Globosuxanthone A
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| Category | Bioactive by-products |
| Catalog number | BBF-04617 |
| CAS | 917091-74-8 |
| Molecular Weight | 304.25 |
| Molecular Formula | C15H12O7 |
| Purity | ≥95% |
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Description
Globosuxanthone A is a fungal metabolite isolated from C. globosum which is a well-known mesophilic member of the mold family Chaetomiaceae. Globosuxanthone A is cytotoxic to various human solid tumor cell lines, including MCF-7, PC3, LNCap and DU145 cells.
Specification
| Synonyms | (1R,2R)-2,9-dihydro-1,2,8-trihydroxy-9-oxo-1H-xanthene-1-carboxylic acid, methyl ester; rel-methyl (1R,2R)-1,2,8-trihydroxy-9-oxo-2,9-dihydro-1H-xanthene-1-carboxylate |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | methyl (1R,2R)-1,2,8-trihydroxy-9-oxo-2H-xanthene-1-carboxylate |
| Canonical SMILES | COC(=O)C1(C(C=CC2=C1C(=O)C3=C(C=CC=C3O2)O)O)O |
| InChI | InChI=1S/C15H12O7/c1-21-14(19)15(20)10(17)6-5-9-12(15)13(18)11-7(16)3-2-4-8(11)22-9/h2-6,10,16-17,20H,1H3/t10-,15+/m1/s1 |
| InChI Key | HEFOWMGZUBJFBY-BMIGLBTASA-N |
Properties
| Appearance | Solid |
| Boiling Point | 506.8±50.0°C at 760 mmHg |
| Density | 1.6±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, DMSO, Methanol |
Reference Reading
1. Antifungal xanthones produced by the endophytic fungus Paraconionthyrium sp. YM 311593
Cuiping Miao, Shaohua Wu, Chuansheng Liu, Junfei Wang, Rong Huang, Yihan Lu, Sisi Liu, Kaixuan Zheng Folia Microbiol (Praha) . 2020 Jun;65(3):567-572. doi: 10.1007/s12223-019-00762-8.
During our investigation on the endophytic fungi of Azadirachta indica, the strain YM 311593 was obtained from the fruit of the plant. The culture extract of the strain showed antifungal activities against four phytopathogenic fungi. Based on the morphological features and phylogenetic definition, the strain YM 311593 was identified as Paraconiothyrium sp. Four xanthones and one anthraquinone were obtained from the extract of the fermentation broth of the strain. They were characterized to be globosuxanthone A (1), vertixanthone (2), hydroxyvertixanthone (3), 3,8-dihydroxy-1-methy1-9H- xanthen-9-one (4), and danthron (5), respectively, by spectroscopic elucidation. Furthermore, the absolute configuration of 1 was deduced by X-ray diffraction analysis. Besides, compound 4 was firstly found from natural sources. The antifungal activities of compounds 1-5 towards four phytopathogens were assayed using broth microdilution method. Among them, globosuxanthone A (1) showed obvious antifungal activity towards Fusarium graminearum, Fusarium solani, and Botrytis cinerea with MIC values of 4, 8, and 16 μg/mL, respectively.
2. A new dibenz[b,e]oxepine derivative, 1-hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione, from a marine-derived fungus, Beauveria bassiana TPU942
Hiroyuki Yamazaki, Kazuyo Ukai, Henki Rotinsulu, Michio Namikoshi, Kazuki Murakami, Hiromu Fujiwara, Tsuyoshi Kaneko Mar Drugs . 2012 Dec;10(12):2691-2697. doi: 10.3390/md10122691.
1-Hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione (1) was obtained from the culture broth of a marine-derived fungus, Beauveria bassiana TPU942, isolated from a marine sponge collected at Iriomote Island in Okinawa, together with two known compounds, chrysazin (2) and globosuxanthone A (3). The structure of 1 was elucidated on the basis of its spectroscopic data (HREIMS, 1D and 2D NMR experiments including ¹H--¹H COSY, HMQC and HMBC spectra). Dibenz[b,e]oxepines are rare in nature, and only six natural products have been reported. Therefore, compound 1 is the seventh natural product in this class. Compounds 2 and 3 showed an antifungal activity against Candida albicans, and 3 inhibited the cell growth against two human cancer cell lines, HCT-15 (colon) and Jurkat (T-cell lymphoma). Compound 1 did not show an apparent activity in the same bioassays.
3. A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity
A A Leslie Gunatilaka, Luke Whitesell, Thomas J Turbyville, Anne Fritz, E M Kithsiri Wijeratne Bioorg Med Chem . 2006 Dec 1;14(23):7917-23. doi: 10.1016/j.bmc.2006.07.048.
Bioassay-guided fractionation of a cytotoxic EtOAc extract of the fungal strain, Chaetomium globosum, inhabiting the rhizosphere of the Christmas cactus, Opuntia leptocaulis, of the Sonoran desert afforded a new dihydroxanthenone, globosuxanthone A (1), a new tetrahydroxanthenone, globosuxanthone B (2), two new xanthones, globosuxanthone C (3) and D (4), 2-hydroxyvertixanthone (5), and two known anthraquinones (6 and 7). The structures of the new compounds 1-4 were elucidated by NMR and MS techniques, and the relative stereochemistry of 1 was determined by X-ray crystallographic analysis. Of the compounds encountered, 1 was found to exhibit strong cytotoxicity against a panel of seven human solid tumor cell lines, disrupt the cell cycle leading to the accumulation of cells in either G2/M or S phase, and induce classic signs of apoptosis.
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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 ╳
