Stachybotrin A
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| Category | Bioactive by-products |
| Catalog number | BBF-02953 |
| CAS | 144373-26-2 |
| Molecular Weight | 401.49 |
| Molecular Formula | C23H31NO5 |
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Description
It is produced by the strain of Stachyborrys sp. It has antimicrobial and antifungal activity.
Specification
| IUPAC Name | (2S,3S)-3,5-dihydroxy-2-[(3E)-4-(hydroxymethyl)-8-methylnona-3,7-dienyl]-2-methyl-3,4,8,9-tetrahydropyrano[2,3-e]isoindol-7-one |
| Canonical SMILES | CC(=CCCC(=CCCC1(C(CC2=C(C=C3C(=C2O1)CNC3=O)O)O)C)CO)C |
| InChI | InChI=1S/C23H31NO5/c1-14(2)6-4-7-15(13-25)8-5-9-23(3)20(27)11-17-19(26)10-16-18(21(17)29-23)12-24-22(16)28/h6,8,10,20,25-27H,4-5,7,9,11-13H2,1-3H3,(H,24,28)/b15-8+/t20-,23-/m0/s1 |
| InChI Key | ZVZKOARXMVUPBB-KWOFNGTCSA-N |
Properties
| Antibiotic Activity Spectrum | Fungi |
| Solubility | Soluble in Methanol, Chloroform, Ethyl Acetate |
Reference Reading
1. Cytotoxicity, fractionation and dereplication of extracts of the dinoflagellate Vulcanodinium rugosum, a producer of pinnatoxin G
Marie Geiger, Gwenaëlle Desanglois, Kevin Hogeveen, Valérie Fessard, Thomas Leprêtre, Florence Mondeguer, Yann Guitton, Fabienne Hervé, Véronique Séchet, Olivier Grovel, Yves-François Pouchus, Philipp Hess Mar Drugs. 2013 Sep 2;11(9):3350-71. doi: 10.3390/md11093350.
Pinnatoxin G (PnTX-G) is a marine toxin belonging to the class of cyclic imines and produced by the dinoflagellate Vulcanodinium rugosum. In spite of its strong toxicity to mice, leading to the classification of pinnatoxins into the class of "fast-acting toxins", its hazard for human health has never been demonstrated. In this study, crude extracts of V. rugosum exhibited significant cytotoxicity against Neuro2A and KB cells. IC₅₀ values of 0.38 µg mL⁻¹ and 0.19 µg mL⁻¹ were estimated on Neuro2A cells after only 24 h of incubation and on KB cells after 72 h of incubation, respectively. In the case of Caco-2 cells 48 h after exposure, the crude extract of V. rugosum induced cell cycle arrest accompanied by a dramatic increase in double strand DNA breaks, although only 40% cytotoxicity was observed at the highest concentration tested (5 µg mL⁻¹). However, PnTX-G was not a potent cytotoxic compound as no reduction of the cell viability was observed on the different cell lines. Moreover, no effects on the cell cycle or DNA damage were observed following treatment of undifferentiated Caco-2 cells with PnTX-G. The crude extract of V. rugosum was thus partially purified using liquid-liquid partitioning and SPE clean-up. In vitro assays revealed strong activity of some fractions containing no PnTX-G. The crude extract and the most potent fraction were evaluated using full scan and tandem high resolution mass spectrometry. The dereplication revealed the presence of a major compound that could be putatively annotated as nakijiquinone A, N-carboxy-methyl-smenospongine or stachybotrin A, using the MarinLit™ database. Further investigations will be necessary to confirm the identity of the compounds responsible for the cytotoxicity and genotoxicity of the extracts of V. rugosum.
2. Synthesis of tricyclic pyrano[2,3-e]isoindolin-3-ones as the core structure of stachybotrin A, B, and C
Seiichi Inoue, Riyoung Kim, Yujiro Hoshino, Kiyoshi Honda Chem Commun (Camb). 2006 May 14;(18):1974-6. doi: 10.1039/b601433j. Epub 2006 Apr 3.
The substituted tricyclic pyrano[2,3-e]isoindolin-3-ones and , as the core structure of stachybotrin A, B, and C (), have been regioselectively synthesized for the first time by a short route which involved Mannich reaction and Claisen rearrangement.
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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 ╳
