Estradiol

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Estradiol
2D structure for Estradiol
Chemical Name	13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Chemical Formula	C₁₈H₂₄O₂
CAS Number	50-28-2
Chemical Information	HMDB00151
Biochemical Taxonomy	Steroids and Steroid Derivatives
Functional Taxonomy	Not Available
Nutritional Taxonomy	Not Available
Metabolic Pathways	Androgen and Estrogen Metabolism Benzoate Degradation via CoA Ligation Butanoate Metabolism Fatty Acid Biosynthesis (Path 2) Fatty Acid Metabolism Lysine Degradation Pentose and Glucuronate Interconversions Porphyrin and Chlorophyll Metabolism Starch and Sucrose Metabolism Valine, Leucine and Isoleucine Degradation
Biofluid Location	Blood Cerebrospinal Fluid (CSF) Saliva
Tissue Location	Adrenal Cortex Adrenal Gland Brain Epidermis Fibroblasts Gonads Muscle Neurons Placenta Platelet Prostate Spleen Stratum Corneum Testes Testis Uterus Adipose Tissue
Normal Biofluid Concentrations	Blood: 0.00009 (0.0-0.00018) uM Cerebrospinal Fluid (CSF): 0.0000007 - 0.000011 uM Cerebrospinal Fluid (CSF): 0.0000011 +/- 0.0000003 uM Saliva: <1.00 uM
Normal Tissue Concentrations	Not Available
Diseases / Conditions Related to Nutrition	Female Follicular phase Female Luteal phase Female Midcycle Postmenopausal
Other (Monogenic Disorders)	Not Available
Abnormal Biofluid Concentrations	Blood (Female Follicular phase): 0.00039 (0.000037-0.00073) uM Blood (Female Luteal phase): 0.00050 (0.000055-0.00095) uM Blood (Female Midcycle): 0.00092 (0.00037-0.0015) uM Blood (Postmenopausal): 0.00009 (0.0-0.00018) uM
Abnormal Tissue Concentrations	Not Available
Physiological Processes	Not Available

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Introduction

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Estradiol is the most potent form of mammalian estrogenic steroids. estradiol is produced in the ovaries. The ovary requires both luteinizing hormone (LH) and follicle-stimulating hormone (FSH) to produce sex steroids. LH stimulates the thecal cells surrounding the follicle to produce progesterone and androgens. The androgens diffuse across the basement membrane to the granulosa cell layer, where, under the action of FSH, they are aromatized to estrogens, mainly estradiol. The ovary shows cyclical activity, unlike the testis that is maintained in a more or less constant state of activity. Hormone secretions vary according to the phase of the menstrual cycle. In the developing follicle LH receptors (LH-R) are only located on the thecal cells and FSH receptors (FSHR) on the granulosa cells. The dominant pre-ovulatory follicle develops LH-Rs on the granulosa cells prior to the LH surge. Thecal cells of the preovulatory follicle also develop the capacity to synthesize estradiol and this persists when the thecal cells become incorporated into the corpus luteum. After ovulation, the empty follicle is remodelled and plays an important role in the second half or luteal phase of the menstrual cycle. This phase is dominated by progesterone and, to a lesser extent, estradiol secretion by the corpus luteum. estradiol is also synthesized locally from cholesterol through testosterone in the hippocampus and acts rapidly to modulate neuronal synaptic plasticity. Localization of estrogen receptor alpha (ERalpha) in spines in addition to nuclei of principal neurons implies that synaptic ERalpha is responsible for rapid modulation of synaptic plasticity by endogenous estradiol. estradiol is a potent endogenous antioxidant which suppresses hepatic fibrosis in animal models, and attenuates induction of redox sensitive transcription factors, hepatocyte apoptosis and hepatic stellate cells activation by inhibiting a generation of reactive oxygen species in primary cultures. This suggests that the greater progression of hepatic fibrosis and hepatocellular carcinoma in men and postmenopausal women may be due, at least in part, to lower production of estradiol and a reduced response to the action of estradiol. estradiol has been reported to induce the production of interferon (INF)-gamma in lymphocytes, and augments an antigen-specific primary antibody response in human peripheral blood mononuclear cells. IFN-gamma is a potent cytokine with immunomodulatory and antiproliferative properties. Therefore, female subjects, particularly before menopause, may produce antibodies against hepatitis B virus e antigen and hepatitis B virus surface antigen at a higher frequency than males with chronic hepatitis B virus infection. The estradiol-Dihydrotestosterone model of prostate cancer (PC) proposes that the first step in the development of most PC and breast cancer (BC) occurs when aromatase converts testosterone to estradiol. (PMID: 17708600, 17678531, 17644764)