Isolation of an α-methylene-γ-butyrolactone derivative, a toxin from the plant pathogen Lasiodiplodia theobromae

He, Guowei; Matsuura, Hideyuki; Yoshihara, Toshio

doi:10.1016/j.phytochem.2004.08.011

Cited by 26 publications

(18 citation statements)

References 11 publications

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“…and Fusarium sp. [ 1 , 2 ] while a toxin compound produced by Lasiodiplodia theobromae was identified as (3S,4R)-3-carboxy-2-methylene-heptan-4-olide [ 25 ]. In this study, although no OTA was detected in longan pulp, it is necessary to further identify other toxic compounds possible present due to latent pathogen infection.…”

Section: Resultsmentioning

confidence: 99%

A Comparative Identification of Ochratoxin A in Longan Fruit Pulp by High Performance Liquid Chromatography-Fluorescence Detection and Electron Spray Ionization-Mass Spectrometry

Xie

Yang

et al. 2010

Molecules

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Harvested longan (Dimocarpus longan Lour.) fruit are susceptible to decay caused by both bacterial and fungal infections. Ochratoxin A (OTA) is a kind of mycotoxin produced by a number of fungi. In this study, OTA was extracted from longan fruit pulp by 80% methanol and then loaded on C-18 solid-phase extraction columns. The extract solution was then analyzed by high-performance liquid chromatography - fluorescence detection (HPLC-FD) and an electron spray ionization-mass spectrometry (ESI-MS), respectively. The HPLC-FD analysis showed that a compound similar to OTA might exist in longan fruit pulp, but further analysis by the ESI-MS method demonstrated that OTA was not present in the longan pulp, indicating that the presence of OTA in longan fruit pulp detected by the HPLC-FD analysis needed to be confirmed by the ESI-MS method.

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Section: Resultsmentioning

confidence: 99%

A Comparative Identification of Ochratoxin A in Longan Fruit Pulp by High Performance Liquid Chromatography-Fluorescence Detection and Electron Spray Ionization-Mass Spectrometry

Xie

Yang

et al. 2010

Molecules

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“…In order to better understand the role of secondary metabolites in the virulence of L. theobromae , investigations were conducted testing in vitro the effect of abiotic factors such as temperature [ 13 , 19 ] and nutrient availability [ 22 ] on the extrolites production. Moreover, studies have compared secondary metabolites produced by L. theobromae in liquid medium with the ones obtained after an incubation period of the fungus in the host tissue, and metabolites detected in this latter condition were named vivotoxins by He and co-workers [ 23 ].…”

Section: Secondary Metabolitesmentioning

confidence: 99%

“…A strain of L. theobromae isolated from rotted mango branches is the first producer of (3 S ,4 R )-3-carboxy-2-methylene-heptan-4-olide ( 52 ), together with its well-known isomer decumbic acid ( 53 ). Furthermore, 52 is also considered a vivotoxin because it was isolated from bananas incubated with the fungal mycelium [ 23 ].…”

Section: Secondary Metabolitesmentioning

confidence: 99%

Secondary Metabolites of Lasiodiplodia theobromae: Distribution, Chemical Diversity, Bioactivity, and Implications of Their Occurrence

Salvatore

Alves

Andolfi

2020

Toxins

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Lasiodiplodia theobromae is a plant pathogenic fungus from the family Botryosphaeriaceae that is commonly found in tropical and subtropical regions. It has been associated with many hosts, causing diverse diseases and being responsible for serious damages on economically important crops. A diverse array of bioactive low molecular weight compounds has been described as being produced by L. theobromae cultures. In this review, the existing literature on secondary metabolites of L. theobromae, their bioactivity, and the implications of their occurrence are compiled. Moreover, the effects of abiotic factors (e.g., temperature, nutrient availability) on secondary metabolites production are highlighted, and possible avenues for future research are presented. Currently, a total of 134 chemically defined compounds belonging to the classes of secondary metabolites and fatty acids have been reported from over 30 L. theobromae isolates. Compounds reported include cyclohexenes and cyclohexenones, indoles, jasmonates, lactones, melleins, phenols, and others. Most of the existing bioactivity studies of L. theobromae metabolites have assessed their potential phytotoxic, cytotoxic, and antimicrobial activities. In fact, its host adaptability and its ability to cause diseases in plants as well as in humans may be related to the capacity to produce bioactive compounds directly involved in host–fungus interactions.

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“…Moreover, some Botryosphaeriaceae isolated from declining grapevines produce phytotoxic metabolites belonging to different classes of natural compounds . So far, literature has been lacking about secondary metabolite production of Lasiodiplodia isolates from grapevines, except for L. theobromae which biosynthesizes several lipophilic and hydrophilic metabolites showing biological activities . Recently, three new jasmonates, lasiojasmonates A – C, and the two natural 16‐ O ‐acetylbotryosphaeriolactones A and C produced by L .…”

Section: Introductionmentioning

confidence: 99%

Lasiolactols A and B Produced by the Grapevine Fungal Pathogen Lasiodiplodia mediterranea

Andolfi

Basso

Giambra

et al. 2016

Chemistry & Biodiversity

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A strain of Lasiodiplodia mediterranea, a fungus associated with grapevine decline in Sicily, produced several metabolites in liquid medium. Two new dimeric γ‐lactols, lasiolactols A and B (1 and 2), were characterized as (2S*,3S*,4R*,5R*,2′S*,3′S*,4′R*,5′R*)‐ and (2R*,3S*,4R*,5R*,2′R*,3′S*,4′R*,5′R*)‐(5‐(4‐hydroxymethyl‐3,5‐dimethyl‐tetrahydro‐furan‐2‐yloxy)‐2,4‐dimethyl‐tetrahydro‐furan‐3‐yl]‐methanols by IR, 1D‐ and 2D‐NMR, and HR‐ESI‐MS. Other four metabolites were identified as botryosphaeriodiplodin, (5R)‐5‐hydroxylasiodiplodin, (–)‐(1R,2R)‐jasmonic acid, and (–)‐(3S,4R,5R)‐4‐hydroxymethyl‐3,5‐dimethyldihydro‐2‐furanone (3 – 6, resp.). The absolute configuration (R) at hydroxylated secondary C‐atom C(7) was also established for compound 3. The compounds 1 – 3, 5, and 6, tested for their phytotoxic activities to grapevine cv. Inzolia leaves at different concentrations (0.125, 0.25, 0.5, and 1 mg/ml) were phytotoxic and compound 5 showed the highest toxicity. All metabolites did not show in vitro antifungal activity against four plant pathogens.

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Isolation of an α-methylene-γ-butyrolactone derivative, a toxin from the plant pathogen Lasiodiplodia theobromae

Cited by 26 publications

References 11 publications

A Comparative Identification of Ochratoxin A in Longan Fruit Pulp by High Performance Liquid Chromatography-Fluorescence Detection and Electron Spray Ionization-Mass Spectrometry

A Comparative Identification of Ochratoxin A in Longan Fruit Pulp by High Performance Liquid Chromatography-Fluorescence Detection and Electron Spray Ionization-Mass Spectrometry

Secondary Metabolites of Lasiodiplodia theobromae: Distribution, Chemical Diversity, Bioactivity, and Implications of Their Occurrence

Lasiolactols A and B Produced by the Grapevine Fungal Pathogen Lasiodiplodia mediterranea

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