WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H562166
CAS#: 3484-37-5
Description: Ovatodiolide is a broad anticancer agent. It acts by upregulating hsa-miR-155, suppressing the BCR-ABL fusion gene and dysregulating the PI3K/AKT/mTOR pathway.
Hodoodo Cat#: H562166
Name: Ovatodiolide
CAS#: 3484-37-5
Chemical Formula: C20H24O4
Exact Mass: 328.17
Molecular Weight: 328.400
Elemental Analysis: C, 73.15; H, 7.37; O, 19.49
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Synonym: Ovatodiolide; NSC 156130; NSC-156130; NSC156130; Melampodin;
IUPAC/Chemical Name: 3,7,11,15(17)-Cembratetraene-16,2:19,6-diolide; (3E,12E)-3,12-Dimethyl-8-methylene-6,18-dioxa-tricyclo(14.2.1.0.5,9)nonadeca-3,12,16(19)-triene-7,17-dione
InChi Key: KTYZKXFERQUCPX-XGKXUXTPSA-N
InChi Code: InChI=1S/C20H24O4/c1-12-5-4-6-15-11-16(23-20(15)22)9-13(2)10-18-17(8-7-12)14(3)19(21)24-18/h5,10-11,16-18H,3-4,6-9H2,1-2H3/b12-5+,13-10+/t16-,17-,18+/m1/s1
SMILES Code: O=C1O[C@@H]2[C@H](CC/C(C)=C/CCC(C(O3)=O)=C[C@H]3C/C(C)=C/2)C1=C
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 328.40 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Tu YX, Wang SB, Fu LQ, Li SS, Guo QP, Wu Y, Mou XZ, Tong XM. Ovatodiolide targets chronic myeloid leukemia stem cells by epigenetically upregulating hsa-miR-155, suppressing the BCR-ABL fusion gene and dysregulating the PI3K/AKT/mTOR pathway. Oncotarget. 2017 Dec 14;9(3):3267-3277. doi: 10.18632/oncotarget.23231. eCollection 2018 Jan 9. PubMed PMID: 29423045; PubMed Central PMCID: PMC5790462.
2: Yu CY, Jerry Teng CL, Hung PS, Cheng CC, Hsu SL, Hwang GY, Tzeng YM. Ovatodiolide isolated from Anisomeles indica induces cell cycle G2/M arrest and apoptosis via a ROS-dependent ATM/ATR signaling pathways. Eur J Pharmacol. 2018 Jan 15;819:16-29. doi: 10.1016/j.ejphar.2017.09.050. Epub 2017 Oct 3. PubMed PMID: 28986085.
3: Wang CN, Lee YL, Lin YP, Chung WH, Tzeng YM, Lee CC. Ovatodiolide suppresses allergic airway inflammation and hyperresponsiveness in a murine model of asthma. Eur J Pharmacol. 2017 Oct 5;812:9-17. doi: 10.1016/j.ejphar.2017.06.036. Epub 2017 Jun 27. PubMed PMID: 28666799.
4: Huang YJ, Yang CK, Wei PL, Huynh TT, Whang-Peng J, Meng TC, Hsiao M, Tzeng YM, Wu AT, Yen Y. Ovatodiolide suppresses colon tumorigenesis and prevents polarization of M2 tumor-associated macrophages through YAP oncogenic pathways. J Hematol Oncol. 2017 Feb 28;10(1):60. doi: 10.1186/s13045-017-0421-3. PubMed PMID: 28241877; PubMed Central PMCID: PMC5329923.
5: Hsieh YJ, Tseng SP, Kuo YH, Cheng TL, Chiang CY, Tzeng YM, Tsai WC. Ovatodiolide of Anisomeles indica Exerts the Anticancer Potential on Pancreatic Cancer Cell Lines through STAT3 and NF-κB Regulation. Evid Based Complement Alternat Med. 2016;2016:8680372. doi: 10.1155/2016/8680372. Epub 2016 May 8. PubMed PMID: 27242913; PubMed Central PMCID: PMC4875986.
6: Lu KT, Wang BY, Chi WY, Chang-Chien J, Yang JJ, Lee HT, Tzeng YM, Chang WW. Ovatodiolide Inhibits Breast Cancer Stem/Progenitor Cells through SMURF2-Mediated Downregulation of Hsp27. Toxins (Basel). 2016 Apr 28;8(5). pii: E127. doi: 10.3390/toxins8050127. PubMed PMID: 27136586; PubMed Central PMCID: PMC4885042.
7: Bamodu OA, Huang WC, Tzeng DT, Wu A, Wang LS, Yeh CT, Chao TY. Ovatodiolide sensitizes aggressive breast cancer cells to doxorubicin, eliminates their cancer stem cell-like phenotype, and reduces doxorubicin-associated toxicity. Cancer Lett. 2015 Aug 10;364(2):125-34. doi: 10.1016/j.canlet.2015.05.006. Epub 2015 May 11. PubMed PMID: 25976769.
8: Rao YK, Chen YC, Fang SH, Lai CH, Geethangili M, Lee CC, Tzeng YM. Ovatodiolide inhibits the maturation of allergen-induced bone marrow-derived dendritic cells and induction of Th2 cell differentiation. Int Immunopharmacol. 2013 Nov;17(3):617-24. doi: 10.1016/j.intimp.2013.08.002. Epub 2013 Aug 31. PubMed PMID: 24001794.
9: Ho JY, Hsu RJ, Wu CL, Chang WL, Cha TL, Yu DS, Yu CP. Ovatodiolide Targets β -Catenin Signaling in Suppressing Tumorigenesis and Overcoming Drug Resistance in Renal Cell Carcinoma. Evid Based Complement Alternat Med. 2013;2013:161628. doi: 10.1155/2013/161628. Epub 2013 May 26. PubMed PMID: 23781255; PubMed Central PMCID: PMC3677612.
10: Lien HM, Wang CY, Chang HY, Huang CL, Peng MT, Sing YT, Chen CC, Lai CH. Bioevaluation of Anisomeles indica extracts and their inhibitory effects on Helicobacter pylori-mediated inflammation. J Ethnopharmacol. 2013 Jan 9;145(1):397-401. doi: 10.1016/j.jep.2012.11.015. Epub 2012 Nov 21. PubMed PMID: 23178270.
11: Kulkarni RR, Shurpali K, Gawde RL, Sarkar D, Puranik VG, Joshi SP. Phyllocladane diterpenes from Anisomeles heyneana. J Asian Nat Prod Res. 2012;14(12):1162-8. doi: 10.1080/10286020.2012.738672. Epub 2012 Nov 19. PubMed PMID: 23157282.
12: Huang HC, Lien HM, Ke HJ, Chang LL, Chen CC, Chang TM. Antioxidative characteristics of Anisomeles indica extract and inhibitory effect of ovatodiolide on melanogenesis. Int J Mol Sci. 2012;13(5):6220-35. doi: 10.3390/ijms13056220. Epub 2012 May 21. PubMed PMID: 22754360; PubMed Central PMCID: PMC3382824.
13: Liao YF, Rao YK, Tzeng YM. Aqueous extract of Anisomeles indica and its purified compound exerts anti-metastatic activity through inhibition of NF-κB/AP-1-dependent MMP-9 activation in human breast cancer MCF-7 cells. Food Chem Toxicol. 2012 Aug;50(8):2930-6. doi: 10.1016/j.fct.2012.05.033. Epub 2012 May 23. PubMed PMID: 22634262.
14: Lin KL, Tsai PC, Hsieh CY, Chang LS, Lin SR. Antimetastatic effect and mechanism of ovatodiolide in MDA-MB-231 human breast cancer cells. Chem Biol Interact. 2011 Nov 15;194(2-3):148-58. doi: 10.1016/j.cbi.2011.10.002. Epub 2011 Oct 19. PubMed PMID: 22033475.
15: Hou YY, Wu ML, Hwang YC, Chang FR, Wu YC, Wu CC. The natural diterpenoid ovatodiolide induces cell cycle arrest and apoptosis in human oral squamous cell carcinoma Ca9-22 cells. Life Sci. 2009 Jul 3;85(1-2):26-32. doi: 10.1016/j.lfs.2009.04.013. Epub 2009 May 3. PubMed PMID: 19409917.
16: Rao YK, Fang SH, Hsieh SC, Yeh TH, Tzeng YM. The constituents of Anisomeles indica and their anti-inflammatory activities. J Ethnopharmacol. 2009 Jan 21;121(2):292-6. doi: 10.1016/j.jep.2008.10.032. Epub 2008 Nov 8. PubMed PMID: 19041702.
17: Chen YL, Lan YH, Hsieh PW, Wu CC, Chen SL, Yen CT, Chang FR, Hung WC, Wu YC. Bioactive cembrane diterpenoids of Anisomeles indica. J Nat Prod. 2008 Jul;71(7):1207-12. doi: 10.1021/np800147z. Epub 2008 Jun 12. PubMed PMID: 18547115.
18: Shahidul Alam M, Quader MA, Rashid MA. HIV-inhibitory diterpenoid from Anisomeles indica. Fitoterapia. 2000 Sep;71(5):574-6. PubMed PMID: 11449512.
19: Arisawa M, Nimura M, Fujita A, Hayashi T, Morita N, Koshimura S. Biological active macrocyclic diterpenoids from chinese drug "Fáng Féng Cáo"; II. Derivatives of ovatodiolids and their cytotoxity. Planta Med. 1986 Aug;(4):297-9. PubMed PMID: 17345312.
20: Ho-Dac-An, Buu-Hoi NP. [Pharmacodynamic properties of ovatodiolide, the active principle of Anisomeles ovata (Labiaceae)]. Therapie. 1969 Jul-Aug;24(4):627-31. French. PubMed PMID: 5822002.
