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MedKoo Cat#: 576869 | Name: Manoalide

Description:

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

Manoalide is a phospholipase A2 inhibitor and antiproliferative agent.

Chemical Structure

Manoalide
Manoalide
CAS#75088-80-1

Theoretical Analysis

MedKoo Cat#: 576869

Name: Manoalide

CAS#: 75088-80-1

Chemical Formula: C25H36O5

Exact Mass: 416.2563

Molecular Weight: 416.56

Elemental Analysis: C, 72.08; H, 8.71; O, 19.20

Price and Availability

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Related CAS #
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Synonym
Manoalide
IUPAC/Chemical Name
2(5H)-Furanone, 4-((2R,6R)-3,6-dihydro-6-hydroxy-5-((3E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexenyl)-2H-pyran-2-yl)-5-hydroxy-, (5R)-
InChi Key
FGJIDQWRRLDGDB-CPIXEKRISA-N
InChi Code
InChI=1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1
SMILES Code
C\C(=C/CCC1=CC[C@@H](O[C@H]1O)C2=CC(=O)O[C@H]2O)\CCC3=C(C)CCCC3(C)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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 416.56 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
1: Soriente A, De Rosa MM, Scettri A, Sodano G, Terencio MC, Payá M, Alcaraz MJ. Manoalide. Curr Med Chem. 1999 May;6(5):415-31. PMID: 10101221. 2: Yao ZK, Jean YH, Lin SC, Lai YC, Chen NF, Tseng CC, Chen WF, Wen ZH, Kuo HM. Manoalide Induces Intrinsic Apoptosis by Oxidative Stress and Mitochondrial Dysfunction in Human Osteosarcoma Cells. Antioxidants (Basel). 2023 Jul 14;12(7):1422. doi: 10.3390/antiox12071422. PMID: 37507960; PMCID: PMC10376204. 3: Wang HR, Tang JY, Wang YY, Farooqi AA, Yen CY, Yuan SF, Huang HW, Chang HW. Manoalide Preferentially Provides Antiproliferation of Oral Cancer Cells by Oxidative Stress-Mediated Apoptosis and DNA Damage. Cancers (Basel). 2019 Sep 4;11(9):1303. doi: 10.3390/cancers11091303. PMID: 31487907; PMCID: PMC6770486. 4: Yeom JH, Kim HY, Lim JH, Yoon KW, Kim HM, Jeong HJ. A calcium channel blocker, manoalide exerts an anti-allergic inflammatory effect through attenuating NF-κB activity. Immunopharmacol Immunotoxicol. 2021 Dec;43(6):799-805. doi: 10.1080/08923973.2021.1988101. Epub 2021 Oct 28. PMID: 34708672. 5: Wang HR, Chen PH, Tang JY, Yen CY, Su YC, Huang MY, Chang HW. Manoalide Shows Mutual Interaction between Cellular and Mitochondrial Reactive Species with Apoptosis in Oral Cancer Cells. Oxid Med Cell Longev. 2021 Mar 2;2021:6667355. doi: 10.1155/2021/6667355. PMID: 33747349; PMCID: PMC7943270. 6: Luo X, Wang Q, Tang X, Xu J, Wang M, Li P, Li G. Cytotoxic Manoalide-Type Sesterterpenes from the Sponge Luffariella variabilis Collected in the South China Sea. J Nat Prod. 2021 Jan 22;84(1):61-70. doi: 10.1021/acs.jnatprod.0c01026. Epub 2020 Dec 28. PMID: 33371684. 7: Ni Y, Liu J, Zeng L, Yang Y, Liu L, Yao M, Chai L, Zhang L, Li Y, Zhang L, Li W. Natural product manoalide promotes EGFR-TKI sensitivity of lung cancer cells by KRAS-ERK pathway and mitochondrial Ca2+ overload-induced ferroptosis. Front Pharmacol. 2023 Jan 11;13:1109822. doi: 10.3389/fphar.2022.1109822. PMID: 36712673; PMCID: PMC9873971. 8: Li C, Lin H, He H, Ma M, Jiang W, Zhou R. Inhibition of the NLRP3 Inflammasome Activation by Manoalide Ameliorates Experimental Autoimmune Encephalomyelitis Pathogenesis. Front Cell Dev Biol. 2022 Feb 16;10:822236. doi: 10.3389/fcell.2022.822236. PMID: 35252186; PMCID: PMC8888861. 9: Peng SY, Tang JY, Lan TH, Shiau JP, Chen KL, Jeng JH, Yen CY, Chang HW. Oxidative-Stress-Mediated ER Stress Is Involved in Regulating Manoalide-Induced Antiproliferation in Oral Cancer Cells. Int J Mol Sci. 2023 Feb 16;24(4):3987. doi: 10.3390/ijms24043987. PMID: 36835397; PMCID: PMC9965613. 10: Wheeler LA, Sachs G, De Vries G, Goodrum D, Woldemussie E, Muallem S. Manoalide, a natural sesterterpenoid that inhibits calcium channels. J Biol Chem. 1987 May 15;262(14):6531-8. PMID: 2437121. 11: Bennett CF, Mong S, Clarke MA, Kruse LI, Crooke ST. Differential effects of manoalide on secreted and intracellular phospholipases. Biochem Pharmacol. 1987 Mar 1;36(5):733-40. doi: 10.1016/0006-2952(87)90727-1. PMID: 3103628. 12: Ettinger-Epstein P, Tapiolas DM, Motti CA, Wright AD, Battershill CN, de Nys R. Production of manoalide and its analogues by the sponge Luffariella variabilis Is hardwired. Mar Biotechnol (NY). 2008 Jan-Feb;10(1):64-74. doi: 10.1007/s10126-007-9037-x. Epub 2007 Sep 25. PMID: 17899268. 13: Lai KH, Peng BR, Hsu YM, El-Shazly M, Du YC, Lu MC, Su JH, Liu YC. The Configuration-Dependent Anti-Leukemic Effect of Manoalide Stereoisomers: Reignite Research Interest in these Sponge-Derived Sesterterpenoids. Bioorg Chem. 2021 Sep;114:105150. doi: 10.1016/j.bioorg.2021.105150. Epub 2021 Jul 7. PMID: 34328853. 14: Glaser KB, de Carvalho MS, Jacobs RS, Kernan MR, Faulkner DJ. Manoalide: structure-activity studies and definition of the pharmacophore for phospholipase A2 inactivation. Mol Pharmacol. 1989 Nov;36(5):782-8. PMID: 2586492. 15: De Vries GW, Amdahl LD, Kramer KD, Wheeler LA. Inhibition by manoalide of fMLP-stimulated elastase release from human neutrophils. Biochem Pharmacol. 1990 Dec 1;40(11):2487-90. doi: 10.1016/0006-2952(90)90090-8. PMID: 2268367. 16: Kanki D, Imai K, Ise Y, Okada S, Matsunaga S. Oshimalides A and B, Sesterterpenes of the Manoalide Class from a Luffariella sp. Deep-Sea Marine Sponge: Application of Asymmetric Dihydroxylation in Structure Elucidation. J Nat Prod. 2021 May 28;84(5):1676-1680. doi: 10.1021/acs.jnatprod.1c00320. Epub 2021 May 9. PMID: 33966383. 17: Zhou GX, Molinski TF. Manoalide derivatives from a sponge, Luffariella sp. J Asian Nat Prod Res. 2006 Jan-Mar;8(1-2):15-20. doi: 10.1080/10286020500246022. PMID: 16753777. 18: Lombardo D, Dennis EA. Cobra venom phospholipase A2 inhibition by manoalide. A novel type of phospholipase inhibitor. J Biol Chem. 1985 Jun 25;260(12):7234-40. PMID: 3997864. 19: Bennett CF, Mong S, Wu HL, Clark MA, Wheeler L, Crooke ST. Inhibition of phosphoinositide-specific phospholipase C by manoalide. Mol Pharmacol. 1987 Nov;32(5):587-93. PMID: 3683364. 20: Long CJ, Sarau HM, Berkowitz BA. The inhibition of release of endothelium- derived relaxant factor by manoalide, a potent inhibitor of phospholipase A2. Br J Pharmacol. 1987 Dec;92(4):843-9. doi: 10.1111/j.1476-5381.1987.tb11389.x. PMID: 2827828; PMCID: PMC1853728.