Sclerotiorin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04102 |
| CAS | 549-23-5 |
| Molecular Weight | 390.86 |
| Molecular Formula | C21H23ClO5 |
| Purity | ≥98% |
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Description
Sclerotiorin is a metabolite isolated from Penicillium species. It inhibits soybean lipoxygenase-1 (LOX-1) with IC50 value of 4.2 µM. It also exhibits antioxidant property by scavenging free radical with an ED50 of 0.12 μM.
Specification
| Synonyms | [(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-7-methyl-6,8-dioxoisochromen-7-yl] acetate |
| Storage | Store at -20°C |
| IUPAC Name | [(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-7-methyl-6,8-dioxoisochromen-7-yl] acetate |
| Canonical SMILES | CCC(C)C=C(C)C=CC1=CC2=C(C(=O)C(C(=O)C2=CO1)(C)OC(=O)C)Cl |
| InChI | InChI=1S/C21H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-26-15)19(24)21(5,27-14(4)23)20(25)18(16)22/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,21+/m0/s1 |
| InChI Key | SWJLTKXURNHVHE-UPWXJBBJSA-N |
Properties
| Appearance | Crystalline Solid |
| Boiling Point | 482.9°C at 760 mmHg |
| Density | 1.23 g/cm3 |
| Solubility | Soluble in DMF, DMSO, ethanol |
Reference Reading
1. Synthesis and antifungal activity of novel sclerotiorin analogues
Nick Mulholland, Qiong-You Wu, David Beattie, Long Lin, Guang-Fu Yang, John Clough, Yu-Cheng Gu, Shao-Wei Huang, Dianne Irwin J Agric Food Chem . 2012 May 9;60(18):4480-91. doi: 10.1021/jf300610j.
Sclerotiorin 1, first isolated from Penicillium sclerotiorum, has weak antifungal activity and belongs to the azaphilone-type family of natural products. Several series of sclerotiorin analogues were designed and synthesized with the aim of discovering novel fungicides with improved activity. The syntheses involved two key steps, cycloisomerization and then oxidation, and used a simple and efficient Sonogashira cross-coupling reaction to construct the required functionalized precursor. With sclerotiorin as a control, the activities of the newly synthesized analogues were evaluated against seven fungal pathogens, and several promising candidates (compounds 3a₁, 3d₂, 3e₂, 3f₂ and 3k₂) with greater activity and simpler structures than sclerotiorin were discovered. In addition, preliminary structure-activity relationships were studied, which revealed that not only the chlorine or bromine substituent at the 5-position of the nucleus but also the phenyl group at the 3-position and the substituent pattern on it contributed crucially to the observed antifungal activity. Analogues with a methyl substituent at the 1-position have reduced levels of activity, while those with a free hydroxyl group in place of acetoxy at the quaternary center of the bicyclic ring system retain activity.
2. Sclerotiorin inhibits protein kinase G from Mycobacterium tuberculosis and impairs mycobacterial growth in macrophages
Dongni Chen, Lei He, Zhigang She, Peibo Yuan, Shuangshuang Ma, Yongjun Lu Tuberculosis (Edinb) . 2017 Mar;103:37-43. doi: 10.1016/j.tube.2017.01.001.
As a eukaryotic-like Ser/Thr protein kinase, Mycobacterium tuberculosis virulent effector protein kinase G (PknG) mediates mycobacterial survival by regulating bacterial cell metabolic processes and preventing phagosome-lysosome fusion in host macrophages. Targeting PknG is an effective strategy for development of anti-tuberculosis (TB) drugs. In the study, we found that sclerotiorin, derived from marine fungi from the South China Sea, exhibited moderately strong inhibitory effects on recombinant PknG, with an IC50value of 76.5 μM, and acted as a non-competitive inhibitor. The dissociation constant (KD) of sclerotiorin determined by MST was 11.4 μM, demonstrating a moderate binding strength between them. Sclerotiorin could substantially impair the mycobacterial survival in infected macrophages while the macrophage viability remained unaffected, though it did not inhibit the mycobacterial growth in culture. When sclerotiorin was used in combination with rifampicin, intracellular mycobacterial growth decreased as sclerotiorin concentration increased. Docking analysis suggested a binding mechanism of inhibition with performing interactions with the P-loop and catalytic loop of PknG. In summary, we reported that sclerotiorin had moderately strong PknG inhibitory activity, but no cytotoxicity, and it could substantially decrease the mycobacterial growth inside macrophages, suggesting that sclerotiorin has potential to supplement antibiotic therapy for TB.
3. Sclerotiorin, from Penicillium frequentans, a potent inhibitor of aldose reductase
C Chidananda, A P Sattur, L Jagan Mohan Rao Biotechnol Lett . 2006 Oct;28(20):1633-6. doi: 10.1007/s10529-006-9133-4.
Aldose reductase, the first key enzyme in the polyol pathway, is involved in complications of diabetes. Sclerotiorin, isolated and purified from the fermented broth of Penicillium frequentans, inhibited aldose reductase with an IC(50 )0.4 microM. The inhibitor also showed antibacterial activity against Bacillus spp.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
