Waol A
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| Category | Bioactive by-products |
| Catalog number | BBF-02972 |
| CAS | |
| Molecular Weight | 236.26 |
| Molecular Formula | C13H16O4 |
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Description
It is a trihydrofuran derivative with cytotoxicity produced by the strain of Myceliophthora lutea TF-0409. It has very weak anti-staphylococcus aureus activity. In cell culture, its cytoplasmic activity against HL 60, P388, T24, HeLa and A549 was 8-10 times weaker than adriamycin, but its cytoplasmic activity against HL 60/ADM was stronger than adriamycin (IC50 is 2.0 μg/mL). IC50 is 0.1 μg/mL.
Specification
| Synonyms | FD-211; NSC726144; NSC-726144; 5H-Furo[3,4-b]pyran-5-one, 2,3,7,7a-tetrahydro-3-hydroxy-2,7-di-(1E)-1-propen-1-yl-, (2R,3R,7S,7aR)- |
| IUPAC Name | (2R,3R,7S,7aR)-3-hydroxy-2,7-bis[(E)-prop-1-enyl]-2,3,7,7a-tetrahydrofuro[3,4-b]pyran-5-one |
| Canonical SMILES | CC=CC1C(C=C2C(O1)C(OC2=O)C=CC)O |
| InChI | InChI=1S/C13H16O4/c1-3-5-10-9(14)7-8-12(16-10)11(6-4-2)17-13(8)15/h3-7,9-12,14H,1-2H3/b5-3+,6-4+/t9-,10-,11+,12-/m1/s1 |
| InChI Key | QXZDESIVIREXNJ-XQJSVKFYSA-N |
Properties
| Appearance | Colorless Oily Matter |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 442.3±45.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. A simple and efficient approach to the synthesis of 4H-furo[3,4-b]pyrans via a three-component reaction of isocyanides
Ahmad Shaabani, Ebrahim Soleimani, Afshin Sarvary, Ali Hossein Rezayan Bioorg Med Chem Lett. 2008 Jul 15;18(14):3968-70. doi: 10.1016/j.bmcl.2008.06.014. Epub 2008 Jun 10.
A three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and tetronic acid in dichloromethane at room temperature afforded 4H-furo[3,4-b]pyran derivatives. These compounds are closely related with ring systems, TAN-2483B, TAN-2483A, and FD-211 which have a broad spectrum of biological activity.
2. Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system. Revision of the structures of and syntheses of (+/-)-Waol A (FD-211) and (+/-)-Waol B (FD-212)
Xiaolei Gao, Barry B Snider J Org Chem. 2004 Aug 20;69(17):5517-27. doi: 10.1021/jo0358628.
The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483A (5). Aldol reaction of hydroxybutanolides 13b,c with 2,4-hexadienal affords 12b,c, which are subjected to iodoetherification with bis(sym-collidine)IPF6 to provide 11b(c). Treatment with Et3N in CH2Cl2 completes the three-step syntheses of TAN-2483A (5) and waol A (6). Aldol reaction of hydroxybutanolide 31 with 2,4-hexadienal affords 32, which is subjected to iodoetherification to provide 34, which in turn is treated with Bu3SnCl, NaBH3CN, and oxygen to provide diol 60. Further elaboration completes the first syntheses of massarilactone B (7) and the fusidilactone B (9) ring system.
3. Waol A, trans-dihydrowaol A, and cis-dihydrowaol A: polyketide-derived γ-lactones from a Volutella species
Tamam El-Elimat, Mario Figueroa, Huzefa A Raja, Audrey F Adcock, David J Kroll, Steven M Swanson, Mansukh C Wani, Cedric J Pearce, Nicholas H Oberlies Tetrahedron Lett. 2013 Aug 7;54(32):4300-4302. doi: 10.1016/j.tetlet.2013.06.008.
An organic extract of a filamentous fungus (MSX 58801), identified as a Volutella sp. (Hypocreales, Ascomycota), displayed moderate cytotoxic activity against NCI-H460 human large cell lung carcinoma. Bioactivity-directed fractionation led to the isolation of three γ-lactones having the furo[3,4-b]pyran-5-one bicyclic ring system [waol A (1), trans-dihydrowaol A (2), and cis-dihydrowaol A (3)]. The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configuration of 2 was established via a modified Mosher's ester method. Compounds 1 and 2 were evaluated for cytotoxicity against a human cancer cell panel.
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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 ╳
