Madangolide and Laingolide A, Two Novel Macrolides from Lyngbya bouillonii (Cyanobacteria)

Abstract

Two new macrolide derivatives, madangolide (2) and laingolide A (3), have been isolated from the cyanobacterium Lyngbya bouillonii, collected in Papua New Guinea. Their structures (without stereochemistry) have been established by detailed high-field 1D and 2D NMR studies and, in the case of 3, by comparison with the spectroscopic data of laingolide (1), previously isolated from the same organism.

Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A

“…In the apratoxins, these domains include highly methylated amino acids joined by proline ester and thiazoline moieties to the novel ketide 3,7-dihydroxy-2,5,8,8-tetramethylnonanoic acid. Similar ketide motifs (e.g., 7-dihydroxy-2,5,8,8-tetramethylnonanoic acid) have been encountered in isolates of the cyanobacterium Lyngbya bouillonii (10,11).…”

A Review Study on Macrolides Isolated from Cyanobacteria

“…Three novel nitrogen-containing macrolides, laingolide ( 62 ) [57], laingolide A ( 63 ) and madangolide ( 64 ) [58], have been identified from the marine cyanobacterium Lyngbya bouillonii harvested in Laing Island, Papua-New Guinea (Figure 12). The structures of these macrolides ( 62–64 ) contain a lactone ring of 15, 15 and 17 members, respectively [58].…”

Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon

“…Lyngbouilloside ( 1 ) is a glycosidic macrolide isolated by Gerwick et al (Tan et al, 2002) from the cyanobacteria Lyngbya bouillonii (Hoffmann and Demoulin, 1991), which also produce several other structurally intriguing natural products including the tetrapeptide lyngbyapeptin (Klein et al, 1999a,b), several macrolides such as laingolide, laingolide A, and madangolide (Klein et al, 1996, 1999a,b), and various lyngbouilloside analogs such as lyngbyaloside ( 2 ) (Klein et al, 1997), lyngbyaloside B ( 3 ) (Luesch et al, 2002; Matthew et al, 2010), and lyngbyaloside C ( 4 ) (Matthew et al, 2010; Figure 1). The structure of lyngbouilloside was determined after exhaustive 1D and 2D NMR analysis, HR-FABMS, IR, and UV absorption experiments, which unveiled the presence of the pendant dienyl side chain, the 14-membered ring lactone, the presence of hydroxyl groups, the chair conformation of the tetrahydropyran ring and the relative configuration of the stereogenic centers in the aglycon portion of the natural product.…”