The absence of steroid estrogens in plants

Jacobsohn, Gert M.; Frey, Michael J.; Hochberg, Richard B.

doi:10.1016/0039-128x(65)90036-x

Cited by 25 publications

(8 citation statements)

References 12 publications

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“…It is of interest to note that, large concentrations of estrogenic hormones have been isolated from males suffering from feminizing adrenal carcinoma (Dempsey & Richardson Hall, 1963). Both estradiol and estrone are metabolized to estrioI, which is often the principal estrogen recoverable from human urine; the only other reported natural source of estriol is female willow catkins (Skarzynski, 1933); however, Jacobsohn, Frey & Hochberg (1965) could not confirm this finding.…”

Section: Introductioncontrasting

confidence: 52%

Estrogenic steroids. III. The crystal and molecular structure of estriol

Cooper¹,

Norton²,

Hauptman³

1969

Acta Crystallogr Sect B

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APPENDIXThe conditional probability distribution of cos (q~h+ %+q~-h-Z)Let the vector h be fixed and assume that k ranges uniformly throughout reciprocal space. Denote by P(xl IEkl, IEh+kl) the conditional probability distribution of the random variable X= cos (~h + ~k + 9-h-k),given that I~1 and IEh+kl have specified, fixed values. Crystal data for estriol (C18H2403) are: a= 9.270, b = 23.001, c= 7.560 A, p= 110.90. Space group P21 with two molecules in the asymmetric unit. The structure was solved from a set of phases derived initially by application of a phase determining formula of the type KIEIE2E3I cos (~,, +~,2+,,3) = ((If,d"-) (If,,,+,,l'-) (lf-,,3+,,l ~°-)>,,+ R and extended by application of the tangent formula. The structure was refined by block diagonal least-squares with anisotropic thermal parameters for the non-hydrogen atoms, to R= 5.6%. All hydrogen atoms were located. Standard deviations of non-hydrogen distances and angles are 0.007/~ and 0.4 ° respectively.Differences in hydrogen bonding, packing environment and intramolecular sterie effects cause the two molecules in the asymmetric unit to be non-identical. The two molecules are hydrogen bonded head-to-tail via the 3-hydroxyl oxygen of one molecule and the 16or-hydroxyl hydrogen of another, in such a way that the 18-methyl group of the first lies under the A ring of the second, producing distortion of this aromatic ring. Steric hindrance between the C ring equatorial hydrogen atom at C(11), and the hydrogen atom at C(1) produces twisting about the C(9)--C(10)bond, in opposite directions in the two molecules, causing the B ring to take up a half chair conformation in the first and a twist boat conformation in the second.The molecules pack with molecules of the first kind and molecules of the second kind, hydrogen bonded in separate chains parallel to b. These chains are cross linked via the asymmetric unit and via weaker hydrogen bonds involving all three hydroxyl groups. Three distinct types of hydrogen bond exist in which the O...H-O angles are 159-177 °, 136 °, and 128 °.

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Section: Introductioncontrasting

confidence: 52%

Estrogenic steroids. III. The crystal and molecular structure of estriol

Cooper¹,

Norton²,

Hauptman³

1969

Acta Crystallogr Sect B

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“…Examples of plant steroids are estrone found in palm (Elaeis guineensis Jacq., Arecaceae) and β-sitosterol which is found in almost all plants (Farnsworth et al, 1975a,b;Duke, 1992). Studies have reported conflicting evidence about estrone found in the seeds of pomegranate (Miksicek, 1994) and the presence of estrone in palm kernel residue could not be confirmed by further investigations (Jacobsohn et al, 1965). The steroidal plant compounds reported in earlier investigations have been questioned due to the limited technology available at the time to isolate and identify compounds (Price and Fenwick, 1985).…”

Section: Classification Of Phytoestrogensmentioning

confidence: 97%

Phytoestrogens: a review of the present state of research

Ososki

Kennelly

2003

Phytotherapy Research

407

278

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Phytoestrogens are a diverse group of plant-derived compounds that structurally or functionally mimic mammalian estrogens and show potential benefits for human health. The number of articles published on phytoestrogens has risen dramatically in the past couple decades. Further research continues to demonstrate the biological complexity of phytoestrogens, which belong to several different chemical classes and act through diverse mechanisms. This paper discusses the classification of phytoestrogens, methods of identification, their proposed mechanisms of action and botanical sources for phytoestrogens. The effects of phytoestrogens on breast and prostate cancers, cardiovascular disease, menopausal symptoms and osteoporosis will also be examined including research on benefits and risks.

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“…Various authors later confirmed the presence of steroidal estrogens in many plant species including date palm, bean, pomegranate, and the species of the Prunus genus [53,56,74,75,76,77,78]. Although numerous authors have described the presence of steroidal estrogens as well as their biosynthetic pathway, some authors have, historically, disputed their presence in plants [79,80]. Nevertheless, in 2001, estrogen receptor-like proteins were isolated from various plant organs and shown to be localized in the nucleus [81].…”

Section: Estrogensmentioning

confidence: 99%

Plants are Capable of Synthesizing Animal Steroid Hormones

Tarkowská

2019

Molecules

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As a result of the findings of scientists working on the biosynthesis and metabolism of steroids in the plant and animal kingdoms over the past five decades, it has become apparent that those compounds that naturally occur in animals can also be found as natural constituents of plants and vice versa, i.e., they have essentially the same fate in the majority of living organisms. This review summarizes the current state of knowledge on the occurrence of animal steroid hormones in the plant kingdom, particularly focusing on progesterone, testosterone, androstadienedione (boldione), androstenedione, and estrogens.

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The absence of steroid estrogens in plants

Cited by 25 publications

References 12 publications

Estrogenic steroids. III. The crystal and molecular structure of estriol

Estrogenic steroids. III. The crystal and molecular structure of estriol

Phytoestrogens: a review of the present state of research

Plants are Capable of Synthesizing Animal Steroid Hormones

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