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MedKoo Cat#: 412974 | Name: Citreoviridin
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Description:

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

Citreoviridin is a mycotoxin isolated from several Penicillium species that has been shown to inhibit the mitochondrial ATP synthetase system.

Chemical Structure

Citreoviridin
Citreoviridin
CAS#25425-12-1

Theoretical Analysis

MedKoo Cat#: 412974

Name: Citreoviridin

CAS#: 25425-12-1

Chemical Formula: C23H30O6

Exact Mass: 402.2042

Molecular Weight: 402.49

Elemental Analysis: C, 68.64; H, 7.51; O, 23.85

Price and Availability

Size Price Availability Quantity
1mg USD 285.00 2 Weeks
5mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Citreoviridin; Citreoviridin A; Citreoviridine; Citreoviridine A; BRN5311865; BRN-5311865; BRN 5311865; NSC 159630; NSC159630; NSC-159630
IUPAC/Chemical Name
2H-Pyran-2-one, 4-methoxy-5-methyl-6-(7-methyl-8-(tetrahydro-3,4-dihydroxy-2,4,5-trimethyl-2-furanyl)-1,3,5,7-octatetraenyl)-
InChi Key
JLSVDPQAIKFBTO-USJRQALFSA-N
InChi Code
InChI=1S/C23H30O6/c1-15(14-22(4)21(25)23(5,26)17(3)29-22)11-9-7-8-10-12-18-16(2)19(27-6)13-20(24)28-18/h7-14,17,21,25-26H,1-6H3/b8-7+,11-9+,12-10+,15-14+
SMILES Code
O=C1C=C(OC)C(C)=C(/C=C/C=C/C=C/C(C)=C/C2(C)OC(C)C(C)(O)C2O)O1
Appearance
Solid powder
Purity
>95% (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
>2 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 402.49 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: Heikkinen T, Küblbeck J, Rysä J. Metabolic disruption by mycotoxins: focus on metabolic endpoints steatosis, adipogenesis and glucose metabolism in vivo and in vitro. Arch Toxicol. 2025 Feb 9. doi: 10.1007/s00204-025-03957-w. Epub ahead of print. PMID: 39923202. 2: Cheng S, Xu Y, Kang M, Zhu W, Wang L, Fu P. Aurovertins from a Marine-Derived Penicillium Species and Nonenzymatic Reactions in Their Formation. J Nat Prod. 2025 Feb 28;88(2):554-562. doi: 10.1021/acs.jnatprod.4c01436. Epub 2025 Jan 25. PMID: 39862218. 3: Yang J, Lu J, Cao L, Dong W, Zheng X, Fu X. Citreoviridin induces apoptosis through oxidative damage and inflammatory response in PC-12 cells. Toxicol Ind Health. 2025 Jan;41(1):32-39. doi: 10.1177/07482337241295474. Epub 2024 Oct 22. PMID: 39437026. 4: Demir Ö, Schulz B, Rabsch L, Steinert M, Surup F. Strong antagonism of an endophyte of Fraxinus excelsior towards the ash dieback pathogen, Hymenoscyphus fraxineus, is mediated by the antifungal secondary metabolite PF1140. Appl Environ Microbiol. 2024 Jun 18;90(6):e0066524. doi: 10.1128/aem.00665-24. Epub 2024 May 30. PMID: 38814060; PMCID: PMC11218641. 5: Wang Z, Liu C, Wei M, Zhu H, Zang Y, Zhu H. Undescribed α-pyrone-containing mycotoxins and an eremophilane-type sesquiterpenoid isolated from Aspergillus aureoterreus and their cytotoxicity. Phytochemistry. 2024 Mar;219:113989. doi: 10.1016/j.phytochem.2024.113989. Epub 2024 Jan 12. PMID: 38218305. 6: Chalyy ZA, Kiseleva MG, Sedova IB, Tutelyan VA. [Mycotoxins in spices consumed in Russia]. Vopr Pitan. 2023;92(2):26-34. Russian. doi: 10.33029/0042-8833-2023-92-2-26-34. Epub 2023 Mar 1. PMID: 37346017. 7: Jeong S, Lee BS, Jung SE, Yoon Y, Song BW, Kim IK, Choi JW, Kim SW, Lee S, Lim S. A Low Concentration of Citreoviridin Prevents Both Intracellular Calcium Deposition in Vascular Smooth Muscle Cell and Osteoclast Activation In Vitro. Molecules. 2023 Feb 10;28(4):1693. doi: 10.3390/molecules28041693. PMID: 36838684; PMCID: PMC9967071. 8: Uchiyama Y, Yamazaki D, Kobayashi N, Kanda Y, Sugita-Konishi Y. Electrophysiological Effect of Citreoviridin on Human InducedPluripotent Stem Cell-derived Cardiomyocytes. Shokuhin Eiseigaku Zasshi. 2022;63(6):210-217. doi: 10.3358/shokueishi.63.210. PMID: 36575035. 9: Zhong YJ, Cao F, Hu LS, Xu CX, Zhu YA, Chen X, Mao XM. Complex Interplay and Catalytic Versatility of Tailoring Enzymes for Efficient and Selective Biosynthesis of Fungal Mycotoxins. J Agric Food Chem. 2023 Jan 11;71(1):311-319. doi: 10.1021/acs.jafc.2c07681. Epub 2022 Dec 26. PMID: 36571252. 10: Zou ZB, Zhang G, Zhou YQ, Xie CL, Xie MM, Xu L, Hao YJ, Luo LZ, Zhang XK, Yang XW, Wang JS. Chemical Constituents of the Deep-Sea-Derived Penicillium citreonigrum MCCC 3A00169 and Their Antiproliferative Effects. Mar Drugs. 2022 Nov 24;20(12):736. doi: 10.3390/md20120736. PMID: 36547883; PMCID: PMC9781865. 11: Rabot C, Chen Y, Bijlani S, Chiang YM, Oakley CE, Oakley BR, Williams TJ, Wang CCC. Conversion of Polyethylenes into Fungal Secondary Metabolites. Angew Chem Int Ed Engl. 2023 Jan 23;62(4):e202214609. doi: 10.1002/anie.202214609. Epub 2022 Nov 23. PMID: 36417558; PMCID: PMC10100090. 12: Luo D, Guan J, Dong H, Chen J, Liang M, Zhou C, Xian Y, Xu X. Simultaneous determination of twelve mycotoxins in edible oil, soy sauce and bean sauce by PRiME HLB solid phase extraction combined with HPLC-Orbitrap HRMS. Front Nutr. 2022 Sep 28;9:1001671. doi: 10.3389/fnut.2022.1001671. PMID: 36245528; PMCID: PMC9555343. 13: Chen C, Ye G, Tang J, Li J, Liu W, Wu L, Long Y. New Polyketides from Mangrove Endophytic Fungus Penicillium sp. BJR-P2 and Their Anti- Inflammatory Activity. Mar Drugs. 2022 Sep 18;20(9):583. doi: 10.3390/md20090583. PMID: 36135772; PMCID: PMC9502265. 14: Dong Z, Yang X, Qiu T, An Y, Zhang G, Li Q, Jiang L, Yang G, Cao J, Sun X, Liu X, Liu D, Yao X. Exosomal miR-181a-2-3p derived from citreoviridin-treated hepatocytes activates hepatic stellate cells trough inducing mitochondrial calcium overload. Chem Biol Interact. 2022 May 1;358:109899. doi: 10.1016/j.cbi.2022.109899. Epub 2022 Mar 16. PMID: 35305974. 15: Yamano Y, Rakotondraibe HL. Understanding the Biosynthesis of Paxisterol in Lichen-Derived Penicillium aurantiacobrunneum for Production of Fluorinated Derivatives. Molecules. 2022 Mar 2;27(5):1641. doi: 10.3390/molecules27051641. PMID: 35268742; PMCID: PMC8911623. 16: Cao F, Zhang MK, Yang X, Xu CX, Cheng JT, Zhao QW, Wu R, Sheng R, Mao XM. A target and efficient synthetic strategy for structural and bioactivity optimization of a fungal natural product. Eur J Med Chem. 2022 Feb 5;229:114067. doi: 10.1016/j.ejmech.2021.114067. Epub 2021 Dec 26. PMID: 34973507. 17: Valente S, Piombo E, Schroeckh V, Meloni GR, Heinekamp T, Brakhage AA, Spadaro D. CRISPR-Cas9-Based Discovery of the Verrucosidin Biosynthesis Gene Cluster in Penicillium polonicum. Front Microbiol. 2021 May 21;12:660871. doi: 10.3389/fmicb.2021.660871. PMID: 34093475; PMCID: PMC8176439. 18: Chiang YM, Lin TS, Chang SL, Ahn G, Wang CCC. An Aspergillus nidulans Platform for the Complete Cluster Refactoring and Total Biosynthesis of Fungal Natural Products. ACS Synth Biol. 2021 Jan 15;10(1):173-182. doi: 10.1021/acssynbio.0c00536. Epub 2020 Dec 29. PMID: 33375785. 19: Okano T, Kobayashi N, Izawa K, Yoshinari T, Sugita-Konishi Y. Whole Genome Analysis Revealed the Genes Responsible for Citreoviridin Biosynthesis in Penicillium citreonigrum. Toxins (Basel). 2020 Feb 15;12(2):125. doi: 10.3390/toxins12020125. PMID: 32075322; PMCID: PMC7077241. 20: Kiseleva M, Chalyy Z, Sedova I, Aksenov I. Stability of Mycotoxins in Individual Stock and Multi-Analyte Standard Solutions. Toxins (Basel). 2020 Jan 30;12(2):94. doi: 10.3390/toxins12020094. PMID: 32019119; PMCID: PMC7076964.