Structural and biosynthetic studies on eremophilenols related to the phytoalexin capsidiol, produced by Botrytis cinerea

Suárez, Ivonne; Lima, Gesiane da Silva; Conti, Rena M.; Pinedo, Cristina; Moraga, Javier; Barúa, Javier; Oliveira, Ana Lígia Leandrini de; Aleu, Josefina; Durán-Patrón, Rosa; Macı́as-Sánchez, Antonio J.; Hanson, James R.; Pupo, Mônica Tallarico; Hernández-Galán, Rosario; Collado, Isidro G.

doi:10.1016/j.phytochem.2018.06.010

Cited by 12 publications

(39 citation statements)

References 27 publications

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“…These molecules activates the host defence response against the microbe (Lim et al, 2017). Accompanied by this, the host plant produces phytoalexins (Suárez et al, 2018) and high protease activity (Asai and Shirasu, 2015). Primarily, such HR is activated at the response of high level of phyto-hormone (Großkinsky et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Phytohormonal cross-talk modulate Bipolaris sorokiniana (Scc.)interaction with Zea mays

Yousaf

Hussain

Hamayun

et al. 2019

Preprint

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16Besides acting as growth inducing molecule, Gibberellin (GA 3 ) also confers the compatibility 17 of microbial interactions with host. We inoculated 11 days old Z. mays seedlings grown under 18 hydroponic conditions and high GA 3 levels with Bipolaris sorokiniana (BIPOL) at the spore 19 density (SD) of OD 0.6 . The high level of GA 3 negatively affected the growth of the seedlings, 20 accompanied by the high level of stress deducing secondary metabolites (proline, total 21 flavanoids, phenylpropanoids, and glucosinolides). Moreover, high level of GA 3 produced a 22 hypersensitive response (HR) in the seedlings. The HR developed cross talks with IAA and 23 trans-zeatins and triggered higher production of hypersensitive inducing biomolecules. The 24 other HR co-related biological processes were demonstrated by high phytoalexins level and 25 high protease activities. Such activities ultimately inhibited the colonization of BIPOL on the 26 roots of maize seedlings. The products of the genes expressed at high GA 3 also conferred the 27 deterrence of BIPOL colonization at SD = OD 0.6 . Intriguingly, when we inhibited GA 3 28 biosynthesis in the seedlings with aerially sprayed uniconizole, prior to BIPOL treatment, the 29 BIPOL colonized and subsequently promoted the seedling growth. This low level of GA 3 30 after BIPOL treatment checked the high level of secondary metabolites and hypersensitivity 31 inducing molecules. The results, thus suggested that the aforementioned processes only 32 happened in the BIPOL at SD (OD 0.6 ), whereas the SD at lower levels (OD 0.2 or OD 0.4 ) 33 neither promoted the growth of uniconizole pre-treated seedlings nor produced HR in control 34 seedlings of maize plant.35

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Section: Introductionmentioning

confidence: 99%

Phytohormonal cross-talk modulate Bipolaris sorokiniana (Scc.)interaction with Zea mays

Yousaf

Hussain

Hamayun

et al. 2019

Preprint

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“…From a general point of view, these toxins are the virulence tools of B. cinerea, but we do not exclude the possibility that they may also act as modulators of QS. In strains of B. cinerea submitted to chemical stress, a QS effect was reported with several sporogenic eremophil-9-ene-1,11-diol derivatives in cultures after more than three weeks of fermentation [28]. The regulation of gene expression in Trichoderma arundinaceum by botrydial and botcinins has been previously established in a process named by the authors as "a metabolic dialogue", but, from a biochemical point of view, can be considered as a QS effect [29].…”

Section: Discussionmentioning

confidence: 96%

The Search for Quorum Sensing in Botrytis cinerea: Regulatory Activity of Its Extracts on Its Development

Rosero-Hernández

Echeverri

2020

Plants

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Botrytis cinerea is a phytopathogenic fungus that causes large crop and post-harvest losses. Therefore, new and effective strategies are needed to control the disease and to reduce resistance to fungicides. Modulating pathogenicity and virulence by manipulating microbial communication is a promising strategy. This communication mechanism, called Quorum Sensing (QS), has already been reported in bacteria and yeasts; however, it has not yet been studied in B. cinerea. To establish the existence of this biochemical process in B. cinerea, we prepared extracts at different growth times (D1-D12), which were applied to fresh cultures of the same fungi. The chemical analysis of the extracts obtained from several fermentations showed different compositions and biological activities. We confirmed the presence of several phytotoxins, as well as compounds 1-phenylethanol and 3-phenylpropanol. Day five extract (0.1%) inhibited conidia germination and elongation of germ tubes, day seven extract (1%) produced the greatest phytotoxic effect in tomato leaves, and day nine extract (0.1%) was a sporulation inhibitor. In contrast, the extracts from days 7, 9, and 12 of fermentation (0.1% and 0.01%) promoted pellet and biofilm formation. Sporulation was slightly induced at 0.01%, while at 0.1% there was a great inhibition. At the highest extract concentrations, a biocidal effect was detected, but at the lowest, we observed a QS-like effect, regulating processes such as filamentation, morphogenesis, and pathogenesis. These results of the biological activity and composition of extracts suggest the existence of a QS-like mechanism in B. cinerea, which could lead to new non-biocidal alternatives for its control through interference in the pathogenicity and virulence mechanisms of the fungi.

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“…Also, abscisic acid (2) which mediates leaf fall in plants (Marumo et al, 1982) and a family of recently reported eremophil-9-en-11-ols (3-13) Fig. 1, which have exhibited interesting activity as effectors involved in different life cycle processes of this pathogen (Pinedo et al, 2016;Suárez et al, 2018); and ii) polyketides, mainly botcinic (14) and botcineric (15) acids and their botcinin derivatives (16, 17), the second family of toxins involved in the infection mechanism (Tani et al, 2005(Tani et al, , 2006. Additionally, botrylactone ( 18), an intermediate in the biosynthesis of 14 and 15 (Moraga et al, 2011) and an interesting different group of polyketides called cinbotolides (19)(20)(21), stereochemically related to botcinins whose biological role is unknown, have been isolated from several strains of B. cinerea (Botubol et al, 2014;Moraga et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

“…We recently reported the biosynthesis of the above-mentioned family of eremophilen-11-ol derivatives by chemical induction with copper sulphate (5 ppm) of a silent biosynthetic pathway of B. cinerea. As a result, a significant number of (+)-4-epieremophil-9-en-11-ol (3-13) and some 11-hydroxyeremophil-1(10)-en-2-one (22-24) were characterized and reported (Pinedo et al, 2016;Suárez et al, 2018Suárez et al, , 2020. In vitro evaluation of the biological role of these metabolites indicated they were involved in the self-regulation of asexual spore production and enhanced the production of complex appressoria (infection cushions), showing for the first time that sesquiterpenoid metabolites participate in the regulation of infective structures.…”

Section: Introductionmentioning

confidence: 99%

“…In vitro evaluation of the biological role of these metabolites indicated they were involved in the self-regulation of asexual spore production and enhanced the production of complex appressoria (infection cushions), showing for the first time that sesquiterpenoid metabolites participate in the regulation of infective structures. Furthermore, these metabolites possess an enantiomeric carbon skeleton resembling that of phytoalexin capsidiol and suggesting that this family of compounds may be effectors that inhibit plant defences or modulate plant immunity to foster the infection process (Suárez et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

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The complemented mutant ΔBcstc7, in the STC7 of Botrytis cinerea led to the characterization of 11,12,13-tri-nor-eremophilenols derivatives

Suárez

Pinedo

Aleu³

et al. 2022

Phytochemistry

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Botrytis cinerea has high potential for the production of specialized metabolites. The recent resequencing of the genome of the B05.10 strain using PacBio technology and the resulting update of the Ensembl Fungi (2017) database in the genome sequence have been instrumental in identifying new genes that could be involved in secondary metabolism. Thus, a new sesquiterpene cyclase (STC) coding gene (Bcstc7) has been included in the gene list from this phytopathogenic fungus. We recently constructed the null and complement transformants in STC7 which enabled us to functionally characterize this STC. Deletion of the Bcstc7 gene abolished (+)-4-epieremophilenol biosynthesis, and could then be re-established by complementing the null mutant with the Bcstc7 gene. Chemical analysis of the complemented transformant suggests that STC7 is the principal enzyme responsible for the key cyclization step of farnesyl diphosphate (FDP) to (+)-4-epi-eremophil-9-en-11-ols.A thorough analysis of the metabolites produced by two wild-type strains, B05.10 and UCA992, and the complemented mutant compl ΔBcstc7 niaD , revealed the isolation and structural characterization of six 11,12,13-trinor-eremophilene derivatives, in addition to a large number of known eremophilen-11-ol derivatives. The structural characterization was carried out by extensive spectroscopic techniques. The biosynthesis of these compounds is explained by a retroaldol reaction or by dehydration and oxidative cleavage of C11-C13 carbons. This is the first time that this interesting family of degraded eremophilenols has been isolated from the phytopathogenous fungus B. cinerea.

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Structural and biosynthetic studies on eremophilenols related to the phytoalexin capsidiol, produced by Botrytis cinerea

Cited by 12 publications

References 27 publications

Phytohormonal cross-talk modulate Bipolaris sorokiniana (Scc.)interaction with Zea mays

Phytohormonal cross-talk modulate Bipolaris sorokiniana (Scc.)interaction with Zea mays

The Search for Quorum Sensing in Botrytis cinerea: Regulatory Activity of Its Extracts on Its Development

The complemented mutant ΔBcstc7, in the STC7 of Botrytis cinerea led to the characterization of 11,12,13-tri-nor-eremophilenols derivatives

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