Cis-heptadeca-1,9-diene-4,6-diyne-3,8-diol, an antifungal polyacetylene from carrot root tissue

https://doi.org/10.1016/0048-4059(78)90039-5Get rights and content

Abstract

A compound isolated from root tissue extracts of Daucus carota L. showed antifungal activity towards Mycocentrospora acerina and Cladosporium cladosporioides. It was identified with the aid of u.v. and infrared spectroscopy, nuclear magnetic resonance and mass spectrometry as cis-heptadeca-1,9-diene-4,6-diyne-3,8-diol with the trivial name of falcarindiol. A concentration gradient in carrot roots varying from 93 μg/g fresh wt in periderm and pericyclic parenchyma to 2 μg/g in xylem parenchyma was demostrated. The ED50 for inhibition of germination of chlamydospores of M. acerina was 31·8 μg/ml. The rôle of this compound in disease resistance is discussed.

References (15)

There are more references available in the full text version of this article.

Cited by (62)

  • Quantifying biochemical quality parameters in carrots (Daucus carota L.) - FT-Raman spectroscopy as efficient tool for rapid metabolite profiling

    2016, Food Chemistry
    Citation Excerpt :

    Among them, bis-acetylenic oxylipins (polyacetylenes) were reported to have a multitude of bioactivities including bitter taste, allergenic, antibacterial, antimycobacterial and antifungal activities (Dawid, Dunemann, Schwab, Nothnagel, & Hofmann, 2015). In addition, polyacetylenes are discussed as potential health-promoting and therapeutic agents due to their anti-tumor and anti-inflammatory properties (Garrod, Lewis, & Coxon, 1978; Olsson & Svensson, 1996; Zaini, Brandt, Clench, & Le Maitre, 2012; Zidorn et al., 2005). Recent studies identified new phenylpropanoids in carrots as bitter taste compounds, comprising laserine and 2-epilaserine and their oxides (Schmiech, Uemura, & Hofmann, 2008; Yang, Yan, & Lu, 2008).

  • Stability of falcarinol type polyacetylenes during processing of Apiaceae vegetables

    2013, Trends in Food Science and Technology
    Citation Excerpt :

    However, the proceeding section provides a very brief overview of this area to contextualise the subject matter. PAs of the falcarinol-type tend to be present constitutively, indicating that they act primarily as pre-infectional compounds in the species producing them, although some increase can be observed in response to infections (Garrod, Lewis, & Coxon, 1978; Harding & Heale, 1980; Harding & Heale, 1981; Olsson and Svensson, 1996). Such as microbial attack, a disease state, or abiotic stress during plant growth and subsequent processing (e.g., UV irradiation, metal salts, detergents) (Lund & White, 1990; Ebel, 1986; Minto & Blacklock, 2008).

  • Secondary metabolites and defense: The story continues

    2012, Physiological and Molecular Plant Pathology
  • Inhibitory effects of the carrot metabolites 6-methoxymellein and falcarindiol on development of the fungal leaf blight pathogen Alternaria dauci

    2012, Physiological and Molecular Plant Pathology
    Citation Excerpt :

    In this paper, relatively strong inhibition of A. dauci development was observed in the presence of the polyacetylene falcarindiol, with IC50 nephelometric values ranging from 34 to 102 μM (Fig. 5). By comparison, in M. acerina, the falcarindiol concentration causing 50% inhibition of chlamydospore germination was 122 μM [9,10]. This value is nearly equivalent to the IC50 obtained with the least susceptible A. dauci strain in our study, while keeping in mind that the IC50 values were determined by different methods in both studies.

  • Antilisterial activity of carrots: Effect of temperature and properties of different carrot fractions

    2010, Food Research International
    Citation Excerpt :

    Additionally, the antimicrobial activity has been reported not to be linked to phenolic compounds but presumably to apolar compounds, such as dodecanoic acid and methyl esters of dodecanoic and pentadecanoic acids (Babic et al., 1994). Falcarinol and falcarindiol, polyacetylenic constituents of carrots with antimicrobial properties (Garrod, Lewis & Coxon, 1978; Garrod, Lea & Lewis, 1979; Hansen, Purup & Christensen, 2003), have been discounted due to their location in the carrot peel, which was removed during the preparation of shredded carrots that have shown higher antilisterial activity than whole ones (Beuchat & Brackett, 1990; Nguyen-the & Lund, 1991). Finally, 6-methoxymellein, a phytoalexin accumulated in carrot tissue after infection or other types of stress (Amin, Kurosaki& Nishi, 1988; Kurosaki & Nishi, 1983), has been suggested due to its wide antimicrobial spectrum, although there is no evidence of its toxicity against L. monocytogenes.

View all citing articles on Scopus
View full text