322. The biosynthesis of polyacetylenes. Part III. Polyacetylenes and triterpenes in Polyporus anthracophilus

Bu’Lock, J. D.; Allport, D. C.; Turner, W. B.

doi:10.1039/jr9610001654

Cited by 14 publications

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“…Circa 1960, Polyporus anthracophilus feeding experiments with [1-14 C]acetate showed labeling of the odd-numbered carbons in matricaria ester 3D (Fig. 5) [55]. A related experiment demonstrated the alternating [1-14 C]acetate labeling of nemotinic and odyssic acids (3F, 3G) from basidiomycete B.…”

Section: 13mentioning

confidence: 95%

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: 13mentioning

confidence: 95%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

297

228

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“…Investigations with the higher fungus Polyporus anthracophilus (3) showed that its polyacetylenes were in a dynamic state, their synthesis de novo accompanying their disappearance. The dry rot fungus Merulius lacrymans (4) produced about 30 mg of poly-PREPARATIONS OF PASSICOL 109 acetylenes per liter of culture fluid when grown on corn steep liquor, and the concentration of polyacetylenes was maximal 50 days after inoculation.…”

Section: Resultsmentioning

confidence: 99%

Passicol, an Antibacterial and Antifungal Agent Produced by Passiflora Plant Species: Preparation and Physicochemical Characteristics

Birner

Nicolls

1973

Antimicrob Agents Chemother

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An increased yield of the crude material with antibacterial and antifungal activity produced by Passiflora species was obtained by aerated bathing of cut rinds of banana passion fruit in water in rotating cylindrical bottles. The crude material was separated into several fractions by thin-layer chromatography with the use of silica gel and ethyl acetate-chloroform (2: 1). The fractions showing ultraviolet absorption maxima in the vicinity of 340, 358, and 375 to 377 nm were biologically active. The data indicate that the active material, here called "Passicol" for the first time, has characteristics of the polyacetylenic group of compounds. The activity can be preserved for a long time when crude material is stored in organic solvent in the dark at 6 C. Gentle bathing of the cut rinds of Passiflora in water in the presence of air and ethylene stimulated the formation of the active principle.As reported previously by Nicolls (8), the antifungal activity found in Passiflora species is constantly produced when the living tissue is wounded. For further investigation of the biological activity of the active principle produced by Passiflora, and possible physicochemical investigations, it was necessary to produce the active compound in greater quantity and higher concentration than in the initial work.For convenience of description, the name "Passicol" has been given here for the first time to the active substance. 24 hr by removing the diffusate and replacing it with an equal volume of fresh distilled water. The operation was continued for 14 to 16 days. The filtered (cotton gauze) diffusate was acidified with 12 N H2SO4 to a pH of 1 to 1.5 and was extracted with 0.35 volume of ethyl acetate by stirring for 5 to 10 min; it was then separated in a separating funnel and finally centrifuged. The organic extract was dried with anhydrous sodium sulfate and stored in the dark at 6 C. The pooled organic extract was concentrated on a rotating flask evaporator to about 2.5% of the original volume. When stored in the dark at 6 C, the crude concentrate has retained its activity for over 2 years. MATERIALS AND METHODSAs a pilot investigation of the possibility of readily increasing the scale of production, a glass column containing loosely packed cut rinds of P. mollissima was set up, and distilled water was percolated through the rinds at a rate sufficient to keep them bathed in fluid. The emerging fluid (total volume in the same ratio to rind weight was as used for the roller apparatus) was continuously recirculated. The level of activity detected in the resultant extract was satisfactory, but was inferior to the yield from the roller apparatus. Precise conditions for optimal yields by this percolation method were not pursued.Spectrophotometric assay. The ultraviolet (UV) spectrum of the ethyl acetate extract from the diffusate exhibited several maxima, and absorbance in these regions was in direct proportion to the biological activity of the extract. The peak at 375 nm was selected for measuring the activity by spectropho-L05

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The natural occurrence of unusual fatty acids Part 3. Acetylenic fatty acids

Diedrich

Henschel

1991

Nahrung

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Acetylenic compounds especially acetylenic fatty acids (Cl, to Cz1) were first of all identified in higher plants. Their structure is very different with regard to the number of the double and triple bonds per molecule, and the functional groups.The mechanism of the biogenesis and the influencing factors are not definitely clarified. A side pathway of the biogenesis of the saturated fatty acids is supposed. Various physiological effects of the acetylenic fatty acids are presented.

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322. The biosynthesis of polyacetylenes. Part III. Polyacetylenes and triterpenes in Polyporus anthracophilus

Cited by 14 publications

References 0 publications

Biosynthesis and function of polyacetylenes and allied natural products

Biosynthesis and function of polyacetylenes and allied natural products

Passicol, an Antibacterial and Antifungal Agent Produced by Passiflora Plant Species: Preparation and Physicochemical Characteristics

The natural occurrence of unusual fatty acids Part 3. Acetylenic fatty acids

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