Oosporein | CAS#475-54-7 | Insecticidal metabolite

MedKoo Cat#: 558995 | Name: Oosporein

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Description:

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

Oosporein is a mycotoxin and bioactive insecticidal metabolite. The transcriptional factor OpS3 has been identified as a positive regulator of a red secondary metabolite oosporein in B. bassiana.

Chemical Structure

Oosporein

CAS#475-54-7

Theoretical Analysis

MedKoo Cat#: 558995

Name: Oosporein

CAS#: 475-54-7

Chemical Formula: C14H10O8

Exact Mass: 306.0376

Molecular Weight: 306.23

Elemental Analysis: C, 54.91; H, 3.29; O, 41.80

Price and Availability

Size	Price	Availability
1mg	USD 500.00	2 Weeks
5mg	USD 870.00	2 Weeks
10mg	USD 1,250.00	2 Weeks

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Synonym

IUPAC/Chemical Name

2,2′,5,5′-tetrahydroxy-4,4′-dimethyl-[bi-1,4-cyclohexadien-1-yl]-3,3′,6,6′-tetrone

InChi Key

DHMPJEGFPQTNFX-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H10O8/c1-3-7(15)11(19)5(12(20)8(3)16)6-13(21)9(17)4(2)10(18)14(6)22/h15,17,20,22H,1-2H3

SMILES Code

CC1=C(O)C(C(C2=C(O)C(C(C)=C(O)C2=O)=O)=C(O)C1=O)=O

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oosporein is a mycotoxin.

In vitro activity:

A negative correlation was seen between fungal growth and oosporein production, with strains producing oosporein (i.e., the ΔBbsmr1 and OpS3 overexpression strains) producing significantly less biomass compared with the WT and ΔBbsmr1ΔOpS1 strains (P < 0.05; SI Appendix, Fig. S4A), although the exogenous addition of oosporein to fungal culture medium had no significant effect on fungal growth (SI Appendix, Fig. S4D). This study confirmed the in vitro antibacterial activity of oosporein using both Gram-positive and Gram-negative test strains, including Staphylococcus aureus N315, Escherichia coli, and Bacillus thuringiensis (SI Appendix, Figs. S7 and S8). Reference: Proc Natl Acad Sci U S A. 2017 Feb 28;114(9):E1578-E1586. https://pubmed.ncbi.nlm.nih.gov/28193896/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 306.23 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. Fan Y, Liu X, Keyhani NO, Tang G, Pei Y, Zhang W, Tong S. Regulatory cascade and biological activity of Beauveria bassiana oosporein that limits bacterial growth after host death. Proc Natl Acad Sci U S A. 2017 Feb 28;114(9):E1578-E1586. doi: 10.1073/pnas.1616543114. Epub 2017 Feb 13. PMID: 28193896; PMCID: PMC5338512. 2. Ramesha A, Venkataramana M, Nirmaladevi D, Gupta VK, Chandranayaka S, Srinivas C. Cytotoxic effects of oosporein isolated from endophytic fungus Cochliobolus kusanoi. Front Microbiol. 2015 Sep 1;6:870. doi: 10.3389/fmicb.2015.00870. PMID: 26388840; PMCID: PMC4556033.

In vitro protocol:

In vivo protocol:

TBD

1: Mao A, Wang J, Zhu S, Jin D, Fan Y. An efficient visual screening of gene knockout mutants in the insect pathogenic fungus Beauveria bassiana. Microb Biotechnol. 2024 Jun;17(6):e14512. doi: 10.1111/1751-7915.14512. PMID: 38923821; PMCID: PMC11201804. 2: Li JX, Fernandez KX, Ritland C, Jancsik S, Engelhardt DB, Coombe L, Warren RL, van Belkum MJ, Carroll AL, Vederas JC, Bohlmann J, Birol I. Genomic virulence features of Beauveria bassiana as a biocontrol agent for the mountain pine beetle population. BMC Genomics. 2023 Jul 10;24(1):390. doi: 10.1186/s12864-023-09473-4. PMID: 37430186; PMCID: PMC10334655. 3: P S, Rani ROP, Chellappan M. Characterization of insecticidal metabolite oosporein in Lecanicillium saksenae (Kushwaha) Kurihara and Sukarno, a geographically distinct isolate from Kerala, India. Toxicon. 2023 Jul;230:107176. doi: 10.1016/j.toxicon.2023.107176. Epub 2023 May 28. PMID: 37253413. 4: Vrabl P, Zottele M, Colleselli L, Schinagl CW, Mayerhofer L, Siewert B, Strasser H. Light in the box-photobiological examination chamber with light trap ventilation system for studying fungal surface cultures illustrated with Metarhizium brunneum and Beauveria brongniartii. Fungal Biol Biotechnol. 2023 May 29;10(1):11. doi: 10.1186/s40694-023-00159-w. PMID: 37248509; PMCID: PMC10228068. 5: Haruma T, Doyama K, Lu X, Arima T, Igarashi T, Tomiyama S, Yamaji K. Oosporein Produced by Root Endophytic Chaetomium cupreum Promotes the Growth of Host Plant, Miscanthus sinensis, under Aluminum Stress at the Appropriate Concentration. Plants (Basel). 2022 Dec 21;12(1):36. doi: 10.3390/plants12010036. PMID: 36616165; PMCID: PMC9824719. 6: Luo Z, Chen Q, Su Y, Hu S, Keyhani NO, Wang J, Zhu C, Zhou T, Pan Y, Bidochka MJ, Zhang Y. The AreA Nitrogen Catabolite Repression Activator Balances Fungal Nutrient Utilization and Virulence in the Insect Fungal Pathogen Beauveria bassiana. J Agric Food Chem. 2023 Jan 11;71(1):646-659. doi: 10.1021/acs.jafc.2c07047. Epub 2022 Dec 30. PMID: 36584226. 7: Chen X, Zhang W, Wang J, Zhu S, Shen X, Chen H, Fan Y. Transcription Factors BbPacC and Bbmsn2 Jointly Regulate Oosporein Production in Beauveria bassiana. Microbiol Spectr. 2022 Dec 21;10(6):e0311822. doi: 10.1128/spectrum.03118-22. Epub 2022 Nov 23. PMID: 36416546; PMCID: PMC9769838. 8: Mascarin GM, Marinho-Prado JS, Assalin MR, Martins LG, Braga ES, Tasic L, Dita M, Lopes RB. Natural occurrence of Beauveria caledonica, pathogenicity to Cosmopolites sordidus and antifungal activity against Fusarium oxysporum f. sp. cubense. Pest Manag Sci. 2022 Nov;78(11):4458-4470. doi: 10.1002/ps.7063. Epub 2022 Jul 22. PMID: 35775394. 9: Altimira F, Arias-Aravena M, Jian L, Real N, Correa P, González C, Godoy S, Castro JF, Zamora O, Vergara C, Vitta N, Tapia E. Genomic and Experimental Analysis of the Insecticidal Factors Secreted by the Entomopathogenic Fungus Beauveria pseudobassiana RGM 2184. J Fungi (Basel). 2022 Mar 1;8(3):253. doi: 10.3390/jof8030253. PMID: 35330256; PMCID: PMC8952764. 10: Ávila-Hernández JG, Aguilar-Zárate P, Carrillo-Inungaray ML, Michel MR, Wong-Paz JE, Muñiz-Márquez DB, Rojas-Molina R, Ascacio-Valdés JA, Martínez-Ávila GCG. The secondary metabolites from Beauveria bassiana PQ2 inhibit the growth and spore germination of Gibberella moniliformis LIA. Braz J Microbiol. 2022 Mar;53(1):143-152. doi: 10.1007/s42770-021-00668-z. Epub 2022 Jan 21. PMID: 35060091; PMCID: PMC8882492. 11: Litwin A, Bernat P, Nowak M, Słaba M, Różalska S. Lipidomic response of the entomopathogenic fungus Beauveria bassiana to pyrethroids. Sci Rep. 2021 Oct 29;11(1):21319. doi: 10.1038/s41598-021-00702-y. PMID: 34716379; PMCID: PMC8556296. 12: Wang H, Peng H, Li W, Cheng P, Gong M. The Toxins of Beauveria bassiana and the Strategies to Improve Their Virulence to Insects. Front Microbiol. 2021 Aug 26;12:705343. doi: 10.3389/fmicb.2021.705343. PMID: 34512581; PMCID: PMC8430825. 13: Lara-Juache HR, Ávila-Hernández JG, Rodríguez-Durán LV, Michel MR, Wong-Paz JE, Muñiz-Márquez DB, Veana F, Aguilar-Zárate M, Ascacio-Valdés JA, Aguilar- Zárate P. Characterization of a Biofilm Bioreactor Designed for the Single-Step Production of Aerial Conidia and Oosporein by Beauveria bassiana PQ2. J Fungi (Basel). 2021 Jul 21;7(8):582. doi: 10.3390/jof7080582. PMID: 34436122; PMCID: PMC8396940. 14: Mc Namara L, Dolan SK, Walsh JMD, Stephens JC, Glare TR, Kavanagh K, Griffin CT. Oosporein, an abundant metabolite in Beauveria caledonica, with a feedback induction mechanism and a role in insect virulence. Fungal Biol. 2019 Aug;123(8):601-610. doi: 10.1016/j.funbio.2019.01.004. Epub 2019 Jan 28. PMID: 31345414. 15: Haruma T, Yamaji K, Ogawa K, Masuya H, Sekine Y, Kozai N. Root-endophytic Chaetomium cupreum chemically enhances aluminium tolerance in Miscanthus sinensis via increasing the aluminium detoxicants, chlorogenic acid and oosporein. PLoS One. 2019 Feb 22;14(2):e0212644. doi: 10.1371/journal.pone.0212644. PMID: 30794662; PMCID: PMC6386393. 16: Zhang X, Hu Q, Weng Q. Secondary metabolites (SMs) of Isaria cicadae and Isaria tenuipes. RSC Adv. 2018 Dec 21;9(1):172-184. doi: 10.1039/c8ra09039d. PMID: 35521576; PMCID: PMC9059538. 17: Moonjely S, Keyhani NO, Bidochka MJ. Hydrophobins contribute to root colonization and stress responses in the rhizosphere-competent insect pathogenic fungus Beauveria bassiana. Microbiology (Reading). 2018 Apr;164(4):517-528. doi: 10.1099/mic.0.000644. Epub 2018 Mar 8. PMID: 29517481. 18: Lu Y, Luo F, Cen K, Xiao G, Yin Y, Li C, Li Z, Zhan S, Zhang H, Wang C. Omics data reveal the unusual asexual-fruiting nature and secondary metabolic potentials of the medicinal fungus Cordyceps cicadae. BMC Genomics. 2017 Aug 30;18(1):668. doi: 10.1186/s12864-017-4060-4. PMID: 28854898; PMCID: PMC5577849. 19: Bengyella L, Yekwa EL, Nawaz K, Iftikhar S, Tambo E, Alisoltani A, Feto NA, Roy P. Global invasive Cochliobolus species: cohort of destroyers with implications in food losses and insecurity in the twenty-first century. Arch Microbiol. 2018 Jan;200(1):119-135. doi: 10.1007/s00203-017-1426-6. Epub 2017 Aug 22. PMID: 28831526. 20: Wei G, Lai Y, Wang G, Chen H, Li F, Wang S. Insect pathogenic fungus interacts with the gut microbiota to accelerate mosquito mortality. Proc Natl Acad Sci U S A. 2017 Jun 6;114(23):5994-5999. doi: 10.1073/pnas.1703546114. Epub 2017 May 22. PMID: 28533370; PMCID: PMC5468619.