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Part of the book series: Handbuch der Pflanzenphysiologie / Encyclopedia of Plant Physiology ((532,volume 10))

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Zusammenfassung

Die Sterine sind hochmolekulare, gut kristallisierte Alkohole mit 27 bis 31 Kohlenstoffatomen. Ihren Namen leitet diese Verbindungsklasse von dem gegen Ende des 18. Jahrhunderts aus Gallensteinen isolierten Cholesterin ab (χολή Galle, στέαϱ Fett1). Ein pflanzliches Sterin scheint erstmals von Husemann beschrieben worden zu sein, der indessen die Verwandschaft des „Hydrocarotins“ mit Cholesterin nicht erkannte. 1862 isolierte dann Beneke aus Erbsen eine Substanz, die er für Cholesterin hielt, jedoch zeigte später Hesse, daß derartige in Pflanzen vorkommende Verbindungen dem Cholesterin zwar sehr nahe stehen, aber mit ihm nicht identisch sind. Es ergab sich somit eine Einteilung in tierische (Zoosterine) und pflanzliche Sterine (Phytosterine); von diesen wurden noch die Algensterine und Pilzsterine (Mycosterine) abgetrennt. Die Grenzen zwischen den einzelnen Gruppen sind jedoch nicht sehr streng. Zwar ist das Vorkommen des Cholesterins selber ausschließlich auf Wirbeltiere beschränkt — ein hydroxyliertes Cholesterin konnte allerdings kürzlich in höheren Pflanzen aufgefunden werden (S. 138) —, aber manche Pflanzensterine finden sich auch bei niederen Tieren.

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Literatur

  • Alt, G. H., and D. H. R. Barton: The constitution of cerevisterol. Chem. a. Ind. 1952, 1103.

    Google Scholar 

  • Anderson, R. J.: The phytosterols of the endosperm of corn. J.Amer. Chem. Soc. 46, 1450–1460 (1924).

    CAS  Google Scholar 

  • Anderson, R. J., F. P. Nabenhauer and R. L. Shriner: The distribution of dihydrositosterol in plant fats. J. of Biol. Chem. 71, 389–399 (1926/1927).

    CAS  Google Scholar 

  • Anderson, R. J., and R. L. Shriner: The phytosterols of corn oil. J. Amer. Chem. Soc. 48, 2976–2986 (1926).

    CAS  Google Scholar 

  • The reductive products of certain plant sterols. J. of Biol. Chem. 71, 401-406 (1926/27).

    Google Scholar 

  • Anderson, R. J., R. L. Shriner and G. O. Burr: The phytosterols of wheat germ oil. J. Amer. Chem. Soc. 48, 2987–2996 (1926).

    CAS  Google Scholar 

  • Appleton, G. S., R. J. Kieber and W. J. Payne: The sterol content of fungi. II. Screening of representative yeasts and molds for sterol content. Appl. Microbiol. 3, 249–251 (1955).

    PubMed  CAS  Google Scholar 

  • Arigoni, D., O. Jeger u. L. Ruzicka: Zur Kenntnis der Triterpene. 183. Mitteilung. Über die Konstitution von Tirucallol, Euphorbol und Elemadienolsäure. Helvet. chim. Acta 38, 222–230 (1955).

    CAS  Google Scholar 

  • Arigoni, D., R. Viterbo, M. Dünnenberger, O. Jeger u. L. Ruzicka: Zur Kenntnis der Triterpene. 182. Mitteilung. Konstitution und Konfiguration von Euphol und iso-Euphenol. Helvet. chim. Acta 37, 2306–2322 (1954).

    CAS  Google Scholar 

  • Arigoni, D., H. Wyler u. O. Jeger: Zur Kenntnis der Triterpene. 179. Mitteilung. Über die gegenseitigen Beziehungen bei Elemadienolsäure, Tirucalladienol und Euphorbadienol. Helvet. chim. Acta 37, 1553–1558 (1954).

    CAS  Google Scholar 

  • Avasthi, B. K., u. J. D. Tewari: Chemische Untersuchung der Samen von „Desmodium gangeticum“. Arch. Pharmaz. 288, 272–275 (1955).

    CAS  Google Scholar 

  • Bachhawat, B. K., W. G. Robinson and M. J. Coon: The enzymatic cleavage of ß-hydroxy-ß-methylglutaryl coenzyme A to acetoacetate and acetyl coenzyme A. J. of Biol. Chem. 216, 727–736 (1955).

    CAS  Google Scholar 

  • Enzymatic carboxylation of β-hydroxyisovaleryl coenzyme A. J. of Biol. Chem. 219, 539-550 (1956).

    Google Scholar 

  • Barbour, J. B., W. A. Lourens, F. L. Warren and K. H. Watling: The structure of tirucallol, euphorbol and the elemi acids. Chem. a. Ind. 1955, 226.

    Google Scholar 

  • Barbour, J. B., F. L. Warren and D. A. Wood: The Euphorbia resins. Part VII. The characterization of the groups in euphorbol. J. Chem. Soc. (Lond.) 1951, 2537-2539.

    Google Scholar 

  • Barnes, C. S., D. H. R. Barton, J. S. Fawcett and B. R. Thomas: Triterpenoids. Part X. The stereochemistry of lanostadienol (lanosterol). J. Chem. Soc. (Lond.) 1953, 576-579.

    Google Scholar 

  • Barton, D. H. R.: Optische Drehung und Molekel-Struktur der Steroide. Angew. Chem. 61, 57–59 (1949).

    CAS  Google Scholar 

  • Triterpenoids. Part III. Cycloartenone, a triterpenoid ketone. J. Chem. Soc. (Lond.) 1951, 1444-1451.

    Google Scholar 

  • The chemistry of the triterpenoids. Progress in Organic Chemistry, Bd. 2, S. 67-103. London: Butterworths Scientific Publications 1953.

    Google Scholar 

  • Barton, D. H. R., and T. Bruun: A new sterol from a strain of Aspergillus niger. J. Chem. Soc. (Lond.) 1951, 2728-2733.

    Google Scholar 

  • Barton, D. H. R., and J. D. Cox: The application of the method of molecular rotation differences to steroids. Part V. Olefinic unsaturation at the 7:8-position. J. Chem. Soc. (Lond.) 1948, 1354-1357.

    Google Scholar 

  • Barton, D. H. R., J. F. McGhie, M. K. Pradhan and S. A. Knight: The constitution and stereochemistry of euphol. J. Chem. Soc. (Lond.) 1955, 576-586.

    Google Scholar 

  • Barton, D. H. R., and K. H. Overton: Triterpenoids. Part XX. The constitution and stereochemistry of a novel tetracyclic triterpenoid. J. Chem. Soc. (Lond.) 1955, 2639-2652.

    Google Scholar 

  • Barton, D. H. R., J. E. Page and E. W. Warnhoff: Triterpenoids. Part XVIII. The constitutions of phyllanthol and cycloartenol. J. Chem. Soc. (Lond.) 1954, 2715-2719.

    Google Scholar 

  • Barton, D.H.R., and E.Seoane: Triterpenoids. Part XXII. The constitution and stereochemistry of masticadienonic acid. J. Chem. Soc. (Lond.) 1956, 4150-4157.

    Google Scholar 

  • Bauer, K. H., u. H. Moll: Zur Kenntnis der unverseifbaren Bestandteile des Sheafetts. Fette und Seifen 46, 560–563 (1939).

    CAS  Google Scholar 

  • Bauer, K. H., u. P. Schenkel: Zur Kenntnis des Euphorbiumharzes. Arch. Pharmaz. 266, 633–638 (1928).

    CAS  Google Scholar 

  • Bauer, K. H., u. G. Schröder: Über Euphorbol. 2. Mitteilung über Euphorbiumharz (5. Mitteilung „Über die Chemie der Harzbestandteile“). Arch. Pharmaz. 269, 209–218 (1931).

    CAS  Google Scholar 

  • Bauer, K. H., u. Y. Yen Hou: Untersuchungen über die Lipide des Sojaöls. Fette u. Seifen 51, 301–307 (1944).

    CAS  Google Scholar 

  • Behring, H. v.: Enthalten Bakterien Sterine? Hoppe-Seylers Z. 192, 112–113 (1930).

    Google Scholar 

  • Beneke, G. M. R.: Cholesterin im Pflanzenreich aufgefunden. Liebigs Ann. 122, 249–255 (1862).

    Google Scholar 

  • Benešová, V., V. Herout and F. Šorm: Über Pflanzenstoffe. 3. Mitt. Über Verbindungen aus echtem Reizker (Lactarius deliciosus L.). Chem. Listy 48, 882–885 (1954) (Chem. Zbl. 1956, 3338)

    Google Scholar 

  • Bengtsson, S. E.: Ein Vergleich zwischen Sitostanol und Stigmastanol. Hoppe-Seylers Z. 237, 46–51 (1935).

    CAS  Google Scholar 

  • Bentley, H. R., J.A. Henry, D.S. Irvine, D. Mukerji and F. S. Spring: Triterpenoids. Part XXXII. Cyclolaudenol, a triterpenoid alcohol from opium. J. Chem. Soc. (Lond.) 1955, 596-602.

    Google Scholar 

  • Bergmann, W.: Marine products. XXV. Comparative biochemical studies on the lipides of marine invertebrates, with special reference to the sterols. J. Marine Res. (Sears Foundation) 8, 137–176 (1949).

    CAS  Google Scholar 

  • The Sterols. Progress in the Chemistry of Fats and Other Lipids, Bd. 1, S. 18–69. London: Pergamon Press Ltd. 1952.

    Google Scholar 

  • The plant sterols. Annual Rev. Plant Physiol. 4, 383 (1953).

    Google Scholar 

  • Bergmann, W., and R. J. Feeney: Sterols of Algae. I. The occurence of chondrillasterol in Scenedesmus obliquus. J. of Org. Chem. 15, 812–814 (1950).

    CAS  Google Scholar 

  • Bergmann, W., and M. Klosty: Sterols of Algae. II. The structure of fucosterol. J. Amer. Chem. Soc. 73, 2935 (1951).

    CAS  Google Scholar 

  • Bergmann, W., and F. H. McTigue: Contribution to the study of marine products. XXI. Chondrillasterol. J. of Org. Chem. 13, 735–741 (1948).

    Google Scholar 

  • Bergmann, W., and R. C. Ottke: Marine products. XXIV. The occurence of brassicasterol in mollusks. J. of Org. Chem. 14, 1085–1088 (1949).

    CAS  Google Scholar 

  • Bernstein, S., and E. S. Wallis: Structure of ß-sitosterol and its preparation from stigmasterol. J. of Org. Chem. 2, 341–345 (1937).

    CAS  Google Scholar 

  • Studies in the sitosterol complex. The isolation of α3-sitosterol. J. Amer. Chem. Soc. 61, 1903–1904 (1939a).

    Google Scholar 

  • Studies in the sitosterol complex. The structure of α1-sitosterol. J. Amer. Chem. Soc. 61, 2308–2313 (1939b).

    Google Scholar 

  • Biochemisches Handlexikon, herausgeg. von E. Abderhalden, Bd. 3, S. 268-309; Bd. 8, S. 473-493; Bd. 10, S. 156-181; Bd. 14, S. 798-869. Berlin: Springer 1911-1933.

    Google Scholar 

  • Birkinshaw, J. H., E. N. Morgan and W. P. K. Findlay: Biochemistry of the wood-rotting fungi. 7. Metabolic products of Polyporus benzoinus (Wahl) Fr. Biochemic. J. 50, 509–516 (1952).

    CAS  Google Scholar 

  • Black, W. A. P., and W. J. Cornhill: A method for the estimation of fucosterol in seaweeds. J. Sci. Food Agric. 2, 387–390 (1951) (Chem. Abstr. 46, 3120).

    CAS  Google Scholar 

  • Blears, J. G., and C. Shoppee: Ergosta-7,22-dien-3β,5α,6β-triol (cerevisterol). Chem. a. Ind. 1953, 947.

    Google Scholar 

  • Blecher, H., and S. Gurin: The conversion of radioactive acetoacetate to cholesterol by surviving rat liver slices. J. of Biol. Chem. 209, 953–962 (1953).

    Google Scholar 

  • Bloch, K.: Biological synthesis of cholesterol. Rec. Chem. Progr. 15, 103–109 (1954).

    CAS  Google Scholar 

  • Bloch, K., L. C. Clark and I. Harary: Utilization of branched chain acids in cholesterol synthesis. J. Amer. Chem. Soc. 76, 3859–3860 (1954); J. of Biol. Chem. 211, 867-699 (1954).

    CAS  Google Scholar 

  • Bonner, J., and B. Arreguin: The biochemistry of rubber formation in the guayule. I. Rubber formation in seedlings. Arch. of Biochem. 21, 109–124 (1949).

    CAS  Google Scholar 

  • Bonner, J., M. W. Parker and J. C. Montermoso: Biosynthesis of rubber. Science (Lancaster, Pa.) 120, 549–551 (1954).

    CAS  Google Scholar 

  • Bonstedt, K.: Über einige Sterine des Pflanzenreichs. Hoppe-Seylers Z. 176, 269–281 (1928).

    CAS  Google Scholar 

  • Bowers, A., T. G. Halsall, E. R. H. Jones and A. J. Lemin: The chemistry of triterpenes and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid C. J. Chem. Soc. (Lond.) 1953, 2548-2560.

    Google Scholar 

  • Bowers, A., T. G. Halsall and G. C. Sayer: The chemistry of triterpenes and related compounds. Part XXV. Some stereochemical problems concerning polyporenic acid C. J. Chem. Soc. (Lond.) 1954, 3970-3984.

    Google Scholar 

  • Bradbury, R. B., and D. E. White: Estrogens and related substances in plants. Vitamins a. Hormones 12, 207–233 (1954).

    CAS  Google Scholar 

  • Breivik, O. N., J. L. Owades and R. F. Light: A new tetraethenoid sterol of yeast. J. of Org. Chem. 19, 1734–1740 (1954).

    CAS  Google Scholar 

  • Bücher, N. L. R., and K. McGarrahan: Rat liver microsomes in cholesterol biosynthesis. Federat. Proc. 14, 187 (1955).

    Google Scholar 

  • Bijrián, R.: Über Sitosterin. Ein Beitrag zur Kenntnis der Phytosterine. Mh. Chem. 18, 551–574 (1897).

    Google Scholar 

  • Callow, R. K.: Occurence of α-dihydroergosterol as an impurity in yeast ergosterol. Biochemic. J. 25, 87–94 (1931).

    CAS  Google Scholar 

  • Carter, P. W., I. M. Heilbron and B. Lythgoe: Lipochromes and sterols of the algal classes. Proc. Roy. Soc. Lond., Ser. B 128, 82–109 (1939).

    CAS  Google Scholar 

  • Chapon, S., et S. David: Sur un constituant secondaire du latex d’ Euphorbia balsamifera. Bull. Soc. chim. France 1952, 456-457.

    Google Scholar 

  • Clayton, R. B., and K. Bloch: Lanosterol as a precursor of cholesterol. Federat. Proc. 14, 194 (1955).

    Google Scholar 

  • Biological synthesis of lanosterol and agnosterol. J. of Biol. Chem. 218, 305-318 (1956a).

    Google Scholar 

  • The biological conversion of lanosterol to cholesterol. J. of Biol. Chem. 218, 319-325 (1956b).

    Google Scholar 

  • Clenshaw, E., and I. Smedley-MacLean: The nature of the unsaponifiable fraction of the lipoid matter extracted from green leaves. Biochemic. J. 23, 107–109 (1929).

    CAS  Google Scholar 

  • Clewer, H. W. B., S. J. Green and F. Tutin: The constituents of Oloriosa superba. J. Chem. Soc. (Lond.) 107, 835–846 (1915).

    CAS  Google Scholar 

  • Cole, A. R. H.: Infrared spectra of natural products. Part III. Cycloartenol and phyllantol. J. Chem. Soc. (Lond.) 1954, 3810-3812.

    Google Scholar 

  • Cook, J. W., and M. F. C. Paige: The sterols of Calycanthus floridus. J. Chem. Soc. (Lond.) 1944, 336 bis 337.

    Google Scholar 

  • Cornforth, J. W.: The biosynthesis of cholesterol. Rev. Pure a. Appl. Chem. 4, 275–302 (1954).

    Google Scholar 

  • Cornforth, J. W., I. Y. Gore and G. Popják: Studies in the biosynthesis of cholesterol. 4. Degradation of rings C and D. Biochemie. J. 65, 94–109 (1957).

    CAS  Google Scholar 

  • Cornforth, J. W., and G. Popják: Studies on the biosynthesis of cholesterol. 3. Distribution of 14C in squalene biosynthesized from [Me-14C] acetate. Biochemie. J. 58, 403–407 (1954).

    CAS  Google Scholar 

  • Cort, L. A., R. M. Gascoigne, J. S. H. Holker, S. J. Ralph, A. Robertson and J. J. H. Simes: The chemistry of fungi. Part XXIII. Tumulosic acid. J. Chem. Soc. (Lond.) 1954, 3713-3721.

    Google Scholar 

  • Corwin, L. M., L. J. Schroeder and W. G. McCullough: The metabolism of squalene by cellfree yeast extracts. J. Amer. Chem. Soc. 78, 1372–1375 (1956).

    CAS  Google Scholar 

  • Cosserat, L., G. Ourisson and T. Takahashi: The constitution of the neutral tetracyclic triterpenes of Dammer resin. Chem. a. Ind. 1956, 190-191.

    Google Scholar 

  • Cox, J. S. G., F. E. King and T. J. King: The chemistry of extractives from hardwoods. Part XXVI. Experiments on cycloeucalenol, a new triterpene from Eucalyptus microcorys. J. Chem. Soc. (Lond.) 1956, 1384-1392.

    Google Scholar 

  • Cross, L. C, C. G. Eliot, I. M. Heilbron and E. R. H. Jones: Constituents of higher fungi. Part I. The triterpene acids of Polyporus betulinus Fr. J. Chem. Soc. (Lond.) 1940, 632-636.

    Google Scholar 

  • Dam, H., A. Geiger, J. Glavind, P. Karrer, W. Karrer, E. Rothschild u. H. Salomon: Isolierung des Vitamins K in hochgereinigter Form. Helvet. chim. Acta 22, 310–313 (1939).

    CAS  Google Scholar 

  • Danielsson, H., and K. Bloch: On the origin of C-28 in ergosterol. J. Amer. Chem. Soc. 79, 500–501 (1957).

    CAS  Google Scholar 

  • Dauben, W. G., Y. Ban and J. H. Richards: The biosynthesis of the triterpene, eburicoic acid: The utilization of methyl-labeled acetate. J. Amer. Chem. Soc. 79, 968–973 (1957).

    CAS  Google Scholar 

  • Dauben, W. G., G. J. Fonken and G. A. Boswell: The biosynthetic precursor of the extra carbon atom in the side-chain of steroids. J. Amer. Chem. Soc. 79, 1000–1001 (1957).

    CAS  Google Scholar 

  • Dauben, W. G., and Th. W. Hutton: The biosynthesis of steroids and triterpenes. The origin of carbons 11 and 12 of ergosterol. J. Amer. Chem. Soc. 78, 2647–2648 (1956).

    CAS  Google Scholar 

  • Dauben, W. G., and J. H. Richards: The biosynthesis of the triterpene eburicoic acid. J. Amer. Chem. Soc. 78, 5329–5335 (1956).

    CAS  Google Scholar 

  • Dawson, M. C, T. G. Halsall, E. R. H. Jones, G. D. Meakins and P. C. Phillips: Butyrospermol and “Basseol”. Chem. a. Ind. 1955, 918-919.

    Google Scholar 

  • The chemistry of the triterpenes and related compounds. Part XXIX. The chemistry of butyrospermol. J. Chem. Soc. (Lond.) 1956, 3172-3178.

    Google Scholar 

  • Dawson, M. C, T. G. Halsall, E. R. H. Jones and P. A. Robins: The chemistry of the triterpenes. Part XVI. The action of hydrogen chloride on butyrospermol. J. Chem. Soc. (Lond.) 1953, 581-589.

    Google Scholar 

  • Dawson, M. C., T. G. Halsall and R. H. E. Swayne: The chemistry of the triterpenes. Part XVII. Some aspects of the chemistry of tetracyclic triterpenes. J. Chem. Soc. (Lond.) 1953, 590-594.

    Google Scholar 

  • Dicker, D. W., and M. C. Whiting: The synthetical preparation of pure squalene. Chem. a. Ind. 1956, 351.

    Google Scholar 

  • Dickhart, W.: The squalene content of various oils. Amer. J. Pharmacy 127, 359–361 (1955).

    CAS  Google Scholar 

  • Dirscherl, W., u. H. Nahm: Die Seitenkette des β- und γ-Sitosterins. Liebigs Ann. 555, 57–69 (1943).

    CAS  Google Scholar 

  • Über die Identität des Cinchols mit ß-Sitosterin und die Konstitution des γ-Sitosterins. Liebigs Ann. 558, 231-234 (1947).

    Google Scholar 

  • Dituri, F., F. A. Cobey, J. V. B. Warms and S. Gurin: Terpenoid intermediates in the biosynthesis of cholesterol. J. of Biol. Chem. 221, 181–189 (1956).

    CAS  Google Scholar 

  • Dulaney, E. L., E. O. Stapley and K. Simpf: Studies on ergosterol production by yeasts. Appl. Microbiol. 2, 371–379 (1954).

    PubMed  CAS  Google Scholar 

  • Eschenmoser, A., L. Ruzicka, O. Jeger u. D. Arigoni: Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen. Helvet. chim. Acta 38, 1890–1904 (1955).

    CAS  Google Scholar 

  • Fagerlund, U. H. M., and D. R. Idler: Marine sterols. II. 24-Methylene-cholesterol in molluscs. J. of Org. Chem. 21, 372–373 (1956).

    CAS  Google Scholar 

  • Fernholz, E.: Über die Konstitution des Stigmasterins. Liebigs Ann. 507, 128–138 (1934 a).

    Google Scholar 

  • Die Lage der Kerndoppelbindung im Stigmasterin. Liebigs Ann. 508, 215-224 (1934b).

    Google Scholar 

  • Fernholz, E., and H. B. MacPhillamy: Isolation of a new phytosterol: Campesterol. J. Amer. Chem. Soc. 63, 1155–1156 (1941).

    CAS  Google Scholar 

  • Fernholz, E., and M.L. Moore: The isolation of α-spinasterol from alfalfa. J. Amer. Chem. Soc. 61, 2467–2468 (1939).

    CAS  Google Scholar 

  • Fernholz, E., and W. L. Ruigh: On the constitution of α-spinasterol. J. Amer. Chem. Soc. 62, 2341–2343 (1940).

    CAS  Google Scholar 

  • On the constitution of campesterol. J. Amer. Chem. Soc. 63, 1157-1159 (1941).

    Google Scholar 

  • Fernholz, E., and H. E. Stavely: Brassicasterol. II. Degradation by ozone. J. Amer. Chem. Soc. 62, 428–430 (1940).

    CAS  Google Scholar 

  • Brassicasterol, the characteristic sterol of rapeseed oil. J. Amer. Chem. Soc. 62, 1875-1877 (1940).

    Google Scholar 

  • Fieser, L. F., and M. Fieser: Natural products related to phenanthrene, 3.Aufl. New York: Reinhold Publishing Corporation 1949.

    Google Scholar 

  • Frantz, I. D., and N. L. R. Bücher: The incorporation of the carboxyl carbon from acetate into cholesterol by rat liver homogenates. J. of Biol. Chem. 206, 471–481 (1954).

    CAS  Google Scholar 

  • Fridrichsons, J., and A. Mc L. Mathieson: Triterpenoids. The crystal structure of lanosteryl iodoacetate. J. Chem. Soc. (Lond.) 1953, 2159-2167.

    Google Scholar 

  • Fröschl, N., u. J. Zellner: Zur Kenntnis der Pilzharze. Mh. Chem. 53/54, 146–152 (1929).

    Google Scholar 

  • Furukawa, S.: Untersuchungen über die Bestandteile von „Gingko biloba L.“-Blätter. Sci. Pap. Inst. Phys. Chem. Res. 19, 27–38 (1932) (Chem. Zbl. 1932, II, 3901).

    CAS  Google Scholar 

  • Gascoigne, R. M., J. S. E. Holker, B. J. Ralph and A. Robertson: The chemistry of fungi. Part XVI. Eburicoic acid. J. Chem. Soc. (Lond.) 1951, 2346-2352.

    Google Scholar 

  • Gascoigne, R. M., A. Robertson and J. J. H. Simes: The chemistry of fungi. Part XVII. Dehydroeburicoic acid. J. Chem. Soc. (Lond.) 1953, 1830-1837.

    Google Scholar 

  • Gisvold, O.: Sterol glucosides. J. Amer. Pharmac. Assoc. 23, 402–403 (1934).

    CAS  Google Scholar 

  • Gloyer, S.W., and H.A. Schuette: The sterols of rye germ oil. J. Amer. Chem. Soc. 61, 1901–1903 (1939).

    CAS  Google Scholar 

  • Godson, D. H., F.E. King and T. J. King: The constitution of the neutral tetracyclic triterpenes of Dammer resin. Chem. a. Ind. 1956, 190.

    Google Scholar 

  • Gonzalez, A. G., J. L. Bretón and C. Bretón: The constitution of handianol. Chem. a. Ind. 1955, 416-417.

    Google Scholar 

  • González, A. G., y M. L. G. Mora: Aportación al estudio del latex de las „Euphorbias Canarias“. VI. Obtencion del germanicol y lanosterol del latex de la Euphorbia balsamifera Ait. An. Real. Soc. españ. Físic. y Quím., Ser B 48, 483–494 (1952) (Chem. Abstr. 48, 7039).

    Google Scholar 

  • Grob, E.C., u. R. Bütler: Über einen möglichen Weg der Biosynthese der Carotinoide bei Mucor hiemalis. Experientia (Basel) 11, 259–261 (1955).

    CAS  Google Scholar 

  • Gruber, W., u. G. Proske: Über Trametenolsäure [aus Trametes odorata (Wulf.) Fr.]. Mh. Chem. 81, 837–842 (1950).

    CAS  Google Scholar 

  • Guider, J. M., T. G. Halsall, R. Hodges and E. R. H. Jones: The chemistry of the triterpenes and related compounds. Part XXVI. The nature of polyporenic acid B. J. Chem. Soc. (Lond.) 1954, 3234-3238.

    Google Scholar 

  • Guider, J. M., T. G. Halsall and E. R. H. Jones: The chemistry of the triterpenes and related compounds. Part XXVII. Pinicolic acid A. J. Chem. Soc. (Lond.) 1954, 4471-4475.

    Google Scholar 

  • Guirard, B. M., E. E. Snell and R. J. Williams: The nutritional role of acetate for lactic acid bacteria. I. The response to substances related to acetate. Arch. of Biochem. 9, 361–379 (1946).

    CAS  Google Scholar 

  • Guiteras, A.: Einwirkung von Ozon auf Stigmasterin. Hoppe-Seylers Z. 214, 89–90 (1934).

    Google Scholar 

  • Haines, D.W., and F. L. Warren: The Euphorbia resins. Part II. The isolation of taraxasterol and a new triterpene, tirucallol, from E. tirucalli. J. Chem. Soc. (Lond.) 1949, 2554-2556.

    Google Scholar 

  • Halsall, T. G., and R. Hodges: The chemistry of the triterpenes and related compounds. Part XXIV. The conversion of polyporenic acid A into a lanosterol derivative. J. Chem. Soc. (Lond.) 1954, 2385-2391.

    Google Scholar 

  • Halsall, T. G., R. Hodges and E. R. H. Jones: The chemistry of the triterpenes and related compounds. Part XIX. Further evidence concerning the structure of polyporenic acid A. J. Chem. Soc. (Lond.) 1953, 3019-3024.

    Google Scholar 

  • Halsall, T. G., and E. R. H. Jones: The chemistry of butyrospermol and of some fungal acids. Referatenband, S. 177, XIV. Internationaler Kongreß für reine und angewandte Chemie. Zürich, 21.–27. Juli 1955.

    Google Scholar 

  • Halsall, T. G., G. D. Meakins and R. E. H. Swayne: The chemistry of the triterpenes and related compounds. Part XXI. Some aspects of the chemistry of the elemi acids. J. Chem. Soc. (Lond.) 1953, 413-4148.

    Google Scholar 

  • Hamilton, B., and W. O. Kermack: The isolation of α-spinasterol from colocynth. J. Chem. Soc. (Lond.) 1952, 5051-5052.

    Google Scholar 

  • Hanahan, D. J., and S. J. Wakil: The biosynthesis of ergosterol from isotopic acetate. Arch. of Biochem. a. Biophysics 37, 167–171 (1952).

    CAS  Google Scholar 

  • Origin of some of the carbon atoms of the side chain of C14-ergosterol. J. Amer. Chem. Soc. 75, 273-275 (1953).

    Google Scholar 

  • Hart, M. C., and F. W. Heyl: Some constituents of jambul. J. Amer. Chem. Soc. 38, 2805–2813 (1916).

    CAS  Google Scholar 

  • Hartmann, E., u. J. Zellner: Zur Chemie der höheren Pilze. XIX. Mitt. Über Polyporus pinicola. Mh. Chem. 50, 193–200 (1928).

    CAS  Google Scholar 

  • Heath-Brown, B., I. M. Heilbron and E. R. H. Jones: Studies in the sterol group. Part XLIL The constitution of zymosterol. J. Chem. Soc. (Lond.) 1940, 1482-1489.

    Google Scholar 

  • Heiduschka, A., u. R. Wallenreuter: Zur Kenntnis des Öles der Samen von Strychnos nux-vomica. Arch. Pharmaz. 250, 398–402 (1912).

    Google Scholar 

  • Zur Kenntnis des Öles der Samen von Strychnos nuxvomica. II. Arch. Pharmaz. 253, 202-213 (1915).

    Google Scholar 

  • Heilbron, I. M.: Some aspects of algal chemistry. J. Chem. Soc. (Lond.) 1942, 79-89.

    Google Scholar 

  • Heilbron, I. M., E. R. H. Jones, K.C. Roberts and P.A. Wilkinson: Studies in the sterol group. Part XLIIL The unsaponifiable portion of the acetone extract of plantation rubber. J. Chem. Soc. (Lond.) 1941, 344-347.

    Google Scholar 

  • Heilbron, I. M., E. R. H. Jones and P. A. Robins: The non-saponifiable matter of shea nut fat. Part IV. A new tetracyclic diethenoid alcohol, butyrospermol. J. Chem. Soc. (Lond.) 1949, 444-449.

    Google Scholar 

  • Heilbron, I. M., G. C. Moffett and F. S. Spring: The non-saponifiable matter of shea nut fat. Part I. J. Chem. Soc. (Lond.) 1934, 1583 bis 1585.

    Google Scholar 

  • Heilbron, I. M., R. F. Phipers and H. R. Wright: The chemistry of algae. Part I. The algal sterol fucosterol. J. Chem. Soc. (Lond.) 1934, 1572-1576.

    Google Scholar 

  • Helmkamp, G., and J. Bonner: Some relationships of sterols to plant growth. Plant Physiol. 29, 428–436 (1953).

    Google Scholar 

  • Henry, J. A., D.S. Irvine and F. S. Spring: Triterpenoids. Part XXXIV. The constitution of cyclolaudenol. J. Chem. Soc. (Lond.) 1955, 1607-1615.

    Google Scholar 

  • Henry, J. A., and F. S. Spring: The structure of cycloartenol. Chem. a. Ind. 1954, 189.

    Google Scholar 

  • Hesse, O.: Über Phytosterin und Cholesterin. Liebigs Ann. 192, 175–179 (1878).

    Google Scholar 

  • Heusner, A.: Die Stereochemie der natürlichen Steroide. Angew. Chem. 63, 59–70 (1951).

    CAS  Google Scholar 

  • Die Chemie der Hormone. (Zwanglose Abhandlungen aus dem Gebiet der inneren Sekretion, Bd. 10.) Leipzig: Johann Ambrosius Barth 1954.

    Google Scholar 

  • Hey, D.H., J. Honeyman and W. I. Peal: The steroid series. Part I. The ozonolysis of fucosterol and some of its derivatives. J. Chem. Soc. (Lond.) 1950, 2881-2884.

    Google Scholar 

  • The steroid series. Part II. Further reactions of fucosterol and 24-ketocholesterol. J. Chem. Soc. (Lond.) 1952, 4833-4839.

    Google Scholar 

  • Heyl, F. W., and D. Larsen: The unsaponifiable fraction from spinach fat. II. J. Amer. Pharmaceut. Assoc. 22, 510–513 (1933).

    CAS  Google Scholar 

  • The unsaponifiable fraction of spinach fat. A glucoside of γ-spinasterol. J. Amer. Chem. Soc. 56, 942-943 (1934).

    Google Scholar 

  • Heyl, F. W., E. C. Wise and J. H. Speer: The unsaponifiable fraction from spinach fat. J. of Biol. Chem. 82, 111–116 (1929).

    Google Scholar 

  • Holker, J. S. E., A. D. G. Powell, A. Robertson, J. J. H. Simes, R. S. Wright and R. M. Gascoigne: The chemistry of fungi. Part XIX. The structure of eburicoic acid. J. Chem. Soc. (Lond.) 1953, 2422-2429.

    Google Scholar 

  • Honeywell, E. M., and Ch. E. Bills: Cerevisterol, a sterol accompanying ergosterol in yeast. J. of Biol. Chem. 99, 71–78 (1932/1933).

    Google Scholar 

  • Cerevisterol: New notes on composition, properties, and relation to other sterols. J. of Biol. Chem. 103, 515–520 (1933).

    Google Scholar 

  • Hüttel, R., u. H. Behringer: Über das Vorkommen von Pflanzensterinen in Kröten. Hoppe-Seylers Z. 245, 175–180 (1937).

    Google Scholar 

  • Husemann, A.: Über Carotin und Hydrocarotin. Diss. Univ. Göttingen 1860; Liebigs Ann. 117, 200-229 (1861).

    Google Scholar 

  • Hutt, H.H.: Lipid nomenclature. Nature (Lond.) 175, 303–304 (1955).

    CAS  Google Scholar 

  • Idler, D. R., and U. H. M. Fagerlund: Marine sterols. I. Isolation of 24-methylene-cholesterol from molluscs. J. Amer. Chem. Soc. 77, 4142–4144 (1955).

    CAS  Google Scholar 

  • Idler, D. R., A. A. Kandutsch and C. A. Baumann: Isolation of Δ7-stigmastenol from wheat. J. Amer. Chem. Soc. 75, 4325 (1953).

    CAS  Google Scholar 

  • Idler, D. R., S. W. Nicksic, D. R. Johnson, V. W. Meloche, H.A. Schuette and C. A. Baumann: Separation and tentative identification of two new sterols from oats. J. Amer. Chem. Soc. 75, 1712–1715 (1953).

    CAS  Google Scholar 

  • Inagaki, M., and T. Takemoto: Constituents of Chinese materia medica. VII. Isolation of α-euphorbol (euphorbadienol). J. Pharmaceut. Soc. Japan 75, 1571–1572 (1955) (Chem. Abstr. 50, 10647).

    CAS  Google Scholar 

  • Irvine, D.S., W. Lawrie, A. S. McNab and F. S. Spring: The constitution of butyrospermol. J. Chem. Soc. (Lond.) 1956, 2029-2033.

    Google Scholar 

  • Isler, O., R. Rüegg, L. Chopard-dit-Jean, H. Wagner u. K. Bernhard: Synthese von Squalen aus natürlichem und synthetischem Nerolidol. Helvet. chim. Acta 39, 897–904 (1956).

    CAS  Google Scholar 

  • Itallie, L. van: Über Dipterocarpol. Arch. Pharmaz. 250, 204–210 (1912).

    Google Scholar 

  • Jantzen, E., u. W. Gohdes: Über das Vorkommen von glucosidisch gebundenen Sterinen im Sojaö1. Biochem. Z. 272, 167–171 (1934).

    CAS  Google Scholar 

  • Jeger, O.: Über die Konstitution der Triterpene. Fortschritte der Chemie organischer Naturstoffe, Bd. 7, S. 1–86. Wien: Springer 1950.

    Google Scholar 

  • Johnston, J. A., D. W. Racusen and J. Bonner: The metabolism of isoprenoid precursors in a plant system. Proc. Nat. Acad. Sci. U.S.A. 40, 1031–1037 (1954).

    CAS  Google Scholar 

  • Jones, E. R. H., and T. G. Halsall: Tetracyclic triterpenes. Fortschritte der Chemie organischer Naturstoffe, Bd. 12, S. 44–130. Wien: Springer 1955.

    Google Scholar 

  • Jones, E. R. H., P. A. Wilkinson and R. H. Kerlogue: Studies in the sterol group. Part XLIV. The oxidation of phytosterols with the Oppenauer reagent. J. Chem. Soc. (Lond.) 1942, 391-393.

    Google Scholar 

  • Kaiser, E., and R. Wulzen: Identification of a sugar-cane sterol antistiffness factor as stigmasterol. Arch. of Biochem. a. Biophysics 31, 327–328 (1951).

    CAS  Google Scholar 

  • Kariyone, T., u. G. Kurono: Bestandteile von Fomes officinalis Fris. J. Pharmaceut. Soc. Japan 60, 110–111, 318-320 (1940) (Chem. Abstr. 35, 461).

    Google Scholar 

  • Karrer, P., u. W. Bürgi: Über Inhaltsstoffe von Cerastium alpinum. Helvet. chim. Acta 34, 832–834 (1951).

    CAS  Google Scholar 

  • Karrer, P., u. A. Helfenstein: Synthese des Squalens. Helvet. chim. Acta 14. 78–85 (1931).

    CAS  Google Scholar 

  • Khanolkar, V. R., T. B. Panse and V. D. Divekar: γ-Sitosteryl-glycoside in tobacco. Science (Lancaster, Pa.) 122, 515–516 (1955).

    CAS  Google Scholar 

  • Kind, C. A., and V. D. Celentano: Steroids of the Virginia snakeroot, Aristolochia serpentaria. J. of Org. Chem. 18, 1473–1477 (1953).

    CAS  Google Scholar 

  • King, F. E., and L. Jurd: The chemistry of extractives from hardwood. Part XII. The cyclitols and steroids of opepe (Sarcocephalus diderrichii). J. Chem. Soc. (Lond.) 1953, 1192-1195.

    Google Scholar 

  • King, L. C., and Ch. D. Ball: The sterols of alfalfa seed oil. I. J. Amer. Chem. Soc. 61, 2910–2912 (1939).

    CAS  Google Scholar 

  • The sterols of alfalfa seed oil. II. Isolation of β-spina-sterol and δ-spinasterol. J. Amer. Chem. Soc. 64, 2488-2492 (1942).

    Google Scholar 

  • Kipnis, F.: Suggested nomenclatural revision for “triterpenoid” steroids. Science (Lancaster, Pa.) 118, 754 (1953).

    CAS  Google Scholar 

  • Klein, H. P.: Relation of coenzyme A to steroid and total lipid synthesis in yeast. Federat. Proc. 10, 209 (1951).

    Google Scholar 

  • Klein, H. P., N. R. Eaton and J. C. Murphy: Net synthesis of sterols in resting cells of Saccharomyces cerevisiae. Biochim. et Biophysica Acta 13, 591 (1954).

    CAS  Google Scholar 

  • Klosty, M., and W. Bergmann: Sterols of algae. III. The occurence of ergosterol in Chlorella pyranoidosa. J. Amer. Chem. Soc. 74, 1601 (1952).

    CAS  Google Scholar 

  • Lahey, F. N., and P. H. A. Strasser: Eburicoic acid. J. Chem. Soc. (Lond.) 1951, 873-877.

    Google Scholar 

  • Langdon, R. G., and K. Bloch: The biosynthesis of squalene. J. of Biol. Chem. 200, 129–134 (1953a).

    CAS  Google Scholar 

  • The utilization of squalene in the biosynthesis of cholesterol. J. of Biol. Chem. 200, 135-144 (1953b).

    Google Scholar 

  • Larsen, C.D.: Spinastanol and its identity with fucostanol and stigmastanol. J. Amer. Chem. Soc. 60, 2431–2434 (1938).

    CAS  Google Scholar 

  • Lawrie, W., W. Hamilton, F. S. Spring and H. S. Watson: Triterpenoids. Part LIII. The constitution and stereochemistry of butyrospermol. J. Chem. Soc. (Lond.) 1956, 3272-3280.

    Google Scholar 

  • Lawrie, W., F. S. Spring and H. S. Watson: Constitution of parkeol. Chem. a. Ind. 1956, 1458.

    Google Scholar 

  • Lettré, H., u. A. Hagedorn: Darstellung von Steringlykosiden. Hoppe-Seylers Z. 242, 210–241 (1936).

    Google Scholar 

  • Lettré-Inhoffen-Tschesche: Über Sterine, Gallensäuren und verwandte Naturstoffe, 2. Aufl., Bd. 1. Bearbeitet von H. Lettré u. R. Tschesche, unter Mitwirkung von H. Fernholz. Stuttgart: Ferdinand Enke 1954.

    Google Scholar 

  • Lipmann, F.: Development of the acetylation problem, a personal account. Science (Lancaster, Pa.) 120, 855–865 (1954).

    CAS  Google Scholar 

  • Lynen, F.: Participation of coenzyme A in the oxidation of fat. Nature (Lond.) 174, 962–965 (1954).

    CAS  Google Scholar 

  • Ma, R. M., and P. S. Schaffer: ß-Sitosteryl-D-glucoside and β-sitosterol from commercially dried grapefruit pulp. Arch. of Biochem. a. Biophysics 47, 419–423 (1953).

    CAS  Google Scholar 

  • MacCorquodale, D. W., H. Steenbock and H. Adkins: The preparation and antirachitic activation of some derivatives of ergosterol and cholesterol. J. Amer. Chem. Soc. 52, 2512–2518 (1930).

    CAS  Google Scholar 

  • MacLachlan, P. L.: Fat metabolism in plants with special reference to sterols. J. of Biol. Chem. 113, 197–204 (1936).

    CAS  Google Scholar 

  • Fat metabolism in plants with special reference to sterols. II. Differential changes in the roots, stems and leaves. J. of Biol. Chem. 114, 185-191 (1936).

    Google Scholar 

  • MacPhillamy, H. B.: On the structure of fucosterol. J. Amer. Chem. Soc. 64, 1732–1733 (1942).

    CAS  Google Scholar 

  • Marion, L.: Nonbasic constituents of the leaves and roots of Adlumia fungosa Greene. Canad. J. Res. 10, 759–764 (1934) (Chem. Zbl. 1934, II, 2993).

    CAS  Google Scholar 

  • Ménard, E., H. Wyler, A. Hiestand, D. Arigoni, O. Jeger u. L. Ruzicka: Zur Kenntnis der Triterpene. 188. Mitteilung. Beweis für die Konstitution und Konfiguration von Tirucallol, Euphol, Euphorbol, Elemadienol-und Elemadienonsäure. Helvet. chim. Acta 38, 1517–1529 (1955).

    Google Scholar 

  • Mills, J. S.: The constitution of the neutral, tetracyclic triterpenes of Dammar resin. J. Chem. Soc. (Lond.) 1956, 2196-2202.

    Google Scholar 

  • Mills, J. S., and A. E. A. Werner: The chemistry of Dammar resin. J. Chem. Soc. (Lond.) 1955, 3132-3140.

    Google Scholar 

  • Mondon, A.: Zur Biogenese der Steroide. Angew. Chem. 65, 333–342 (1953).

    CAS  Google Scholar 

  • Die Synthese des Isosqualens. Chem. Ber. 88, 724-732 (1955).

    Google Scholar 

  • Murakami, S. T., T. Takemoto and M. Inagaki: Constituents of Chinese materia medica. VI. Identity of kanzuiol and tirucallol. J. Pharmaceut. Soc. Japan 75, 1171–1172 (1955) (Chem. Abstr. 50, 2121).

    CAS  Google Scholar 

  • Nath, M. C.: Untersuchung über die Konstitution von „Artostenon“, einem Sterinketon aus der indischen Sommerpflanze „Artocarpus integrifolia“. I. Isolierung und Reinigung. II. Nachweis einer Doppelbindung. III. Reduktion von Artostenon. Hoppe-Seylers Z. 247, 9–22 (1937).

    CAS  Google Scholar 

  • Newbold, G. T., and F. S. Spring: The isolation of euphol and α-euphorbol from Euphorbium. J. Chem. Soc. (Lond.) 1944, 249-252.

    Google Scholar 

  • Nicolaides, N., and F. Laves: The stereochemistry of squalene. A new method for the determination of cis-trans-isomerism. J. Amer. Chem. Soc. 76, 2596–2597 (1954).

    CAS  Google Scholar 

  • Nicolaides, N., O. K. Reiss and R. G. Langdon: Studies of the in vitro metabolism of the human skin. I. Biosynthesis in scalp skin. J. Amer. Chem. Soc. 77, 1535–1538 (1955).

    CAS  Google Scholar 

  • Oppenauer, R. V.: Synthesis of dehydroisoandrosterone by the decomposition of γ-sito-sterol from soybeans. Nature (Lond.) 135, 1039 (1935).

    CAS  Google Scholar 

  • Ottke, R. C, S. Simmonds and E. L. Tatum: Deuterioacetate in the biogenesis of ergosterol by Neurospora. J. of Biol. Chem. 186, 581–589 (1950).

    CAS  Google Scholar 

  • Ottke, R. C., E. L. Tatum, I. Zabin and K. Bloch: Isotopic acetate and isovalerate in the synthesis of ergosterol by Neurospora. J. of Biol. Chem. 189, 429–433 (1951).

    CAS  Google Scholar 

  • Oxford, A. E., and H. Raistrick: Studies in the biochemistry of microorganisms. XXXII. The mycelial constituents of Pénicillium brevi-compactum Diercks and related species. 1. Ergosteryl palmitate. Biochemic. J. 27, 1176–1180 (1933).

    CAS  Google Scholar 

  • Pascher, A.: Über die Übereinstimmung zwischen den Diatomeen, Heterokonten und Chrysomonaden. Ber. dtsch. bot. Ges. 39, 236–248 (1921).

    Google Scholar 

  • Popjak, G.: Biosynthesis of squalene and cholesterol in vitro from acetate-1-C14. Arch. of Biochem. a. Biophysics 48, 102–106 (1954).

    CAS  Google Scholar 

  • Power, F. B., and H. Browning jr.: The constituents of the flowers of Anthemis nobilis. J. Chem. Soc. (Lond.) 105, 1829–1845 (1914).

    CAS  Google Scholar 

  • Power, F. B., and Ch. W. Moore: The constituents of colocynth. J. Chem. Soc. (Lond.) 97, 99–110 (1910).

    CAS  Google Scholar 

  • Power, F. B., and A. H. Salway: The identification of ipuranol and some allied compounds as phytosterol glucosides. J. Chem. Soc. (Lond.) 103, 399–406 (1913).

    CAS  Google Scholar 

  • Rabinowitz, J. L.: The biosynthesis of radioactive senecioic acid (γ-methylcrotonic acid) in particle-free extracts of rat liver. J. Amer. Chem. Soc. 76, 3037–3830 (1954).

    CAS  Google Scholar 

  • Rabinowitz, J. L., and S. Gurin: The biosynthesis of radiaoctive cholesterol, β-methyl-glutaconic acid and β-methylcrotonic acid by aqueous extracts of liver. J. Amer. Chem. Soc. 76, 5168 (1954).

    CAS  Google Scholar 

  • Reindel, F., u. A. Weickmann: Zur Kenntnis des Zymosterins. II. Liebigs Ann. 482, 120–129 (1930).

    CAS  Google Scholar 

  • Ritter, E.: Beiträge zur Kenntnis des Sitosterins. Hoppe-Seylers Z. 34, 461–480 (1902).

    CAS  Google Scholar 

  • Rosenkrantz, H., A. T. Milhorat, M. Farber and A. E. Milman: Purification and identification of the antistiffness factor. Proc. Soc. Exper. Biol. a. Med. 76, 408–410 (1951).

    CAS  Google Scholar 

  • Roth, M., G. Saucy, R. Anliker, O. Jeger u. H. Heusser: Über Steroide und Sexualhormone. 195. Mitteilung. Die Konstitution der Polyporensäure A. Helvet. chim. Acta 36, 1908–1918 (1953).

    CAS  Google Scholar 

  • Rudney, H.: The synthesis of γ-hydroxy-γ-methylglutaric acid in rat liver homogenates. J. Amer. Chem. Soc. 76, 2595–2596 (1954).

    CAS  Google Scholar 

  • The synthesis of γγ-dimethylacrylic acid in rat liver homogenates. J. Amer. Chem. Soc. 77, 1698-1699 (1955).

    Google Scholar 

  • Ruzicka, L.: The isoprene rule and the biogenesis of terpene compounds. Experientia (Basel) 9, 357–367 (1953).

    CAS  Google Scholar 

  • Ruzicka, L., R. Denss u. O. Jeger: Zur Kenntnis der Triterpene (96. Mitteilung). Beweis der Identität von Lanosterin und Kryptosterin. Helvet. chim. Acta 28, 759–766 (1945).

    Google Scholar 

  • Salway, A. H.: The synthetic preparation of the α-glucosides of sitosterol, cholesterol, and some fatty alcohols. J. Chem. Soc. (Lond.) 103, 1022–1029 (1913).

    CAS  Google Scholar 

  • Sandermann, W., u. H. Stockmann: Untersuchungen über die Biogenese von Sterinen. Naturwiss. 43, 581 (1956).

    Google Scholar 

  • Sandqvist, H., u. E. Bengtsson: Zur Frage der Bruttoformel des Sitosterins. Ber. dtsch. chem. Ges. 64, 2167–2171 (1931).

    Google Scholar 

  • Schaffner, K., R. Viterbo, D. Arigoni u. O. Jeger: Zur Kenntnis der Triterpene. 191. Mitt. Zur Stereochemie des α-Onocerins. Helvet. chim. Acta 39, 174–183 (1956).

    CAS  Google Scholar 

  • Schenck, G.O., K. Gollnick u. O. A. Neumüller: Zur photosensibilisierten Autoxydation der Steroide. Darstellung von Steroid-Hydroperoxyden mittels phototoxischer Photosensibilisatoren. Liebigs Ann. 603, 46–59 (1957).

    CAS  Google Scholar 

  • Schmid, L., u. A. Waschkaij: Über die Phytosterine des Rüböls. Mh. Chem. 48, 139–144 (1927).

    CAS  Google Scholar 

  • Schönheimer, R., H. v. Behring u. R. Hummel: Über die Bedeutung gesättigter Sterine im Organismus. 4. Mitteilung: Untersuchung der Sterine aus verschiedenen Organen auf ihren Gehalt an gesättigten Sterinen. Hoppe-Seylers Z. 192, 93–96 (1930).

    Google Scholar 

  • Schuette, H.A., and W.E. Link: Isolation of campesterol and ⊿7-stigmastenol from rye germ oil. J. Amer. Chem. Soc. 76, 4192 (1954).

    CAS  Google Scholar 

  • Schulze, H.: Über die Abgrenzung der Sterine gegenüber anderen Alkoholen der Polyterpen-Reihe und über den Bau des Lanosterins und Onocerins. Hoppe-Seylers Z. 238, 35–53 (1936).

    CAS  Google Scholar 

  • Schwab, G. E.: Überblick über die Chemie der Sterine und ihre Verbreitung in der Natur. Diss. Univ. Zürich. Zürich: J. Bollmann A.-G. 1941.

    Google Scholar 

  • Schwenk, E., G. J. Alexander, Th. H. Stoudt and Ch. A. Fish: Studies on the biosynthesis of cholesterol. VII. Formation of cholesterol precursors by yeast. Arch. of Biochem. a. Biophysics 55, 274–285 (1955).

    CAS  Google Scholar 

  • Schwenk, E., D. Todd and Ch. A. Fish: Studies on the biosynthesis of cholesterol. VI. Companions of cholesterol-C14 in liver perfusions, including squalene-C14, as possible precursors in its biosynthesis. Arch. of Biochem. a. Biophysics 49, 187–206 (1954).

    CAS  Google Scholar 

  • Seitz, K., u. O. Jeger: Zur Kenntnis der Triterpene. 142. Mitteilung. Über die Isolierung eines unbekannten tetracyclischen Alkohols C30H50O aus „shea-nut“-Öl. Helvet. chim. Acta 32, 1626–1632 (1949).

    CAS  Google Scholar 

  • Sen, N. K., and J. K. Chakravarti: Sterols of jute-seed oil (Corchorus capsularis). J. Indian Chem. Soc. 28, 727–731 (1951) (Chem. Zbl. 1952,7679.

    CAS  Google Scholar 

  • Seoane, E.: Further crystalline constituents of gum mastic. J. Chem. Soc. (Lond.) 1956, 4158-4160.

    Google Scholar 

  • Sifferd, R. H., u. R. J. Anderson: Über das Vorkommen von Sterinen in Bakterien. Hoppe-Seylers Z. 239, 270–272 (1936).

    CAS  Google Scholar 

  • Simpson, I. C. E.: The constituents of senega root. Part I. Spinasterol. J. Chem. Soc. (Lond.) 1937, 730-733.

    Google Scholar 

  • Smedley-MacLean, I., and D. Hoffert: The carbohydrate and fat metabolism of yeast. Part III. The nature of the intermediate stages. Biochemic. J. 20, 343–357 (1926).

    Google Scholar 

  • Smedley-MacLean, I., and E. M. Thomas: The isolation of a second sterol from yeast fat. (Preliminary communication.) Biochemic. J. 22, 22–26 (1928).

    CAS  Google Scholar 

  • Soliman, G., and W. Saleh: Constituents of the seeds of Corchorus olitorius L. Part II. Isolation of β-sitosterol and corchorolic acid. J. Chem. Soc. (Lond.) 1954, 1506-1508.

    Google Scholar 

  • Sonderhoff, R., u. H. Thomas: Die enzymatische Dehydrierung der Trideutero-essigsäure. Liebigs Ann. 530, 195–213 (1937).

    CAS  Google Scholar 

  • Stabursvik, A.: A steroidal glycol, 22-hydroxycholesterol from Narthecium ossifragum Huds. Acta chem. scand. (Copenh.) 7, 1120 (1953).

    Google Scholar 

  • Steiner, M., u. H. Holtzem: Triterpene und Triterpen-saponine. Moderne Methoden der Pflanzenanalyse, herausgeg. von K. Paech u. M. V. Tracey, Bd. III, S. 58–140. Berlin-Göttingen-Heidelberg: Springer 1955.

    Google Scholar 

  • Stoll, A., u. E. Jucker: Phytosterine, Steroid-saponine und Herzglykoside. Moderne Methoden der Pflanzenanalyse, herausgeg. von K. Paech u. M. V. Tracey, Bd. III, S. 141–271. Berlin-Göttingen-Heidelberg: Springer 1955.

    Google Scholar 

  • Stork, G., and A. W. Burgstaller: The stereochemistry of polyene cyclization. J. Amer. Chem. Soc. 77, 5068–5077 (1955).

    CAS  Google Scholar 

  • Swift, L. J.: Isolation of ß-sitosteryl-D-glucoside from the juice of Florida Valencia oranges (Citrus sinensis L.). J. Amer. Chem. Soc. 74, 1099–1100 (1952).

    CAS  Google Scholar 

  • Täufel, K.: Zur Frage der Verbreitung von Squalen in pflanzlichen Fetten. Biochem. Z. 303, 324–328 (1939).

    Google Scholar 

  • Täufel, K., u. W. Heimann: Weitere Untersuchungen über die Verbreitung des Squalens in pflanzlichen und tierischen Fetten. Biochem. Z. 306, 123–124 (1940).

    Google Scholar 

  • Täufel, K., H. Thaler u. H. Schreyegg: Squalen als Bestandteil des Hefefettes. Fettchem. Umschau 43, 26–29 (1936).

    Google Scholar 

  • Tanret, Ch.: Sur un nouveau principe immédiat de l’ergot de seigle, l’ergostérine. C. r. Acad. Sci. (Paris) 106, 98–100 (1889).

    Google Scholar 

  • Sur l’ergostérine et la fongistérine. C. r. Acad. Sci. (Paris) 147, 75-77 (1908).

    Google Scholar 

  • Tavormina, P.A., and M. H. Gibbs: The metabolism of βγ-dihydroxy-β-methylvaleric acid by liver homogenates. J. Amer. Chem. Soc. 78, 6210 (1956).

    CAS  Google Scholar 

  • Tavormina, P. A., M. H. Gibbs and J. W. Huff: The utilization of β-hydroxy-β-methyl-γ-valerolactone in cholesterol biosynthesis. J. Amer. Chem. Soc. 78, 4498–4499 (1956).

    CAS  Google Scholar 

  • Tchen, T. T., and K. Bloch: In vitro conversion of squalene to lanosterol and cholesterol. J. Amer. Chem. Soc. 77, 6085–6086 (1955).

    CAS  Google Scholar 

  • On the mechanism of cyclization of squalene. J. Amer. Chem. Soc. 78, 1516-1517 (1956).

    Google Scholar 

  • Thorbjarnarson, T., and J. C. Drummond: Occurence of an unsaturated hydrocarbon in olive oil. Analyst (Lond.) 60, 23–29 (1935).

    CAS  Google Scholar 

  • Thornton, M. H., H. R. Kraybill and J. H. Mitchell jr.: Sterol glucosides from expressed soy bean oil. J. Amer. Chem. Soc. 62, 2006–2008 (1940).

    CAS  Google Scholar 

  • Tischer, J.: Über die epiphasischen Carotinoide und einige farblose Begleitstoffe einer roten Euglene (Carotinoide der Süßwasseralgen. VI. Teil). Hoppe-Seylers Z. 259, 163–170 (1939).

    CAS  Google Scholar 

  • Tomkins, G. M., I. L. Chaikoff, W.G. Dauben, H. L. Bradlow and P. A. Srere: Synthetic C14-„squalene“: Concerning its incorporation into cholesterol by liver. J. Amer. Chem. Soc. 74, 6445–6446 (1952).

    Google Scholar 

  • Toyama, Y., and T. Takagi: Sterols and other unsaponifiable substances in the lipids of shell fishes, crustaceae, and echinoderms. XVI. Reinvestigation of hitodesterol and its identity with α-spinasterol. Bull. Chem. Soc. Japan 28, 469–473 (1955).

    CAS  Google Scholar 

  • XVII. Mono-unsaturated sterol components of the starfish, Asterina pectinifera. Bull. Chem. Soc. Japan 29, 317-319 (1956).

    Google Scholar 

  • Toyama, Y., T. Takagi and T. Tanaka: Sterols and other unsaponifiable substances in the fats of shell fishes, Crustacea and echinodermata. XI. Sterols in the fat of the clam. Bull. Chem. Soc. Japan 26, 154–156 (1953) (Chem. Abstr. 48, 12770).

    Google Scholar 

  • Trippett, S.: The synthesis of squalene. Chem. a. Ind. 1956, 80.

    Google Scholar 

  • Tschesche, R.: Neuere Vorstellungen auf dem Gebiete der Biosynthese der Steroide und verwandter Naturstoffe. Fortschritte der Chemie organischer Naturstoffe, Bd. XII, S. 131–168. Wien: Springer 1955.

    Google Scholar 

  • Tsukamoto, T., and T. Ohtaki: Fatty substances from ovaries of Bufo melanosticus. IV. J. Pharmaceut. Soc. Japan 71, 751–753 (1951) (Chem. Abstr. 45, 10406).

    Google Scholar 

  • Turnbull, J.H., S. K. Vasistha, W. Wilson and R. Woodger: Nycthantic acid, a constituent of Nycthantes arbor-tnstis. J. Chem. Soc. (Lond.) 1957, 569-573.

    Google Scholar 

  • Vilkas, M.: Contribution à l’étude des triterpènes tetracycliques. Sur la structure de l’a-euphol. Ann. de Chim. 6, 325–366 (1951).

    CAS  Google Scholar 

  • Vogel, Chr., O. Jeger u. L. Ruzizka: Zur Kenntnis der Triterpene. 171. Mitteilung. Über Euphorbadienol. Helvet. chim. Acta 35, 510–519 (1952).

    CAS  Google Scholar 

  • Vogel, H., u. H. Knobloch: Chemie und Technik der Vitamine, 3. Aufl., Bd. 1, Die fettlöslichen Vitamine. Stuttgart: Ferdinand Enke 1950.

    Google Scholar 

  • Voser, W., Hs. H. Günthard, H. Heusser, O. Jeger u. L. Ruzicka: Zur Kenntnis der Triterpene. 175. Mitteilung. Ein neuer Weg zur Öffnung des Ringes C bei Lanostadienol. Helvet. chim. Acta 35, 2065–2072 (1952).

    Google Scholar 

  • Voser, W., Hs. H. Günthard, O. Jeger u. L. Ruzicka: Zur Kenntnis der Triterpene. 167. Mitteilung. Über die Größe des Ringes D im Lanostadienol. Helvet. chim. Acta 35, 66–75 (1952).

    CAS  Google Scholar 

  • Wagtendonck, W. J. van, and R. Wulzen: Physiological and chemical aspects of the antistiffness factor essential for Guinea pigs. Vitamins a. Hormones 8, 69–125 (1950).

    Google Scholar 

  • Wallis, E. S., and P. N. Chakravorty: Nature of the sterols in cottonseed oil. J. of Org. Chem. 2, 335–340 (1937).

    CAS  Google Scholar 

  • Wallis, E. S., and E. Fernholz: α-Sitosterol. J. Amer. Chem. Soc. 58, 2446–2448 (1936).

    CAS  Google Scholar 

  • Warren, F. L., and K. H. Watling: The structure of tirucallol and euphol. Chem. a. Ind. 1956, 24-25.

    Google Scholar 

  • Wehmer, C., W. Thies u. M. Hadders: Systematische Verbreitung und Vorkommen von Phytosterinen. Handbuch der Pflanzenanalyse, herausgeg. von G. Klein, Bd. II, Teil I, S. 749–763. Wien: Springer 1932.

    Google Scholar 

  • Wieland, H., u. M. Asano: Zur Kenntnis der Sterine der Hefe. Liebigs Ann. 473, 300–313 (1929).

    CAS  Google Scholar 

  • Wieland, H., u. W. Benend: Einige Beobachtungen über die Hydrierung von Sterinen. Liebigs Ann. 554, 1–8 (1943).

    CAS  Google Scholar 

  • Wieland, H., u. G. Coutelle: Zur Kenntnis des Fungisterins und anderer Inhaltsstoffe von Pilzen. Liebigs Ann. 548, 270–283 (1941).

    CAS  Google Scholar 

  • Wieland, H., u. G. A. C. Gough: Zur Kenntnis der Sterine der Hefe. II. Liebigs Ann. 482, 36–49 (1930).

    CAS  Google Scholar 

  • Wieland, H., u. Y. Kanaoka: Über die Nebensterine der Hefe. V. Zymosterin und Ascosterin. Liebigs Ann. 530, 146–151 (1937).

    CAS  Google Scholar 

  • Wieland, H., H. Pasedach u. A. Ballauf: Über die Nebensterine der Hefe. IV. Kryptosterin. Liebigs Ann. 529, 68–83 (1937).

    CAS  Google Scholar 

  • Wieland, H., F. Rath u. W. Benend: Über die Nebensterine der Hefe. VII. Zur Kenntnis des Zymosterins. Liebigs Ann. 548, 19–33 (1941).

    CAS  Google Scholar 

  • Wieland, H., F. Rath u. H. Hesse: Die Nebensterine der Hefe. VIII. Zur Konstitution von Ascosterin, Faecosterin, Episterin und Neosterin. Liebigs Ann. 548, 34–49 (1941).

    CAS  Google Scholar 

  • Wieland, H., u. W. M. Stanley: Zur Kenntnis der Sterine der Hefe. III. Liebigs Ann. 489, 31–42 (1931).

    CAS  Google Scholar 

  • Wieland, H., u. F. Wille: Weitere Versuche über die Dehydrierung von Alkohol durch Hefe. Über den Mechanismus der Oxydationsvorgänge. XLI. Liebigs Ann. 515, 260–272 (1935).

    CAS  Google Scholar 

  • Wieland, P., u. V. Prelog: Über die Isolierung von Ergosterin, Ergosterinpalmitat und Ergosterin-peroxyd aus dem Mycel von Aspergillus fumigatus, mut. helvola, Yuill. Helvet. chim. Acta 30, 1028–1030 (1947).

    CAS  Google Scholar 

  • Wiesner, J. v.: Die Rohstoffe des Pflanzenreichs, 4. Aufl., Bd. I, S. 1041–1043 u. 1057-1058. Leipzig: W. Engelmann 1927.

    Google Scholar 

  • Willaman, J. J., and F. M. Wadley: Steroidal sapogenins. XXXVII. Association of sapogenins and unsaturated sterols in Agave, Dioscorea, and Yucca. Arch. of Biochem. a. Biophysics 62, 238–240 (1956).

    CAS  Google Scholar 

  • Willstätter, R., u. H.J. Page: Untersuchungen über Chlorophyll. XXIV. Über die Pigmente der Braunalgen. Liebigs Ann. 404, 237–271 (1914).

    Google Scholar 

  • Windaus, A., u. A. Hauth: Über Stigmasterin, ein neues Phytosterin aus Calabar-Bohnen. Ber. dtsch. chem. Ges. 39, 4378–4384 (1906).

    Google Scholar 

  • Windaus, A., u. R. Tschesche: Über das sogenannte „Isocholesterin“ des Wollfetts. Hoppe-Seylers Z. 190, 51–61 (1930).

    CAS  Google Scholar 

  • Windaus, A., u. W. Welsch: Über die Phytosterine des Rüböls. Ber. dtsch. chem. Ges. 42, 612–616 (1909).

    CAS  Google Scholar 

  • Wolf, D. E., C. H. Hoffman, P. E. Aldrich, H. R. Skeggs, L. D. Wright and K. Folkers: ß-Hydroxy-β-methyl-γ-valerolactone (divalonic acid), a new biological factor. J. Amer. Chem. Soc. 78, 4499 (1956).

    CAS  Google Scholar 

  • Woodward, R. B., and K. Bloch: The cyclization of squalene in cholesterol synthesis. J. Amer. Chem. Soc. 75, 2023–2024 (1953).

    CAS  Google Scholar 

  • Woodward, R. B., A. A. Patchett, D. H. R. Barton, D. A. J. Ives and R. B. Kelly: The synthesis of lanosterol (lanostadienol). J. Chem. Soc. (Lond.) 1957, 1131-1144.

    Google Scholar 

  • Yoshida, S., R. Takasaki and H. Sueyoshi: Structure of a triterpenoid from rice bran oil. J. Pharmaceut. Soc. Japan 76, 1335–1336 (1956) (Chem. Abstr. 51, 3650).

    CAS  Google Scholar 

  • Zabin, I.: The formation of radioactive lycopene in ripening tomatoes. J. of Biol. Chem. 226, 851–866 (1957).

    CAS  Google Scholar 

  • Zabin, L, and K. Bloch: Utilization of isovalerc acid for the synthesis of cholesterol. J. of Biol. Chem. 185, 131–138 (1950).

    CAS  Google Scholar 

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Heusner, A. (1958). Phytosterine. In: Der Stoffwechsel Sekundärer Pflanzenstoffe / The Metabolism of Secondary Plant Products. Handbuch der Pflanzenphysiologie / Encyclopedia of Plant Physiology, vol 10. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-26784-4_4

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