Pure Appl. Chem., 1981, Vol. 53, No. 4, pp. 873-890
http://dx.doi.org/10.1351/pac198153040873
Recent studies in the marine sterol field
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- Bradley Marcia D., Ku��era Milo��, Loeb Marcia, Bennettov�� Blanka, Miralles Joseph, Diop Moussoukhoye, Ferrer Alain, Kornprobst Jean-Michel, Andersson Tommy, Nilsson Eva: Alterations in proteases, protease inhibitors and ecdysone levels: a profile of stress in insects. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1989, 94, 85. <http://dx.doi.org/10.1016/0305-0491(89)90016-3>
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- 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>
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- 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>
- 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>
- Ayanoglu Eser, Li Huiting, Djerassi Carl, Düzgünes Nejat: Unusual sponge phospholipids and their analogs. Synthesis and interactions with conventional phospholipids and cholesterol in model membranes. J Chem Phys Lipids 1988, 47, 165. <http://dx.doi.org/10.1016/0009-3084(88)90010-2>
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- 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>
- 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)90145-9>
- Miralles Joseph, Diop Moussoukhoye, Ferrer Alain, Kornprobst Jean-Michel, Meyran Jean-Claude, Fran��ois Jean, Graf Fran��ois, Dash Janet A.: Sterol composition of the ahermatypic zoantharia: Palythoa senegambiensis carter and its commensal, the decapoda Diogenes ovatus miers. Inadequacy of sterol content for chemotaxonomy of Palythoa genus. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1988, 89, 209. <http://dx.doi.org/10.1016/0305-0491(88)90212-X>
- Malik Sohail, Stoilov Ivan L., Djerassi Carl: Biosynthetic studies of marine lipids 18. Biosynthesis of 3β-(hydroxymethyl)-A-nor-5α-cholest-15-ene in the marine sponge phakellia aruensis. Tetrahetron Lett 1988, 29, 4081. <http://dx.doi.org/10.1016/S0040-4039(00)80422-0>
- Summons Roger E., Volkman John K., Boreham Christopher J.: Dinosterane and other steroidal hydrocarbons of dinoflagellate origin in sediments and petroleum. Geochimica et Cosmochimica Acta 1987, 51, 3075. <http://dx.doi.org/10.1016/0016-7037(87)90381-4>
- Sica Donato, Piccialli Vincenzo, Pronzato Roberto: ��5,7Sterols from the sponges Ircinia pipetta and Dysidea avara identification of cholesta-5,7,24-trien-3B-OL. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1987, 88, 293. <http://dx.doi.org/10.1016/0305-0491(87)90117-9>
- Stoilov Ivan L., Bladocha-Moreau Michele, Thompson Janice E., Djerassi Carl: Biosynthetic studies of marine lipids 12. Tetrahedron 1987, 43, 2213. <http://dx.doi.org/10.1016/S0040-4020(01)86804-6>
- Ayanoğlu Eser, Düzgüneş Nejat, Wijekoon W.M.Donald, Djerassi Carl: Biophysical properties of unusual phospholipids and sterols from marine invertebrates. Biochim Biophys Acta Biomembr 1986, 863, 110. <http://dx.doi.org/10.1016/0005-2736(86)90392-5>
- 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>
- Goad L.J., Garneau F.-X., Simard J.L., Apsimon J.W., Girard M.: Composition of the free, esterified and sulphated sterols of the sea cucumber Psolus fabricii. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1986, 84, 189. <http://dx.doi.org/10.1016/0305-0491(86)90204-X>
- Stoilov Ivan L., Thompson Janice E., Djerassi Carl: Biosynthetic studes of marine lipids 7. Tetrahedron 1986, 42, 4147. <http://dx.doi.org/10.1016/S0040-4020(01)87637-7>
- 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>
- Stoilov Ivan L., Thompson Janice E., Djerassi Carl: Biosynthetic studies of marine lipids 10. Double side chain extension in the triply alkylated sponge sterol xestosterol. Tetrahetron Lett 1986, 27, 4821. <http://dx.doi.org/10.1016/S0040-4039(00)85072-8>
- 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>
- Stevens Earl V.J., Husbands David R., Koubi Harry, Fr��minet Alain, Dini A., Piccialli V., Pronzato R., Sica D.: Insulin-dependent production of low-molecular-weight compounds that modify keenzymes in metabolism. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1985, 81, 1. <http://dx.doi.org/10.1016/0305-0491(85)90169-5>
- Sica Donato, Piccialli Vincenzo: A new C30 sterol, (24Z)-24-propylcholesta-5,7,24(28)-trien-3��-ol, and other ��5,7 sterols from the sponge Spongionella gracilis. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1985, 81, 115. <http://dx.doi.org/10.1016/0305-0491(85)90170-1>
- Seldes A.M., Rovirosa J., San Mart��n A., Gros E.G.: Sterols from the sponge Haliclona chilensis. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1985, 81, 119. <http://dx.doi.org/10.1016/0305-0491(85)90171-3>
- 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>
- Goad L.J., Garneau F.-X., Simard J.-L., ApSimon J.W., Girard M.: Isolation ofΔ9(11)-sterols from the sea cucumber . Implications for holothurin biosynthesis. Tetrahetron Lett 1985, 26, 3513. <http://dx.doi.org/10.1016/S0040-4039(00)98678-7>
- Zaikin V. G., Mikaya A. I.: Mass spectrometry of bioorganic molecules containing small carbocycles. Mass Spectrom Rev 1984, 3, 479. <http://dx.doi.org/10.1002/mas.1280030403>
- Shubina L. K., Makar'eva T. N., Stonik V. A.: Steroid compounds of marine sponges. III. 24-Ethyl-25-methylcholesta-5,22-dien-3β-OL — A new marine sterol from the spongeHalichondria sp. Chem Nat Compd 1984, 20, 438. <http://dx.doi.org/10.1007/BF00574330>
- Dini A., Falco B., Ferrigni M., Marino A., Sica D.: The sterols of two hadromerida sponges. CMLS Cell Mol Life Sci 1984, 40, 170. <http://dx.doi.org/10.1007/BF01963582>
- Dasgupta Amitava, Ayanoglu Eser, Djerassi Carl: Phospholipid studies of marine organisms: New branched fatty acids fromStrongylophora durissima. Lipid 1984, 19, 768. <http://dx.doi.org/10.1007/BF02534470>
- Volkman John K., Gagosian Robert B., Wakeham Stuart G.: Free and esterified sterols of the marine dinoflagellateGonyaulax polygramma. Lipid 1984, 19, 457. <http://dx.doi.org/10.1007/BF02537408>
- Moldowan J.Michael: C30-steranes, novel markers for marine petroleums and sedimentary rocks. Geochimica et Cosmochimica Acta 1984, 48, 2767. <http://dx.doi.org/10.1016/0016-7037(84)90321-1>
- Djerassi Carl: A Steroid autobiography. Steroid 1984, 43, 351. <http://dx.doi.org/10.1016/0039-128X(84)90010-2>
- 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>
- Mendis A.H.W., Evans A.A.F., Dini A., Sica D., Boniforti L., Durliat Michele: Major volatile metabolites produced by two isolates of Aphelenchus avenae under aerobic and anaerobic conditions. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1984, 78, 737. <http://dx.doi.org/10.1016/0305-0491(84)90128-7>
- Nichols Peter D., Jones Gary J., De Leeuw Jan W., Johns R.B.: The fatty acid and sterol composition of two marine dinoflagellates. Phytochemisry 1984, 23, 1043. <http://dx.doi.org/10.1016/S0031-9422(00)82605-9>
- 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>
- Alam Maktoob, Sanduja Radhika, Watson David A., Loeblich Alfred R.: STEROL DISTRIBUTION IN THE GENUSHETEROCAPSA(PYRRHOPHYTA)1. Journal of Phycology 1984, 20, 331. <http://dx.doi.org/10.1111/j.0022-3646.1984.00331.x>
- Koch Patrick, Djerassi Carl, Lakshmi Vijai, Schmitz Francis J.: Identification de stérols à chaîne latérale oxygénée dans une éponge de l'espèceHyrtios. HCA 1983, 66, 2431. <http://dx.doi.org/10.1002/hlca.19830660806>
- Ayanoglu Eser, Popov Simeon, Kornprobst J. M., Aboud-Bichara Amira, Djerassi Carl: Phospholipid studies of marine organisms: V1 new α-methoxy acids fromHigginsia tethyoides. Lipid 1983, 18, 830. <http://dx.doi.org/10.1007/BF02534643>
- de Leeuw J.W., Rijpstra W.Irene C., Schenck P.A., Volkman J.K.: Free, esterified and residual bound sterols in Black Sea Unit I sediments. Geochimica et Cosmochimica Acta 1983, 47, 455. <http://dx.doi.org/10.1016/0016-7037(83)90268-5>
- Goad L.John, Holz George G., Beach David H.: Identification of (24S)-24-methylcholesta-5,22-dien-3β-ol as the major sterol of a marine cryptophyte and a marine prymnesiophyte. Phytochemisry 1983, 22, 475. <http://dx.doi.org/10.1016/0031-9422(83)83028-3>
- 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>
- Djerassi Carl, Popov S., Carlson R.M.K.: Occurrence and seasonal variation of 19-norcholest-4-EN-3-one and 3β-monohydroxy sterols in the Californian gorgonian, Muricea californica. Steroid 1983, 41, 537. <http://dx.doi.org/10.1016/0039-128X(83)90093-4>
- di Giacomo G., Dini A., Falco B., Marino A., Sica D.: Sterols from the sponge Agelas oroides. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1983, 74, 499. <http://dx.doi.org/10.1016/0305-0491(83)90217-1>
- Kalinovskaya N.I., Kuznetsova T.A., Elyakov G.B.: Sterol composition of Pacific holothurian Stichopus japonicus selenka. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1983, 74, 597. <http://dx.doi.org/10.1016/0305-0491(83)90235-3>
- Khan A.Sattar, Goad L.John: The sterol constituents and ��5,7-sterol content of some bivalve molluscs. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1983, 76, 569. <http://dx.doi.org/10.1016/0305-0491(83)90295-X>
- Nichols Peter D., Volkman John K., Johns R.B.: Sterols and fatty acids of the marine unicellular alga, fcrg 51. Phytochemisry 1983, 22, 1447. <http://dx.doi.org/10.1016/S0031-9422(00)84033-9>
- Dow W.C., Gebreyesus T., Popov S., Carlson R.M.K., Djerassi Carl: Marine 4-methyl sterols: Synthesis of C-24 epimers of 4α,24-dimethyl-5α-cholestan-3β-OL and 360 MHz 1HNMR comparisons to the natural product from Plexaura homomalla. Steroid 1983, 42, 217. <http://dx.doi.org/10.1016/S0039-128X(83)90220-9>
- 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>
- Catalan Cesar A.N., Djerassi Carl: Chemical proof of absolute configuration of 24,26-cyclocholesterol by biomimetic conversion to 27-norergostenes. Tetrahetron Lett 1983, 24, 3461. <http://dx.doi.org/10.1016/S0040-4039(00)86013-X>
- Jones Gary J., Nichols Peter D., Johns R. B.: THE LIPID COMPOSITION OF THORACOSPHAERA HEIMII: EVIDENCE FOR INCLUSION IN THE DINOPHYCEAE1. J Phycol 1983, 19, 416. <http://dx.doi.org/10.1111/j.0022-3646.1983.00416.x>
- 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>
- Goad L. John, Withers Nancy: Identification of 27-nor-(24R)-24-methylcholesta-5,22-dien-3β-ol and brassicasterol as the major sterols of the marine dinoflagellateGymnodinium simplex. Lipid 1982, 17, 853. <http://dx.doi.org/10.1007/BF02534578>
- 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>
- Catalan Cesar A.N., Lakshmi Vijai, Schmitz Francis J., Djerassi Carl: Minor and trace sterols in marine invertebrates 39.11For part 38, see ref. 10. 24ξ,25ξ-24,26-cyclocholest-5-en-3β-ol, a novel cyclopropyl sterol. Steroid 1982, 40, 455. <http://dx.doi.org/10.1016/0039-128X(82)90022-8>
- Kokke W.C.M.C., Fenical William, Djerassi Carl: Sterols of the cultured dinoflagellate Pyrocystis lunula. Steroid 1982, 40, 307. <http://dx.doi.org/10.1016/0039-128X(82)90042-3>
- Burnell D.Jean, ApSimon John W., Gilgan Michael W.: Seasonal and geographic variations of the sterols from the starfish asterias vulgaris (verrill). Steroid 1982, 39, 357. <http://dx.doi.org/10.1016/0039-128X(82)90060-5>
- Zielinski Jan, Milkova T., Popov S., Marekov N., Djerassi Carl: Minor and trace sterols in marine invertebrates. 34★★For No. 33 in this series, see: Bohlin, L., Sjöstrand, U., Sodano, G. and Djerassi, C., J. ORG. CHEM., submitted for publication. Isolation and structure elucidation of 24-methyl-5α-cholesta-7,9(11), 24(28)-trien-3β-ol, the first naturally occurring Δ7, 9(11) unsaturated marine sterol. Steroid 1982, 39, 675. <http://dx.doi.org/10.1016/0039-128X(82)90138-6>
- Gebreyesus T., Djerassi Carl: Synthesis of the putative marine sterols [24R]- and [24S]-23,24-dimethyl-5α-cholest-23(29)-en-3β-ol. Tetrahetron Lett 1982, 23, 4427. <http://dx.doi.org/10.1016/S0040-4039(00)85619-1>
- 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>
- 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>
- 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>
- 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>