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Pure Appl. Chem., 1978, Vol. 50, No. 3, pp. 171-184

http://dx.doi.org/10.1351/pac197850030171

Recent advances in the mass spectrometry of steroids

C. Djerassi

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  • Seeman Jeffrey I.: Carl Djerassi: In His Own Words. Angew. Chem. 2014, 126, 3334. <http://dx.doi.org/10.1002/ange.201308367>
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  • Silva Marina V., Perlat Marie -Claude, Tabet Jean -Claude, Giorgi Gianluca, Salvini Laura, Ponticelli Fabio: Application of self-ionization for enhancing stereochemical and positional effects from arylglycosides under electron ionization conditions in an ion trap mass spectrometer. j am soc mass spectrom 2003, 14, 851. <http://dx.doi.org/10.1016/S1044-0305(03)00332-5>
  • Duan Yi, Ma Lanhua: Lipid geochemistry in a sediment core from Ruoergai Marsh deposit (Eastern Qinghai-Tibet plateau, China). Geochem 2001, 32, 1429. <http://dx.doi.org/10.1016/S0146-6380(01)00105-X>
  • Carballeira Nstor M., Guzmn Aikomari, Nechev Jordan T., Lahtchev Kantcho, Ivanova Albena, Stefanov Kamen: Unusual lipid composition of a Bacillus sp. Isolated from Lake Pomorie in Bulgaria. Lipid 2000, 35, 1371. <http://dx.doi.org/10.1007/s11745-000-0654-3>
  • Williams T. M., Kind A. J., Houghton E., Hill D. W.: Electrospray collision-induced dissociation of testosterone and testosterone hydroxy analogs. J Mass Spectrom 1999, 34, 206. <http://dx.doi.org/10.1002/(SICI)1096-9888(199903)34:3<206::AID-JMS785>3.0.CO;2-1>
  • Ramaroson-Raonizafinimanana Béatrice, Gaydou Emile M., Bombarda Isabelle: Occurrence of 5α-cholesta-7,24-dien-3β-ol and 23-dehydrolophenol in the bean lipids of Vanilla madagascariensis . J Amer Oil Chem Soc 1998, 75, 1325. <http://dx.doi.org/10.1007/s11746-998-0179-4>
  • Kostova Ivanka, Simeonov Mario, Iossifova Tanya, Tappe Robert, Pardeshi Nalini, Budzikiewicz Herbert: Three 9,19-cyclotetracyclic triterpenes from Skimmia wallichii. Phytochemisry 1996, 43, 643. <http://dx.doi.org/10.1016/0031-9422(96)00320-2>
  • Djerassi Carl: Steroids made it possible: Organic mass spectrometry. Org Mass Spectrom 1992, 27, 1341. <http://dx.doi.org/10.1002/oms.1210271203>
  • Kamilova T. A., Ekhvalova T. V.: Episterol and fungisterol from mutant strains of the yeast Saccharomyces cerevisiae. Chem Nat Compd 1989, 25, 624. <http://dx.doi.org/10.1007/BF00598097>
  • Rashkes Ya. V., Rashkes A. M., Kiktev M. M., Khidyrova N. K., Shakhidoyatov Kh. M., Abdullaev A. A.: Amount of sterols and triterpenoids in leaves and petioles of leaf-shedding and standard lines of cotton plant. Chem Nat Compd 1989, 25, 676. <http://dx.doi.org/10.1007/BF00598264>
  • Malik Sohail, Djerassi Carl: Minor and trace sterols in marine invertebrates. 61. Isolation and structure elucidation of new A-nor sterols from the marine sponge Phakellia aruensis. Steroid 1989, 53, 271. <http://dx.doi.org/10.1016/0039-128X(89)90015-9>
  • Vanden Bossche Hugo, Opperdoes Fred R., Hart David T., Lauwers Wim J., Willemsens Gustaaf: Perturbation of sterol biosynthesis by itraconazole and ketoconazole in Leishmania mexicana mexicana infected macrophages. Mol Bioch Parasitol 1989, 33, 123. <http://dx.doi.org/10.1016/0166-6851(89)90026-1>
  • Carballeira N��stor M., Bou Carlos R., van Eyk Armor��l D, Naud�� Ryno J, Oelofsen Willem, Davidson William S., Bartlett Sylvia E., Birt Tim P., Birt Victoria L., Green John M.: The sterol composition of the marine sponge Aplysina (= Verongia) archeri: A comparative study of the verongidae. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1989, 93, 175. <http://dx.doi.org/10.1016/0305-0491(89)90232-0>
  • Zaretskii Z. V. I., Kustanovich Z., Kingston E. E., Beynon J. H., Djerassi Carl, Tökes L.: Translational energy release and stereochemistry of steroids. VII—the loss of angular methyl groups after the dehydration of molecular ions of cholesterol and related C(5)-unsaturated 3β-hydroxy steroids. Org Mass Spectrom 1986, 21, 125. <http://dx.doi.org/10.1002/oms.1210210306>
  • Grantham P.J.: Sterane isomerisation and moretane/hopane ratios in crude oils derived from Tertiary source rocks. Geochem 1986, 9, 293. <http://dx.doi.org/10.1016/0146-6380(86)90110-5>
  • Lauwers W. F. J., Jeune L. Le, Bossche H. Vanden, Willemsens G.: Identification of 17α, 20α-dihydroxyprogesterone in testicular extracts after incubation with ketoconazole. Biol Mass Spectrom 1985, 12, 296. <http://dx.doi.org/10.1002/bms.1200120608>
  • Zaretskii Z. V. I., Kingston E. E., Beynon J. H., Guilhaus M., Kingston R. G., Brenton A. G., Beynon J. H., Welch Michael J., Pereles Daniel J., Edward White V: Letters to the editor. Org Mass Spectrom 1985, 20, 422. <http://dx.doi.org/10.1002/oms.1210200608>
  • Zaretskii Z. V. I., Kustanovich Z., Kingston E. E., Beynon J. H., Lauber R., Schlunegger U. P., Djerassi Carl: Translational energy release and stereochemistry of steroids 6—Contribution of the 18- and 19-methyl groups to the translational energy release for the angular methyl loss in unsaturated steroids. Org Mass Spectrom 1985, 20, 471. <http://dx.doi.org/10.1002/oms.1210200709>
  • Patterson Donald G., Haley M. J., Midgley I., Djerassi Carl: Mass spectrometry in structural and stereochemical problems. 2617—The effect of stereochemistry on the course of the characteristic ringD fragmentation of steroid hydrocarbons. Org Mass Spectrom 1984, 19, 531. <http://dx.doi.org/10.1002/oms.1210191102>
  • Mahato Shashi B., Banerjee Sukdeb, Sahu Niranjan P.: Metabolism of progesterone and testosterone by a Bacillus sp. Steroid 1984, 43, 545. <http://dx.doi.org/10.1016/S0039-128X(84)90180-6>
  • Wakeham S. G., Gagosian R. B., Farrington J. W., Canuel E. A.: Sterenes in suspended particulate matter in the eastern tropical North Pacific. Appl Opt 1984, 308, 840. <http://dx.doi.org/10.1038/308840a0>
  • Teshima Shin-Ichi, Kanazawa Akio, Yamada Ichimaro, Tanaka Yoshito: Sterols of the spongeTethya amamensis: Occurrence of (24E)-24-ethylidenecholesta-5,7-dienol, (24E)-24-propylidenecholesta-5,7-dienol, and (24Z)-24-propylidenecholesta-5,7-dienol. Lipid 1983, 18, 193. <http://dx.doi.org/10.1007/BF02534547>
  • Li Xian, Djerassi Carl: Minor and trace sterols in marine invertebrates 40. Structure and synthesis of axinyssasterol, 25-methylfucosterol and 24-ethyl-24-methylcholesterol -- novel sponge sterols with highly branched side chains. Tetrahetron Lett 1983, 24, 665. <http://dx.doi.org/10.1016/S0040-4039(00)81493-8>
  • Dias Jerry Ray: Mass spectral fragmentation of 24, 24-diphenyl-23-ene derivatives of cholic acid. J Pharm Sci 1982, 71, 285. <http://dx.doi.org/10.1002/jps.2600710305>
  • Gagosian Robert B., Smith Steven O., Nigrelli Gale E.: Vertical transport of steroid alcohols and ketones measured in a sediment trap experiment in the equatorial Atlantic Ocean. Geochimica et Cosmochimica Acta 1982, 46, 1163. <http://dx.doi.org/10.1016/0016-7037(82)90002-3>
  • Dissanayake C.B., Senaratne A., Gunatilaka A.A.Leslie: Organic geochemical studies of the Muthurajawela peat deposit of Sri Lanka. Geochem 1982, 4, 19. <http://dx.doi.org/10.1016/0146-6380(82)90004-3>
  • García F., Cruz R., González M.: The mass spectra of13C labelled methylene derivatives of steroids—IV. Biol Mass Spectrom 1981, 8, 93. <http://dx.doi.org/10.1002/bms.1200080302>
  • Sica D., Di Giacomo G., Anderson L.C., Johnson D.A.: Contents of volume 70A number 3 1981. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1981, 70, i. <http://dx.doi.org/10.1016/0305-0491(81)90007-9>
  • Bohlin Lars, Kokke W.C.M.C., Fenical William, Djerassi Carl: 4α-methyl-24S-ethyl-5α-cholestan-3β-ol and 4α-methyl-24S-ethyl-5α-cholest-8(14)-en-3β-ol, two new sterols from a cultured marine di. Phytochemisry 1981, 20, 2397. <http://dx.doi.org/10.1016/S0031-9422(00)82674-6>
  • Wright Jeffrey L.C.: Minor and trace sterols of Dunaliella tertiolecta. Phytochemisry 1981, 20, 2403. <http://dx.doi.org/10.1016/S0031-9422(00)82675-8>
  • Carmely S., Kashman Y.: Isolation and structure elucidation of lobophytosterol, depresosterol and three other closely related sterols. Tetrahedron 1981, 37, 2397. <http://dx.doi.org/10.1016/S0040-4020(01)88896-7>
  • Li Lian Niang, Djerassi Carl: Minor and trace sterols in marine invertebrates 30. Isolation, structure elucidation and partial synthesis of 26-methylstrongylosterol and 28-methylxestosterol - two marine sterols arising by a novel quadruple biomethylation sequence. Tetrahetron Lett 1981, 22, 4639. <http://dx.doi.org/10.1016/S0040-4039(01)83001-X>
  • Dürbeck Hans Werner, Büker Ingrid: Studies on anabolic steroids. The mass spectra of 17α-methyl-17β-hydroxy-1,4-androstadien-3-one (dianabol) and its metabolites. Biol Mass Spectrom 1980, 7, 437. <http://dx.doi.org/10.1002/bms.1200071007>
  • Patterson Donald G., Lavanchy André, Djerassi Carl: Electron impact induced fragmentation of steroidal diketones with ‘abnormal’ stereochemistry. Org Mass Spectrom 1980, 15, 41. <http://dx.doi.org/10.1002/oms.1210150113>
  • Lavanchy Andre, Varkony Tomas, Smith Dennis H., Gray Neil A. B., White William C., Carhart Raymond E., Buchanan Bruce G., Djerassi Carl: Rule-based mass spectrum prediction and ranking: Applications to structure elucidation of novel marine sterols. Org Mass Spectrom 1980, 15, 355. <http://dx.doi.org/10.1002/oms.1210150709>
  • Delseth Claude, Tolela Luhata, Djerassi Carl, Scheuer Paul J., Wells Robert J.: 5α-24-Norcholestan-3β-ol and (24Z)-Stigmasta-5,7,24(28)-trien-3β-ol, Two New Marine Sterols from the Pacific SpongesTerpios zeteki andDysidea herbacea. HCA 1979, 62, 101. <http://dx.doi.org/10.1002/hlca.19790620115>
  • Ayanoglu Eser, Chan Andrea, Djerassi Carl: Use of n-lithioethylenediamine in the double bond isomerization and degradation of sterol side chains. Tetrahedron 1979, 35, 1591. <http://dx.doi.org/10.1016/0040-4020(79)80020-4>
  • GAGOSIAN ROBERT B., SMITH STEVEN O.: Steroids ketones in surface sediments from the south-west African shelf. Appl Opt 1979, 277, 287. <http://dx.doi.org/10.1038/277287a0>
  • Kokke W.C.M.C., Fenical W.H., Pak C.S., Djerassi Carl: Minor and trace sterols in marine invertebrates IX. Verongulasterol - a marine sterol with a novel side chain alkylation pattern. Tetrahetron Lett 1978, 19, 4373. <http://dx.doi.org/10.1016/S0040-4039(01)95227-X>
  • Ravi B.N., Kokke W.C.M.C., Delseth Claude, Djerassi Carl: Isolation and structure of 26,27-cycloaplysterol (petrosterol) a cyclopropane-containing marine sterol. Tetrahetron Lett 1978, 19, 4379. <http://dx.doi.org/10.1016/S0040-4039(01)95229-3>