Microbial transformations of terpenoids with 1-p-menthene skeleton

Abraham, Wolf‐Rainer; Stumpf, Burghard; Kieslich, Klaus

doi:10.1007/bf00266280

Cited by 37 publications

(26 citation statements)

References 8 publications

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“…Its biotransformation by Diplodia gossypina and Corynespora cassiicola resulted in the hydroxylation of positions 1 and 2 (Abraham et al, 1986). With Aspergillus cellulosae the same diol mentioned above was produced as well as (+)-isopiperitone, (+)-peryllil alcohol (2) and (+)-cis-carveol (Noma, 1992).…”

Section: R(+)limonenementioning

confidence: 74%

Biotransformation of the monoterpene, limonene, by Fusarium verticilloides

Oliveira

Strapasson

2000

Braz. arch. biol. technol.

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Section: R(+)limonenementioning

confidence: 74%

Biotransformation of the monoterpene, limonene, by Fusarium verticilloides

Oliveira

Strapasson

2000

Braz. arch. biol. technol.

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“…The authors suggested that the limonene-1,2-trans-diol is formed by hydrolysis of the initially formed epoxide. The specific activity was not reported, but sufficed for the production of 900 g of the (1S, 2S)-trans-diol from d-limonene in a 70-l reactor within 96 h (Abraham et al 1986b;Kieslich et al 1986). The same screening of 800 strains also yielded a variety of other less regiospecific fungi converting d-limonene to mixtures of multiple oxidation products at relatively low rates (Kieslich et al 1986).…”

Section: Bioconversions By Fungi and Yeastsmentioning

confidence: 99%

Biotransformation of limonene by bacteria, fungi, yeasts, and plants

Duetz

Bouwmeester²,

Beilen

et al. 2003

Appl Microbiol Biotechnol

231

147

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The past 5 years have seen significant progress in the field of limonene biotransformation, especially with regard to the regiospecificity of microbial biocatalysts. Whereas earlier only regiospecific biocatalysts for the 1,2 position (limonene-1,2-diol) and the 8-position (a-terpineol) were available, recent reports describe microbial biocatalysts specifically hydroxylating the 3-position (isopiperitenol), 6-position (carveol and carvone), and 7-position (perillyl alcohol, perillylaaldehyde, and perillic acid). The present review also includes the considerable progress made in the characterization of plant P-450 limonene hydroxylases and the cloning of the encoding genes.

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“…Compound 1 gave essentially identical 1 H and 13 C NMR data as one of these products, which is (+)-(1R)-2-oxo-3-p-menthenol). However, optical rotation data obtained for 1 suggest that it is the enantiomer of the compound described in the literature (1 gave [α] D -85º (c 0.455, CHCl 3 ), while the literature compound gave [α] D + 92.9 (c 1.00, CHCl 3 , [9]. Based on this notion, the absolute configuration around C-1 in compound 1 was indirectly deduced to be "S".…”

Section: (-)-(1s)-2-oxo-3-p-menthenol (1)mentioning

confidence: 87%

Terpenoids of the Heartwood of Chamaecyparis Nootkatensis

Khasawneh¹,

Karchesy²

2012

AJOC

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Two monoterpenes and two sesquiterpene diols were isolated and identified for the first time from the methanol extract of the heartwood of Alaska yellow cedar (AYC) tree. The two monoterpenes were identified as (1S)-2-oxo-3-p-menthenol (1) and (4R)-4-hydroxy-4-isopropylcyclohex-1-enecarboxylic acid (2). The two sesquiterpenes were identified as (5S, 7R, 10R, 11R)-eudesm-4(14)-ene-11, 12-diol (kudtdiol, 3) and (4R, 5S, 7R)-1(10)-eremophilene-11,12-diol (tedonodiol, 4). Structures for these compounds were confirmed on the basis of spectroscopic data and in comparison with related known compounds. In addition, 10 other previously known AYC constituents were also isolated from the methanol extract of the heartwood of AYC including nootkatin, chamic acid, chaminic acid, carvacrol, methyl carvacrol, chanootin, nootkatene, nootkatone, valencene and valencene-13-ol.

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Microbial transformations of terpenoids with 1-p-menthene skeleton

Cited by 37 publications

References 8 publications

Biotransformation of the monoterpene, limonene, by Fusarium verticilloides

Biotransformation of the monoterpene, limonene, by Fusarium verticilloides

Biotransformation of limonene by bacteria, fungi, yeasts, and plants

Terpenoids of the Heartwood of Chamaecyparis Nootkatensis

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