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Biochemistry

Title:		Structural characterization of sulfated steroids that activate mouse pheromone-sensing neurons
Author(s):		Hsu FF; Nodari F; Kao LF; Fu X; Holekamp TF; Turk J; Holy TE;
Address:		"Department of Internal Medicine, Mass Spectrometry Resource, Division of Endocrinology, Diabetes, Metabolism, Washington University School of Medicine, St. Louis, Missouri 63110, USA. fhsu@im.wustl.edu"
Journal Title:		Biochemistry
Year:		2008
Volume:		47
Issue:		52
Page Number:		14009 - 14019
DOI:		10.1021/bi801392j
ISSN/ISBN:		1520-4995 (Electronic) 0006-2960 (Print) 0006-2960 (Linking)
Abstract:		"In many species, social behavior is organized via chemical signaling. While many of these signals have been identified for insects, the chemical identity of these social cues (often called pheromones) for mammals is largely unknown. We recently isolated these chemical cues that caused firing in the pheromone-sensing neurons of the vomeronasal organ from female mouse urine [Nodari, F., et al. (2008) J. Neurosci. 28, 6407-6418]. Here, we report their structural characterization. Mass spectrometric approaches, including tandem quadrupole, multiple-stage linear ion trap, high-resolution mass spectrometry, and H-D exchange followed by ESI mass spectrometry, along with (1)H and (13)C nuclear magnetic resonance spectroscopy, including two-dimensional correlation spectroscopy, total correlation spectroscopy, heteronuclear multiple-quantum coherence, and NOE, were used to identify two sulfated steroids, 4-pregnene-11beta,20,21-triol-3-one 21-sulfate (I) (the configuration at C20 was not deduced) and 4-pregnene-11beta,21-diol-3,20-dione 21-sulfate (II), whose presence is sex-specific. The identification of this novel class of mammalian social signaling compounds suggests that steroid hormones, upon conjugation, assume a new biological role, conveying information about the organism's identity and physiological state"
Keywords:		Animals Female Magnetic Resonance Spectroscopy Male Mass Spectrometry Mice Molecular Structure *Neurons *Pheromones Pregnenediones/*chemistry Steroids/*chemistry Sulfates/*chemistry;
Notes:		"MedlineHsu, Fong-Fu Nodari, Francesco Kao, Lung-Fa Fu, Xiaoyan Holekamp, Terrence F Turk, John Holy, Timothy E eng P41 RR000954-260004/RR/NCRR NIH HHS/ P41 GM103422/GM/NIGMS NIH HHS/ P41 RR000954-296488/RR/NCRR NIH HHS/ P41 RR000954-220005/RR/NCRR NIH HHS/ R37-DK34388/DK/NIDDK NIH HHS/ P60 DK020579/DK/NIDDK NIH HHS/ R37 DK034388/DK/NIDDK NIH HHS/ P41 RR000954-210030/RR/NCRR NIH HHS/ R01-DC005964/DC/NIDCD NIH HHS/ P60-DK20579/DK/NIDDK NIH HHS/ P41 RR000954-240004/RR/NCRR NIH HHS/ R01 DC005964-05/DC/NIDCD NIH HHS/ P30 DK056341-08/DK/NIDDK NIH HHS/ P30 DK056341/DK/NIDDK NIH HHS/ P30 DK056341-07/DK/NIDDK NIH HHS/ R01 DC005964/DC/NIDCD NIH HHS/ P41 RR000954/RR/NCRR NIH HHS/ P41 RR000954-250004/RR/NCRR NIH HHS/ P41-RR00954/RR/NCRR NIH HHS/ P30-DK56341/DK/NIDDK NIH HHS/ Research Support, N.I.H., Extramural 2008/12/05 Biochemistry. 2008 Dec 30; 47(52):14009-19. doi: 10.1021/bi801392j"