Betaenone B
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| Category | Mycotoxins |
| Catalog number | BBF-00140 |
| CAS | 85269-23-4 |
| Molecular Weight | 368.51 |
| Molecular Formula | C21H36O5 |
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Description
Betaenone B is a phytotoxin produced by Phoma betae PS-14.
Specification
| Synonyms | 1(2H)-Naphthalenone, octahydro-2,7-dihydroxy-4-(3-hydroxy-1-oxopropyl)-2,4,5,7-tetramethyl-3-((1R)-1-methylpropyl)-, (2S,3R,4R,4aS,5R,7R,8aS)- |
| IUPAC Name | (2S,3R,4R,4aS,5R,7R,8aS)-3-[(2R)-butan-2-yl]-2,7-dihydroxy-4-(3-hydroxypropanoyl)-2,4,5,7-tetramethyl-3,4a,5,6,8,8a-hexahydronaphthalen-1-one |
| Canonical SMILES | CCC(C)C1C(C2C(CC(CC2C(=O)C1(C)O)(C)O)C)(C)C(=O)CCO |
| InChI | InChI=1S/C21H36O5/c1-7-12(2)17-20(5,15(23)8-9-22)16-13(3)10-19(4,25)11-14(16)18(24)21(17,6)26/h12-14,16-17,22,25-26H,7-11H2,1-6H3/t12-,13-,14+,16+,17-,19-,20-,21+/m1/s1 |
| InChI Key | PUZNAAVWFXQUDM-HBKHSIGZSA-N |
Reference Reading
1. Chemical constituents of the fermented broth of the ascomycete Theissenia cinerea 89091602
Wen-Li Liang, Che-Jen Hsiao, Yu-Ming Ju, Liang-Hsin Lee, Tzong-Huei Lee Chem Biodivers. 2011 Dec;8(12):2285-90. doi: 10.1002/cbdv.201000329.
One new betaenone, theissenoic acid (1), together with three new acetogenins, theissenolactones A-C (2-4, resp.), were isolated from the fermented broth of Theissenia cinerea 89091602 isolated in Taiwan. The structures of 1-4 were elucidated by spectroscopic methods. Biological tests revealed that 3 and 4 exhibited moderate growth-inhibitory activities against A549 lung cancer cell line with GI(50) values of 14.9 and 47.9 μM, respectively.
2. α,β-Enone Borylation by Bis(Pinacolato)Diboron Catalyzed by Cu3(BTC)2 Using Cesium Carbonate as a Base
Amarajothi Dhakshinamoorthy, Mercedes Alvaro, Abdullah M Asiri, Hermenegildo Garcia Nanomaterials (Basel). 2021 May 25;11(6):1396. doi: 10.3390/nano11061396.
Cu3(BTC)2 (BTC: 1,3,5-benzenetricarboxylate) as a heterogeneous catalyst in the presence of cesium carbonate as a base is reported for the borylation of α,β-conjugated enones by bis(pinacolato)diboron (B2pin2). According to the hot-filtration test, Cu3(BTC)2 is acting as a heterogeneous catalyst. Further, Cu3(BTC)2 exhibits a wide substrate scope and can be reused in consecutive runs, maintaining a crystal structure as evidenced by powder X-ray diffraction (XRD). A suitable mechanism is also proposed for this transformation using Cu3(BTC)2 as catalyst.
3. Kabiramides J and K, trisoxazole macrolides from the sponge Pachastrissa nux
Thanchanok Sirirak, Siriporn Kittiwisut, Chittrawan Janma, Supreeya Yuenyongsawad, Khanit Suwanborirux, Anuchit Plubrukarn J Nat Prod. 2011 May 27;74(5):1288-92. doi: 10.1021/np100886y. Epub 2011 Mar 16.
Three trisoxazole macrolides possessing a 30-α,β-enone moiety, including the known kabiramide G (1) and the new kabiramides J (2) and K (3), were isolated from the sponge Pachastrissa nux, along with the previously reported kabiramides B (4), C (5), and D (6). To date, the enone moiety has been found to associate solely with the trisoxazole macrolides from P. nux. All of the isolated macrolides showed moderate to strong antimalarial and cytotoxic activities, except for 1, which possessed only potent cytotoxicity.
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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 ╳
