The microbiological production of 10-Hydroxystearic acid from oleic acid

Wallen, Lowell L.; Benedict, R. G.; Jackson, Richard W.

doi:10.1016/0003-9861(62)90006-1

Cited by 143 publications

(63 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…strain 3266 in 1962 ( Fig. 1) (12). In the following years, many other strains were identified that were also able to convert OA into 10-HSA or to further oxidize it to 10-ketostearic acid (2,3,5,7).…”

mentioning

confidence: 99%

Oleate Hydratase Catalyzes the Hydration of a Nonactivated Carbon-Carbon Bond

et al. 2009

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Oleate Hydratase Catalyzes the Hydration of a Nonactivated Carbon-Carbon Bond

et al. 2009

View full text Add to dashboard Cite

show abstract

“…deed 1 0 -hydroxystearic acid was found as original constituent (not generated by hydrogenation) in tissue homogenates (H erold and Spiteller, 1996). We show in this communication that 10-hydroxy stearic acid is generated from oleic acid by water addition in a regio-and enantioselective reaction by bacteria (Wallen et a l, 1962;Niehaus and Schröpfer, 1965;Schröpfer, 1966;Yang et a l, 1993) introduced from the surrounding.…”

Section: Introductionmentioning

confidence: 84%

“…1 0 i?-hydroxystearic acid is a well known water addition product to oleic acid generated by bacte ria (Wallen et al, 1962), especially pseudomonades (Niehaus and Schröpfer, 1965;Wallen et al, 1962). Schröpfer has investigated this reaction in detail and determined the stereochemistry of the pro duct (Schröpfer and Bloch, 1965).…”

Section: Discussionmentioning

confidence: 99%

10-Hydroxystearic Acid - Identified after Homogenization of Tissue - Is Derived from Bacteria

Adam

Hannemann

Reiner

et al. 2000

Zeitschrift Für Naturforschung C

View full text Add to dashboard Cite

10-Hydroxystearic acid seems to be widely distributed in nature: Bacteria generate it by hydroxylation of oleic acid, but it was found also as constituent of plants, in cancer cell cultures and in mammalian tissue homogenates. Investigation of 10-hydroxystearic acid, obtained from mammalian tissue homogenates, revealed its identity with that of bacteria. Thus not 10-hydroxystearic acid is widely distributed in nature but its producers: bacteria. When biological material is processed in aqueous media, lipases are activated, these cleave membrane phospholipids. Thus liberated oleic acid is the substrate for widespread bacteria which are introduced into the media when the work up procedure is done in not sterile surrounding. The bacteria transform then oleic acid to 10R-hydroxystearic acid.

show abstract

“…A number of microbial systems that convert oleic acid to monohydroxy and dihydroxy fatty acids have been found (1,2,6,10,14,15,27). Bioconversion of polyunsaturated fatty acids, such as linoleic acid and ␣-and ␥-linolenic acids, has also been studied (10,22,28,30).…”

mentioning

confidence: 99%

Production of Novel Tetrahydroxyfuranyl Fatty Acids from α-Linolenic Acid by Clavibacter sp. Strain ALA2

Hosokawa¹,

Hou²,

Weisleder

2003

Appl Environ Microbiol

View full text Add to dashboard Cite

Previously, it was reported that a newly isolated microbial culture, Clavibacter sp. strain ALA2, produced trihydroxy unsaturated fatty acids, diepxoy bicyclic fatty acids, and tetrahydroxyfuranyl fatty acids ( ). In this study, we found that Clavibacter sp. strain ALA2 produced novel THFAs, including 13,16-dihydroxy-12-THFA, 15-epoxy-9(Z)-octadecenoic acid (13,16-dihydroxy-THFA), and 7,13,16-trihydroxy-12, 15-epoxy-9(Z)-octadecenoic acid (7,13,16-trihydroxy-THFA), from ␣-linolenic acid (9,12,15-octadecatrienoic acid). The chemical structures of these products were determined by gas chromatography-mass spectrometry and proton and 13 C nuclear magnetic resonance analyses. The optimum incubation temperature was 30°C for production of both hydroxyTHFAs. 13,16-Dihydroxy-THFA was detected after 2 days of incubation, and the concentration reached 45 mg/50 ml after 7 days of incubation; 7,13,16-trihydroxy-THFA was not detected after 2 days of incubation, but the concentration reached 9 mg/50 ml after 7 days of incubation. The total yield of both 13,16-dihydroxy-THFA and 7,13,16-trihydroxy-THFA was 67% (wt/wt) after 7 days of incubation at 30°C and 200 rpm. In previous studies, it was reported that Clavibacter sp. strain ALA2 oxidized the C-7, C-12, C-13, C-16, and C-17 positions of linoleic acid (n-6) into hydroxy groups. In this case, the bond between the C-16 and C-17 carbon atoms is saturated. In ␣-linolenic acid (n-3), however, the bond between the C-16 and C-17 carbon atoms is unsaturated. It seems that enzymes of strain ALA2 oxidized the C-12-C-13 and C-16-C-17 double bonds into dihydroxy groups first and then converted them to hydroxy-THFAs.

show abstract

The microbiological production of 10-Hydroxystearic acid from oleic acid

Cited by 143 publications

References 9 publications

Oleate Hydratase Catalyzes the Hydration of a Nonactivated Carbon-Carbon Bond

Oleate Hydratase Catalyzes the Hydration of a Nonactivated Carbon-Carbon Bond

10-Hydroxystearic Acid - Identified after Homogenization of Tissue - Is Derived from Bacteria

Production of Novel Tetrahydroxyfuranyl Fatty Acids from α-Linolenic Acid by Clavibacter sp. Strain ALA2

Contact Info

Product

Resources

About