Off-odorous compounds produced by molds on oatmeal agar: Identification and relation to other growth characteristics

Börjesson, Thomas; Stöllman, U.; Schnürer, Johan

doi:10.1021/jf00035a053

Cited by 103 publications

(50 citation statements)

References 19 publications

(26 reference statements)

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“…3-Methylfuran and 1-octen-3-ol are commonly produced by mold (Borjesson et al, 1992;Borjesson et al, 1993;Korpi et al, 1997;Matysik et al, 2008). In human chamber studies, these compounds caused acute effects, such as objective and/or subjective signs of mild mucosal irritation of the eyes and airways due to exposure (Wålinder et al, 2005;Walinder et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

Relationship between selected indoor volatile organic compounds, so-called microbial VOC, and the prevalence of mucous membrane symptoms in single family homes

Araki

Kawai

Eitaki

et al. 2010

Science of The Total Environment

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Abstract:Micro-organisms are known to produce a range of volatile organic compounds, so-called microbial VOC (MVOC). Chamber studies where humans were exposed to MVOC addressed the acute effects of objective and/or subjective signs of mucosal irritation. However, the effect of MVOC on inhabitants due to household exposure is still unclear. The purpose of this epidemiological study was to measure indoor MVOC levels in single family homes and to evaluate the relationship between exposure to them and sick building syndrome (SBS). All inhabitants of the dwellings were given a self-administered questionnaire with standardized questions to assess their symptoms.Air samples were collected and the concentrations of eight selected compounds in indoor air were analyzed by gas chromatography/mass spectrometry -selective ion monitoring mode (GC/MS-SIM). The most frequently detected MVOC was 1-pentanol at a detection rate of 78.6% and geometric mean of 0.60 μg/m 3 . Among 620 participants, 120 (19.4%) reported one or more mucous symptoms; irritation of the eyes, nose, airway, or coughing every week (weekly symptoms), and 30 (4.8%) reported that the symptoms were home-related (home-related symptoms). Weekly symptoms were not associated with any of MVOC, whereas significant associations between home-related mucous symptoms and 1-octen-3-ol (per log 10 -unit: odds ratio (OR) 5.6, 95% confidence interval (CI): 2.1 to 14.8) and 2-pentanol (per log 10 -unit: OR 2.3, 95%CI: 1.0 to 4.9) were obtained after adjustment for gender, age, and smoking.Associations between home-related symptoms and 1-octen-3-ol remained after mutual adjustment. However, concentrations of the selected compounds in indoors were lower than the estimated safety level in animal studies. Thus, the statistically significant association between 1-octen-3-ol may be due to a direct effect of the compounds or the associations may be being associated with other offending compounds. Additional studies are needed to evaluate these possibilities.

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Section: Introductionmentioning

confidence: 99%

Relationship between selected indoor volatile organic compounds, so-called microbial VOC, and the prevalence of mucous membrane symptoms in single family homes

Araki

Kawai

Eitaki

et al. 2010

Science of The Total Environment

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“…1) are well-known as volatile odoriferous microbial metabolites. The two terpene alcohols are, in fact, the most frequently found secondary metabolites in actinomycetes (8,11,17), filamentous Cyanobacteria (18)(19)(20), and Myxobacteria (21), and they are also produced by a small number of fungi (22)(23)(24). The production of 2-methylisoborneol is associated with a characteristic scent, whereas albaflavenone, which was first isolated from cultures of a highly odoriferous Streptomyces albidoflavus species, is best described as earthy and camphor-like (25).…”

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confidence: 99%

Terpene synthases are widely distributed in bacteria

Yamada

Kuzuyama

Komatsu

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

441

366

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Odoriferous terpene metabolites of bacterial origin have been known for many years. In genome-sequenced Streptomycetaceae microorganisms, the vast majority produces the degraded sesquiterpene alcohol geosmin. Two minor groups of bacteria do not produce geosmin, with one of these groups instead producing other sesquiterpene alcohols, whereas members of the remaining group do not produce any detectable terpenoid metabolites. Because bacterial terpene synthases typically show no significant overall sequence similarity to any other known fungal or plant terpene synthases and usually exhibit relatively low levels of mutual sequence similarity with other bacterial synthases, simple correlation of protein sequence data with the structure of the cyclized terpene product has been precluded. We have previously described a powerful search method based on the use of hidden Markov models (HMMs) and protein families database (Pfam) search that has allowed the discovery of monoterpene synthases of bacterial origin. Using an enhanced set of HMM parameters generated using a training set of 140 previously identified bacterial terpene synthase sequences, a Pfam search of 8,759,463 predicted bacterial proteins from public databases and in-house draft genome data has now revealed 262 presumptive terpene synthases. The biochemical function of a considerable number of these presumptive terpene synthase genes could be determined by expression in a specially engineered heterologous Streptomyces host and spectroscopic identification of the resulting terpene products. In addition to a wide variety of terpenes that had been previously reported from fungal or plant sources, we have isolated and determined the complete structures of 13 previously unidentified cyclic sesquiterpenes and diterpenes.terpene synthase | bacteria | heterologous expression

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“…1), 2-methylisoborneol (2-MIB), geosmin, and albaflavenone are known as odorous and volatile microbial metabolites. The former two terpenoid alcohols are the most frequently found secondary metabolites of actinomycetes (3)(4)(5), filamentous cyanobacteria (6)(7)(8), myxobacteria (9), and fungi (10,11), and account for many odor problems encountered with freshwater or with fish (7,(12)(13)(14). Geosmin is also known to contribute to the characteristic earthy red beet flavor (15).…”

mentioning

confidence: 99%

Identification and functional analysis of genes controlling biosynthesis of 2-methylisoborneol

Komatsu

Tsuda

Ōmura

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

216

210

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To identify the genes for biosynthesis of the off-flavor terpenoid alcohol, 2-methylisoborneol (2-MIB), the key genes encoding monoterpene cyclase were located in bacterial genome databases by using a combination of hidden Markov models, protein-family search, and the sequence alignment of their gene products. Predicted terpene cyclases were classified into three groups: sesquiterpene, diterpene, and other terpene cyclases. Genes of the terpene cyclase group that form an operon with a gene encoding S-adenosyl-L-methionine (SAM)-dependent methyltransferase were found in genome data of seven microorganisms belonging to actinomycetes, Streptomyces ambofaciens ISP5053, Streptomyces coelicolor A3(2), Streptomyces griseus IFO13350, Streptomyces lasaliensis NRRL3382R, Streptomyces scabies 87.22, Saccharopolyspora erythraea NRRL2338, and Micromonospora olivasterospora KY11048. Among six microorganisms tested, S. ambofaciens, S. coelicolor A3(2), S. griseus, and S. lasaliensis produced 2-MIB but M. olivasterospora produced 2-methylenebornane (2-MB) instead. The regions containing monoterpene cyclase and methyltransferase genes were amplified by PCR from S. ambofaciens, S. lasaliensis, and Saccharopolyspora erythraea, respectively, and their genes were heterologously expressed in Streptomyces avermitilis, which was naturally deficient of 2-MIB biosynthesis by insertion and deletion. All exoconjugants of S. avermitilis produced 2-MIB. Full-length recombinant proteins, monoterpene cyclase and methyltransferase of S. lasaliensis were expressed at high level in Escherichia coli. The recombinant methyltransferase catalyzed methylation at the C2 position of geranyl diphosphate (GPP) in the presence of SAM. 2-MIB was generated by incubation with GPP, SAM, recombinant methyltransferase, and terpene cyclase. We concluded that the biosynthetic pathway involves the methylation of GPP by GPP methyltransferase and its subsequent cyclization by monoterpene cyclase to 2-MIB.genome mining ͉ methyltransferase ͉ monoterpene cyclase T erpenoid metabolites, monoterpenes, sesquiterpenes, and diterpenes, have been isolated from terrestrial and marine plants or from fungi, with only a relatively minor fraction from prokaryotes. Their compounds are used as antibiotics, hormones, flavor or odor constituents, and pigments. Some of them possess other physiologically or commercially important properties (1, 2). Three terpenoid compounds (Fig. 1), 2-methylisoborneol (2-MIB), geosmin, and albaflavenone are known as odorous and volatile microbial metabolites. The former two terpenoid alcohols are the most frequently found secondary metabolites of actinomycetes (3-5), filamentous cyanobacteria (6-8), myxobacteria (9), and fungi (10, 11), and account for many odor problems encountered with freshwater or with fish (7,(12)(13)(14). Geosmin is also known to contribute to the characteristic earthy red beet flavor (15). 2-MIB is related to the musty-earthy notes in Brie and Camembert cheese flavor (16). An ␣,␤-unsaturated sesquiterpene ketone, albaflavenone, ...

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Off-odorous compounds produced by molds on oatmeal agar: Identification and relation to other growth characteristics

Cited by 103 publications

References 19 publications

Relationship between selected indoor volatile organic compounds, so-called microbial VOC, and the prevalence of mucous membrane symptoms in single family homes

Relationship between selected indoor volatile organic compounds, so-called microbial VOC, and the prevalence of mucous membrane symptoms in single family homes

Terpene synthases are widely distributed in bacteria

Identification and functional analysis of genes controlling biosynthesis of 2-methylisoborneol

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