Distomadines A and B, Novel 6-Hydroxyquinoline Alkaloids from the New Zealand Ascidian, Pseudodistoma aureum.

Abstract

Alkaloids Alkaloids U 0600Distomadines A and B, Novel 6-Hydroxyquinoline Alkaloids from the New Zealand Ascidian, Pseudodistoma aureum. -Distomadines A and B, (I), tetracyclic guanidine-containing hydroxyquinoline alkaloids, are isolated from the plant and characterized by spectroscopic methods and chemical derivatization. Distomadine A (Ia) is obtained as an optically active, fluorescent yellow powder while distomadine B (Ib) is obtained as a 1:2 mixture of (Ib) and 2'-deoxyadenosine. Distomadine A displays mild antifungal activity but is inactive in a range of antitumor, antiviral, anti-inflammatory and antimycobacterial assays. In addition, three known methyl esters of fatty acids are also identified. Eicosapentaenoic acid methyl ester shows mild cytotoxicity to a non-malignant cell line. -(PEARCE, A. N.; APPLETON, D. R.; BABCOCK, R. C.; COPP*, B. R.; Tetrahedron Lett. 44 (2003) 20, 3897-3899; Dep. Chem., Univ. Auckland, Auckland, N. Z.; Eng.) -H. Hoennerscheid 33-203

Biologically active quinoline and quinazoline alkaloids part I

“…Distomadine B ( 197 ) and its analog (+)‐distomadine A ( 198 ) (Fig. ) with furo[3′,4′:5,6]pyrano[2,3,4‐ de ]quinoline skeletons were isolated from Pseudodistoma aureum . Compound 198 showed moderate antifungal activity toward C. albicans , but was inactive in various antitumor, antiviral, anti‐inflammatory, and antimycobacterial assays.…”

Cu(OTf)2-Catalyzed Intramolecular Radical Cascade Reactions for the Diversity-Oriented Synthesis of Quinoline-Annulated Polyheterocyclic Frameworks

“…T he privileged polyheterocyclic compounds containing a quinoline fragment are widely present in numerous natural products and bioactive molecules, and such compounds have proven to possess a wide variety of pharmacological properties, such as anticancer, antiviral, and antiangiogenic activity (Figure 1). 1−3 Representative quinoline-containing natural products are trisphaeridine (an alkaloid isolated from amaryllidaceae species with potential antitumor activity), 4 camptothecin (a topoisomerase inhibitor isolated from camptotheca acuminate with remarkable anticancer activity), 5 fagaronine (a benzophenanthridine alkaloid found in zanthoxylum zanthoxyloides with potential antimalarial activity), 6 and distomadine A (a tetracyclic alkaloid isolated from Pseudodistoma aureum with antifungal activity) 7 (Figure 1A). In addition, quinoline-containing polyheterocyclic fragments are also prevalent in bioactive molecules, such as torin 1 (a potent and selective mTOR inhibitor), 8 topovale (a Top1 targeting antitumor drug), 9 KuFal194 (a highly potent and selective DYRK1A inhibitor), 10 and QL47 (a potent, selective and irreversible BTK inhibitor) 11 (Figure 1B).…”