalling and tumour occurrence in mice with chronic inflammation- induced colorectal cancer. Pharm Biol. 2020 Dec;58(1):886-897. doi: 10.1080/13880209.2020.1812673. PMID: 32878512.

6: Lang X, Zhang X, Wang D, Zhou W. In Vitro and In Vivo Metabolic Activation of Obacunone, A Bioactive and Potentially Hepatotoxic Constituent of Dictamni Cortex. Planta Med. 2020 Jul;86(10):686-695. doi: 10.1055/a-1152-8169. Epub 2020 May 4. PMID: 32365393.

7: Luo X, Yue B, Yu Z, Ren Y, Zhang J, Ren J, Wang Z, Dou W. Obacunone Protects Against Ulcerative Colitis in Mice by Modulating Gut Microbiota, Attenuating TLR4/NF-κB Signaling Cascades, and Improving Disrupted Epithelial Barriers. Front Microbiol. 2020 Mar 31;11:497. doi: 10.3389/fmicb.2020.00497. PMID: 32296403; PMCID: PMC7136403.

8: Xie J, Zhang AH, Qiu S, Zhang TL, Li XN, Yan GL, Sun H, Liu L, Wang XJ. Identification of the perturbed metabolic pathways associating with prostate cancer cells and anticancer affects of obacunone. J Proteomics. 2019 Aug 30;206:103447. doi: 10.1016/j.jprot.2019.103447. Epub 2019 Jul 19. PMID: 31326558.

9: Zhou J, Wang T, Wang H, Jiang Y, Peng S. Obacunone attenuates high glucose- induced oxidative damage in NRK-52E cells by inhibiting the activity of GSK-3β. Biochem Biophys Res Commun. 2019 May 21;513(1):226-233. doi: 10.1016/j.bbrc.2019.03.201. Epub 2019 Apr 3. PMID: 30954216.

10: Gao Y, Hou R, Liu F, Liu H, Fei Q, Han Y, Cai R, Peng C, Qi Y. Obacunone causes sustained expression of MKP-1 thus inactivating p38 MAPK to suppress pro- inflammatory mediators through intracellular MIF. J Cell Biochem. 2018 Jan;119(1):837-849. doi: 10.1002/jcb.26248. Epub 2017 Aug 3. PMID: 28657665.

11: Xu S, Chen W, Xie Q, Xu Y. Obacunone activates the Nrf2-dependent antioxidant responses. Protein Cell. 2016 Sep;7(9):684-8. doi: 10.1007/s13238-016-0297-y. PMID: 27530494; PMCID: PMC5003787.

12: Horiba T, Katsukawa M, Mita M, Sato R. Dietary obacunone supplementation stimulates muscle hypertrophy, and suppresses hyperglycemia and obesity through the TGR5 and PPARγ pathway. Biochem Biophys Res Commun. 2015 Aug 7;463(4):846-52. doi: 10.1016/j.bbrc.2015.06.022. Epub 2015 Jun 5. PMID: 26051277.

13: Murthy KN, Jayaprakasha GK, Patil BS. Cytotoxicity of obacunone and obacunone glucoside in human prostate cancer cells involves Akt-mediated programmed cell death. Toxicology. 2015 Mar 2;329:88-97. doi: 10.1016/j.tox.2015.01.008. Epub 2015 Jan 12. PMID: 25592883.

14: Kim J, Jayaprakasha GK, Patil BS. Obacunone exhibits anti-proliferative and anti-aromatase activity in vitro by inhibiting the p38 MAPK signaling pathway in MCF-7 human breast adenocarcinoma cells. Biochimie. 2014 Oct;105:36-44. doi: 10.1016/j.biochi.2014.06.002. Epub 2014 Jun 11. PMID: 24927687.

15: Vikram A, Jayaprakasha GK, Jesudhasan PR, Pillai SD, Patil BS. Obacunone represses Salmonella pathogenicity islands 1 and 2 in an envZ-dependent fashion. Appl Environ Microbiol. 2012 Oct;78(19):7012-22. doi: 10.1128/AEM.01326-12. Epub 2012 Jul 27. PMID: 22843534; PMCID: PMC3457478.

16: Chidambara Murthy KN, Jayaprakasha GK, Patil BS. Obacunone and obacunone glucoside inhibit human colon cancer (SW480) cells by the induction of apoptosis. Food Chem Toxicol. 2011 Jul;49(7):1616-25. doi: 10.1016/j.fct.2011.04.014. Epub 2011 Apr 15. PMID: 21515332.

17: Chidambara Murthy KN, Jayaprakasha GK, Patil BS. Apoptosis mediated cytotoxicity of citrus obacunone in human pancreatic cancer cells. Toxicol In Vitro. 2011 Jun;25(4):859-67. doi: 10.1016/j.tiv.2011.02.006. Epub 2011 Feb 17. PMID: 21333732.

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