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Pure Appl. Chem., 1979, Vol. 51, No. 9, pp. 1815-1828

http://dx.doi.org/10.1351/pac197951091815

Recent progress in the marine sterol field

C. Djerassi, N. Theobald, W. C. M. C. Kokke, C. S. Pak and R. M. K. Carlson

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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>
  • Seeman Jeffrey I.: Carl Djerassi: In His Own Words. Angew. Chem. Int. Ed. 2014, 53, 3268. <http://dx.doi.org/10.1002/anie.201308367>
  • Sünnemann Hans Wolf, Banwell Martin G., de Meijere Armin: Diversity-Oriented Synthesis of Enantiomerically Pure Steroidal Tetracycles Employing Stille/Diels-Alder Reaction Sequences. Chem Eur J 2008, 14, 7236. <http://dx.doi.org/10.1002/chem.200800601>
  • Hu Jin-Feng, Kelly Michelle, Hamann Mark T: 26-Nor-25-isopropyl-ergosta-5,7,22E-trien-3β-ol: a new C29 sterol from the sponge Agelas sceptrum from Jamaica. Steroid 2002, 67, 743. <http://dx.doi.org/10.1016/S0039-128X(02)00033-8>
  • Kanazawa Akio: Sterols in marine invertebrates. Fisheries Sci 2001, 67, 997. <http://dx.doi.org/10.1046/j.1444-2906.2001.00354.x>
  • Suzuki Noriyuki, Sampei Yoshikazu, Koga Osamu: Norcholestane in Miocene Onnagawa siliceous sediments, Japan. Geochimica et Cosmochimica Acta 1993, 57, 4539. <http://dx.doi.org/10.1016/0016-7037(93)90509-U>
  • Akihisa Toshihiro, Kokke W.C.M.C., Yokota Takao, Tamura Toshitake, Matsumoto Taro: 4α,14α-Dimethyl-5α-ergosta-7,9(11),24(28)-trien-3β-ol from Phaseolus vulgaris and Gynostemma pentaphyllum. Phytochemisry 1990, 29, 1647. <http://dx.doi.org/10.1016/0031-9422(90)80139-8>
  • Pakrashi Satyesh C., Duffa Pradeep K., Achari Basudeb, Misra Suniti, Choudhury Amalesh, Chattopadhyay Subhashis, Ghosh Amitabha: Lipids and fatty acids of the horseshoe crabsTachypleus gigas andCarcinoscorpius rotundicauda. Lipid 1989, 24, 443. <http://dx.doi.org/10.1007/BF02535154>
  • Zimmerman Mary P., Thomas Frances C., Thompson Janice E., Djerassi Carl, Streiner Heidi, Evans Elizabeth, Murphy Peter T.: The distribution of lipids and sterols in cell types from the marine spongePseudaxinyssa sp. Lipid 1989, 24, 210. <http://dx.doi.org/10.1007/BF02535236>
  • Kerr Russell G., Stoilov Ivan L., Thompson Janice E., Djerassi Carl: Biosynthetic studies of marine lipids 16. De novo sterol biosynthesis in sponges. Incorporation and transformation of cycloartenol and lanosterol into unconventional sterols of marine and freshwater sponges. Tetrahedron 1989, 45, 1893. <http://dx.doi.org/10.1016/S0040-4020(01)80054-5>
  • Lawson Mishelle P., Thompson Janice E., Djerassi Carl: Localization of long-chain fatty acids and unconventional sterols in spherulous cells of a marine sponge. Lipid 1988, 23, 1037. <http://dx.doi.org/10.1007/BF02535649>
  • Carballeira Néstor M., Maldonado Maria E.: 6-methyl-8-hexadecenoic acid: A novel fatty acid from the marine spongeDesmapsama anchorata. Lipid 1988, 23, 690. <http://dx.doi.org/10.1007/BF02535670>
  • Lawson Mishelle P., Thompson Janice E., Djerassi Carl: Cell membrane localization of long chain C24−C30 fatty acids in two marine demosponges. Lipid 1988, 23, 741. <http://dx.doi.org/10.1007/BF02536215>
  • Lawson Mishelle P., Stoilov Ivan L., Thompson Janice E., Djerassi Carl: Cell membrane localization of sterols with conventional and unusual side chains in two marine demonsponges. Lipid 1988, 23, 750. <http://dx.doi.org/10.1007/BF02536216>
  • Bloch Konrad: Technical news feature. J Am Oil Chem Soc 1988, 65, 1763. <http://dx.doi.org/10.1007/BF02542377>
  • Manconi R., Piccialli V., Pronzato R., Sica D., Kleinow W., Garson Mary J., Partali Vassilia, Liaaen-Jensen Synn��ve, Stoilov Ivan L.: Steroids in porifera, sterols from freshwater sponges Ephydatia fluviatilis (L.) and Spongilla lacustris (L.). Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1988, 91, 237. <http://dx.doi.org/10.1016/0305-0491(88)90138-1>
  • Garson Mary J., Partali Vassilia, Liaaen-Jensen Synn��ve, Stoilov Ivan L.: Isoprenoid biosynthesis in a marine sponge of the Amphimedon genus: Incorporation studies with [1-14C] acetate, [4-14C] cholesterol and [2-14C] mevalonate. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1988, 91, 293. <http://dx.doi.org/10.1016/0305-0491(88)90145-9>
  • Genet J.P., Gaudin J.M.: Stereoselective synthesis of side chain of glaucasterol using palladium (O) catalyst. Tetrahedron 1987, 43, 5315. <http://dx.doi.org/10.1016/S0040-4020(01)87708-5>
  • Dutta Ashis K., Pal Prasanta K., Ghosh Amitabha, Misra Suniti, Nandi S., Choudhury A.: Lipids and fatty acids of the gastropod molluscCerethidea cingulata. J Am Oil Chem Soc 1986, 63, 223. <http://dx.doi.org/10.1007/BF02546142>
  • Maxwell James R., McEvoy James: A-norsteroidal ketones in deep sea sediments. Geochem 1986, 9, 101. <http://dx.doi.org/10.1016/0146-6380(86)90090-2>
  • H. Buist Peter, Dimnik Gerald P.: Use of sulfur as a chemical connector. Tetrahetron Lett 1986, 27, 1457. <http://dx.doi.org/10.1016/S0040-4039(00)84284-7>
  • Back Thomas G, Proudfoot John R, Djerassi Carl: Application of selenosulfonation to marine sterol synthesis. Preparation of 24,28-dehydroaplysterol, xestosterol and ostreasterol from a common acetylenic intermediate. Tetrahetron Lett 1986, 27, 2187. <http://dx.doi.org/10.1016/S0040-4039(00)84483-4>
  • Proudfoot John R., Catalan C.A.N., Djerassi Carl, Sica D., Sodano G.: Biosynthetic studies of marine lipids. 6. Evidence for an unprecedented biomethylation pathway in the biosynthesis of the cyclopropyl-containing marine sterol, petrosterol. Tetrahetron Lett 1986, 27, 423. <http://dx.doi.org/10.1016/S0040-4039(00)85495-7>
  • Misra Suniti, Ghosh Mrinal K., Choudhury A., Dutta Ashis K., Pal Prasanta K., Ghosh Amitabha: Fatty acids fromMacoma sp. of bivalve mollusc. J Sci Food Agric 1985, 36, 1193. <http://dx.doi.org/10.1002/jsfa.2740361125>
  • Tam Ha T.B., Kokke W.C.M.C., Proudfoot John R., Djerassi Carl, Thompson Janice: Minor and trace sterols in marine invertebrates 53: Further novel marine sterols resulting from triple and quadruple biomethylation of the cholesterol side-chain. Steroid 1985, 45, 263. <http://dx.doi.org/10.1016/0039-128X(85)90075-3>
  • Julia M., Marazano C.: Biomimetic methyl transfer to olefins. Tetrahedron 1985, 41, 3717. <http://dx.doi.org/10.1016/S0040-4020(01)91392-4>
  • Catalan Cesar A.N., Thompson Janice E., Kokke W.C.M.C., Djerassi Carl: Biosynthetic studies of marine lipids—3. Tetrahedron 1985, 41, 1073. <http://dx.doi.org/10.1016/S0040-4020(01)96475-0>
  • Ksebati Mohamad B., Schmitz Francis J.: 24ξ-Methyl-5α-cholestane-3β,5,6β.22r.24-pentol 6-acetate: New polyhydroxylated sterol from the soft coral asterospicularia randalli. Steroid 1984, 43, 639. <http://dx.doi.org/10.1016/0039-128X(84)90026-6>
  • Cranwell P.A.: Lipid geochemistry of sediments from Upton Broad, a small productive lake. Geochem 1984, 7, 25. <http://dx.doi.org/10.1016/0146-6380(84)90134-7>
  • Buist P.H., Kendall J., Barradas R.G.: Biomimetic methylation of unactivated olefins by electrochemically generated methyl cations. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry 1984, 161, 393. <http://dx.doi.org/10.1016/S0022-0728(84)80197-7>
  • Buist Peter H., Findlay Judy M.: Fluorine substituent effects on bio-methylenation of olefinic fatty acids. Tetrahetron Lett 1984, 25, 1433. <http://dx.doi.org/10.1016/S0040-4039(01)80179-9>
  • Proudfoot John R., Djerassi Carl: Minor and trace sterols in marine invertebrates 48. The isolation, structure elucidation and synthesis of 23(R),24(R)-methylenecholesterol. Tetrahetron Lett 1984, 25, 5493. <http://dx.doi.org/10.1016/S0040-4039(01)81608-7>
  • Fujimoto Yoshinori, Kimura Miki, Terasawa Takeshi, Khalifa Fathy A.M., Ikekawa Nobuo: Stereocontrolled synthesis and determination of the c-24 and 25 stereochemistry of glaucasterol. Tetrahetron Lett 1984, 25, 1805. <http://dx.doi.org/10.1016/S0040-4039(01)90046-2>
  • Rovirosa Juana, Muñoz Orlando, Martín Aurelio San, Seldes Alicia M., Gros Eduardo G.: Sterols from the gorgonianLephogorgia subcompressa. Lipid 1983, 18, 570. <http://dx.doi.org/10.1007/BF02535400>
  • Makarieva T.N., Shubina L.K., Kalinovsky A.I., Stonik V.A., Elyakov G.B.: Steroids in porifera. II. Steroid derivatives from two sponges of the family Halichondriidae. Sokotrasterol sulfate,a marine steroid with a new pattern of side chain alkylation. Steroid 1983, 42, 267. <http://dx.doi.org/10.1016/0039-128X(83)90039-9>
  • Bonini Carlo, Kinnel Robin B., Li Michael, Scheuer Paul J., Djerassai Carl: Minor and trace sterols in marine invertebrates 38: isolation, structure elucidation and partial synthesis of papakusterol, a new biosynthetically unusual marine sterol with a cyclopropyl-containing side chain. Tetrahetron Lett 1983, 24, 277. <http://dx.doi.org/10.1016/S0040-4039(00)81384-2>
  • Bloch Konrad E.: Sterol, Structure and Membrane Functio. Crit Rev Biochem Mol Biol 1983, 14, 47. <http://dx.doi.org/10.3109/10409238309102790>
  • Lang Robert W., Djerassi Carl: Stereochemical Aspects of Acid-Catalyzed Cyclopropane Ring-Opening Reactions. A Stereospecific Pathway to Crinosterol and Brassicasterol. HCA 1982, 65, 407. <http://dx.doi.org/10.1002/hlca.19820650144>
  • 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>
  • Ayanoglu Eser, Walkup Robert D., Sica Donato, Djerassi Carl: Phospholipid studies of marine organisms: III. New phospholipid fatty acids fromPetrosia ficiformis. Lipid 1982, 17, 617. <http://dx.doi.org/10.1007/BF02535368>
  • 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>
  • Zielinski Jan, Kokke W.C.M.C., Fenical William, Djerassi Carl: Sterols of the cultured euglenid Eutreptia viridis: A novel Δ23-unsaturated sterol. Steroid 1982, 40, 403. <http://dx.doi.org/10.1016/0039-128X(82)90018-6>
  • Zagalsky P.F., Jones R., Dini A., Minale L., Pizza C., Riccio R., Zollo F., Mohamed A.M., Ishak M.M.: Quaternary structures of the astaxanthin-proteins of Velella velella, and of ��-crustacyanin of lobster carapace, as revealed in electron microscopy. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1982, 71, 237. <http://dx.doi.org/10.1016/0305-0491(82)90255-3>
  • Ritter Karla S., Weiss Burton A., Norrbom Allen L., Nes William R.: Identification of ��5,7-24-methylene- and methylsterols in the brain and whole body of Atta cephalotes isthmicola. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1982, 71, 345. <http://dx.doi.org/10.1016/0305-0491(82)90393-5>
  • Lang Robert W., Djerassi Carl: Stereospecific cyclopropane ring-opening of petrosterol. A possible biomimetic process. Tetrahetron Lett 1982, 23, 2063. <http://dx.doi.org/10.1016/S0040-4039(00)87261-5>
  • Gray Neil A. B., Buchs Armand, Smith Dennis H., Djerassi Carl: Computer Assisted Structural Interpretation of Mass Spectral Data. HCA 1981, 64, 458. <http://dx.doi.org/10.1002/hlca.19810640210>
  • Walkup Robert D., Jamieson Gene C., Ratcliff Milton R., Djerassi Carl: Phospholpid studies of marine organisms: 2.1 Phospholipids, phospholipid-bound fatty acids and free sterols of the spongeAplysina fistularis (Pallas) formafulva (Pallas) (=Verongia thiona)2. Isolation and structure elucidation of unprecedented branched fatty acids. Lipid 1981, 16, 631. <http://dx.doi.org/10.1007/BF02535058>
  • Sjöstrand U., Kornprobst J.M., Djerassi Carl: Minor and trace sterols from marine invertebrates 29. (22E)-ergosta-5,22,25-trien-3β-ol and (22E,24R)-24,26-dimethylcholesta-5,22,25(27)-trien-3β-ol. Two new marine sterols from the sponge Pseudaxinella lunacharta. Steroid 1981, 38, 355. <http://dx.doi.org/10.1016/0039-128X(81)90070-2>
  • Zielinski Jan, Li Hui-tinq, Milkova T.S., Popov S., Marekov N.L., Djerassi Carl: Isolation of 22-methylenecholesterol. Further evidence for direct bioalkylation of 22-dehydrocholesterol. Tetrahetron Lett 1981, 22, 2345. <http://dx.doi.org/10.1016/S0040-4039(01)82902-6>
  • Shu Arthur Y.L., Djerassi Carl: Stereospecific synthesis of dinosterol. Tetrahetron Lett 1981, 22, 4627. <http://dx.doi.org/10.1016/S0040-4039(01)82998-1>
  • Fusetani N., Matsunaga S., Konosu S.: Bioactive marine metabolites II. Halistanol sulfate, an antimicrobial novel steroid sulfate from the marine sponge halichondria cf. moorei bergquist. Tetrahetron Lett 1981, 22, 1985. <http://dx.doi.org/10.1016/S0040-4039(01)92885-0>
  • Brassell S. C., Eglinton G.: Biogeochemical significance of a novel sedimentary C27 stanol. Appl Opt 1981, 290, 579. <http://dx.doi.org/10.1038/290579a0>
  • Harel Zvi, Djerassi Carl: Dinosterol in model membranes: Fluorescence polarization studies. Lipid 1980, 15, 694. <http://dx.doi.org/10.1007/BF02534022>
  • Wahid Khalil M., Djerassi Carl, Sica D.: Minor and trace sterols in marine invertebrates XVII. 1 (24R)-24,26-dimethylcholesta-5,26-dien-3β-01, a new sterol from the sponge Petrosia ficiformis. Steroid 1980, 35, 707. <http://dx.doi.org/10.1016/0039-128X(80)90095-1>
  • Swenson Wendy, Tagle Bruce, Clardy Jon, Withers Nancy W., Kokke W.C.M.C., Fenical William, Djerassi Carl: Peridinosterol - a new Δ17-unsaturated sterol from two cultured marine algae. Tetrahetron Lett 1980, 21, 4663. <http://dx.doi.org/10.1016/0040-4039(80)88088-9>