New Lipopeptides from the Caribbean Cyanobacterium Lyngbya majuscula

Jiménez, Jorge I.; Scheuer, Paul J.

doi:10.1021/np000462q

Cited by 100 publications

(64 citation statements)

References 20 publications

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“…Subsequently, the total synthesis of dragonamide A led to reassignment of the natural product as 35S based on comparisons of its NMR and optical rotation data with both synthetic enantiomers (35R and 35S). 18 NMR and optical rotation data for the dragonamide A that we have isolated closely matches those reported for both the natural product 16 and the 35S synthetic product, but differs significantly from the 35R synthetic product. 18 Therefore, we conclude that dragonamide A (3), dragonamide B (4), and dragomabin (2) all contain 2S-methyloct-7-ynoic acid.…”

Section: Resultssupporting

confidence: 79%

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Antimalarial Linear Lipopeptides from a Panamanian Strain of the Marine Cyanobacterium Lyngbya majuscula

et al. 2007

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As part of the Panama International Cooperative Biodiversity Groups (ICBG) project, two new (2, 4) and two known (1, 3) linear alkynoic lipopeptides have been isolated from a Panamanian strain of the marine cyanobacterium Lyngbya majuscula. Carmabin A (1), dragomabin (2), and dragonamide A (3) showed good antimalarial activity (IC 50 4.3, 6.0, and 7.7 μM, respectively) whereas the non-aromatic analog, dragonamide B (4), was inactive. The planar structures of all four compounds were determined by NMR spectroscopy in combination with mass spectrometry, and their stereoconfigurations were established by chiral HPLC and by comparison of their optical rotations and NMR data with literature values.Artemisinin Combination Treatments (ACTs) for falciparum malaria are currently the only first-line antimalarial drugs amenable to widespread use against all chloroquine-resistant malaria parasites. 1 However, their effective distribution to combat malaria in economically disadvantaged regions could require an annual global subsidy of $300-500 million. 2 Furthermore, in the event of successful widespread use of the artemisinins, the development of resistance to these drugs before effective replacements or alternatives are at hand is a cause for profound concern. Therefore, the development of new classes of antimalarial drugs remains an enormous challenge and is a focus of many collaborative research efforts, including the International Cooperative Biodiversity Groups project in Panama, which investigates Panamanian terrestrial plants, endophytes and marine organisms as sources of tropical disease treatments. 3 As part of this program, we have been investigating marine cyanobacteria as a source of antimalarial agents, and found that the organic extracts of a red Panamanian strain of the marine cyanobacterium Lyngbya majuscula were active against chloroquine-resistant Plasmodium falciparum. To the best of our knowledge, there are only three reports of marine cyanobacterial metabolites isolated with antimalarial activity. Most recently, members of our * To whom correspondence should be addressed. Tel: 541 737 5808. Fax: 541 737 3999. E-mail: kerry.mcphail@oregonstate.edu. Supporting Information Available: 1 H and 13 C NMR spectra in CDCl 3 for carmabin A (1), dragomabin (2), dragonamide A (3) and dragonamide B (4). Results and DiscussionThe organic extracts of two collections of L. majuscula from different sites in Bocas del Toro, Panama (2002 and2003) showed significant activity against chloroquine-resistant Plasmodium falciparum (IC 50 = 6 and 26 μg/mL). Crude fractionation by normal-phase vacuum-liquid chromatography (NP-VLC) of the most active collection from Isla Bastimentos (Bocas del Toro, 2002) produced two relatively polar fractions (100% EtOAc and 25% MeOH-EtOAc) with good antimalarial activity (<2 and 1 μg/mL, respectively). Solid-phase extraction (SPE) and reversed-phase HPLC of the 25% MeOH-EtOAc NP-VLC fraction yielded carmabin A (1) and dragomabin (2) as the active components.Structure elucidation of li...

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Section: Resultssupporting

confidence: 79%

“…(3). 16 A parallel investigation was undertaken of a small, biologically inactive 2003 Isla Bastimentos collection of red L. majuscula, which was collected separately due to its "fuzzy" appearance. Upon microscopic investigation, this "fuzzy" facade resulted from a thick coating of epiphytic chain diatoms on the cyanobacterial filaments.…”

Section: Resultsmentioning

confidence: 99%

Antimalarial Linear Lipopeptides from a Panamanian Strain of the Marine Cyanobacterium Lyngbya majuscula

et al. 2007

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“…Apramides A-B (44A-B) and D-E contained variably methylated 7-octanoic acid termini and had negligible bioactivity [435]. The related planar metabolites dragomabin (44C) [436], carmabin (44D) [437], and dragonamides A-B (44E-F) [436,438] are also known; 44A-C were isolated with 7-alkenoate and 42-keto lipid modifications, respectively. α-Methylation of the fatty amide group was (S) in each case (the original assignment for 44E was corrected by total synthesis).…”

Section: Acetylenic Lipopeptides and Cyclodepsipeptidesmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

296

228

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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“…Three polychlorinated metabolites, pseudodysidenin (5), nordysidenin (6), and dysidenamide (7) were identified from a marine free-living red cyanobacterium, Lyngbya majuscule, collected at Boca del Drago Beach, Bocas del Toro, Panama (Jiménez et al, 2001). Compounds 5-7 are closely related to dysidenin (4) and isodysidenin (8) isolated from Australian and New Guinean specimens of Dysidea herbacea, respectively.…”

Section: Acyclic Polypeptidesmentioning

confidence: 99%

“…Six structurally-related linear lipopeptides, including dragonamide A (11) (Jiménez et al, 2001), carmabin A (13), dragomabin (14) and dragonamide B (12) (Mcphail et. al., 2007), dragonamide C (15) and D (16) (Gunasekera et al, 2008a) (Sone et al, 1995).…”

Section: Acyclic Polypeptidesmentioning

confidence: 99%

Absolute Configuration and Biosynthesis of Pahayokolide A from Lyngbya sp. Strain 15-2 of the Florida Everglades

Liu¹

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New Lipopeptides from the Caribbean Cyanobacterium Lyngbya majuscula

Cited by 100 publications

References 20 publications

Antimalarial Linear Lipopeptides from a Panamanian Strain of the Marine Cyanobacterium Lyngbya majuscula

Antimalarial Linear Lipopeptides from a Panamanian Strain of the Marine Cyanobacterium Lyngbya majuscula

Biosynthesis and function of polyacetylenes and allied natural products

Absolute Configuration and Biosynthesis of Pahayokolide A from Lyngbya sp. Strain 15-2 of the Florida Everglades

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