Microbial conversion of β‐ionone by immobilized <i>Aspergillus niger</i> in the presence of an organic solvent

Sode, Koji; Karube, Isao; Araki, Reiko; Mikami, Yoichi

doi:10.1002/bit.260330915

Cited by 25 publications

(12 citation statements)

References 15 publications

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“…The reaction system contained 40 µM heteranthin and 0.05 µg purified protein. (Sode et al, 1989;Larroche et al, 1995;Yamazaki et al, 1998), Streptomyces (Lutz-Wahl et al, 1998), Geotrichum spp. (Maldonado-Robledo et al, 2003), Thricosporon asahii (Rodríguez-Bustamante et al, 2006, 2009, and other filamentous fungi, yeasts, and bacteria (Uenojo and Pastore, 2010).…”

Section: Discussionmentioning

confidence: 96%

Identification of Bioproducts Generated Enzymatically by Cell-Free Extracts ofSaccharomyces cerevisiaefrom Cells Grown in the Presence or Absence of Heteranthin

2015

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Ditaxis heterantha seeds are a source of the apocarotenoid heteranthin (methyl 3-oxo-12´-apo-ε-caroten-12´-oate). Saccharomyces cerevisiae can degrade, utilize this apocarotenoid, and produce seven aromas (3-oxo-α-ionone, 3-oxo-α-ionol, 3-oxo-7,8-dihydro-α-ionone, 3-hydroxy-β-cyclocitral, safranal, 4-oxo-isophorone, and isophorone). However, nothing is known about the enzymology of this process or the steps to produce them. In the present work, cell-free extracts of S. cerevisiae from cells grown in the presence or absence of heteranthin were evaluated for its degradation. When grown in heteranthin, cell-free extracts produced the same seven aromas, while in its absence only four aromas (3-hydroxy-β-cyclocitral, safranal, 4-oxo-isophorone, and isophorone) were detected. Polyacrylamide gel electrophoresis (PAGE) of cell extracts previously grown in heteranthin yielded a protein band of 27.6 kDa able to cleave this apocarotenoid. Band intensity was proportional to the heteranthin concentration and was not present in extracts from cultures grown in the absence of heteranthin. A purified sample of 27.6 kDa protein produced 3-oxo-α-ionone from heteranthin as the only reaction product, suggesting oxidation of the apocarotenoid at the 9-10 position of its moiety. Maximal enzymatic production of 3-oxo-α-ionone was observed at pH 5.5 and 35 • C with activation energy of 7.23 kJ mol −1 . The enzyme exhibited a K m value of 27 µM for heteranthin and a V max of 135 µmoles min −1 mg −1 . Our findings clearly supported the presence of at least two ways for heteranthin degradation in S. cerevisiae: one that is probably committed to the heteranthin-induced synthesis of 3-oxo-α-ionol, and the other, constitutive, likely committed to safranal production.

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Section: Discussionmentioning

confidence: 96%

Identification of Bioproducts Generated Enzymatically by Cell-Free Extracts ofSaccharomyces cerevisiaefrom Cells Grown in the Presence or Absence of Heteranthin

2015

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“…Sesquiterpene류는 monoterpene류보다 구조가 다양하고 항 진균, 진통 등 다양한 생리활성에 효과가 높다고 알려져 있다 (Sode et al, 1989). 이러한 이유로 본 연구 결과에서도 높은 항 진균 및 항산화 효과를 유도하였을 것으로 사료된다.…”

Section: 편백나무(Chamaecyparis Obtuse)는 상록침엽교목으로 일본 이 원산지이며 1904년에 도입되어 unclassified

Antifungal and Antioxidant Activities of Volatile Organic Compounds Generated During the Drying Process of Chamaecyparis obtuse

Seo¹,

Lee²

2012

The Korean Journal of Microbiology

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In this study, we evaluated antifungal and antioxidant activities of condensed liquid of volatile organic compounds generated during the drying process of Chamaecyparis obtuse. Condensed liquid of volatile organic compounds were extracted with hexane and ethyl acetate, respectively. The extracts were used for antifungal activity at range from 100 to 500 mg/L Antifungal activity of extracts increased as the extracts concentration increased, the activity against tested dermatophytes was high at 500 mg/L. Among extract solvents, antifungal activity was higher at hexane extract than the ethyl acetate. Especially, the antifungal activity against Trichophyton rubrum was higher than other tested dermatophytes. Antioxidant activity was 90% above 25 mg/L regardless of the extractive solvents, while the hexane extract showed high antioxidant activity below 25 mg/L. Major compounds of hexane extract were torreyol, alpha-cadinol, and tau-cadinol. However, major compounds of ethyl acetate extract were alpha-amorphene, alpha-cadinol, and gamma-cadinene.

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“…Geranylgeraniol은 diterpene류의 일종으로 생물체에서 다양한 terpenoids 합성에 관여하는 물질이며 식물체 내에서 carotenoids, gibberellins, tocopherols, chlorophylls의 합성을 위 한 전구 물질이다. 이 외에도 geranylgeraniol의 진통작용에 대한 연구가 보고된 바 있다 (Sode et al, 1989). Isoborneol은 2개의 고리환을 가지고 있는 terpenoid로 다양한 정유의 구성성분이며, Jacobson에 의해 천연 살충제로 알려져 있다 (Jacobson, 1990).…”

Section: Fig 2 Resistance Of Fomitopsis Pinicola (A) and Coriolus Vunclassified

Biotransformation of trans,trans-farnesol by Wood Rot Fungi

Kim¹,

Lee²,

Park³

et al. 2012

The Korean Journal of Microbiology

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In this study, we screened and evaluated possibility of wood rot fungi as biocatalyst for biotransformation of sesquiterpenes. Screening were performed to select the most promising microorganisms with ability to biotransformation the substrate trans,trans-fanesol. Trans,trans-farnesol which is synthesized precursor of sesquiterpenes was used for resistance test on 19 of wood rot fungi. From the 19 tested wood rot fungi, 5 were selected by resistance test on different concentration of trans,trans-fanesol. Biotransformation was performed with selected wood rot fungi on liquid culture. The metabolites detected by GC-MS analysis were nerolidol for Laetiporus sulphureus var. miniatus (jungh) Imaz and eicosane for Coriolus versicolor (L.Fr) Prlar and isoborneol for Fomitopsis pinicola and isocyclocitral for Lampteromyces japonicas. As the results, wood rot fungi could be potential biocatalyst for biotransformation of sesquiterpenes.

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Microbial conversion of β‐ionone by immobilized Aspergillus niger in the presence of an organic solvent

Cited by 25 publications

References 15 publications

Identification of Bioproducts Generated Enzymatically by Cell-Free Extracts ofSaccharomyces cerevisiaefrom Cells Grown in the Presence or Absence of Heteranthin

Identification of Bioproducts Generated Enzymatically by Cell-Free Extracts ofSaccharomyces cerevisiaefrom Cells Grown in the Presence or Absence of Heteranthin

Antifungal and Antioxidant Activities of Volatile Organic Compounds Generated During the Drying Process of Chamaecyparis obtuse

Biotransformation of trans,trans-farnesol by Wood Rot Fungi

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