Butyrolactone I
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-04270 |
| CAS | 87414-49-1 |
| Molecular Weight | 424.44 |
| Molecular Formula | C24H24O7 |
| Purity | >95% by HPLC |
Online Inquiry
Description
It is one of a family of three butyrolactones isolated from aspergillus fumigatus. It exhibits antitumor activity and inhibits the cell cycle at the G1/S and G2/M transitions. It is a selective inhibitor of cyclin-dependent kinases CDK1/cyclin B, CDK2 and CDK5.
Specification
| Synonyms | Olomoucin; 4'-O-Demethylversicolactone D; (2R)-2,5-Dihydro-4-hydroxy-2-[[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-oxo-2-furancarboxylic Acid Methyl Ester; (+)-3''-Dimethylallyl-butyrolactone II |
| Storage | Store at -20°C |
| IUPAC Name | methyl (2R)-4-hydroxy-2-[[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate |
| Canonical SMILES | CC(=CCC1=C(C=CC(=C1)CC2(C(=C(C(=O)O2)O)C3=CC=C(C=C3)O)C(=O)OC)O)C |
| InChI | InChI=1S/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-24(23(29)30-3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m1/s1 |
| InChI Key | NGOLMNWQNHWEKU-XMMPIXPASA-N |
| Source | Aspergillus sp. |
Properties
| Appearance | Light Yellow Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 660.1±55.0°C (Predicted) |
| Melting Point | 95°C (dec.) |
| Density | 1.353±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Deep-Sea-Derived Butyrolactone I Suppresses Ovalbumin-Induced Anaphylaxis by Regulating Mast Cell Function in a Murine Model
Guang-Ming Liu, Yuan-Yuan Gao, Wen-Jin Su, Bo Liu, Xian-Wen Yang, Hong Liu, Chun-Lan Xie, Wei-Xiang Lin, Qing-Mei Liu, Min-Jie Cao J Agric Food Chem . 2018 Jun 6;66(22):5581-5592. doi: 10.1021/acs.jafc.8b01674.
Deep-sea-derived butyrolactone I (BTL-I), which was identified as a type of butanolide, was isolated from Aspergillus sp. Ovalbumin (OVA)-induced BALB/c anaphylaxis was established to explore the antifood allergic activity of BTL-I. As a result, BTL-I was able to alleviate OVA-induced allergy symptoms, reduce the levels of histamine and mouse mast cell proteinases, inhibit OVA-specific IgE, and decrease the population of mast cells in the spleen and mesenteric lymph nodes. BTL-I also significantly suppressed mast-dependent passive cutaneous anaphylaxis. Additionally, the maturation of bone marrow-derived mast cells (BMMCs) declined as BTL-I caused down-regulation of c-KIT receptors. Furthermore, molecular docking analyses revealed that BTL-I interacted with the inhibitory receptor, FcγRIIB. In conclusion, the reduction of mast cell function by deep-sea-derived BTL-I as well as its interactions with the inhibitory receptor, FcγRIIB, may contribute to BTL-I-related protection against food anaphylaxis.
2. Synthesis and Biological Evaluation of Analogues of Butyrolactone I as PTP1B Inhibitors
Chaochun Fan, Qingqing Le, Chao Tang, Kaikai Bai, Jianlin He, Meitian Xiao, Bihong Hong, Siwen Niu Mar Drugs . 2020 Oct 23;18(11):526. doi: 10.3390/md18110526.
In recent years, a large number of pharmacologically active compounds containing a butenolide functional group have been isolated from secondary metabolites of marine microorganisms. Butyrolactone I was found to be produced byAspergillus terreusisolated from several marine-derived samples. The hypoglycemic activity of butyrolactone I has aroused our great interest. In this study, we synthesized six racemic butenolide derivatives (namely BL-1-BL-6) by modifying the C-4 side chain of butyrolactone I. Among them, BL-3 and BL-5 improved the insulin resistance of HepG2 cells and did not affect the proliferation of RIN-m5f cell line, which indicated the efficacy and safety of BL-3 and BL-5. Furthermore, BL-3, BL-4, BL-5, and BL-6 displayed a significant protein tyrosine phosphatase 1B (PTP1B) inhibitory effect, while the enantiomers of BL-3 displayed different 50% percentage inhibition concentration (IC50) values against PTP1B. The results of molecular docking simulation of the BLs and PTP1B explained the differences of biological consequences observed between the enantiomers of BL-3, which supported BLs as PTP1B inhibitors, and also indicated that the chirality of C-4 might influence the inhibitory effect of the BLs. Our findings provide a novel strategy for the development of butyrolactone derivatives as potential PTP1B inhibitors for the treatment of type 2 diabetes mellitus.
3. Butyrolactone I Quantification from Lovastatin Producing Aspergillus terreus Using Tandem Mass Spectrometry-Evidence of Signalling Functions
Sheetal Raina, Tajalli Keshavarz, Elina K Palonen, Juhani Soini, Jussi Meriluoto, Annika Brandt, Milla-Riina Neffling Microorganisms . 2014 Jun 4;2(2):111-27. doi: 10.3390/microorganisms2020111.
Aspergillus terreus is an industrially important filamentous fungus producing a wide spectrum of secondary metabolites, including lovastatin and itaconic acid. It also produces butyrolactone I which has shown potential as an antitumour agent. Additionally, butyrolactone I has been implicated to have a regulating role in the secondary metabolism and morphology of A. terreus. In this study, a quantitative time-course liquid chromatography-electrospray ionisation-tandem mass spectrometry (LC-ESI-MS-MS) analysis of butyrolactone I is reported for the first time in nine-day long submerged cultures of A. terreus. Butyrolactone I was fragmented in the mass analysis producing a reproducible fragmentation pattern of four main daughter ions (m/z 307, 331, 363 and 393) in all the samples tested. Supplementing the cultures with 100 nM butyrolactone I caused a statistically significant increase (up to two-fold) in its production, regardless of the growth stage but was constitutive when butyrolactone I was added at high cell density during the stationary phase. Furthermore, the extracellular butyrolactone I concentration peaked at 48 h post inoculation, showing a similar profile as has been reported for bacterial quorum sensing molecules. Taken together, the results support the idea of butyrolactone I as a quorum sensing molecule in A. terreus.
Recommended Products
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
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 ╳
