Calycopterin
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MedKoo CAT#: 412253

CAS#: 481-52-7

Description: Calycopterin is an immunoinhibitory compound from the extract of Dracocephalum kotschyi.


Chemical Structure

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Calycopterin
CAS# 481-52-7

Theoretical Analysis

MedKoo Cat#: 412253
Name: Calycopterin
CAS#: 481-52-7
Chemical Formula: C19H18O8
Exact Mass: 374.1002
Molecular Weight: 374.34
Elemental Analysis: C, 60.96; H, 4.85; O, 34.19

Price and Availability

Size Price Availability Quantity
10.0mg USD 694.8 2 Weeks
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Synonym: Calycopterin; UNII8794DO3YB5; UNII 8794DO3YB5; UNII-8794DO3YB5

IUPAC/Chemical Name: 4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-3,6,7,8-tetramethoxy-

InChi Key: PIUSRRUXGNYCSS-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H18O8/c1-23-16-12(21)11-13(22)17(24-2)19(26-4)18(25-3)15(11)27-14(16)9-5-7-10(20)8-6-9/h5-8,20,22H,1-4H3

SMILES Code: O=C1C(OC)=C(C2=CC=C(O)C=C2)OC3=C(OC)C(OC)=C(OC)C(O)=C13

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: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 374.34 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

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1: Mourenza Á, Gil JA, Mateos LM, Letek M. Novel Treatments against Mycobacterium tuberculosis Based on Drug Repurposing. Antibiotics (Basel). 2020 Aug 28;9(9):550. doi: 10.3390/antibiotics9090550. PMID: 32872158; PMCID: PMC7557778.

2: Moradi M, Gholipour H, Sepehri H, Attari F, Delphi L, Arefian E, Moridi Farimani M. Flavonoid calycopterin triggers apoptosis in triple-negative and ER- positive human breast cancer cells through activating different patterns of gene expression. Naunyn Schmiedebergs Arch Pharmacol. 2020 Nov;393(11):2145-2156. doi: 10.1007/s00210-020-01917-y. Epub 2020 Jul 2. PMID: 32617603.

3: Froes TQ, Nicastro GG, de Oliveira Pereira T, de Oliveira Carneiro K, Alves Reis IM, Conceição RS, Branco A, Ifa DR, Baldini RL, Castilho MS. Calycopterin, a major flavonoid from Marcetia latifolia, modulates virulence-related traits in Pseudomonas aeruginosa. Microb Pathog. 2020 Jul;144:104142. doi: 10.1016/j.micpath.2020.104142. Epub 2020 Mar 13. PMID: 32173496.

4: Heydari P, Yavari M, Adibi P, Asghari G, Ghanadian SM, Dida GO, Khamesipour F. Medicinal Properties and Active Constituents of Dracocephalum kotschyi and Its Significance in Iran: A Systematic Review. Evid Based Complement Alternat Med. 2019 May 6;2019:9465309. doi: 10.1155/2019/9465309. Erratum in: Evid Based Complement Alternat Med. 2019 Jul 21;2019:5607329. PMID: 31198431; PMCID: PMC6526565.

5: Moridi Farimani M, Nazarianpoor E, Rustaie A, Akhbari M. Phytochemical constituents and biological activities of Cleome iberica DC. Nat Prod Res. 2017 Jun;31(11):1329-1332. doi: 10.1080/14786419.2016.1239093. Epub 2016 Oct 12. PMID: 27731648.

6: Zamani SS, Hossieni M, Etebari M, Salehian P, Ebrahimi SA. Pharmacokinetics of calycopterin and xanthmicrol, two polymethoxylated hydroxyflavones with anti- angiogenic activities from Dracocephalum kotschyi Bioss. Daru. 2016 Oct 4;24(1):22. doi: 10.1186/s40199-016-0161-x. PMID: 27716340; PMCID: PMC5051066.

7: Esmaeili MA, Farimani MM, Kiaei M. Anticancer effect of calycopterin via PI3K/Akt and MAPK signaling pathways, ROS-mediated pathway and mitochondrial dysfunction in hepatoblastoma cancer (HepG2) cells. Mol Cell Biochem. 2014 Dec;397(1-2):17-31. doi: 10.1007/s11010-014-2166-4. Epub 2014 Jul 25. PMID: 25060910; PMCID: PMC5868363.

8: Abbaszadeh H, Ebrahimi SA, Akhavan MM. Antiangiogenic activity of xanthomicrol and calycopterin, two polymethoxylated hydroxyflavones in both in vitro and ex vivo models. Phytother Res. 2014 Nov;28(11):1661-70. doi: 10.1002/ptr.5179. Epub 2014 Jun 3. PMID: 24895220.

9: Fattahi M, Nazeri V, Torras-Claveria L, Sefidkon F, Cusido RM, Zamani Z, Palazon J. Identification and quantification of leaf surface flavonoids in wild- growing populations of Dracocephalum kotschyi by LC-DAD-ESI-MS. Food Chem. 2013 Nov 1;141(1):139-46. doi: 10.1016/j.foodchem.2013.03.019. Epub 2013 Mar 13. PMID: 23768339.

10: Sarvestani NN, Khodagholi F, Ansari N, Farimani MM. Involvement of p-CREB and phase II detoxifying enzyme system in neuroprotection mediated by the flavonoid calycopterin isolated from Dracocephalum kotschyi. Phytomedicine. 2013 Jul 15;20(10):939-46. doi: 10.1016/j.phymed.2013.03.013. Epub 2013 Apr 29. PMID: 23639191.

11: Moghaddam G, Ebrahimi SA, Rahbar-Roshandel N, Foroumadi A. Antiproliferative activity of flavonoids: influence of the sequential methoxylation state of the flavonoid structure. Phytother Res. 2012 Jul;26(7):1023-8. doi: 10.1002/ptr.3678. Epub 2011 Dec 20. PMID: 22184071.

12: Farimani MM, Sarvestani NN, Ansari N, Khodagholi F. Calycopterin promotes survival and outgrowth of neuron-like PC12 cells by attenuation of oxidative- and ER-stress-induced apoptosis along with inflammatory response. Chem Res Toxicol. 2011 Dec 19;24(12):2280-92. doi: 10.1021/tx200420a. Epub 2011 Nov 21. Erratum in: Chem Res Toxicol. 2013 May 20;26(5):837. PMID: 22081883.

13: Lewin G, Shridhar NB, Aubert G, Thoret S, Dubois J, Cresteil T. Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk. Bioorg Med Chem. 2011 Jan 1;19(1):186-96. doi: 10.1016/j.bmc.2010.11.035. Epub 2010 Nov 20. PMID: 21146994.

14: Faham N, Javidnia K, Bahmani M, Amirghofran Z. Calycopterin, an immunoinhibitory compound from the extract of Dracocephalum kotschyi. Phytother Res. 2008 Sep;22(9):1154-8. doi: 10.1002/ptr.2382. PMID: 18683896.

15: Saeidnia S, Gohari AR, Ito M, Kiuchi F, Honda G. Bioactive constituents from Dracocephalum subcapitatum (O. Kuntze) Lipsky. Z Naturforsch C J Biosci. 2005 Jan-Feb;60(1-2):22-4. doi: 10.1515/znc-2005-1-204. PMID: 15787238.