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MedKoo Cat#: 574235 | Name: Pyranonigrin A
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Description:

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

Pyranonigrin A is a fungal metabolite with antioxidant activity. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radicals in a cell-free assay. Pyranonigrin A suppresses TNF-α-induced expression of vascular cell adhesion molecule 1 (VCAM-1) in human umbilical vein endothelial cells (HUVECs).

Chemical Structure

Pyranonigrin A
Pyranonigrin A
CAS#773855-65-5

Theoretical Analysis

MedKoo Cat#: 574235

Name: Pyranonigrin A

CAS#: 773855-65-5

Chemical Formula: C10H9NO5

Exact Mass: 223.0481

Molecular Weight: 223.18

Elemental Analysis: C, 53.82; H, 4.06; N, 6.28; O, 35.84

Price and Availability

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1mg USD 525.00
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Related CAS #
No Data
Synonym
7-hydroxy Pyranonigrin S, Pyranonigrin A
IUPAC/Chemical Name
(7R)-6,7-dihydro-3,7-dihydroxy-2-(1E)-1-propen-1-yl-pyrano[2,3-c]pyrrole-4,5-dione
InChi Key
OALBJWDVDNROSF-VMZHVLLKSA-N
InChi Code
InChI=1S/C10H9NO5/c1-2-3-4-6(12)7(13)5-8(16-4)10(15)11-9(5)14/h2-3,10,12,15H,1H3,(H,11,14)/b3-2+/t10-/m1/s1
SMILES Code
C/C=C/C1=C(O)C(C(C(N[C@@H]2O)=O)=C2O1)=O
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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 223.18 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: Chen Z, Liu H, Ding B, Guo S, Huang H, Tao Y. Two new alkaloids from the endophytic fungus Aspergillus fumigatus SAS10 isolated from the mangrove tree Sonneratia apetala. Nat Prod Res. 2023 Oct 24:1-6. doi: 10.1080/14786419.2023.2272289. Epub ahead of print. PMID: 37874626. 2: Blachowicz A, Romsdahl J, Chiang AJ, Masonjones S, Kalkum M, Stajich JE, Torok T, Wang CCC, Venkateswaran K. The International Space Station Environment Triggers Molecular Responses in Aspergillus niger. Front Microbiol. 2022 Jun 30;13:893071. doi: 10.3389/fmicb.2022.893071. PMID: 35847112; PMCID: PMC9280654. 3: Mohamed H, Ebrahim W, El-Neketi M, Awad MF, Zhang H, Zhang Y, Song Y. In Vitro Phytobiological Investigation of Bioactive Secondary Metabolites from the Malus domestica-Derived Endophytic Fungus Aspergillus tubingensis Strain AN103. Molecules. 2022 Jun 11;27(12):3762. doi: 10.3390/molecules27123762. PMID: 35744888; PMCID: PMC9228098. 4: Kitagaki H. Medical Application of Substances Derived from Non-Pathogenic Fungi Aspergillus oryzae and A. luchuensis-Containing Koji. J Fungi (Basel). 2021 Mar 24;7(4):243. doi: 10.3390/jof7040243. PMID: 33804991; PMCID: PMC8063943. 5: Quang TH, Phong NV, Anh LN, Hanh TTH, Cuong NX, Ngan NTT, Trung NQ, Nam NH, Minh CV. Secondary metabolites from a peanut-associated fungus Aspergillus niger IMBC-NMTP01 with cytotoxic, anti-inflammatory, and antimicrobial activities. Nat Prod Res. 2022 Mar;36(5):1215-1223. doi: 10.1080/14786419.2020.1868462. Epub 2020 Dec 30. PMID: 33375869. 6: Romsdahl J, Blachowicz A, Chiang YM, Venkateswaran K, Wang CCC. Metabolomic Analysis of Aspergillus niger Isolated From the International Space Station Reveals Enhanced Production Levels of the Antioxidant Pyranonigrin A. Front Microbiol. 2020 May 21;11:931. doi: 10.3389/fmicb.2020.00931. PMID: 32670208; PMCID: PMC7326050. 7: Rao P, Shukla A, Parmar P, Rawal RM, Patel B, Saraf M, Goswami D. Reckoning a fungal metabolite, Pyranonigrin A as a potential Main protease (Mpro) inhibitor of novel SARS-CoV-2 virus identified using docking and molecular dynamics simulation. Biophys Chem. 2020 Sep;264:106425. doi: 10.1016/j.bpc.2020.106425. Epub 2020 Jul 6. PMID: 32663708; PMCID: PMC7836334. 8: Tang MC, Zou Y, Yee D, Tang Y. Identification of the Pyranonigrin A Biosynthetic Gene Cluster by Genome Mining in Penicillium thymicola IBT 5891. AIChE J. 2018 Dec;64(12):4182-4186. doi: 10.1002/aic.16324. Epub 2018 Jun 11. PMID: 31588145; PMCID: PMC6777573. 9: Aerts D, Hauer EE, Ohm RA, Arentshorst M, Teertstra WR, Phippen C, Ram AFJ, Frisvad JC, Wösten HAB. The FlbA-regulated predicted transcription factor Fum21 of Aspergillus niger is involved in fumonisin production. Antonie Van Leeuwenhoek. 2018 Mar;111(3):311-322. doi: 10.1007/s10482-017-0952-1. Epub 2017 Sep 30. PMID: 28965153; PMCID: PMC5816093. 10: Kishimoto S, Tsunematsu Y, Sato M, Watanabe K. Elucidation of Biosynthetic Pathways of Natural Products. Chem Rec. 2017 Nov;17(11):1095-1108. doi: 10.1002/tcr.201700015. Epub 2017 Apr 7. PMID: 28387469. 11: Lamboni Y, Nielsen KF, Linnemann AR, Gezgin Y, Hell K, Nout MJ, Smid EJ, Tamo M, van Boekel MA, Hoof JB, Frisvad JC. Diversity in Secondary Metabolites Including Mycotoxins from Strains of Aspergillus Section Nigri Isolated from Raw Cashew Nuts from Benin, West Africa. PLoS One. 2016 Oct 21;11(10):e0164310. doi: 10.1371/journal.pone.0164310. PMID: 27768708; PMCID: PMC5074577. 12: Yamamoto T, Tsunematsu Y, Noguchi H, Hotta K, Watanabe K. Elucidation of Pyranonigrin Biosynthetic Pathway Reveals a Mode of Tetramic Acid, Fused γ-Pyrone, and exo-Methylene Formation. Org Lett. 2015 Oct 16;17(20):4992-5. doi: 10.1021/acs.orglett.5b02435. Epub 2015 Sep 28. PMID: 26414728. 13: Riko R, Nakamura H, Shindo K. Studies on pyranonigrins-isolation of pyranonigrin E and biosynthetic studies on pyranonigrin A. J Antibiot (Tokyo). 2014 Feb;67(2):179-81. doi: 10.1038/ja.2013.91. Epub 2013 Oct 2. PMID: 24084681. 14: Kim AJ, Choi JN, Kim J, Kim HY, Park SB, Yeo SH, Choi JH, Liu KH, Lee CH. Metabolite profiling and bioactivity of rice koji fermented by Aspergillus strains. J Microbiol Biotechnol. 2012 Jan;22(1):100-6. doi: 10.4014/jmb.1106.06033. PMID: 22297225. 15: Perrone G, Stea G, Epifani F, Varga J, Frisvad JC, Samson RA. Aspergillus niger contains the cryptic phylogenetic species A. awamori. Fungal Biol. 2011 Nov;115(11):1138-50. doi: 10.1016/j.funbio.2011.07.008. Epub 2011 Jul 23. PMID: 22036292. 16: Varga J, Frisvad JC, Kocsubé S, Brankovics B, Tóth B, Szigeti G, Samson RA. New and revisited species in Aspergillus section Nigri. Stud Mycol. 2011 Jun 30;69(1):1-17. doi: 10.3114/sim.2011.69.01. PMID: 21892239; PMCID: PMC3161757. 17: Sørensen LM, Lametsch R, Andersen MR, Nielsen PV, Frisvad JC. Proteome analysis of Aspergillus niger: lactate added in starch-containing medium can increase production of the mycotoxin fumonisin B2 by modifying acetyl-CoA metabolism. BMC Microbiol. 2009 Dec 10;9:255. doi: 10.1186/1471-2180-9-255. PMID: 20003296; PMCID: PMC2807875. 18: Miyake Y, Mochizuki M, Ito C, Itoigawa M, Osawa T. Antioxidative pyranonigrins in rice mold starters and their suppressive effect on the expression of blood adhesion molecules. Biosci Biotechnol Biochem. 2008 Jun;72(6):1580-5. doi: 10.1271/bbb.80077. Epub 2008 Jun 7. PMID: 18540108. 19: Miyake Y, Ito C, Itoigawa M, Osawa T. Isolation of the antioxidant pyranonigrin-A from rice mold starters used in the manufacturing process of fermented foods. Biosci Biotechnol Biochem. 2007 Oct;71(10):2515-21. doi: 10.1271/bbb.70310. Epub 2007 Oct 7. PMID: 17928714. 20: Schlingmann G, Taniguchi T, He H, Bigelis R, Yang HY, Koehn FE, Carter GT, Berova N. Reassessing the structure of pyranonigrin. J Nat Prod. 2007 Jul;70(7):1180-7. doi: 10.1021/np070175n. Epub 2007 Jun 30. PMID: 17604395.

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