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MedKoo Cat#: 599073 | Name: Sphaeropsidin A

Description:

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

Sphaeropsidin A is the main phytotoxin produced by Diplodia cupressi.

Chemical Structure

Sphaeropsidin A
Sphaeropsidin A
CAS#38991-80-9

Theoretical Analysis

MedKoo Cat#: 599073

Name: Sphaeropsidin A

CAS#: 38991-80-9

Chemical Formula: C20H26O5

Exact Mass: 346.1780

Molecular Weight: 346.42

Elemental Analysis: C, 69.34; H, 7.57; O, 23.09

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Sphaeropsidin A; LL-S491beta; LL S491beta; LLS491beta; Antibiotic LL-S491beta; Sphaeropsidin A, (+)-;
IUPAC/Chemical Name
(2R,4aR,4bR,8aS,9S)-4a,9-dihydroxy-2,8,8-trimethyl-2-vinyl-2,3,4,4a,5,6,7,8,8a,9-decahydro-10H-9,4b-(epoxymethano)phenanthrene-10,12-dione
InChi Key
FEKFUWWVNCCROX-SQWSIXGCSA-N
InChi Code
InChI=1S/C20H26O5/c1-5-17(4)9-10-19(23)12(11-17)13(21)20(24)14-16(2,3)7-6-8-18(14,19)15(22)25-20/h5,11,14,23-24H,1,6-10H2,2-4H3/t14-,17-,18-,19+,20+/m0/s1
SMILES Code
O=C1C2=C[C@@](C)(C=C)CC[C@]2(O)[C@@]34CCCC(C)(C)[C@]3([H])[C@]1(O)OC4=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 346.42 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: Mathieu V, Chantôme A, Lefranc F, Cimmino A, Miklos W, Paulitschke V, Mohr T, Maddau L, Kornienko A, Berger W, Vandier C, Evidente A, Delpire E, Kiss R. Sphaeropsidin A shows promising activity against drug-resistant cancer cells by targeting regulatory volume increase. Cell Mol Life Sci. 2015 Oct;72(19):3731-46. doi: 10.1007/s00018-015-1902-6. Epub 2015 Apr 14. PubMed PMID: 25868554; PubMed Central PMCID: PMC4943577. 2: Cimmino A, Andolfi A, Avolio F, Ali A, Tabanca N, Khan IA, Evidente A. Cyclopaldic acid, seiridin, and sphaeropsidin A as fungal phytotoxins, and larvicidal and biting deterrents against Aedes aegypti (Diptera: Culicidae): structure-activity relationships. Chem Biodivers. 2013 Jul;10(7):1239-51. doi: 10.1002/cbdv.201200358. Erratum in: Chem Biodivers. 2013 Dec;10(12):2302. PubMed PMID: 23847068. 3: Cimmino A, Fernández-Aparicio M, Andolfi A, Basso S, Rubiales D, Evidente A. Effect of fungal and plant metabolites on broomrapes (Orobanche and Phelipanche spp.) seed germination and radicle growth. J Agric Food Chem. 2014 Oct 29;62(43):10485-92. doi: 10.1021/jf504609w. Epub 2014 Oct 16. PubMed PMID: 25272312. 4: Wang XN, Bashyal BP, Wijeratne EM, U'Ren JM, Liu MX, Gunatilaka MK, Arnold AE, Gunatilaka AA. Smardaesidins A-G, isopimarane and 20-nor-isopimarane diterpenoids from Smardaea sp., a fungal endophyte of the moss Ceratodon purpureus. J Nat Prod. 2011 Oct 28;74(10):2052-61. doi: 10.1021/np2000864. Epub 2011 Oct 14. PubMed PMID: 21999655; PubMed Central PMCID: PMC3371368. 5: Evidente A, Venturi V, Masi M, Degrassi G, Cimmino A, Maddau L, Andolfi A. In vitro antibacterial activity of sphaeropsidins and chemical derivatives toward Xanthomonas oryzae pv. oryzae, the causal agent of rice bacterial blight. J Nat Prod. 2011 Dec 27;74(12):2520-5. doi: 10.1021/np200625m. Epub 2011 Nov 29. PubMed PMID: 22124378. 6: Atala A. Re: Sphaeropsidin A Shows Promising Activity against Drug-Resistant Cancer Cells by Targeting Regulatory Volume Increase. J Urol. 2016 Jul;196(1):280-1. doi: 10.1016/j.juro.2016.03.156. Epub 2016 Apr 5. PubMed PMID: 27321539. 7: Schrader KK, Andolfi A, Cantrell CL, Cimmino A, Duke SO, Osbrink W, Wedge DE, Evidente A. A survey of phytotoxic microbial and plant metabolites as potential natural products for pest management. Chem Biodivers. 2010 Sep;7(9):2261-80. doi: 10.1002/cbdv.201000041. PubMed PMID: 20860028. 8: Evidente A, Masi M, Linaldeddu BT, Franceschini A, Scanu B, Cimmino A, Andolfi A, Motta A, Maddau L. Afritoxinones A and B, dihydrofuropyran-2-ones produced by Diplodia africana the causal agent of branch dieback on Juniperus phoenicea. Phytochemistry. 2012 May;77:245-50. doi: 10.1016/j.phytochem.2012.01.011. Epub 2012 Feb 10. PubMed PMID: 22326509. 9: Ingels A, Dinhof C, Garg AD, Maddau L, Masi M, Evidente A, Berger W, Dejaegher B, Mathieu V. Computed determination of the in vitro optimal chemocombinations of sphaeropsidin A with chemotherapeutic agents to combat melanomas. Cancer Chemother Pharmacol. 2017 May;79(5):971-983. doi: 10.1007/s00280-017-3293-x. Epub 2017 Apr 7. PubMed PMID: 28389780. 10: Li Y, Scott R, Hooper AR, Bartholomeusz GA, Kornienko A, Bills GF. Aspergillus candidus is a newly recognized source of sphaeropsidin A: Isolation, semi-synthetic derivatization and anticancer evaluation. Bioorg Med Chem Lett. 2017 Dec 15;27(24):5436-5440. doi: 10.1016/j.bmcl.2017.11.001. Epub 2017 Nov 4. PubMed PMID: 29138030. 11: Weber RW, Kappe R, Paululat T, Mösker E, Anke H. Anti-Candida metabolites from endophytic fungi. Phytochemistry. 2007 Mar;68(6):886-92. Epub 2007 Feb 6. PubMed PMID: 17286994. 12: Evidente A, Sparapano L, Bruno G, Motta A. Sphaeropsidins D and E, two other pimarane diterpenes, produced in vitro by the plant pathogenic fungus Sphaeropsis sapinea f. sp. cupressi. Phytochemistry. 2002 Apr;59(8):817-23. PubMed PMID: 11937160.