Biotransformation of constituents of essential oils by germinating wheat seed

Dudai, Nativ; Larkov, Olga; Putievsky, E.; Lerner, H. R.; Ravid, Uzi; Lewinsohn, Efraim; Mayer, Alfred M.

doi:10.1016/s0031-9422(00)00333-2

Cited by 52 publications

(50 citation statements)

References 18 publications

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“…Almost all strains produced the reduction product (S)-citronellol (12) in high yields ( > 50%) and, in some cases, in quantitative yields (i.e., 2A17, 1B20, and 2D15) as previously observed with various microorganisms [12] [13] [20] [21], germinating wheat seed [22], and tissue cultures of Petrosellinum crispum [16]. Many strains gave also the oxidation product (S)-citronellic acid (11), although in lower yields (4 -62%).…”

Section: Results Andsupporting

confidence: 63%

Biotransformations of Terpenes by Fungi from Amazonian Citrus Plants

Rueda

Guerrini

Giovannini

et al. 2013

Chemistry & Biodiversity

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The biotransformations of (RS)-linalool (1), (S)-citronellal (2), and sabinene (3) with fungi isolated from the epicarp of fruits of Citrus genus of the Amazonian forest (i.e., C. limon, C. aurantifolia, C. aurantium, and C. paradisiaca) are reported. The more active strains have been characterized, and they belong to the genus Penicillium and Fusarium. Different biotransformation products have been obtained depending on fungi and substrates. (RS)-Linalool (1) afforded the (E)- and (Z)-furanlinalool oxides (7 and 8, resp.; 39 and 37% yield, resp.) with Fusarium sp. (1D2), 6-methylhept-5-en-2-one (4; 49%) with F. fujikuroi, and 1-methyl-1-(4-methypentyl)oxiranemethanol (6; 42%) with F. concentricum. (S)-Citronellal (2) gave (S)-citronellol (12; 36-76%) and (S)-citronellic acid (11; 5-43%) with Fusarium species, while diastereoisomeric p-menthane-3,8-diols 13 and 14 (20 and 50% yield, resp.) were obtained as main products with Penicillium paxilli. Finally, both Fusarium species and P. paxilli biotransformed sabinene (3) to give mainly 4-terpineol (19; 23-56%), and (Z)- and (E)-sabinene hydrates (17 (3-21%) and 18 (11-17%), resp.).

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Section: Results Andsupporting

confidence: 63%

Biotransformations of Terpenes by Fungi from Amazonian Citrus Plants

Rueda

Guerrini

Giovannini

et al. 2013

Chemistry & Biodiversity

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“…Em geral, concentrações de vanilina acima de 1 g/L inibem o crescimento de microrganismos. Neste caso, torna-se difícil encontrar vanilina no sistema microbiano, mas pode-se encontrar álcool vanílico ou ácido vanílico 21 . A álcool vanílico oxidase do fungo Penicillium simplicissimum foi descrita como um catalisador da oxidação de álcool vanílico para vanilina 22,23 .…”

Section: Introductionunclassified

Obtenção de vanilina: oportunidade biotecnológica

Daugsch¹,

Pastore²

2005

Quím. Nova

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“…Monoterpenes are one of the largest and most important groups of secondary metabolites found in essential oils, and some of them are phytotoxic, making them potential bioherbicides (Abrahim et al 2000;Dudai et al 2000a). Monoterpenes are inhibitors of seed germination and plant growth (Abrahim et al 2000;Dudai et al 2000a;Einhellig and Leather 1988;Fischer 1986;Gouda et al 2016;Grana et al 2012;Reynolds 1987;Weidenhamer et al 1994).…”

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confidence: 99%

Herbicidal Activity of Monoterpenes Is Associated with Disruption of Microtubule Functionality and Membrane Integrity

et al. 2016

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Aromatic plants and their volatile compounds affect seed germination and plant growth, and therefore hold potential for agriculture uses as plant growth regulators and bioherbicides. In the present study 17 major monoterpenes were selected, and their mechanisms of plant toxicity were elucidated using transgenic Arabidopsis thaliana at various growth stages. Microtubulin and the plant cell membrane were identified as the focal targets through which phytotoxicity and herbicidal activity acted. Variability in monoterpene mechanisms was observed. Limonene and (+ )-citronellal had strong antimicrotubule efficacy, whereas citral, geraniol, (−)-menthone, (+)-carvone, and (−)-citronellal demonstrated moderate antimicrotubule efficacy. Pulegone, (−)-carvone, carvacrol, nerol, geranic acid, (+)/(−)-citronellol, and citronellic acid lacked antimicrotubule capacity. An enantioselective disruption of microtubule assembly was recorded for (+)/(−)-citronellal and (+)/(−)-carvone. The (+) enatiomers were more potent than their (−) counterparts. Citral, limonene, carvacrol, and pulegone were also tested for phytotoxicity and herbicidal activity. Pulegone had no detectable effect on microtubules or membranes. Citral disrupted microtubules but did not cause membrane damage. Carvacrol lacked a detectable effect on microtubules but incited membrane leakage, and limonene disrupted microtubules and membrane leakage. Therefore, only limonene was herbicidal at the tested concentrations. In planta quantification of residues revealed that citral was biotransformed into nerol and geraniol, and limonene was converted into carvacrol, which could explain its dual capacity with respect to microtubules and membrane functionality. The results obtained are an important added value to commercial efforts in selecting appropriate aromatic plants to be sources of bioherbicidal compounds for sustainable weed management with a limited potential for herbicide resistance evolution in weed populations.

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Biotransformation of constituents of essential oils by germinating wheat seed

Cited by 52 publications

References 18 publications

Biotransformations of Terpenes by Fungi from Amazonian Citrus Plants

Biotransformations of Terpenes by Fungi from Amazonian Citrus Plants

Obtenção de vanilina: oportunidade biotecnológica

Herbicidal Activity of Monoterpenes Is Associated with Disruption of Microtubule Functionality and Membrane Integrity

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