Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet

Natural hydroxy fatty acids are relevant starting materials for the production of a number of industrial fine chemicals, such as different high-value flavour ingredients. Only a few of the latter hydroxy acid derivatives are available on a large scale. Therefore, their preparation by microbial hydration of unsaturated fatty acids, affordable from vegetable oils, is a new biotechnological challenge. In this study, we describe the use of the probiotic bacterium Lactobacillus rhamnosus (ATCC 53103) as whole-cell biocatalyst for the hydration of the most common unsaturated octadecanoic acids, namely oleic acid, linoleic acid, and linolenic acid. We discovered that the addition of the latter fatty acids to an anaerobic colture of the latter strain, during the early stage of its exponential growth, allows the production of the corresponding mono-hydroxy derivatives. In these experimental conditions, the hydration reaction proceeds with high regio-and stereoselectivity. Only 10-hydroxy derivatives were formed and the resulting (R)-10-hydroxystearic acid, (S)-(12Z)-10-hydroxy-octadecenoic acid, and (S)-(12Z,15Z)-10-hydroxy-octadecadienoic acid were obtained in very high enantiomeric purity (ee > 95%). Although overall conversions usually do not exceed 50% yield, our biotransformation protocol is stereoselective, scalable, and holds preparative significance.

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“…The recorded 1 H-and 13 C-NMR spectra are in very good agreement with those previously reported in the literature [42] for the same HFAs.…”

Section: Resultssupporting

confidence: 90%

Use of Lactobacillus rhamnosus (ATCC 53103) as Whole-Cell Biocatalyst for the Regio- and Stereoselective Hydration of Oleic, Linoleic, and Linolenic Acid

Serra

Simeis

2018

Catalysts

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“…By comparison of the NMR, MS, and OR data with the references, 14 known compounds were identified as cyclo[Trp‐Gly] (3), [10] cyclo(Trp‐Ana) (4), [11] cyclo‐(Trp‐Ser) (5), [12] glioperazine C (6), [13] cyclo(Ala‐Tyr) (7), indazole (8), [14] 2‐(4‐hydroxyphenyl)‐2‐oxoethanol (9), [15] 2,2‐[bis‐4‐(2,3‐dihydroxypropoxy)phenyl]propane (10), [16] 2‐[4‐(2,3‐dihydroxypropoxy)phenyl]‐2‐[4′‐hydroxyphenyl]propane (11), furan‐2,5‐diyldimethanol (12), [17] 2,3‐butanediol (13), [18] ergosterol (14), [19] 10‐hydroxy‐cis‐12‐octadecenoic acid (15), [20] and oleic acid (16) [21] …”

Section: Resultsmentioning

confidence: 99%

“…On the basis of above evidence, 2 was then established as (2S,3S)-3-(1H-indol-3-yl)-3methoxypropane-1,2-diol, and named cladosporiole B. By comparison of the NMR, MS, and OR data with the references, 14 known compounds were identified as cyclo[Trp-Gly] (3), [10] cyclo(Trp-Ana) (4), [11] cyclo-(Trp-Ser) (5), [12] glioperazine C (6), [13] cyclo(Ala-Tyr) (7), indazole (8), [14] 2-(4-hydroxyphenyl)-2-oxoethanol (9), [15] 2,2-[bis-4-(2,3-dihydroxypropoxy)phenyl]propane (10), [16] 2-[4-(2,3dihydroxypropoxy)phenyl]-2-[4'-hydroxyphenyl]propane (11), furan-2,5-diyldimethanol (12), [17] 2,3-butanediol (13), [18] ergosterol ( 14), [19] 10-hydroxy-cis-12-octadecenoic acid (15), [20] and oleic acid (16). [21] All compounds were tested for antimicrobial activity against Vibrio parahaemolyticus.…”

Section: Resultsmentioning

confidence: 99%

Cladosporioles A and B, Two New Indole Derivatives from the Deep‐Sea‐Derived Fungus Cladosporium cladosporioides 170056

Zou

Chen

et al. 2022

Chemistry & Biodiversity

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Two new (cladosporioles A and B, 1 and 2) and fourteen known (3–16) compounds were isolated from the deep‐sea‐derived fungus Cladosporium cladosporioides 170056. The relative structures of the new compounds were elucidated mainly by detailed analysis of their NMR and HR‐ESI‐MS spectroscopic data. Their absolute configurations were determined by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. All isolates were tested for antimicrobial activity against Vibrio parahaemolyticus. Compound 15 exhibited weak effect with the MIC value of 156.25 μg/mL.

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“…However, many studies have shown that epinephrine and its analogue are crucial in the flowering. First, epinephrine can partly overcome the inhibition posed by sucrose-ammonium of flowering in [ 62 ] L.paucicostata [ 62 , 63 ]. Second, the antagonist of epinephrine and propranolol can inhibit the flowering of Lemna with an ammonium-free medium.…”

Section: Discussionmentioning

confidence: 99%

Metabolomics Analysis of Litchi Leaves during Floral Induction Reveals Metabolic Improvement by Stem Girdling

Xiao

Chen

et al. 2021

Molecules

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Prolonged exposure to cold temperatures often results in a relatively low flowering rate in litchi (Litchi chinensis Sonn.) trees with younger leaves. This study aimed to verify the impact of stem girdling on litchi flowering by identifying and characterizing the induced metabolic changes. After a 60 day exposure to cold treatment at 15 °C/10 °C (12 h/12 h), the flowering rate of the girdled trees was 100%, while that of the non-girdled trees was 20%, indicating that girdling improved litchi flowering at its turning stage. The metabolic profiles of litchi leaves with and without stem girdling during floral induction were compared and 505 metabolites potentially associated with litchi flowering were detected. Most metabolites were involved in the metabolism of starch and sucrose, fatty acid, and phenylpyruvic acid. The metabolic pathways concerned with the biosynthesis of epinephrine, sucrose, and d-maltose were induced in leaves after girdling treatment. The level of galactitol, phenylpyruvic acid, acetyl-CoA, linoleic acid, alpha-linolenic acid, and 13-HPOT biosynthesis remained stable in the leaves from girdled trees but changed drastically in the leaves from non-girdled trees. In addition, 379 metabolites concerning flowering rate were characterized. Metabolism pathways of starch and sucrose, galactose, and linoleic acid are of great significance to the flowering of litchi. Linoleic acid exhibited the most significant variations between girdled trees and non-girdled trees with fold changes of up to 13.62. These results contribute to understanding the biological mechanism of litchi floral induction and the metabolic changes after stem girdling.

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Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet

Cited by 5 publications

References 13 publications

Use of Lactobacillus rhamnosus (ATCC 53103) as Whole-Cell Biocatalyst for the Regio- and Stereoselective Hydration of Oleic, Linoleic, and Linolenic Acid

Use of Lactobacillus rhamnosus (ATCC 53103) as Whole-Cell Biocatalyst for the Regio- and Stereoselective Hydration of Oleic, Linoleic, and Linolenic Acid

Cladosporioles A and B, Two New Indole Derivatives from the Deep‐Sea‐Derived Fungus Cladosporium cladosporioides 170056

Metabolomics Analysis of Litchi Leaves during Floral Induction Reveals Metabolic Improvement by Stem Girdling

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