Preparation of aroma compounds by microbial transformation of isophorone with Aspergillus niger.

Mikami, Yoichi; Fukunaga, Yumiko; Arita, Masatoshi; Obi, Yukiteru; Kisaki, Takuro

doi:10.1271/bbb1961.45.791

Cited by 16 publications

(12 citation statements)

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“…The same metabolites have also been reported previously as biotransformation products of isophorone by Aspergillus niger [6]. All the spectral data obtained in this study are in good agreement with the literature values.…”

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confidence: 91%

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Microbial Transformations of Isophorone by Alternaria alternata and Neurospora crassa

Kıran

Özşen

Çelik

et al. 2013

Natural Product Communications

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Isophorone (3,5,5-trimethyl-2-cyclohexen-1-one), a monoterpene, and the structurally related 1,8-cineole and camphor, have demonstrated a protective effect against cancer, biological activity against a variety of microorganisms, and anti-oxidant properties. The derivatization of isophorone is, therefore, an important field of xenobiochemistry, pharmacology and toxicology. The aim of this study was to obtain derivatives of isophorone through microbial biotransformation and evaluate the biotransformation metabolites as potential antimicrobial agents. Incubation of isophorone with the fungi Alternaria alternata and Neurospora crassa afforded 4α-hydroxy-and 7-hydroxy-isophorone as transformation metabolites. The antimicrobial activities of isophorone and the metabolites were evaluated in vitro both by using agar dilution and microdilution methods. However, no significant antibacterial activity was observed when compared with those of standard substances.

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supporting

confidence: 91%

“…Figure 2). The absolute configuration was determined by comparison of the sign of rotation between 4α-hydroxy-isophorone and the one reported by Mikami et al [6].…”

mentioning

confidence: 99%

Microbial Transformations of Isophorone by Alternaria alternata and Neurospora crassa

Kıran

Özşen

Çelik

et al. 2013

Natural Product Communications

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“…It is surprising to find (I) and (II) both as odour components in the secretions of flowers and insects, particularly since the butterflies (at least originally) are not sympatric with Buddleja. Oxoisophorone (I) is a widespread natural product of plants and is also known to be produced by microorganisms [17] along with the related cyclic ketones (II), (V) and (VI). (E,E)-aFarnesene represents the second main component in the odour bouquet of Buddleja, which besides benzylalcohol and benzaldehyde contains the monoterpenes (E)-and (Z)-ocimene, a-pinene, geraniol and ß-cyclocitral.…”

Section: Resultsmentioning

confidence: 99%

Volatile compounds from androconial organs of danaine and ithomiine butterflies

Schulz

Francke

Edgar

et al. 1988

Zeitschrift Für Naturforschung C

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Pyrrolizidine alkaloid derivatives are present in the androconial (male scent) organs of Prittwitzia hymenaea, Mechanitis isthmia veritabilis, Tithorea harmónia fúria (Lep., Ithomiinae), Amauris echeria and Euploea sylvester (Lep., Danainae). While the ithomiines contain the new pyrrolizidine alkaloid derivative methyl hydroxydanaidoate, the danaines contain the known derivatives danaidone and hydroxydanaidal. In addition, 2,2,6-trimethyl-2-cyclohexen-l,4-dione (oxoisophorone) and related terpenoids have been identified from Amauris, Euploea and Prittwitzia as well as from the flowers of Buddleja davidii (Loganiaceae). Three new naturally occurring bishomoterpenes as well as mono-and sesquiterpenes and aromatic compounds add to the formation of species specific blends in the scent organs of the butterflies.

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“…The latter is transformed further to 3,5,5-trimethyl-2-cyclohexene-1,4-dione (CLXVI) and 3,5,5-trimethylcyclohexane-1,4-dione (CLXVII), which are also used for tobacco flavoring (Mikami et al 1981b). …”

Section: Transformation Of Other Organic Compoundsmentioning

confidence: 99%

Biotransformations of organic compounds mediated by cultures of Aspergillus niger

Parshikov

Woodling

Sutherland

2015

Appl Microbiol Biotechnol

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Many different organic compounds may be converted by microbial biotransformation to high-value products for the chemical and pharmaceutical industries. This review summarizes the use of strains of Aspergillus niger, a well-known filamentous fungus used in numerous biotechnological processes, for biochemical transformations of organic compounds. The substrates transformed include monocyclic, bicyclic, and polycyclic aromatic hydrocarbons; azaarenes, epoxides, chlorinated hydrocarbons, and other aliphatic and aromatic compounds. The types of reactions performed by A. niger, although not unique to this species, are extremely diverse. They include hydroxylation, oxidation of various functional groups, reduction of double bonds, demethylation, sulfation, epoxide hydrolysis, dechlorination, ring cleavage, and conjugation. Some of the products may be useful as new investigational drugs or chemical intermediates.

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Preparation of aroma compounds by microbial transformation of isophorone with Aspergillus niger.

Cited by 16 publications

References 1 publication

Microbial Transformations of Isophorone by Alternaria alternata and Neurospora crassa

Microbial Transformations of Isophorone by Alternaria alternata and Neurospora crassa

Volatile compounds from androconial organs of danaine and ithomiine butterflies

Biotransformations of organic compounds mediated by cultures of Aspergillus niger

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