Structure–activity relationship of neuritogenic spongean acetylene alcohols, lembehynes

Aoki, Shunji; Matsui, Kouhei; Wang, Hong; Murakami, Nobutoshi; Kobayashi, Mariko

doi:10.1016/s0040-4020(02)00519-7

Cited by 46 publications

(38 citation statements)

References 9 publications

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“…A photoaffinity probe based on 33J, [ 125 I]-azido-LB-18, specifically labeled in vivo a 30-kDa protein in Neuro 2A cells that is anticipated to be the target of 33J [357]. The presence of a (3R)-propargylic alcohol on a minimally C 18 alkyl chain were necessary for strong neuritogenic activity [358].…”

Section: Marine Fatty Acids Andmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

297

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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Section: Marine Fatty Acids Andmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

297

228

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“…[21] NMR experiments NMR experiments were performed on a 17.6 T Varian INOVA NMR spectrometer operating at a 1 H frequency of 750 MHz. The spectrometer was equipped with a gradient shielded 1 H/ 13 C/ 31 P probe and the control software was VNMRJ 1.1d.…”

Section: Experimental Synthesismentioning

confidence: 99%

Determination of the geometry of acetoxyendiynes and acetoxyenynes by NMR heteronuclear ¹³C¹H scalar couplings and ¹³C NMR chemical shifts. Structural assignment of the oxylipin natural products peyssonenynes A and B

Garcia

Martín-Pastor

Lera

et al. 2010

Magnetic Reson in Chemistry

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Solution NMR methods were used for the structural characterization of the acetoxyendiyne E/Z configuration of the marine natural products peyssonenynes A and B and their synthetic analogs derived from palmitic acid. The scarcity of protons in the proximity of the olefin precluded the determination of the double bond geometry using (1)H NMR methods that rely on proton-proton scalar couplings or experiments such as NOESY or ROESY. Long range (1)H-(13)C heteronuclear scalar couplings, (n)J(CH), measured with the 2D excitation sculptured indirect detection experiment (EXSIDE) proved useful and highly reliable for the analysis of the enol acetate geometry. In addition, it was found that the chemical shift of some carbon atoms in the proximity of the olefin was also sensitive to the double bond configuration of these molecules providing an even simpler way to determine their geometry. This protocol showed its robustness by similar analysis of simpler silyl-protected acetoxyenynes derived from fatty acids. These NMR experimental results and stereochemical predictions were rationalized by DFT calculations.

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“…As described herein, the 1,4-dialkyn-3-ol part, jointly to the stereochemistry at the hydroxy position, are implicated in the bioactivity of these hydroxylated polyacetylenes [31,32,33,38]. As described herein, the 1,4-dialkyn-3-ol part, jointly to the stereochemistry at the hydroxy position, are implicated in the bioactivity of these hydroxylated polyacetylenes [31,32,33,38].…”

Section: Studies In Natural Products Chemistrymentioning

confidence: 61%

“…Lembehyne A (19A) induced neurite outgrowth of rat pheochromocytoma PC12 cells at a minimal concentration of 2 mg/mL and induced neuritogenesis in mouse neuroblastoma Neuro 2A cells at 0.1 mg/mL (Fig. The presence of a (3R)-propargylic alcohol increased the neurogenic activity showing the importance of the stereochemistry of the hydroxyl group at C-3 [32]. In a structure-activity relationship study of lembehynes, several analogues with different long-chain parts were synthesized from suitable fatty acids.…”

Section: Haliclonamentioning

confidence: 99%

Marine Polyacetylenes: Distribution, Biological Properties, and Synthesis

Legrave¹,

Fahmi²,

Mendili³

et al. 2015

Studies in Natural Products Chemistry

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Structure–activity relationship of neuritogenic spongean acetylene alcohols, lembehynes

Cited by 46 publications

References 9 publications

Biosynthesis and function of polyacetylenes and allied natural products

Biosynthesis and function of polyacetylenes and allied natural products

Determination of the geometry of acetoxyendiynes and acetoxyenynes by NMR heteronuclear ¹³C¹H scalar couplings and ¹³C NMR chemical shifts. Structural assignment of the oxylipin natural products peyssonenynes A and B

Marine Polyacetylenes: Distribution, Biological Properties, and Synthesis

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Structure–activity relationship of neuritogenic spongean acetylene alcohols, lembehynes

Cited by 46 publications

References 9 publications

Biosynthesis and function of polyacetylenes and allied natural products

Biosynthesis and function of polyacetylenes and allied natural products

Determination of the geometry of acetoxyendiynes and acetoxyenynes by NMR heteronuclear 13C1H scalar couplings and 13C NMR chemical shifts. Structural assignment of the oxylipin natural products peyssonenynes A and B

Marine Polyacetylenes: Distribution, Biological Properties, and Synthesis

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Determination of the geometry of acetoxyendiynes and acetoxyenynes by NMR heteronuclear ¹³C¹H scalar couplings and ¹³C NMR chemical shifts. Structural assignment of the oxylipin natural products peyssonenynes A and B