Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Drug Metabolism: Phase I Reactions01:17

Drug Metabolism: Phase I Reactions

A phase I reaction is a biochemical process that introduces a functionally reactive polar group to a substance. This transformation predominantly occurs in the liver, facilitated by the cytochrome P450 system of hemoproteins situated in the lipophilic endoplasmic reticulum of cells. The metabolite generated through this process can have varying polarities. If it is sufficiently polar, it can be easily excreted in the urine due to its water compatibility. However, if the metabolite is nonpolar,...
Major Hormones and Their Functions01:27

Major Hormones and Their Functions

Hormones, the biochemical messengers produced by endocrine glands, are pivotal in regulating bodily functions and maintaining homeostasis. Each hormone's balance is crucial; imbalances can lead to significant physiological disruptions. Major hormones include oxytocin, cortisol, epinephrine, estrogen, testosterone, thyroxine, growth hormone, insulin, and glucagon.
Oxytocin, produced in the hypothalamus and released by the pituitary gland, plays a role in social bonding, childbirth, and lactation.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

The nutritional herb <i>Epimedium grandiflorum</i> inhibits the growth in a model for the Luminal A molecular subtype of breast cancer.

Oncology letters·2017
Same author

The effect of oral 3,3'-diindolylmethane supplementation on the 2:16α-OHE ratio in BRCA1 mutation carriers.

Familial cancer·2015
Same author

Obesity and the gut microbiome: pathophysiological aspects.

Hormone molecular biology and clinical investigation·2014
Same author

Comparative efficacy of extracts from Lycium barbarum bark and fruit on estrogen receptor positive human mammary carcinoma MCF-7 cells.

Nutrition and cancer·2014
Same author

Evaluation of 3,3'-diindolylmethane with gardasil quadrivalent HPV vaccine in K14-HPV16-transgenic mice cervical histology.

In vivo (Athens, Greece)·2013
Same author

Polychlorinated biphenyl exposure, diabetes and endogenous hormones: a cross-sectional study in men previously employed at a capacitor manufacturing plant.

Environmental health : a global access science source·2012

Related Experiment Video

Updated: Jun 25, 2026

An In Vivo Estrogen Deficiency Mouse Model for Screening Exogenous Estrogen Treatments of Cardiovascular Dysfunction After Menopause
06:18

An In Vivo Estrogen Deficiency Mouse Model for Screening Exogenous Estrogen Treatments of Cardiovascular Dysfunction After Menopause

Published on: August 13, 2019

Estrogen hydroxylation--the good and the bad.

Daniel W Sepkovic1, H Leon Bradlow

  • 1The David and Alice Jurist Institute for Research, Hackensack University Medical Center, Hackensack, New Jersey 07601, USA. dsepkovic@humed.com

Annals of the New York Academy of Sciences
|March 3, 2009
PubMed
Summary

Estradiol metabolism through hydroxylation produces compounds influencing estrogen

Area of Science:

  • Endocrinology and Metabolism
  • Molecular Biology
  • Oncology

Background:

  • Estradiol, the primary female development hormone, exerts diverse effects through its metabolites.
  • Estrogen metabolism, particularly Phase I oxidative hydroxylation, is crucial for understanding both beneficial and detrimental estrogen properties.
  • Specific hydroxylation pathways are influenced by endogenous and exogenous compounds affecting cytochrome enzymes.

Purpose of the Study:

  • To discuss the various hydroxylation pathways of estradiol and the effects of their products.
  • To evaluate the role of estrogen metabolites in predicting breast cancer risk.
  • To examine the interaction between human papilloma virus (HPV) and estrogen metabolites in cervical pathologies and hormonal cancers.

Main Methods:

More Related Videos

Systems Biology of Metabolic Regulation by Estrogen Receptor Signaling in Breast Cancer
10:36

Systems Biology of Metabolic Regulation by Estrogen Receptor Signaling in Breast Cancer

Published on: March 17, 2016

In Silico Modeling Method for Computational Aquatic Toxicology of Endocrine Disruptors: A Software-Based Approach Using QSAR Toolbox
05:47

In Silico Modeling Method for Computational Aquatic Toxicology of Endocrine Disruptors: A Software-Based Approach Using QSAR Toolbox

Published on: August 28, 2019

Related Experiment Videos

Last Updated: Jun 25, 2026

An In Vivo Estrogen Deficiency Mouse Model for Screening Exogenous Estrogen Treatments of Cardiovascular Dysfunction After Menopause
06:18

An In Vivo Estrogen Deficiency Mouse Model for Screening Exogenous Estrogen Treatments of Cardiovascular Dysfunction After Menopause

Published on: August 13, 2019

Systems Biology of Metabolic Regulation by Estrogen Receptor Signaling in Breast Cancer
10:36

Systems Biology of Metabolic Regulation by Estrogen Receptor Signaling in Breast Cancer

Published on: March 17, 2016

In Silico Modeling Method for Computational Aquatic Toxicology of Endocrine Disruptors: A Software-Based Approach Using QSAR Toolbox
05:47

In Silico Modeling Method for Computational Aquatic Toxicology of Endocrine Disruptors: A Software-Based Approach Using QSAR Toolbox

Published on: August 28, 2019

  • Review of existing literature on estrogen hydroxylation pathways and their products.
  • Analysis of prospective and case-control studies on estrogen metabolites and breast cancer risk.
  • Discussion of pilot studies investigating inhibitors of estrogen C-2 hydroxylation and the impact of environmental toxins like phthalate esters.

    • Main Results:

    • Certain estrogen metabolites are linked to increased risk for hormone-related cancers, including breast and cervical cancer.
    • The interaction between human papilloma virus (HPV) and 16alpha-hydroxyestrone is associated with cervical dysplasia and cancer.
    • Pilot studies identified a body fat component inhibiting estrogen C-2 hydroxylation and phthalate esters increasing hormonal cancer risk.

    Conclusions:

    • Modulation of estrogen hydroxylation is critical for mitigating cancer risk.
    • Estrogen metabolites play a significant role in the development of hormone-related cancers.
    • Environmental factors and endogenous compounds can influence estrogen metabolism and cancer susceptibility.