catechol estrogen

カテコールエストロゲン

WordNet

a general term for female steroid sex hormones that are secreted by the ovary and responsible for typical female sexual characteristics (同)oestrogen

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エストロゲン(動物の雌を発情させる卵胞ホルモン)(《英》oestrogen)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/01/31 09:11:08」(JST)

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Structure of 2-hydroxyestradiol, a catechol estrogen.

A catechol estrogen is a steroidal estrogen that contains catechol (1,2-dihydroxybenzene) within its structure.^[1] The catechol estrogens are endogenous metabolites of estradiol and estrone and include the following compounds:^[1]^[2]

2-Hydroxylated:
- 2-Hydroxyestradiol
- 2-Hydroxyestrone
- 2-Hydroxyestriol
4-Hydroxylated:
- 4-Hydroxyestradiol
- 4-Hydroxyestrone
- 4-Hydroxyestriol

The most abundant catechol estrogen in serum and urine is 2-hydroxyestrone, with 2-hydroxyestradiol and 2-hydroxyestriol also being formed, while the principal 4-hydroxy catechol estrogen, 4-hydroxyestrone, is present in only small amounts in urine.^[1] 4-Hydroxyestriol has been detected in the urine of pregnant women.^[3] The catechol estrogens are formed from estradiol and estrone by cytochrome P450 enzymes predominantly in the liver but also in extrahepatic tissues, and are metabolized by catechol O-methyltransferase (COMT) into methoxylated estrogens such as 2-methoxyestradiol and 4-methoxyestrone as well as by conjugation via other phase II enzymes.^[1]^[2] Under poor conditions of inactivation by phase II enzymes, catechol estrogens can undergo oxidation to reactive quinones and semiquinones, and this has been hypothesized to contribute to estrogen-induced carcinogenesis.^[2]

ER (rat uterine cytosol) RBA + estrogenicity (change in rat uterine wet weight) of estrogen metabolites^[4]
Compound	RBA	Uterine weight (%)
Control	–	100
Estradiol	100	506
Estriol	10	468
2-Hydroxyestradiol	24	285
2-Methoxyestradiol	0.05	101
4-Hydroxyestradiol	45	?
4-Methoxyestradiol	13	260
2-Hydroxyestrone	2	130
2-Methoxyestrone	0.01	?
4-Hydroxyestrone	11	351
4-Methoxyestrone	0.13	338

Similarly to estradiol and estrone, catechol estrogens possess estrogenic activity.^[1] 2-Hydroxylated catechol estrogens are weak and possibly antiestrogenic estrogens, whereas their 4-hydroxylated counterparts are more potent in their estrogenic activity.^[1] For instance, 2-hydroxyestrone reportedly shows negligible uterotrophic effect in animals, whereas 4-hydroxy catechol estrogens show moderate changes in stimulating uterine weight.^[1] In addition to being substrates for COMT similarly to catecholamines like dopamine, norepinephrine, and epinephrine, catechol estrogens are potent competitive inhibitors of COMT as well as of tyrosine hydroxylase, and may affect both catecholamine biosynthesis and metabolism.^[1]^[2]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h H.J. Buchsbaum (6 December 2012). The Menopause. Springer Science & Business Media. pp. 65–. ISBN 978-1-4612-5525-3.
^ ^a ^b ^c ^d Shufeng Zhou (6 April 2016). Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism. CRC Press. pp. 241–242. ISBN 978-1-4665-9788-4.
^ Fotsis T, Järvenpää P, Adlercreutz H (1980). "Identification of 4-hydroxyestriol in pregnancy urine". J. Clin. Endocrinol. Metab. 51 (1): 148–51. doi:10.1210/jcem-51-1-148. PMID 6892918.
^ Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". J. Soc. Gynecol. Investig. 7 (3): 175–83. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.

UpToDate Contents

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1. エストロゲン作用の分子生物学および生理学molecular biology and physiology of estrogen action [show details]
… responses to estrogen and the clinical consequences for the activity of estrogen in both females and males are summarized in the figure Their major actions are genomic, mediated by nuclear estrogen receptors …
2. エストロゲン・プロゲスチン配合経口避妊薬：患者の選択、カウンセリング、使用法combined estrogen progestin oral contraceptives patient selection counseling and use [show details]
… and estrogen component of the COC working synergistically, but estrogen suppression of FSH, which in turn prevents folliculogenesis, is likely the most important mechanism The additional estrogen exposure …
3. エストロゲン関連片頭痛estrogen associated migraine [show details]
… in estrogen concentration after exposure to high levels of the hormone for several days (estrogen priming), as in the following settings : Natural declines in endogenous estrogen, such as at the beginning …
4. エストロゲンと認知機能estrogen and cognitive function [show details]
…and benefits of postmenopausal estrogen therapy are reviewed separately. Substantial biologic evidence supports the importance of estrogen to cognitive function. Estrogen receptors have been identified …
5. 骨粗鬆症の予防および治療のための選択的エストロゲン受容体調節剤selective estrogen receptor modulators for prevention and treatment of osteoporosis [show details]
… The selective estrogen receptor modulators (SERMs) bind with high affinity to the estrogen receptor and have estrogen agonist and antagonist properties that vary depending upon the individual target organ …

English Journal

Liquid chromatography-tandem mass spectrometric analysis of ten estrogen metabolites at sub-picogram levels in breast cancer women.

Khedr A1, Alahdal AM2.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.J Chromatogr B Analyt Technol Biomed Life Sci.2016 Sep 15;1031:181-8. doi: 10.1016/j.jchromb.2016.07.051. Epub 2016 Jul 30.
The measurement of estrogens at sub-picogram levels is essential for research on breast cancer and postmenopausal plasma. Heretofore, these concentration levels have rarely been achieved. However, it is possible through derivatization but still represent problems for monitoring catechol estrogens an
PMID 27497156

Cigarette smoking and hormones.

Marom-Haham L1, Shulman A.
Current opinion in obstetrics & gynecology.Curr Opin Obstet Gynecol.2016 Aug;28(4):230-5. doi: 10.1097/GCO.0000000000000283.
PURPOSE OF REVIEW: The purpose is to provide a summary of the effects of cigarette smoking on steroid hormone metabolism and how it affects female fertility.RECENT FINDINGS: Components of tobacco smoke such as polycyclic aromatic hydrocarbons lead to transcriptional upregulation of a number of genes
PMID 27285958

Revealing ecological risks of priority endocrine disrupting chemicals in four marine protected areas in Hong Kong through an integrative approach.

Xu EG1, Ho PW2, Tse Z2, Ho SL2, Leung KM3.
Environmental pollution (Barking, Essex : 1987).Environ Pollut.2016 Aug;215:103-12. doi: 10.1016/j.envpol.2016.04.090. Epub 2016 May 11.
Marine Protected Areas (MPAs) in Hong Kong are situated in close proximity to urbanized areas, and inevitably influenced by wastewater discharges and antifouling biocides leached from vessels. Hence, marine organisms inhabiting these MPAs are probably at risk. Here an integrative approach was employ
PMID 27179329

Japanese Journal

Catechol estrogens mediated activation of Nrf2 through covalent modification of its quinone metabolite to Keap1

Sumi Daigo,Numasawa Yumiko,Endo Akiko,Iwamoto Noriko,Kumagai Yoshito
Journal of toxicological sciences 34(6), 627-635, 2009-12-01
… The catechol metabolites (2-OHE and 4-OHE) of estrogen enter a redox cycle, thereby generating not only reactive oxygen species (ROS) but also electrophilic quinones. … The purpose of the present study is to explore the roles of oxidative and electrophilic stress in Nrf2 activation caused by redox-active catechol estrogens. …
NAID 110007485673