Isoaltenuene
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Bioactive by-products |
| Catalog number | BBF-04470 |
| CAS | 126671-80-5 |
| Molecular Weight | 292.28 |
| Molecular Formula | C15H16O6 |
| Purity | 97.5% |
Online Inquiry
Description
Isoaltenuene is isolated from the solid cultures of the fungus Colletotrichum sp, and it shows antibacterial activity against gram-positive bacteria and exhibits cytotoxic activity against sevral cancer cells.
Specification
| Synonyms | 6H-Dibenzo[b,d]pyran-6-one, 2,3,4,4a-tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-, (2α,3β,4aα)-; 6H-Dibenzo[b,d]pyran-6-one, 2,3,4,4a-tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-, (2R,3R,4aS)-rel-; rel-(2R,3R,4aS)-2,3,4,4a-Tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-6H-dibenzo[b,d]pyran-6-one; (2α,3β,4aα)-(±)-2,3,4,4a-Tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-6H-dibenzo[b,d]pyran-6-one |
| Storage | Store at -20°C |
| IUPAC Name | (2R,3R,4aS)-2,3,7-trihydroxy-9-methoxy-4a-methyl-3,4-dihydro-2H-benzo[c]chromen-6-one |
| Canonical SMILES | CC12CC(C(C=C1C3=CC(=CC(=C3C(=O)O2)O)OC)O)O |
| InChI | InChI=1S/C15H16O6/c1-15-6-12(18)10(16)5-9(15)8-3-7(20-2)4-11(17)13(8)14(19)21-15/h3-5,10,12,16-18H,6H2,1-2H3/t10-,12-,15+/m1/s1 |
| InChI Key | MMHTXEATDNFMMY-HCKVZZMMSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 609.4±55.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone |
Reference Reading
1. Neuroprotective Activities of Constituents from Phyllosticta capitalensis, an Endophyte Fungus of Loropetalum chinense var. rubrum
Xiaoxia Zhu, Ying Liu, Yunwei Hu, Xin Lv, Zhaoxia Shi, Yuanyuan Yu, Xueyang Jiang, Feng Feng, Jian Xu Chem Biodivers. 2021 Aug;18(8):e2100314. doi: 10.1002/cbdv.202100314. Epub 2021 Jun 22.
One new dioxolanone derivative, guignardianone G (1) and twelve known compounds (2-13) were isolated from the 95 % ethanol extract of the plant endophytic fungus Phyllosticta capitalensis cultured in rice medium. Among these known compounds, isoaltenuene (3), brassicasterol (7), 5,6-epoxyergosterol (8), citreoanthrasteroid A (9), demethylincisterol A (10), and chaxine C (11) were reported from Phyllosticta sp. for the first time. The structure of 1 was elucidated by 1D- and 2D-NMR experiments and HR-ESI-MS data analysis, and its absolute configuration was established through the comprehensive use of the methods of modified Mosher methods, calculations of ECD spectra and optical rotation values. The neuroprotective activity of compounds (1-9, 11-13) were evaluated on PC12 cells damage induced by glutamate, and compounds 9 and 12 showed potential neuroprotective activities with half effective concentration (EC50 ) of 24.2 and 33.9 μM, respectively.
2. Tracking emerging mycotoxins in food: development of an LC-MS/MS method for free and modified Alternaria toxins
Hannes Puntscher, Mary-Liis Kütt, Philipp Skrinjar, Hannes Mikula, Joachim Podlech, Johannes Fröhlich, Doris Marko, Benedikt Warth Anal Bioanal Chem. 2018 Jul;410(18):4481-4494. doi: 10.1007/s00216-018-1105-8. Epub 2018 May 16.
Mycotoxins produced by Alternaria fungi are ubiquitous food contaminants, but analytical methods for generating comprehensive exposure data are rare. We describe the development of an LC-MS/MS method covering 17 toxins for investigating the natural occurrence of free and modified Alternaria toxins in tomato sauce, sunflower seed oil, and wheat flour. Target analytes included alternariol (AOH), AOH-3-glucoside, AOH-9-glucoside, AOH-3-sulfate, alternariol monomethyl ether (AME), AME-3-glucoside, AME-3-sulfate, altenuene, isoaltenuene, tenuazonic acid (TeA), tentoxin (TEN), altertoxin I and II, alterperylenol, stemphyltoxin III, altenusin, and altenuic acid III. Extensive optimization resulted in a time- and cost-effective sample preparation protocol and a chromatographic baseline separation of included isomers. Overall, adequate limits of detection (0.03-9 ng/g) and quantitation (0.6-18 ng/g), intermediate precision (9-44%), and relative recovery values (75-100%) were achieved. However, stemphyltoxin III, AOH-3-sulfate, AME-3-sulfate, altenusin, and altenuic acid III showed recoveries in wheat flour below 70%, while their performance was stable and reproducible. Our pilot study with samples from the Austrian retail market demonstrated that tomato sauces (n = 12) contained AOH, AME, TeA, and TEN in concentrations up to 20, 4, 322, and 0.6 ng/g, while sunflower seed oil (n = 7) and wheat flour samples (n = 9) were contaminated at comparatively lower levels. Interestingly and of relevance for risk assessment, AOH-9-glucoside, discovered for the first time in naturally contaminated food items, and AME-3-sulfate were found in concentrations similar to their parent toxins. In conclusion, the established multi-analyte method proved to be fit for purpose for generating comprehensive Alternaria toxin occurrence data in different food matrices. Graphical abstract ᅟ.
3. A new alternariol glucoside from fungus Alternaria alternate cib-137
Guo-Bo Xu, Xiang Pu, Huan-Huan Bai, Xiao-Zhen Chen, Guo-You Li Nat Prod Res. 2015;29(9):848-52. doi: 10.1080/14786419.2014.990905. Epub 2014 Dec 18.
A new secondary metabolite, 2-O-methylalternariol 4-O-β-[4-methoxyl-glucopyranoside] (1), together with four known compounds alternariol methyl ether (2), altenuene (3), isoaltenuene (4) and 2-(2'S-hydroxypropyl)-5-methyl-7-hydroxychromone (5), was isolated from the fungus Alternaria alternate cib-137. Its structure was elucidated on the basis of spectroscopic data. Compounds 3 and 4 demonstrated moderate activity against Staphylococcus aureus.
Recommended Products
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-03754 | Castanospermine | Inquiry |
| BBF-01826 | Deoxymannojirimycin | 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 ╳
