Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C18 13-Hydroxy, C1810-Hydroxy, and C1914-Hydroxy Unsaturated Fatty Acids

Rosanna Cardillo; Giovanni Fronza; Claudio Fuganti; Piero Grasselli; Andrea Mele; Domenica Pizzi; Gianna Allegrone; Massimo Barbeni; Antonella Pisciotta

doi:10.1021/jo00018a001

Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C₁₈ 13-Hydroxy, C₁₈10-Hydroxy, and C₁₉14-Hydroxy Unsaturated Fatty Acids

Rosanna Cardillo, Giovanni Fronza, Claudio Fuganti, Piero Grasselli, Andrea Mele, Domenica Pizzi, Gianna Allegrone, Massimo Barbeni, Antonella Pisciotta

Research output: Contribution to journal › Article › peer-review

Abstract

(S)-δ-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)- 10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-γ-dodecanolide. When (S)-homocoriolic acid (3) was fed to C. suaveolens, γ-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to fi, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.

Original language	English
Pages (from-to)	5237-5239
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	56
Issue number	18
DOIs	https://doi.org/10.1021/jo00018a001
Publication status	Published - 1 Aug 1991
Externally published	Yes

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Cardillo, R., Fronza, G., Fuganti, C., Grasselli, P., Mele, A., Pizzi, D., Allegrone, G., Barbeni, M., & Pisciotta, A. (1991). Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C₁₈ 13-Hydroxy, C₁₈10-Hydroxy, and C₁₉14-Hydroxy Unsaturated Fatty Acids. Journal of Organic Chemistry, 56(18), 5237-5239. https://doi.org/10.1021/jo00018a001

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title = "Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C18 13-Hydroxy, C1810-Hydroxy, and C1914-Hydroxy Unsaturated Fatty Acids",

abstract = "(S)-δ-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)- 10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-γ-dodecanolide. When (S)-homocoriolic acid (3) was fed to C. suaveolens, γ-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to fi, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.",

author = "Rosanna Cardillo and Giovanni Fronza and Claudio Fuganti and Piero Grasselli and Andrea Mele and Domenica Pizzi and Gianna Allegrone and Massimo Barbeni and Antonella Pisciotta",

year = "1991",

month = aug,

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doi = "10.1021/jo00018a001",

language = "English",

volume = "56",

pages = "5237--5239",

journal = "Journal of Organic Chemistry",

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Cardillo, R, Fronza, G, Fuganti, C, Grasselli, P, Mele, A, Pizzi, D, Allegrone, G, Barbeni, M & Pisciotta, A 1991, 'Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C₁₈ 13-Hydroxy, C₁₈10-Hydroxy, and C₁₉14-Hydroxy Unsaturated Fatty Acids', Journal of Organic Chemistry, vol. 56, no. 18, pp. 5237-5239. https://doi.org/10.1021/jo00018a001

Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C₁₈ 13-Hydroxy, C₁₈10-Hydroxy, and C₁₉14-Hydroxy Unsaturated Fatty Acids. / Cardillo, Rosanna; Fronza, Giovanni; Fuganti, Claudio et al.
In: Journal of Organic Chemistry, Vol. 56, No. 18, 01.08.1991, p. 5237-5239.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C18 13-Hydroxy, C1810-Hydroxy, and C1914-Hydroxy Unsaturated Fatty Acids

AU - Cardillo, Rosanna

AU - Fronza, Giovanni

AU - Fuganti, Claudio

AU - Grasselli, Piero

AU - Mele, Andrea

AU - Pizzi, Domenica

AU - Allegrone, Gianna

AU - Barbeni, Massimo

AU - Pisciotta, Antonella

PY - 1991/8/1

Y1 - 1991/8/1

N2 - (S)-δ-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)- 10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-γ-dodecanolide. When (S)-homocoriolic acid (3) was fed to C. suaveolens, γ-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to fi, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.

AB - (S)-δ-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)- 10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-γ-dodecanolide. When (S)-homocoriolic acid (3) was fed to C. suaveolens, γ-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to fi, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.

UR - https://www.scopus.com/pages/publications/0025784904

U2 - 10.1021/jo00018a001

DO - 10.1021/jo00018a001

M3 - Article

SN - 0022-3263

VL - 56

SP - 5237

EP - 5239

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Stereochemistry of the Microbial Generation of δ-Decanolide, γ-Dodecanolide, and γ-Nonanolide from C₁₈ 13-Hydroxy, C₁₈10-Hydroxy, and C₁₉14-Hydroxy Unsaturated Fatty Acids

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