Allenoic Acids Research Articles

Transcriptional regulation of estrogen-responsive genes by non-steroidal estrogens: Doisynolic and allenolic acids

Estrogen receptor (ER), a member of the nuclear receptor superfamily, exerts prominent physiological roles in both humans and other species by acting directly as a transcription factor, altering nuclear gene expression. One peculiarity of estrogenic regulation is that it is affected by a wide variety of non-steroidal compounds in addition to the natural hormone, estradiol. Doisynolic and allenolic acid compounds are non-steroidal compounds that act as potent estrogens in animal studies, yet bind to ER extremely poorly in competitive binding assays, raising the possibility of alternative molecular mechanisms for the observed estrogenic effects. In this work we demonstrate that (±)- Z-bisdehydrodoisynolic acid, (±)- Z-bisdehydrodoisynolic acid 3-methyl ether, and (−) allenolic acid can interact directly with ER. These compounds all serve as ligands for ER in mechanism-specific tissue culture-based reporter gene assays for both positive and negative gene regulation. We have also used a novel assay based on electromobility shift by ER for directly determining relative binding affinities for ER. In addition, we show cell-type-specific activity differences for (±)- Z-bisdehydrodoisynolic acid 3-methyl ether, supporting clinical observations indicating a higher potency of this compound in female animals than in humans.

Microbial transformation of artificial estrogens of the allenolic group.

When 2,2-dimethyl 3-(2'-naphthyl 6'-hydroxy) pentanoic acid, an artificial estrogen of the allenolic acid group, was added to an exponential-phase growth culture of Neurospora crassa (in Horowitz medium), it was transformed into its hydroxylated derivative, 2,2-dimethyl 3-(2'-naphthyl 4',6'-dihydroxy)pentaoic acid. To study this transformation, radioactive 2-methyl-[2-14-C=A1methyl 3-(2'-naphthyl 6'-hydroxy) pentanoic acid has been prepared. The rate of metabolism of allenolic acids varies in the same way as their estrogenic activity.

Structure moleculaire et activite oestrogene—XVII : Comparaison des configurations absolues des acides bisdehydrodoisynolique normal et α, α-dimethyl β-ethyl allenolique physiologiquement actifs

A stereochemical correlation has been established between the two highly estrogenic acids: levorotatory α,α-diméthyl β-éthyl allenolic acid (I) and levorotatory n-bisdehydrodoisynolic acid (III). The configuration of the corresponding asymmetric centre is opposite in these compounds.

Experimental and clinical studies on a new synthetic estrogen, an allenolic acid derivative, vallestril

In general, there are few chemical structural characteristics of substances with estrogenic activities, and it has been widely known that even substances with other than steroid structure have marked estrogenic activity and produce physiologic effects similar to those of the natural estrogens.1 These substances, for clinical use, should show remarkable estrogenic activity without side effects.Studies on the chemistry of stilbene derivatives by Dodds and associates5 in 1938 have been monumental in the field of synthetic chemistry, and it was highlighted by the synthesis of marrianolic acid, doisynolic acid and derivatives of each, followed by that of estrone.22–26Following this, in 1947–1948, Courrier, Horeau and Jacques2, 3, 4 were able to synthesize allenolic acid, a naphthalene compound derivative, which was studied in detail by Julia.8 The present report deals with the experimental results of work with 3-(6-methoxy-2-naphthyl)-2-2-dimethyl pentanoic acid, a derivative of allenolic acid, manufactured under the trade name Vallestril.

The use of various endocrine preparations in the suppression of lactation: A comparative study in 800 cases

1.1. In view of the increasing popularity of artificial suppression of lactation, we have presented a comparative study of 800 cases, illustrating the effects of various endocrines on the market.2.2. Eleven criteria for the ideal endocrine for inhibition of lactation are listed.3.3. Eight hundred cases were followed during the five days post partum and some by questionnaires given to patients and returned to the hospital three to four weeks post partum.4.4. Four tables show the effects of the various products on the suppression of lactation, breast engorgement, vaginal (withdrawal) bleeding, and vaginal discharge.5.5. A brief review of the pertinent literature is presented.6.6. Some explanation of the possible modus operandi of the suppression of lactation is offered.7.7. We conclude that ethyl dimethyl allenolic acid (Vallestril), 20 mg. daily for four to five days post partum, is effective in the suppression of lactation.8.8. We feel that these preliminary results warrant further studies to confirm our present findings.

Clinical assay of a new synthetic estrogen: vallestril.

IN 1947 and 1948 Courrier, Horeau and Jacques1 2 3 4 5 published a series of chemical and biologic studies of certain derivatives of a compound that they called "allenolic acid," in honor of Dr. E. Allen.2 This compound is known chemically as 6-hydroxy-2-naphthaleneproprionic acid. The name allenolic acid has been used widely in France and is recognized, although not officially accepted, by Chemical Abstracts. The derivatives found to possess strong estrogenic acitivity were 3- (6-methoxy-2-naphthyl)-2–2-dimethylpentanoic acid and the corresponding hydroxy compound, referred to by the French interchangeably as dimethyl-ethyl allenolic acid. The authors studied the biologic effects of these two dimethylpentanoic acid . . .

A New Route to the Allenolic Acid Type of Compound1

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA New Route to the Allenolic Acid Type of Compound1B. BelleauCite this: J. Am. Chem. Soc. 1951, 73, 11, 5443–5444Publication Date (Print):November 1, 1951Publication History Published online1 May 2002Published inissue 1 November 1951https://doi.org/10.1021/ja01155a505RIGHTS & PERMISSIONSArticle Views34Altmetric-Citations1LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (317 KB) Get e-Alerts Get e-Alerts