22225-63-4Relevant academic research and scientific papers
New antitumour fungal metabolites from Alternaria porri
Phuwapraisirisan, Preecha,Rangsan, Jakaphan,Siripong, Pongpan,Tip-Pyang, Santi
, p. 1063 - 1071 (2009)
Chemical investigation of the onion pathogenic fungus Alternaria porri resulted in the isolation of two new phthalides named zinnimide (2) and deprenylzinnimide (8), along with a new bianthraquinone, alterporriol F (10). The structures of the new metabolites were characterised by spectroscopic analysis and chemical degradation. Of the new compounds isolated, alterporriol F was highly cytotoxic towards HeLa and KB cells, with IC50 values of 6.5 and 7.0 g mL-1.
ANTHRAQUINONES FROM THE GENUS CORTINARIUS
Archard, Michelle A.,Gill, Melvyn,Strauch, Richard J.
, p. 2755 - 2758 (1985)
The anthraquinones 6-methylxanthopurpurin-3-methyl ether, xanthorin, and 1,4-dihydroxy-2-methoxy-7-methyl-9,10-anthraquinone (austrocortitnin) have been isolated from fruit bodies of a red Australian toadstool belonging to the genus Cortinarius; austrocortinin is reported for the first time as a natural product. Key Word Index - Cortinarius; Dermocybe; basidiomycete; anthraquinones.
Applications of [4+2] Anionic Annulation and Carbonyl-Ene Reaction in the Synthesis of Anthraquinones, Tetrahydroanthraquinones, and Pyranonaphthoquinones
Basak, Shyam,Mal, Dipakranjan
, p. 11035 - 11051 (2017/10/27)
Hexa-2,5-dienoates, susceptible to isomerization by acids and bases, are suitable for the [4+2] anionic annulation to give 3-(2-alkenyl)naphthoates in regiospecific manner. When combined with intramolecular carbonyl-ene reaction (ICE), the accessibility of the naphthoates culminates in a new synthesis of anthraquinones and diastereoselective synthesis of tetrahydroanthraquinones. This strategy has also resulted in a 3-step synthesis of dehydroherbarin from a 3-methallylnaphthoate.
Pigments of fungi. LXV Tetrahydroanthraquinone and anthraquinone gentiobiosides from the fungus Dermocybe splendida
Gill, Melvyn,Smrdel, Albin F.
, p. 47 - 58 (2007/10/03)
The tetrahydroanthraquinones (1S,3S)-austrocortirubin (7) and (1S,3S)-austrocortilutein (10) and the anthraquinones austrocortinin (13), xanthorin (14) and 3-methylxanthopurpurin 6-O-methyl ether (15) occur in the fungus Dermocybe splendida mainly in the form of their respective 8-O-β-D-gentiobiosides (26), (11), (16), (19) and (22) (gentiobiose = 6-O-β-D-glucopyranosyl-β-D-glucopyranose). The various gentiobiosides are isolated from lyophilized fruit bodies, separated by chromatography and characterized, in the main, as their acetyl derivatives by spectroscopic and chemical methods. A method for the selective cleavage of phenolic acetyl groups in peracetylated anthraquinone and tetrahydroanthraquinone glycosides is described. CSIRO 2000.
Pigments of Fungi. XXII Synthesis of (+/-) Austrocortirubin and Related Tetrahydroanthraquinones
Burns, Christopher J.,Gill, Melvyn
, p. 1447 - 1458 (2007/10/02)
The fungal tetrahydroanthraquinones austrocortirubin (1) and austrocortilutein (3) and their deoxy derivatives (2) and (4), respectively, are synthesized in racemic form from naphthopurpurin (6).
Regiospecific Addition of Monooxygenated Dienes to Halo Quinones
Boisvert, Louise,Brassard, Paul
, p. 4052 - 4059 (2007/10/02)
In spite of their decreased polarity with respect to previously studied electron-rich analogues, monooxygenated dienes also react regiospecifically with halo quinones.The corresponding adducts can easily be aromatized on silica gel to isomeric polysubstituted naphthoquinones of unambiguous structure and therefore provide ready access to substrates for subsequent regiospecific annulations.The scope of this approach is illustrated by advantageous syntheses of several natural products: chimaphilin, 6-methylalizarin, 6-methylxantopurpurin, and barleriaquinone.The adductscan also give rise to a series of products in which the oxygen function of the dienes is preserved as a hydroxyl group in the quinone.To this end adducts derived from 1-oxygenated dienes and halo quinones were oxidized effectively with Jones reagent while those obtained from the 2-oxygenated isomers responded better to manganese dioxide.Relative positions of substituens in the adducts were readily confirmed by comparison of some of the hydroxylated oxidation products with known compounds of unambiguous structure.The method is again illustrated by the ready synthesis of a number of natural products including plumbagin, soranjidiol, isochrysophanol and its 8-methyl ether, and isozyganein and its 5-methyl ether.
rac-Altersolanol A and Related Tetrahydroanthraquinones, Total Synthesis and Cytotoxic Properties
Krohn, Karsten,Markus, Helga,Kraemer, Hans Peter,Frank, Walter
, p. 1033 - 1042 (2007/10/02)
A key step in the first synthesis of racemic altersolanol A (1a) is the regioselective Diels-Alder reaction of 5-acetoxy-7-methoxy-1,4-naphthoquinone (12) with 2-methyl-1-(trimethylsiloxy)-1,3-butadiene (13) to afford the adduct 14.The structure of 14 has been confirmed by X-ray measurements.The hydroxy groups of ring A are introduced by epoxidation of 14 to 20, rearrangement to the allylic alcohol 26, epoxidation to 31, and opening of the oxirane to rac-altersolanol A (1a).Similar products were obtained starting from juglone (15).Many of the intermediate epoxidesand also compounds 42-44 show remarkable cytotoxicity in cell cultures but all compounds were too toxic to be useful as anticancer agents.
REGIOSPECIFIC ADDITIONS OF SOME SIMPLE DIENES TO HALOQUINONES
Boisvert, Louise,Brassard, Paul
, p. 2453 - 2456 (2007/10/02)
Some simple dienes have been shown to react regiospecifically with haloquinones; the adducts can be oxidized without loss of the oxygenated function or aromatized to a variety of natural products and useful intermediates.
