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MedKoo Cat#: 599121 | Name: Lobaric acid

Description:

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

Lobaric acid is a depsidone metabolite that has been isolated from Stereocaulon lichen species with antioxidant, antiproliferative, antiviral, and enzyme inhibitory activites. It scavenges superoxide radicals in a cell-free assay (IC50 = 97.9 μmol) and inhibits proliferation in a panel of leukemia, colorectal, gastric, breast, ovarian, prostate, pancreatic, and lung cancer cell lines (EC50s = 15.2-63.9 μg/ml). Lobaric acid inhibits protein tyrosine phosphatase 1B (PTP1B; IC50 = 0.87 μM for the human recombinant enzyme) and production of 12(S)-HETE (Item No. 34570) by 12(S)-lipoxygenase (IC50 = 28.5 μM). In vivo, lobaric acid (250 μM) decreases lesion number, but not lesion diameter, in tobacco leaves infected with tobacco mosaic virus (TMV).

Chemical Structure

Lobaric acid
Lobaric acid
CAS#522-53-2

Theoretical Analysis

MedKoo Cat#: 599121

Name: Lobaric acid

CAS#: 522-53-2

Chemical Formula: C25H28O8

Exact Mass: 456.1784

Molecular Weight: 456.49

Elemental Analysis: C, 65.78; H, 6.18; O, 28.04

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Lobaric acid;
IUPAC/Chemical Name
8-hydroxy-3-methoxy-11-oxo-1-pentanoyl-6-pentyl-11H-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid
InChi Key
JHEWMLHQNRHTQX-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H28O8/c1-4-6-8-9-15-21(24(28)29)18(27)13-20-23(15)32-19-12-14(31-3)11-16(17(26)10-7-5-2)22(19)25(30)33-20/h11-13,27H,4-10H2,1-3H3,(H,28,29)
SMILES Code
O=C(C1=C(O)C=C(C(OC2=CC(OC)=CC(C(CCCC)=O)=C23)=C1CCCCC)OC3=O)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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 456.49 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: Kwon IS, Yim JH, Lee HK, Pyo S. Lobaric Acid Inhibits VCAM-1 Expression in TNF-α-Stimulated Vascular Smooth Muscle Cells via Modulation of NF-κB and MAPK Signaling Pathways. Biomol Ther (Seoul). 2016 Jan;24(1):25-32. doi: 10.4062/biomolther.2015.084. Epub 2016 Jan 1. PubMed PMID: 26759698; PubMed Central PMCID: PMC4703349. 2: Majmudar CY, Højfeldt JW, Arevang CJ, Pomerantz WC, Gagnon JK, Schultz PJ, Cesa LC, Doss CH, Rowe SP, Vásquez V, Tamayo-Castillo G, Cierpicki T, Brooks CL 3rd, Sherman DH, Mapp AK. Sekikaic acid and lobaric acid target a dynamic interface of the coactivator CBP/p300. Angew Chem Int Ed Engl. 2012 Nov 5;51(45):11258-62. doi: 10.1002/anie.201206815. Epub 2012 Oct 8. PubMed PMID: 23042634; PubMed Central PMCID: PMC3711073. 3: Joo YA, Chung H, Yoon S, Park JI, Lee JE, Myung CH, Hwang JS. Skin Barrier Recovery by Protease-Activated Receptor-2 Antagonist Lobaric Acid. Biomol Ther (Seoul). 2016 Sep 1;24(5):529-35. doi: 10.4062/biomolther.2016.011. PubMed PMID: 27169822; PubMed Central PMCID: PMC5012879. 4: Morita H, Tsuchiya T, Kishibe K, Noya S, Shiro M, Hirasawa Y. Antimitotic activity of lobaric acid and a new benzofuran, sakisacaulon A from Stereocaulon sasakii. Bioorg Med Chem Lett. 2009 Jul 1;19(13):3679-81. doi: 10.1016/j.bmcl.2009.03.170. Epub 2009 May 12. PubMed PMID: 19481447. 5: Gissurarson SR, Sigurdsson SB, Wagner H, Ingolfsdottir K. Effect of lobaric acid on cysteinyl-leukotriene formation and contractile activity of guinea pig taenia coli. J Pharmacol Exp Ther. 1997 Feb;280(2):770-3. PubMed PMID: 9023290. 6: Hidalgo ME, Bascuñan L, Quilhot W, Fernández E, Rubio C. Spectroscopic and photochemical properties of the lichen compound lobaric acid. Photochem Photobiol. 2005 Nov-Dec;81(6):1447-9. PubMed PMID: 16107188. 7: Ingolfsdottir K, Gissurarson SR, Müller-Jakic B, Breu W, Wagner H. Inhibitory effects of the lichen metabolite lobaric acid on arachidonate metabolism in vitro. Phytomedicine. 1996 Jan;2(3):243-6. doi: 10.1016/S0944-7113(96)80049-3. PubMed PMID: 23194623. 8: Sundset MA, Kohn A, Mathiesen SD, Praesteng KE. Eubacterium rangiferina, a novel usnic acid-resistant bacterium from the reindeer rumen. Naturwissenschaften. 2008 Aug;95(8):741-9. doi: 10.1007/s00114-008-0381-0. Epub 2008 Apr 18. PubMed PMID: 18421431. 9: Brisdelli F, Perilli M, Sellitri D, Piovano M, Garbarino JA, Nicoletti M, Bozzi A, Amicosante G, Celenza G. Cytotoxic activity and antioxidant capacity of purified lichen metabolites: an in vitro study. Phytother Res. 2013 Mar;27(3):431-7. doi: 10.1002/ptr.4739. Epub 2012 May 25. PubMed PMID: 22628260. 10: Ogmundsdóttir HM, Zoëga GM, Gissurarson SR, Ingólfsdóttir K. Anti-proliferative effects of lichen-derived inhibitors of 5-lipoxygenase on malignant cell-lines and mitogen-stimulated lymphocytes. J Pharm Pharmacol. 1998 Jan;50(1):107-15. PubMed PMID: 9504441. 11: Bucar F, Schneider I, Ogmundsdóttir H, Ingólfsdóttir K. Anti-proliferative lichen compounds with inhibitory activity on 12(S)-HETE production in human platelets. Phytomedicine. 2004 Nov;11(7-8):602-6. PubMed PMID: 15636173. 12: Thadhani VM, Choudhary MI, Ali S, Omar I, Siddique H, Karunaratne V. Antioxidant activity of some lichen metabolites. Nat Prod Res. 2011 Nov;25(19):1827-37. doi: 10.1080/14786419.2010.529546. Epub 2011 Jun 30. PubMed PMID: 22136374. 13: Ingólfsdóttir K, Chung GA, Skúlason VG, Gissurarson SR, Vilhelmsdóttir M. Antimycobacterial activity of lichen metabolites in vitro. Eur J Pharm Sci. 1998 Apr;6(2):141-4. PubMed PMID: 9795033. 14: Ozgencli I, Budak H, Ciftci M, Anar M. Lichen acids may be used as a potential drug for cancer therapy; by inhibiting mitochondrial thioredoxin reductase purified from rat lung. Anticancer Agents Med Chem. 2016 May 3. [Epub ahead of print] PubMed PMID: 27141875. 15: Seo C, Sohn JH, Ahn JS, Yim JH, Lee HK, Oh H. Protein tyrosine phosphatase 1B inhibitory effects of depsidone and pseudodepsidone metabolites from the Antarctic lichen Stereocaulon alpinum. Bioorg Med Chem Lett. 2009 May 15;19(10):2801-3. doi: 10.1016/j.bmcl.2009.03.108. Epub 2009 Mar 26. PubMed PMID: 19362837. 16: Hong JM, Suh SS, Kim TK, Kim JE, Han SJ, Youn UJ, Yim JH, Kim IC. Anti-Cancer Activity of Lobaric Acid and Lobarstin Extracted from the Antarctic Lichen Stereocaulon alpnum. Molecules. 2018 Mar 14;23(3). pii: E658. doi: 10.3390/molecules23030658. PubMed PMID: 29538328. 17: Ismed F, Lohézic-Le Dévéhat F, Delalande O, Sinbandhit S, Bakhtiar A, Boustie J. Lobarin from the Sumatran lichen, Stereocaulon halei. Fitoterapia. 2012 Dec;83(8):1693-8. doi: 10.1016/j.fitote.2012.09.025. Epub 2012 Oct 4. PubMed PMID: 23041521. 18: Kim TK, Kim JE, Youn UJ, Han SJ, Kim IC, Cho CG, Yim JH. Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum. J Nat Prod. 2018 Jun 22;81(6):1460-1467. doi: 10.1021/acs.jnatprod.8b00227. Epub 2018 Jun 7. PubMed PMID: 29878768. 19: Nguyen KH, Chollet-Krugler M, Gouault N, Tomasi S. UV-protectant metabolites from lichens and their symbiotic partners. Nat Prod Rep. 2013 Dec;30(12):1490-508. doi: 10.1039/c3np70064j. Review. PubMed PMID: 24170172. 20: Haraldsdóttir S, Guolaugsdóttir E, Ingólfsdóttir K, Ogmundsdóttir HM. Anti-proliferative effects of lichen-derived lipoxygenase inhibitors on twelve human cancer cell lines of different tissue origin in vitro. Planta Med. 2004 Nov;70(11):1098-100. PubMed PMID: 15549672.