Antioestrogenic and antifertility compounds. III. Enantiomers of (±)-hexoestrol and its homologues

1970 ◽  
Vol 23 (8) ◽  
pp. 1605 ◽  
Author(s):  
DJ Collins ◽  
JJ Hobbs
Keyword(s):  
Butyric Acid ◽  
Active Site ◽  
Oestrogen Receptor ◽  
Optically Active ◽  
Valeric Acid ◽  
Absolute Stereochemistry

(�)-2,3-Bis(p-hydroxyphenyl)butane (5a) and (&)-3,4-bis(p-hydroxyphenyl)-hexane (5c) were resolved, and absolute stereochemistry of the former was established as (-)-(2R,3R) by correlation with (+)-(R)-2,3-bis(p-methoxyphenyl)but-1-en. The (+) and (-) isomers of erythro-2,3-bis(p-hydroxyphenyl)pentane (Sb) were synthesized from (-)- and (+)-erythro-2,3-bis(p-methoxyphenyl)valeric acid, respectively. (+)-erythro-2,3-Bis(p-hydroxyphenyl)pentane (5b) was shown to have the (2R,3S) configuration, and (+)-threo-(b) the (2S,3S) configuration, by correlation with (-)-(8)-2,3-bis(p-methoxyphenyl)pent-1-ene. It follows that the configuration of erythro-2,3-bis(p-methoxyphenyl)-valeric and the corresponding-butyric acid is (+)-(2S,3R). Interaction of optically active hexoestrol and its homologues with the oestrogen receptor active site is discussed in terms of steroid stereochemistry.

scholarly journals Isolation and Absolute Stereochemistry of Optically Active Sydonic Acid fromGloniumsp. (Hysteriales, Ascomycota)

2009 ◽  
Vol 73 (1) ◽  
pp. 203-204 ◽  
Author(s):  
Shinji KUDO ◽  
Takanori MURAKAMI ◽  
Junsuke MIYANISHI ◽  
Kazuaki TANAKA ◽  
Noboru TAKADA ◽  
...  
Keyword(s):  
Optically Active ◽  
Absolute Stereochemistry

scholarly journals Human gut bacteria as potent class I histone deacetylase inhibitors in vitro through production of butyric acid and valeric acid

PLoS ONE ◽  
2018 ◽  
Vol 13 (7) ◽  
pp. e0201073 ◽  
Author(s):  
Samantha Yuille ◽  
Nicole Reichardt ◽  
Suchita Panda ◽  
Hayley Dunbar ◽  
Imke E. Mulder
Keyword(s):  
Histone Deacetylase ◽  
Butyric Acid ◽  
Histone Deacetylase Inhibitors ◽  
Gut Bacteria ◽  
Valeric Acid ◽  
Class I ◽  
Human Gut

scholarly journals Stereochemistry of 1-(4′-hydroxyphenyl)ethanol produced by hydroxylation of 4-ethylphenol by p-cresol methylhydroxylase

1984 ◽  
Vol 224 (2) ◽  
pp. 617-621 ◽  
Author(s):  
W McIntire ◽  
D J Hopper ◽  
J C Craig ◽  
E T Everhart ◽  
R V Webster ◽  
...  
Keyword(s):  
Pseudomonas Putida ◽  
Active Site ◽  
Optically Active

Enzymic hydroxylation of 4-ethylphenol by (a) Pseudomonas putida and (b) highly purified p-cresol methylhydroxylase gave optically active 1-(4′-hydroxyphenyl)-ethanol. The products were transformed into the phenolic methyl ethers and shown to contain 69.5% and 65.6%, respectively, of the (S)-(-)-isomer. The stereochemistry of the reaction is discussed in terms of three distinct steps occurring at the active site of the enzyme.

The absolute configuration of (+)-3,4-Bis(p-hydroxyphenyl)hexane (hexoestrol) and related compounds

1974 ◽  
Vol 27 (8) ◽  
pp. 1753 ◽  
Author(s):  
DJ Collins ◽  
JJ Hobbs
Keyword(s):  
Absolute Configuration ◽  
Valeric Acid ◽  
The Absolute ◽  
Related Compounds ◽  
Absolute Stereochemistry

(+)-(2S,3R)-2,3-Bis(p-methoxyphenyl)valeric acid, previously converted into (-)-(2R,3R)-2,3-bis(p-methoxyphenyl)pentane, has now been converted into (+)-(3R,4R)-3,4-bis(p-methoxyphenyl)hexane via (+)-(3S,4R)-3,4-bis(p-methoxyphenyl)hexan-2-one and (-)-(4s)-3,4-bis(p-methoxypheny1)hex-2-ene. This provides unequivocal correlation of the absolute stereochemistry of a series of homologous diarylalkanes, and a corresponding series of diarylalkenes.

scholarly journals Effects of Industrial and Ruminant Trans-fatty Acids-Enriched Diet on Fecal Microbiome and Short Chain Fatty Acid Metabolites of C57BL/6 Mice

2021 ◽  
Vol 5 (Supplement_2) ◽  
pp. 1171-1171
Author(s):  
Farzad Mohammadi ◽  
Emma Tolsdorf ◽  
Karine Greffard ◽  
Élodie Chotard ◽  
Jean-François Bilodeau ◽  
...  
Keyword(s):  
Fatty Acids ◽  
16S Rrna ◽  
Gut Microbiota ◽  
Butyric Acid ◽  
Relative Abundance ◽  
Trans Fatty Acids ◽  
Valeric Acid ◽  
Short Chain ◽  
16S Rrna Analysis ◽  
Fecal Microbiome

Abstract Objectives We hypothesized that the intake of industrially originated trans-fatty acids (elaidic acid (EA trans 18: 1n-9)) and ruminant trans fatty acids (trans-palmitoleic acid (TPA t16:1 n-7)) will differentially modify gut microbiota and short-chain fatty acids (SCFA) profiles. The objective is to compare the long- and short-term effects of EA and TPA on the fecal microbiome and SCFAs profiles in mice. Methods Forty C57BL/6 mice were divided to 4 groups. Each group was given one of the following 4 formulations in the drinking water: lecithin nanovesicles, nanovesicles containing either lecithin with EA or TPA (86:14 (w/w)) or water alone (control) for 28 days with a normal fat diet. Fecal samples were collected at days 0, 7 and 28. Gut microbiota profiles were determined by 16S rRNA gene sequencing. SCFAs were measured by headspace gas chromatography coupled to a single quadrupole mass spectrometer. Baseline data (relative abundance of bacteria or levels of SCFAs) was pooled and then compared with data from day 7 or day 28 for each formulation. Results After 7 days of lecithin, 16S rRNA analysis revealed an increase in the relative abundance of Lactobacillus. After 28 days of lecithin, an increase in the relative abundance of Lactobacillus, Erysipelotrichaceae, and Enterobacteriaceae together with a decrease in Bacteroidaceae was observed. Further, a tendency to increase level of butyric acid (P = 0.053) was observed after 28 days of lecithin. After 7 days of EA, an increase in the relative abundance of Lactobacillus, whereas a decrease in the relative abundance of Parabacteroides, Bacteroides, Rumininococcaceae, Lachnospiraceae and Peptococcaceae was observed. After 7 days of TPA, results show a decreased level of isovaleric acid (P = 0.04) and valeric acid (P = 0.03). After 28 days of TPA, data demonstrates an increase in the level of butyric acid (P = 0.01) and propionic acid (P = 0.01). Water intake for 28 days decreased the level of valeric acid (P = 0.02). Conclusions Consumption of industrial and ruminant trans-fatty acids modify differentially bacterial taxa present in the gut microbiome and SCFA profiles. Funding Sources NSERC, CMDO.

scholarly journals Influence of the Mediterranean diet on the production of short-chain fatty acids in women at risk for breast cancer (LIBRE)

2020 ◽  
Vol 79 (OCE2) ◽  
Author(s):  
Benjamin Seethaler ◽  
Jacqueline Beutel ◽  
Marie Kogel ◽  
Maryam Basrai ◽  
Jens Walter ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Physical Activity ◽  
Fatty Acids ◽  
Acetic Acid ◽  
Mediterranean Diet ◽  
Butyric Acid ◽  
Short Chain Fatty Acids ◽  
Valeric Acid ◽  
Short Chain ◽  
Control Group

AbstractBackground: A number of small intervention studies suggested that a Mediterranean diet (MedD) and physical activity can lower the risk for breast cancer. LIBRE is the first large multicenter RCT to test the effect of these lifestyle factors on the incidence of breast cancer in women at risk because of BRCA mutations(1). LIBRE also offers to unravel underlying mechanisms such as the role of short-chain fatty acids (SCFA) for beneficial effects of such lifestyle interventions.Methods: We examined the effect of the lifestyle intervention on the production of SCFA measured in feces by gas chromatography. From the ongoing LIBRE trial we included all complete datasets (171 women; mean age 44 ± 11 years). Both women with and without previous breast cancer diagnosis were recruited (diseased; non-diseased). The participants were randomized into an intervention group (IG) trained for MedD and physical activity, and a usual care control group (CG). Adherence to the MedD was assessed at baseline and after 3 months (V1) using the validated Mediterranean Diet Adherence Screener (MEDAS) and the EPIC food frequency questionnaire (FFQ).Results: At baseline there was no difference in SCFA levels between the groups. In the IG the MEDAS score increased substantially by 2.5 points (p < 0.001), in the CG only mildly by 0.4 points (p < 0.05). Correspondingly, the intake of fibers increased solely in the IG. In the course of the study the amount of caproic acid decreased in the control group (p < 0.001). At V1 non-diseased women showed higher amounts of acetic acid (p = 0.042), n-butyric acid (p = 0.023), n-valeric acid (p = 0.018) and iso-valeric acid (p = 0.031). There were several correlations between the intake of different fibers and fecal SCFA. For example, the sum of poly- and oligosaccharides correlated with acetic acid (p = 0.001; r = 0.316), propionic acid (p = 0.034; r = 0,251), n-butyric acid (p = 0.010; r = 0.316) and iso-valeric acid (p = 0.012; r = 0.306). There was no correlation between the MEDAS and SCFA.Discussion: A lifestyle change towards a MedD and increased physical activity did not change the levels of SCFA in feces, although an increase of fiber intake was documented in the IG. To further analyze SCFA metabolism in this target population, gut microbiota composition and function (metabolites) are currently analyzed.

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