Lecanoric acid | CAS#480-56-8 | depside polypheno

MedKoo Cat#: 598536 | Name: Lecanoric acid

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Description:

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

Lecanoric acid is a naturally occurring depside polyphenol isolated from a variety of lichens. It is a potent antioxidant, surpassing ascorbic acid in a 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) free radical scavenging assay (IC50s = 424.51 and 6.42 μg/ml for lecanoric and ascorbic acid, respectively). Lecanoric acid has antibacterial and antifungal activities with minimum inhibitory concentrations ranging from 0.5 to 1 mg/ml for a panel of fifteen microorganisms. In a cell viability assay, lecanoric acid exhibits antiproliferative activity against HeLa cells (IC50 = 123.97 μg/ml). Lecanoric acid also exhibits antidiabetic and hypolipidemic properties.

Chemical Structure

Lecanoric acid

CAS#480-56-8

Theoretical Analysis

MedKoo Cat#: 598536

Name: Lecanoric acid

CAS#: 480-56-8

Chemical Formula: C16H14O7

Exact Mass: 318.0740

Molecular Weight: 318.28

Elemental Analysis: C, 60.38; H, 4.43; O, 35.19

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 450.00	2 Weeks

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Synonym

Lecanoric acid; NSC 249981; NSC-249981; NSC249981;

IUPAC/Chemical Name

4-((2,4-dihydroxy-6-methylbenzoyl)oxy)-2-hydroxy-6-methylbenzoic acid

InChi Key

HEMSJKZDHNSSEW-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H14O7/c1-7-3-9(17)5-11(18)14(7)16(22)23-10-4-8(2)13(15(20)21)12(19)6-10/h3-6,17-19H,1-2H3,(H,20,21)

SMILES Code

O=C(OC1=CC(C)=C(C(O)=O)C(O)=C1)C2=C(C)C=C(O)C=C2O

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lecanoric acid is a histidine-decarboxylase inhibitor isolated from fungus.

In vitro activity:

Lecanoric acid inhibited cell colony formation already at 0.03 µg/ml in HCT-116 cells and induced a G2 cell cycle block in several cell lines. Moreover, lecanoric acid arrested the cell cycle, presumably in the M phase, since expression of cyclin B1 and phosphorylated histone H3 was upregulated, whereas the inactive cyclin-dependent kinase 1 (CDK1) was reduced in HCT-116 cells. Reference: Biomed Pharmacother. 2022 Apr;148:112734. https://pubmed.ncbi.nlm.nih.gov/35190352/

In vivo activity:

All of the lichen acids, especially lecanoric and vulpinic acid, exhibited much stronger inhibitory effect on TrxR purified from rat lung than the anticancer drugs cisplatin and doxorubicin. Reference: Anticancer Agents Med Chem. 2018;18(11):1599-1605. https://pubmed.ncbi.nlm.nih.gov/29793415/

Preparing Stock Solutions

The following data is based on the product molecular weight 318.28 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. Roser LA, Erkoc P, Ingelfinger R, Henke M, Ulshöfer T, Schneider AK, Laux V, Geisslinger G, Schmitt I, Fürst R, Schiffmann S. Lecanoric acid mediates anti-proliferative effects by an M phase arrest in colon cancer cells. Biomed Pharmacother. 2022 Apr;148:112734. doi: 10.1016/j.biopha.2022.112734. Epub 2022 Feb 18. PMID: 35190352. 2. Nakashima K, Tanabe H, Fujii-Kuriyama Y, Hayashi H, Inoue M. Atranorin and lecanoric acid antagonize TCDD-induced xenobiotic response element-driven activity, but not xenobiotic response element-independent activity. J Nat Med. 2016 Jul;70(3):476-82. doi: 10.1007/s11418-016-0983-3. Epub 2016 Mar 15. PMID: 26979434. 3. 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. 2018;18(11):1599-1605. doi: 10.2174/1871520618666180525095520. PMID: 29793415.

In vitro protocol:

In vivo protocol:

1. 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. 2018;18(11):1599-1605. doi: 10.2174/1871520618666180525095520. PMID: 29793415.

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Anticancer Agents Med Chem. 2016 May 3. [Epub ahead of print] PubMed PMID: 27141875. 5: Ristić S, Ranković B, Kosanić M, Stanojković T, Stamenković S, Vasiljević P, Manojlović I, Manojlović N. Phytochemical study and antioxidant, antimicrobial and anticancer activities of Melanelia subaurifera and Melanelia fuliginosa lichens. J Food Sci Technol. 2016 Jun;53(6):2804-16. doi: 10.1007/s13197-016-2255-3. Epub 2016 Jun 22. PubMed PMID: 27478237; PubMed Central PMCID: PMC4951434. 6: de Pedro N, Cantizani J, Ortiz-López FJ, González-Menéndez V, Cautain B, Rodríguez L, Bills GF, Reyes F, Genilloud O, Vicente F. Protective effects of isolecanoric acid on neurodegenerative in vitro models. Neuropharmacology. 2016 Feb;101:538-48. doi: 10.1016/j.neuropharm.2015.09.029. Epub 2015 Oct 9. PubMed PMID: 26455662. 7: Gaikwad S, Verma N, Sharma BO, Behera BC. Growth promoting effects of some lichen metabolites on probiotic bacteria. J Food Sci Technol. 2014 Oct;51(10):2624-31. doi: 10.1007/s13197-012-0785-x. Epub 2012 Aug 2. PubMed PMID: 25328204; PubMed Central PMCID: PMC4190253. 8: Umezawa K, Matsushima T, Sawa T, Takeuchi T, Hirono I. Inhibition of tumor promotion by a lecanoric acid analogue. Experientia. 1984 Jan 15;40(1):100-1. PubMed PMID: 6420182. 9: Huneck S, Follmann G. [On the occurrence of erythrine and lecanoric acid in some Dinaria species. 51. On the lichen contents]. Pharmazie. 1968 Mar;23(3):156-7. German. PubMed PMID: 5682056. 10: 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. 11: Yamazaki M, Matsuo M, Shibata S. Biosynthesis of lichen depsides, lecanoric acid and atranorin. Chem Pharm Bull (Tokyo). 1965 Aug;13(8):1015-7. PubMed PMID: 5867825. 12: Umezawa H, Shibamoto N, Naganawa H, Ayukawa S, Matsuzaki M, Takeuchi T, Kono K, Sakamoto T. Isolation of lecanoric acid, an inhibitor of histidine decarboxylase from a fungus. J Antibiot (Tokyo). 1974 Aug;27(8):587-96. PubMed PMID: 4436144. 13: Zhang HJ, Zhu DQ, Sun LY, Ge ZH, Xu JJ, Feng SC. [Study on the chemical constituents of two lichen plants from Meng Mountain]. Zhong Yao Cai. 2013 Sep;36(9):1454-6. Chinese. PubMed PMID: 24620693. 14: Ivanova V, Backor M, Dahse HM, Graefe U. Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta. Prep Biochem Biotechnol. 2010;40(4):377-88. doi: 10.1080/10826068.2010.525432. PubMed PMID: 21108141. 15: Schroeckh V, Scherlach K, Nützmann HW, Shelest E, Schmidt-Heck W, Schuemann J, Martin K, Hertweck C, Brakhage AA. Intimate bacterial-fungal interaction triggers biosynthesis of archetypal polyketides in Aspergillus nidulans. Proc Natl Acad Sci U S A. 2009 Aug 25;106(34):14558-63. doi: 10.1073/pnas.0901870106. Epub 2009 Aug 6. PubMed PMID: 19666480; PubMed Central PMCID: PMC2732885. 16: Qiu C, Ding Y. [Studies on chemical constituents of Umbilicaria esculenta (Miyoshi) minks]. Zhongguo Zhong Yao Za Zhi. 2001 Sep;26(9):608-10. Chinese. PubMed PMID: 12776427. 17: Rama Krishna B, Ramakrishna S, Rajendra S, Madhusudana K, Mallavadhani UV. Synthesis of some novel orsellinates and lecanoric acid related depsides as α-glucosidase inhibitors. J Asian Nat Prod Res. 2018 Jul 3:1-15. doi: 10.1080/10286020.2018.1490274. [Epub ahead of print] PubMed PMID: 29968482. 18: Parrot D, Peresse T, Hitti E, Carrie D, Grube M, Tomasi S. Qualitative and spatial metabolite profiling of lichens by a LC-MS approach combined with optimised extraction. Phytochem Anal. 2015 Jan-Feb;26(1):23-33. doi: 10.1002/pca.2532. Epub 2014 Aug 6. PubMed PMID: 25130294. 19: Seo C, Choi YH, Ahn JS, Yim JH, Lee HK, Oh H. PTP1B inhibitory effects of tridepside and related metabolites isolated from the Antarctic lichen Umbilicaria antarctica. J Enzyme Inhib Med Chem. 2009 Oct;24(5):1133-7. doi: 10.1080/14756360802667811. PubMed PMID: 19619069. 20: Jayaprakasha GK, Rao LJ. Phenolic constituents from the lichen Parmotrema stuppeum (Nyl.) Hale and their antioxidant activity. Z Naturforsch C. 2000 Nov-Dec;55(11-12):1018-22. PubMed PMID: 11204179.