On gonads and gadflies: the estrus angle

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   Figure 1

   Pure estrone. (left) Platelet crystals of estrone. Reproduced, with permission, from EA Doisy, CD Veler & S Thayer (1930) The preparation of the crystalline ovarian hormone from the urine of pregnant women, Journal of Biological Chemistry, volume 86, pages 499–509. Copyright 1930, the American Society for Biochemistry and Molecular Biology. (top right) Estrone steroidal structure. (bottom right) Gonane, the nuclear hydrocarbon structure upon which the systematic nomenclature of all natural and synthetic steroidal substances is based.
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   Figure 2

   Crystal structure of cholesteryl iodide. X-ray diffraction analysis, showing an electron-density map with the tetracyclic gonane nucleus and alkyl side-chain contour drawn in. Adapted, with permission, from Carlisle CH & Crowfoot D (1945) The crystal structure of cholesteryl iodide. Proceedings of the Royal Society of London: Series A, Mathematical and Physical Sciences, volume 184, pages 64–83. Quoted text reproduced from Hodgkin DC (1972) The X-ray analysis of complicated molecules. [Nobel Lecture, December 11, 1964]. In Nobel Lectures, Chemistry 1963–1970, 71–91. Amsterdam: Elsevier Publishing Co.
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   Figure 3

   Moult-inducing steroids. (left) Crystals of ecdysone isolated from silk-moth pupae. Reproduced, with permission, from Butenandt A & Karlson P, ‘Über die isolierung eines metamorphose-hormons der insekten in kristallisierter form’; in: Zeitschrift für Naturforschung B, vol 9 issue 6, Berlin: De Gruyter, 1954, pp. 389–391, fig. 3. (right) Steroid structure of ecdysone. Ecdysone is a prohormone for the more potent moult-inducing hormone 20-hydroxyecdysone (ecdysterone), which is formed by hydroxylation at C20 (asterisk).
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   Figure 4

   Structure of the steroidal pheromone, androstenone. (left) Stereoscopic view of the crystal packing diagram. Reprinted from Tetrahedron, vol 40, issue 16, PJ Cox & AB Turner, Synthesis, X-ray structure and molecular mechanics studies of the boar taint steroid (5-androst-16-en-3-one), pp. 3135–3138, Copyright (1984), with permission from Elsevier. (right) Steroidal structure of androstenone deduced by Prelog et al. (1944).

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