Polyacetylenes in araliaceae: Their chemistry, biosynthesis and biological significance

Hansen, Lulu Anne; Boll, Per M.

doi:10.1016/s0031-9422(00)85468-0

Cited by 161 publications

(104 citation statements)

References 52 publications

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“…families are strong indicators of the interrelationships between species and have been used extensively for chemotaxonomy [12,169,170]. One trend, the presence of a 3-hydroxy or 3-oxohept-1-ene-4,6-diyne ω subunit, is characteristic for all compounds from Araliaceae (Fig.…”

Section: ω-Modification Of Acetylenic Fatty Acids-compounds Found Ubimentioning

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: ω-Modification Of Acetylenic Fatty Acids-compounds Found Ubimentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

297

228

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“…[1][2][3][4] Thus, much attention has been paid to the development of efficient procedures for the synthesis of diyne derivatives. An oxidative alkyne-alkyne homocoupling reaction is one of the most widely used procedures for the synthesis of symmetrical diyne derivatives.…”

mentioning

confidence: 99%

“…In addition, no reaction proceeded with a physical mixture of Cu(OH) 2 1 ]ethynylbenzene (1 a', deuterium content at the terminal position: 98 %, 0.32 m, 1.5 mL) with Cu(OH) x /TiO 2 at 20 8C for 5 h resulted in a decrease in the deuterium content (98!57 %). In contrast, the H/D-exchange reaction hardly proceeded with CuCl 2 /TiO 2 or TiO 2 under the same conditions.…”

mentioning

confidence: 99%

Heterogeneously Catalyzed Efficient Alkyne–Alkyne Homocoupling by Supported Copper Hydroxide on Titanium Oxide

Oishi

Katayama

Yamaguchi

et al. 2009

Chemistry A European J

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The supported copper hydroxide on titanium oxide (Cu(OH)x/TiO2) has been shown to act as an efficient heterogeneous catalyst for the oxidative alkyne–alkyne homocoupling. A wide variety of alkynes including aromatic, aliphatic, double‐bond‐containing, and silylacetylene derivatives were selectively converted into the corresponding diyne derivatives in high yields without any additives such as bases.

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“…Falcarinol (8) and 10,12-octadecdiynoic acid (12) were reported to be phytoalexins [14][15][16][17][18]. Its age-dependent increase supports the idea that older ginseng requires a higher concentration of falcarinol to prevent the ginseng root from being harmed by phytopathogenic fungi in the soil.…”

Section: Discussionmentioning

confidence: 90%

Analysis of Nonpolar Components from Ginseng of Different Ages

Zhang¹,

Lyu²,

Liu³

et al. 2013

AJPS

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Nonpolar components from ginseng of different ages were extracted and analysed using a GC-MS technique to determine their chemical compositions. In total, 23 ingredients, mostly aliphatic compounds, were identified. The compounds extracted included 10,12-octadecadiynoic acid (12.81% -36.43%), falcarinol (4.95% -36.79%), n-hexadecanoic acid (0.60% -9.70%), 9,12-octadecadienoic acid, ethyl ester (0.33% -5.63%), 5,7-dodecadiyn-1,12-diol (0.97% -3.85%), (Z)-9-octadecenamide (2.66% -5.38%) and (Z,Z)-9,12-octadecadienoic acid (0.46% -5.27%). The two major diyne compositions, falcarinol (8) and 10,12-octadecadiynoic acid (12), were the predominant components (over 50%) of the nonpolar extract of older ginseng. Moreover, the 10,12-octadecadiynoic acid obviously accumulated as the ginseng grew. Sitosterol, a universal metabolite in higher plants, makes up 55.80% of the content of 6-year-old ginseng, but markedly decreases in older ginseng. There was not much difference between the extracts of 8, 10, 12 and 16-year ginsengs, but the extracts of 6-year-old ginseng were distinctive.

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Polyacetylenes in araliaceae: Their chemistry, biosynthesis and biological significance

Cited by 161 publications

References 52 publications

Biosynthesis and function of polyacetylenes and allied natural products

Biosynthesis and function of polyacetylenes and allied natural products

Heterogeneously Catalyzed Efficient Alkyne–Alkyne Homocoupling by Supported Copper Hydroxide on Titanium Oxide

Analysis of Nonpolar Components from Ginseng of Different Ages

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