Maclurin | CAS#519-34-6 | phenolic component

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

MedKoo CAT#: 598232

CAS#: 519-34-6

Description: Maclurin is isolated from Maclura pomifera. Maclurin is composed of two isoforms (isolectins); some sequence similarity to jacalin; potent non-specific blood-group hemagglutinin.

Chemical Structure

Maclurin

CAS# 519-34-6

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 598232
Name: Maclurin
CAS#: 519-34-6
Chemical Formula: C13H10O6
Exact Mass: 262.05
Molecular Weight: 262.217
Elemental Analysis: C, 59.55; H, 3.84; O, 36.61

Price and Availability

Size	Price	Availability
5mg	USD 550	2 Weeks
10mg	USD 950	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: Maclurin; Morintannic acid; NSC 83240; Fustic extract;

IUPAC/Chemical Name: (3,4-dihydroxyphenyl)(2,4,6-trihydroxyphenyl)methanone

InChi Key: XNWPXDGRBWJIES-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H10O6/c14-7-4-10(17)12(11(18)5-7)13(19)6-1-2-8(15)9(16)3-6/h1-5,14-18H

SMILES Code: O=C(C1=CC=C(O)C(O)=C1)C2=C(O)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:

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Biological target:	Maclurin is composed of two isoforms (isolectins); some sequence similarity to jacalin; potent non-specific blood-group hemagglutinin.
In vitro activity:	Maclurin suppressed UVB-mediated tyrosinase activation and melanin accumulation in B16F10 cells without changes in mRNA levels of melanogenesis-related genes including tyrosinase, TRP1, TRP2, CREB, and MITF. Moreover, maclurin reduced melanin contents in melan-a cells, a cell line for normal melanocytes. When applied to a human skin model consisting of the epidermis and melanocytes, maclurin significantly reduced UVB-induced melanin accumulation (~47%) in a concentration-dependent manner based on microscopic observation and Fontana-Masson staining. Reference: Antioxidants (Basel). 2022 Jun 14;11(6):1164. https://pubmed.ncbi.nlm.nih.gov/35740060/
In vivo activity:	TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 262.22 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. Moon KM, Yang JH, Lee MK, Kwon EB, Baek J, Hwang T, Kim JI, Lee B. Maclurin Exhibits Antioxidant and Anti-Tyrosinase Activities, Suppressing Melanogenesis. Antioxidants (Basel). 2022 Jun 14;11(6):1164. doi: 10.3390/antiox11061164. PMID: 35740060; PMCID: PMC9220237. 2. Kong J, Zhou X, Lu J, Han Q, Ouyang X, Chen D, Liu A. Maclurin Promotes the Chondrogenic Differentiation of Bone Marrow Mesenchymal Stem Cells by Regulating miR-203a-3p/Smad1. Cell Reprogram. 2022 Feb;24(1):9-20. doi: 10.1089/cell.2021.0122. PMID: 35180001.
In vitro protocol:	1. Moon KM, Yang JH, Lee MK, Kwon EB, Baek J, Hwang T, Kim JI, Lee B. Maclurin Exhibits Antioxidant and Anti-Tyrosinase Activities, Suppressing Melanogenesis. Antioxidants (Basel). 2022 Jun 14;11(6):1164. doi: 10.3390/antiox11061164. PMID: 35740060; PMCID: PMC9220237. 2. Kong J, Zhou X, Lu J, Han Q, Ouyang X, Chen D, Liu A. Maclurin Promotes the Chondrogenic Differentiation of Bone Marrow Mesenchymal Stem Cells by Regulating miR-203a-3p/Smad1. Cell Reprogram. 2022 Feb;24(1):9-20. doi: 10.1089/cell.2021.0122. PMID: 35180001.
In vivo protocol:	TBD

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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1: Li X, Gao Y, Li F, Liang A, Xu Z, Bai Y, Mai W, Han L, Chen D. Maclurin protects against hydroxyl radical-induced damages to mesenchymal stem cells: antioxidant evaluation and mechanistic insight. Chem Biol Interact. 2014 Aug 5;219:221-8. doi: 10.1016/j.cbi.2014.06.014. Epub 2014 Jun 25. PubMed PMID: 24973644.

2: Ku MJ, Kim JH, Lee J, Cho JY, Chun T, Lee SY. Maclurin suppresses migration and invasion of human non-small-cell lung cancer cells via anti-oxidative activity and inhibition of the Src/FAK-ERK-β-catenin pathway. Mol Cell Biochem. 2015 Apr;402(1-2):243-52. doi: 10.1007/s11010-015-2331-4. Epub 2015 Jan 29. PubMed PMID: 25630491.

3: Healey M. Note on the supposed production of maclurin from acacatechin. Biochem J. 1932;26(2):388-91. PubMed PMID: 16744836; PubMed Central PMCID: PMC1260917.

4: Kaya D, Jäger AK, Yalçin FN, Ersöz T. MAO-A inhibition profiles of some benzophenone glucosides from Gentiana verna subsp. pontica. Nat Prod Commun. 2014 Apr;9(4):505-6. PubMed PMID: 24868869.

5: Kokotkiewicz A, Luczkiewicz M, Pawlowska J, Luczkiewicz P, Sowinski P, Witkowski J, Bryl E, Bucinski A. Isolation of xanthone and benzophenone derivatives from Cyclopia genistoides (L.) Vent. (honeybush) and their pro-apoptotic activity on synoviocytes from patients with rheumatoid arthritis. Fitoterapia. 2013 Oct;90:199-208. doi: 10.1016/j.fitote.2013.07.020. Epub 2013 Aug 3. PubMed PMID: 23916580.

6: Kumar V, Sood H, Chauhan RS. Detection of intermediates through high-resolution mass spectrometry for constructing biosynthetic pathways for major chemical constituents in a medicinally important herb, Swertia chirayita. Nat Prod Res. 2015;29(15):1449-55. doi: 10.1080/14786419.2015.1004175. Epub 2015 Jan 27. PubMed PMID: 25622657.

7: Xu YJ, Luo F, Gao Q, Shang Y, Wang C. Metabolomics reveals insect metabolic responses associated with fungal infection. Anal Bioanal Chem. 2015 Jun;407(16):4815-21. doi: 10.1007/s00216-015-8648-8. Epub 2015 Apr 21. PubMed PMID: 25895944.

8: Abdallah HM, El-Bassossy HM, Mohamed GA, El-Halawany AM, Alshali KZ, Banjar ZM. Phenolics from Garcinia mangostana alleviate exaggerated vasoconstriction in metabolic syndrome through direct vasodilatation and nitric oxide generation. BMC Complement Altern Med. 2016 Sep 13;16:359. doi: 10.1186/s12906-016-1340-5. PubMed PMID: 27618982; PubMed Central PMCID: PMC5020522.

9: Beelders T, de Beer D, Stander MA, Joubert E. Comprehensive phenolic profiling of Cyclopia genistoides (L.) Vent. by LC-DAD-MS and -MS/MS reveals novel xanthone and benzophenone constituents. Molecules. 2014 Aug 7;19(8):11760-90. doi: 10.3390/molecules190811760. PubMed PMID: 25105916.

10: Fromentin Y, Grellier P, Wansi JD, Lallemand MC, Buisson D. Yeast-mediated xanthone synthesis through oxidative intramolecular cyclization. Org Lett. 2012 Oct 5;14(19):5054-7. doi: 10.1021/ol302283p. Epub 2012 Sep 17. PubMed PMID: 22984826.

11: Hearn MT, Smith PK, Mallia AK. Isolation of the Maclura pomifera hemagglutinin on a deoxymelibiotol affinity support and preliminary characterization by buffer electrofocusing and high-performance liquid chromatography. Biosci Rep. 1982 Apr;2(4):247-55. PubMed PMID: 6896160.

12: Sugimori H, Ookuma Y, Iwasaka T. Immunohistochemical properties of the endometrial and cervical adenocarcinoma. Nihon Sanka Fujinka Gakkai Zasshi. 1986 Dec;38(12):2287-8. PubMed PMID: 2433372.

13: Lee SY. Synergistic effect of maclurin on ginsenoside compound K induced inhibition of the transcriptional expression of matrix metalloproteinase-1 in HaCaT human keratinocyte cells. J Ginseng Res. 2018 Apr;42(2):229-232. doi: 10.1016/j.jgr.2017.11.003. Epub 2017 Nov 21. PubMed PMID: 29719471; PubMed Central PMCID: PMC5925616.

14: Ajila CM, Rao LJ, Rao UJ. Characterization of bioactive compounds from raw and ripe Mangifera indica L. peel extracts. Food Chem Toxicol. 2010 Dec;48(12):3406-11. doi: 10.1016/j.fct.2010.09.012. Epub 2010 Sep 21. PubMed PMID: 20851730.

15: Chiang YM, Kuo YH, Oota S, Fukuyama Y. Xanthones and benzophenones from the stems of Garcinia multiflora. J Nat Prod. 2003 Aug;66(8):1070-3. PubMed PMID: 12932126.

16: Allen PZ. Interaction of Salmonella telaviv with Maclura pomifera lectin. Infect Immun. 1985 Jan;47(1):90-3. PubMed PMID: 3838092; PubMed Central PMCID: PMC261475.

17: Chang LW, Juang LJ, Wang BS, Wang MY, Tai HM, Hung WJ, Chen YJ, Huang MH. Antioxidant and antityrosinase activity of mulberry (Morus alba L.) twigs and root bark. Food Chem Toxicol. 2011 Apr;49(4):785-90. doi: 10.1016/j.fct.2010.11.045. Epub 2010 Dec 3. PubMed PMID: 21130832.

18: Imamura Y, Sugihara H, Miyake T, Ikeda T, Noriki S, Miyoshi N, Nakanishi K, Fukuda M. Lectin histochemistry in rat thyroid tumours. Basic Appl Histochem. 1989;33(3):185-96. PubMed PMID: 2818422.

19: Weller NK, Karnovsky MJ. Isolation of pulmonary alveolar type I cells from adult rats. Am J Pathol. 1986 Sep;124(3):448-56. PubMed PMID: 2945439; PubMed Central PMCID: PMC1888347.

20: Rooney SA, Gobran LI, Umstead TM, Phelps DS. Secretion of surfactant protein A from rat type II pneumocytes. Am J Physiol. 1993 Dec;265(6 Pt 1):L586-90. PubMed PMID: 8279574.

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