A Volatile Metabolite of Actinomycetes, 2-Methylisoborneol

Gerber, Nancy N.

doi:10.7164/antibiotics.22.508

Cited by 139 publications

(81 citation statements)

References 7 publications

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“…Despite neither 2-MIB nor geosmin having any known adverse biological and pathological effects, the offensive odor and taste of these compounds may lead to psychosomatic effects, such as headaches, stress, or stomach upsets (Young et al 1996;Lauderdale et al 2004;Giglio et al 2011). 2-MIB (1,2,7,7-tetramethyl-exo-bicyclo[2,2,1]heptan-2-ol), an alicyclic tertiary alcohol, is a crystalline solid with a strong musty odor, which was first isolated from three Streptomyces and one Actinomadura species by Gerber (Gerber 1969;Newcombe et al 2002). Later, it was found in cyanobacteria (Tabachek and Yurkowski 1976), fungi (Fravel et al 2002), and myxobacteria (Dickschat et al 2007).…”

Section: Introductionmentioning

confidence: 99%

2-Methylisoborneol production characteristics of Pseudanabaena sp. FACHB 1277 isolated from Xionghe Reservoir, China

Zhang

Zheng

et al. 2016

J Appl Phycol

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The cyanobacterium Pseudanabaena sp. FACHB 1277, a 2-methylisoborneol (2-MIB) producer isolated from Xionghe Reservoir, was identified by molecular biological methods based on the 16S rDNA sequence. Pseudanabaena sp. FACHB 1277 is a planktonic freshwater species with relatively high 2-MIB per cell density value (7.76 × 10 ). The effects of temperature and light intensity on 2-MIB production of Pseudanabaena sp. FACHB 1277 were investigated. Of the six temperatures tested, 10, 15, 20, 25, 30, and 35°C, the maximum total 2-MIB per cell density and minimum cell density were observed at 10°C, while the total 2-MIB and dissolved 2-MIB (including extracellular and dissolved intracellular 2-MIB) increased with increasing temperature. . The present study indicates that increasing temperature could favor the conversion of bound intracellular to dissolved 2-MIB, while increasing light intensity stimulates the release of dissolved intracellular 2-MIB into the environment.

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Section: Introductionmentioning

confidence: 99%

2-Methylisoborneol production characteristics of Pseudanabaena sp. FACHB 1277 isolated from Xionghe Reservoir, China

Zhang

Zheng

et al. 2016

J Appl Phycol

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“…Their attempts to assign a structure to the isolated odor constituent failed;, however, when the neutral alcohol resisted oxidative degradation or other conventional chemical modification. The first modern studies of volatile bacterial terpenes were carried out some 75 years later by Gerber and Lechevalier (2) and Gerber (3)(4)(5)(6)(7), who speculated that the characteristic odor of cultures of Actinomycetales microorganisms, which are widely distributed in soil, might be caused by volatile terpenes. In addition to determining the structure of Berthelot's geosmin, shown to be a C 12 degraded sesquiterpene alcohol (and giving it its name, which means earth odor) (2, 3), Gerber (4) also isolated and determined the structures of the methylated monoterpene 2-methylisoborneol as well as several other cyclic sesquiterpenes produced by streptomycetes (5-7).…”

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Terpene synthases are widely distributed in bacteria

Yamada

Kuzuyama

Komatsu

et al. 2014

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

440

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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“…An ␣,␤-unsaturated sesquiterpene ketone, albaflavenone, was isolated from highly odorous Streptomyces culture and is an unusual odorous metabolite with antibacterial activity (17). The structures of both 2-MIB and geosmin originally isolated from actinomycetes were determined by Gerber (18,19) and Medsker et al (20). Geosmin is a degraded sesquiterpenoid alcohol, and biochemical and molecular genetic studies of its biosynthesis have been carried out in actinomycete strains Streptomyces coelicolor A3 (2) (21) and Streptomyces avermitilis (22).…”

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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.

215

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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A Volatile Metabolite of Actinomycetes, 2-Methylisoborneol

Abstract: During the past five years we have isolated geosmin, trans-1, 10-dimethyl-£n2«s-9-deca-

Cited by 139 publications

References 7 publications

2-Methylisoborneol production characteristics of Pseudanabaena sp. FACHB 1277 isolated from Xionghe Reservoir, China

2-Methylisoborneol production characteristics of Pseudanabaena sp. FACHB 1277 isolated from Xionghe Reservoir, China

Terpene synthases are widely distributed in bacteria

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

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