Thiophene interconversions in Tagetes patula hairy-root cultures

Arroo, R. R. J.; Jacobs, John; Dekoning, E.A.H.; Dewaard, M.; Westerlo, E. van de; Galen, P.M. van; Swolfs, A.E.M.; Klunder, A. J. H.; Croes, A. F.; Wullems, G. J.

doi:10.1016/0031-9422(94)00763-j

Cited by 20 publications

(6 citation statements)

References 21 publications

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“…Thiophenes are derived from polyacetylenes by thiophene ring formation (Arroo et al . ). Less polar C12‐thiophenes, such as BBT (5‐(3‐buten‐1‐ynyl)‐2,20‐bithienyl) extracted from roots of Tagetes (French marigold), can be considered moderately volatile (Szarka et al .…”

Section: Vocs From Plant Roots and Rhizomesmentioning

confidence: 99%

Biogenic volatile emissions from the soil

Peñuelas

Asensio

Tholl

et al. 2014

Plant Cell & Environment

326

327

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Volatile compounds are usually associated with an appearance/presence in the atmosphere. Recent advances, however, indicated that the soil is a huge reservoir and source of biogenic volatile organic compounds (bVOCs), which are formed from decomposing litter and dead organic material or are synthesized by underground living organism or organs and tissues of plants. This review summarizes the scarce available data on the exchange of VOCs between soil and atmosphere and the features of the soil and particle structure allowing diffusion of volatiles in the soil, which is the prerequisite for biological VOC-based interactions. In fact, soil may function either as a sink or as a source of bVOCs. Soil VOC emissions to the atmosphere are often 1-2 (0-3) orders of magnitude lower than those from aboveground vegetation. Microorganisms and the plant root system are the major sources for bVOCs. The current methodology to detect belowground volatiles is described as well as the metabolic capabilities resulting in the wealth of microbial and root VOC emissions. Furthermore, VOC profiles are discussed as non-destructive fingerprints for the detection of organisms. In the last chapter, belowground volatile-based bi-and multitrophic interactions between microorganisms, plants and invertebrates in the soil are discussed.

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Section: Vocs From Plant Roots and Rhizomesmentioning

confidence: 99%

Biogenic volatile emissions from the soil

Peñuelas

Asensio

Tholl

et al. 2014

Plant Cell & Environment

326

327

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“…The demethylation of bithienyl derivatives has been explored by feeding [ 35 S]-labeled 11F, 11Ca, 11Cb, and 11Cl and it was found that methyl cleavage occurs prior to the formation of the second thiophene ring (Fig. 14C) [190]. Additionally, 11F was not incorporated into α-T (11Ch), bringing into question the order of sulfur additions leading to this important metabolite.…”

Section: Sulfurmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

291

233

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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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“…However, Margl et al ( 2001 ) stated that a polyketide-like biosynthesis via a carbocyclic intermediate cannot be excluded. The monothiophene 2-(but-3-en-l-ynyl)-5-(penta-1,3-diynyl)-thiophene, present in small amounts in Tagetes patula hairy roots, was found to be the precursor of all bithienyls that had been described for this species but not of α-terthienyl (Arroo et al 1995 ). They found that 5′-methyl-5-(3-buten-lynyl)-2,2′-bithienyl was converted into (5′-but-3-en-l-ynyl-[2,2′]bithiophenyl-5-yl)-methyl acetate, probably via (5′-but-3-en-l-ynyl-[2,2′] bithiophenyl-5-yl)-methanol.…”

Section: Root Phytochemicalsmentioning

confidence: 94%

“…Plasmolytic and autolytic changes resulted in plasma membrane breakage and in cell wall aberrations. 5-(4-hydroxy-1-butynyl)-2,2′-bithienyl (BBTOH), the thiophene from the roots, was found to be biocidal to Fusarium oxysporum (Arroo et al 1995 ).…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Tagetes patula

Lim¹

2013

Edible Medicinal and Non-Medicinal Plants

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Thiophene interconversions in Tagetes patula hairy-root cultures

Cited by 20 publications

References 21 publications

Biogenic volatile emissions from the soil

Biogenic volatile emissions from the soil

Biosynthesis and function of polyacetylenes and allied natural products

Tagetes patula

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