Microbial Oxidation of (-)-α-pinene to Verbenol Production by Newly Isolated Strains

Rottava, Ieda; Cortina, Priscila F.; Zanella, Camila A.; Cansian, Rogério Luís; Toniazzo, Geciane; Treichel, Helen; Antunes, O. A. C.; Oestreicher, Enrique G.

doi:10.1007/s12010-010-8996-y

Cited by 21 publications

(19 citation statements)

References 29 publications

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“…and Candida piceae , the most frequently isolated microorganisms in D. valens surroundings (Lou et al ., ; Xu et al ., ), could reduce more than 40% of α‐pinene‐amended media within 24 h compared to controls. The metabolization of α‐pinene by yeasts and bacteria has also been reported in the utility of terpene for commercial bioprocessing (Wright et al ., ; Yoo et al ., ; Rottava et al ., ). The α‐pinene degradation by microorganisms may benefit microbes sensitive to α‐pinene, such as Ca.…”

Section: Discussionmentioning

confidence: 97%

Invasive bark beetle‐associated microbes degrade a host defensive monoterpene

Lü

Sun

2015

Insect Science

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Conifers respond to herbivore attack with defensive chemicals, which are toxic to both insects and their associated microorganisms. Microorganisms associated with insects have been widely reported to metabolize toxic chemicals, which may help both microorganisms and host insects overcome host conifer defense. Dendroctonus valens LeConte, an introduced exotic pest from North America to China, has killed millions of healthy pines. Alpha-pinene is the most abundant defensive monoterpene in Chinese Pinus tabuliformis. Although microorganisms associated with D. valens have already been investigated, little is known about their bioactivities when encountering host defensive monoterpenes. In this study, we evaluated the influences of different concentrations of α-pinene to D. valens and the three most frequently isolated yeasts and bacteria of D. valens, and further assayed microorganisms' capabilities to degrade α-pinene. Results showed that the gallery lengths and body weight changes of bark beetles were significantly affected by 6 mg/mL and 12 mg/mL of α-pinene applied in media compared to controls. The tolerance of experimental microorganisms to α-pinene varied depending on the microbial species. Two out of three yeast strains and all three bacterial strains degraded 20%-50% of α-pinene compared to controls in 24 h in vitro. The microorganisms capable of α-pinene degradation in vitro and their tolerance to high levels of α-pinene suggested that D. valens-associated microorganisms may help both microorganisms and the bark beetle overcome host α-pinene defense.

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Section: Discussionmentioning

confidence: 97%

Invasive bark beetle‐associated microbes degrade a host defensive monoterpene

Lü

Sun

2015

Insect Science

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“…Given that aa similarities between the CYP52P6, Meyerozyma , and the various bark beetle CYP450s are only in the range of 40–55%, there is potential for differing substrate specificities. It is also well known that trees, including members of the Ulmaceae, produce a large suite of related terpenes (including the highly abundant limonene) and that infecting fungi may be responsible for stimulating the tree’s overproduction of these compounds and/or they may directly degrade/transform many of them ( Duetz et al 2003 ; McLeod et al 2005 ; Rottava et al 2010 ).…”

Section: Resultsmentioning

confidence: 99%

Functional Annotation of the Ophiostoma novo-ulmi Genome: Insights into the Phytopathogenicity of the Fungal Agent of Dutch Elm Disease

Comeau

Dufour

Bouvet

et al. 2014

Genome Biology and Evolution

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The ascomycete fungus Ophiostoma novo-ulmi is responsible for the pandemic of Dutch elm disease that has been ravaging Europe and North America for 50 years. We proceeded to annotate the genome of the O. novo-ulmi strain H327 that was sequenced in 2012. The 31.784-Mb nuclear genome (50.1% GC) is organized into 8 chromosomes containing a total of 8,640 protein-coding genes that we validated with RNA sequencing analysis. Approximately 53% of these genes have their closest match to Grosmannia clavigera kw1407, followed by 36% in other close Sordariomycetes, 5% in other Pezizomycotina, and surprisingly few (5%) orphans. A relatively small portion (∼3.4%) of the genome is occupied by repeat sequences; however, the mechanism of repeat-induced point mutation appears active in this genome. Approximately 76% of the proteins could be assigned functions using Gene Ontology analysis; we identified 311 carbohydrate-active enzymes, 48 cytochrome P450s, and 1,731 proteins potentially involved in pathogen–host interaction, along with 7 clusters of fungal secondary metabolites. Complementary mating-type locus sequencing, mating tests, and culturing in the presence of elm terpenes were conducted. Our analysis identified a specific genetic arsenal impacting the sexual and vegetative growth, phytopathogenicity, and signaling/plant–defense–degradation relationship between O. novo-ulmi and its elm host and insect vectors.

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“…Verbenol and verbenone have previously been obtained by biotransformation of α-pinene with fungi [ 3 , 24 , 47 , 48 ] and bacteria [ 14 , 39 , 42 ], but in yields that were insufficient for industrial-scale production. In nature, these terpenoids are active components of Verbena triphylla plants, hyssop and rosemary oils, and are also known as pheromones of many insects and tree pests such as bark beetles.…”

Section: Resultsmentioning

confidence: 99%

Bioconversion of α-pinene by a novel cold-adapted fungusChrysosporium pannorum

Trytek

Jędrzejewski

Fiedurek

2015

Journal of Industrial Microbiology and Biotechnology

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The psychrotrophic fungus Chrysosporium pannorum A-1 is reported for the first time as a novel biocatalyst for O2-promoted oxidation of α-pinene. GC–MS analysis indicated that the main products of the reaction were compounds of a high commercial value, verbenol (1) and verbenone (2). Exponentially growing cells (days 2–3) were about twice as active as cells in the late stationary phase in terms of the total concentration of products. The highest yields of 1 and 2 were obtained using three-day and two-day-old mycelia and a medium containing 1.5 and 1 % (v/v) of the substrate, respectively. The optimal time for the bioconversion of α-pinene varied from 1 to 3 days, and depended on the kind of product desired. Most of 1 was produced at a relatively high concentration of 360 mg/L after the first six hours of α-pinene bioconversion [with an average yield of 69 mg/(g dry cell L aqueous phase)]. The oxidative activity of C. pannorum was identified across a wide temperature range of 5–25 °C, 10 °C being the optimum for the production of 1 and 20 °C for the production of 2. Sequential addition of the substrate during 3 days of the biotransformation resulted in a significant increase in 1 and 2 up to 722 and 176 mg/L, respectively, and a 2-fold enhancement of product yield as compared to bioconversion with a single supply of α-pinene. The concentration of total conversion products in the culture medium reached 1.33 g/L [which corresponded product yield of 225 mg/(g dry cell L)]. This represents probably the most promising result reported to date for oxidative biotransformation of α-pinene by a wild-type microorganism.Electronic supplementary materialThe online version of this article (doi:10.1007/s10295-014-1550-0) contains supplementary material, which is available to authorized users.

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Microbial Oxidation of (-)-α-pinene to Verbenol Production by Newly Isolated Strains

Cited by 21 publications

References 29 publications

Invasive bark beetle‐associated microbes degrade a host defensive monoterpene

Invasive bark beetle‐associated microbes degrade a host defensive monoterpene

Functional Annotation of the Ophiostoma novo-ulmi Genome: Insights into the Phytopathogenicity of the Fungal Agent of Dutch Elm Disease

Bioconversion of α-pinene by a novel cold-adapted fungusChrysosporium pannorum

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