Epiisoshamixanthone
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| Category | Others |
| Catalog number | BBF-05454 |
| CAS | 55826-54-5 |
| Molecular Weight | 406.47 |
| Molecular Formula | C25H26O5 |
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Description
It is a minor metabolite of Aspergillus variecolor.
Specification
| Synonyms | epi-Isoshamixanthone; (-)-2,3-Dihydro-1,11-dihydroxy-5-methyl-10-(3-methyl-2-butenyl)-2-(1-methylethenyl)pyrano[3,2-a]xanthen-12(1H)-one; Pyrano[3,2-a]xanthen-12(1H)-one, 2,3-dihydro-1,11-dihydroxy-5-methyl-10-(3-methyl-2-butenyl)-2-(1-methylethenyl)-, (10R,11R)-rel-(-)-; 2,3-Dihydro-1beta,11-dihydroxy-5-methyl-10-(3-methyl-2-butenyl)-2beta-(1-methylvinyl)pyrano[3,2-a]xanthen-12(1H)-one; (1S,2S)-1,11-dihydroxy-5-methyl-10-(3-methylbut-2-en-1-yl)-2-(prop-1-en-2-yl)-2,3-dihydropyrano[3,2-a]xanthen-12(1H)-one |
| IUPAC Name | (1S,2S)-1,11-dihydroxy-5-methyl-10-(3-methylbut-2-enyl)-2-prop-1-en-2-yl-2,3-dihydro-1H-pyrano[3,2-a]xanthen-12-one |
| Canonical SMILES | CC1=CC2=C(C3=C1OCC(C3O)C(=C)C)C(=O)C4=C(O2)C=CC(=C4O)CC=C(C)C |
| InChI | InChI=1S/C25H26O5/c1-12(2)6-7-15-8-9-17-20(22(15)26)24(28)19-18(30-17)10-14(5)25-21(19)23(27)16(11-29-25)13(3)4/h6,8-10,16,23,26-27H,3,7,11H2,1-2,4-5H3/t16-,23+/m1/s1 |
| InChI Key | UAGOXGIYOPSKFF-MWTRTKDXSA-N |
Properties
| Appearance | Yellow Needles |
| Boiling Point | 581.6±50.0°C at 760 mmHg |
| Melting Point | 114-115°C |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Chloroform, Methanol |
Reference Reading
1. Secoemestrin D, a cytotoxic epitetrathiodioxopiperizine, and emericellenes A-E, five sesterterpenoids from Emericella sp. AST0036, a fungal endophyte of Astragalus lentiginosus1
Ya-Ming Xu, Patricia Espinosa-Artiles, Mangping X Liu, A Elizabeth Arnold, A A Leslie Gunatilaka J Nat Prod. 2013 Dec 27;76(12):2330-6. doi: 10.1021/np400762k. Epub 2013 Nov 19.
A new epitetrathiodioxopiperizine, secoemestrin D (1), and five sesterterpenoids bearing a new carbon skeleton, emericellenes A-E (2-6), together with previously known fungal metabolites, sterigmatocystin (7), arugosin C (8), and epiisoshamixanthone (9), were obtained from the endophytic fungal strain Emericella sp. AST0036 isolated from a healthy leaf tissue of Astragalus lentiginosus. The planar structures and relative configurations of the new metabolites 1-6 were elucidated using MS and 1D and 2D NMR spectroscopic data. All compounds were evaluated for their potential anticancer activity using a panel of six tumor cell lines and normal human fibroblast cells. Only metabolites 1 and 7 showed cytotoxic activity. More importantly, secoemestrin D (1) exhibited significant cytotoxicity with IC50 values ranging from 0.06 to 0.24 μM and moderate selectivity to human glioma (SF-268) and metastatic breast adenocarcinoma (MDA-MB-231) cell lines.
2. Isoshamixanthone: a new pyrano xanthone from endophytic Aspergillus sp. ASCLA and absolute configuration of epiisoshamixanthone
Reem A Kamel, Ahmed S Abdel-Razek, Abdelaaty Hamed, Reham R Ibrahim, Hans Georg Stammler, Marcel Frese, Norbert Sewald, Mohamed Shaaban Nat Prod Res. 2020 Apr;34(8):1080-1090. doi: 10.1080/14786419.2018.1548458. Epub 2019 Jan 19.
Isoshamixanthone (1), a new stereoisomeric pyrano xanthone together with the previously known fungal metabolites, epiisoshamixanthone (2), sterigmatocystin (3), arugosin C (4), norlichexanthone (5), diorcinol (6), ergosterol and methyllinoleate, were obtained from the endophytic fungal strain Aspergillus sp. ASCLA isolated from leaf tissues of the medicinal plant Callistemon subulatus. The chemical structure of the new xanthone (1) was elucidated by extensive 1D, 2D NMR, and ESI HR mass measurements, and by comparison with literature data. The constitutions and absolute configurations of 1 and epiisoshamixanthone (2) were additionally confirmed by X-ray crystallography. Compounds 1,2 were evaluated for their potential anticancer activity using the human cervix carcinoma cell line (KB-3-1). The antimicrobial activities of the fungal extract and compounds 1,2 were studied using a panel of pathogenic microorganisms as well.
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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 ╳
