Abstract
Veratrum alkaloids, like solanum and kurchi alkaloids, form a group of steroid alkaloids. The veratrum group, unlike the other two, have largely a modified steroid skeleton and exist as glyco and ester alkaloids in liliaceous plants belonging to the sub-order Melanthaceae. Although investigations on these compounds are recorded since the early nineteenth century (153), their complex structures were elucidated only during the last two decades by the independent and collaborative work of some of the world’s leading organic chemists. An added reason for recent interest in these alkaloids is the high hypotensive activity of some of their natural esters. Although this interest has waned since the discovery of the superior hypotensive ester alkaloid reserpine, extensive work on veratrum alkaloids has revealed a wealth of interesting, and at times intriguing, chemistry.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Ahrens, F. B.: Über krystallisiertes Veratrin. Ber. dtsch. chem. Ges. 23, 2700 (1890).
Anliker, R., H. Heusser und O. Jeger: Über Steroide und Sexualhormone. 179. Mitt. Notiz zur Herstellung von Dihydro-jervin. Helv. Chim. Acta 35, 838 (1952).
Aslanov, KH. A. and A. S. Sadykov : Alkaloids of Fritillaria. I. Alkaloids of Fritillaria raddeana. II. Products of Chlorination of Raddeanine. III. Structure of Raddeanine. J. Gen. Chem. (USSR) 26, 579, 1790, 1794 (1956) [Chem. Abstr. 50, 13971 (1956); 51, 1993 (1957)7.
Augustine, R. L.: Stereochemistry of Ring F in Jervine. Chem. and Ind. 1961, 1448.
Auterhoff, H.: Zur Kenntnis der isomeren Formen des Veratrin-Alkamins. 2. Mitt. Arch. Pharmaz. 286, 319 (1953).
Auterhoff, H.: Hydrierungsprodukte der Veratrin-Alkamine. 6. Mitt. Veratrin-VeratrumAlkaloide. Arch. Pharmaz. 287, 380 (1954).
Auterhoff, H.: Sabadilla-Nebenalkaloide. 8. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 288, 549 (1955).
Auterhoff, H. und F. Günther: Beiträge zur Kenntnis verschiedener Veratrum-Drogen und ihrer Alkaloide. 7. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 288, 455 (1955).
Auterhoff, H. und H. P. Kraft: Zur Kenntnis der isomeren Formen des Germins. 5. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 287, 332 (1954).
Auterhoff, H. und H. Möhrle: Über Neosabadin - ein neues SabadillaAlkamin. 9. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 291, 288 (1958).
Auterhoff, H. und H. Staúsberg: Über einige Eigenschaften des handelsüblichen Veratrins. 3. Mitt. Arch. Pharmaz. 287, 27 (1954).
Auterhoff, H. und G. Zeisner: Über die Konstitution der Veratrin-Alkamine. 4. Mitt. Arch. Pharmaz. 286, 525 (1953).
Bartlett, M. F., D. F. Diokel and W. I. Taylor: The Alkaloids of Tabernanthe iboga. IV. The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine. J. Amer. Chem. Soc. 80, 126 (1958).
Barton, D. H. R.: unpublished.
Barton, D. H. R., C. J. W. Brooks and P. de Mayo: Steroidal Alkaloids. Part III. The Constitution and Stereochemistry of Cevine. J. Chem. Soc. (London) 1954, 3950.
Barton, D. H. R., C. J. W. Brooks and J. S. Fawcett: Steroidal Alkaloids. Part II. Some Observations on the Constitution of Cevine. J. Chem. Soc. (London) 1954. 2137.
Barton, D. H. R. and J. F. Eastham: Steroidal Alkaloids. Part I. The Functional Groups of Cevine. J. Chem. Soc. (London) 1953, 424.
Barton, D. H. R., O. Jeger, V. Prelog and R. B. Woodward : The Constitutions of Cevine and Some Related Alkaloids. Experientia 10, 81 (1954).
Barton, D. H. R., F. Mccapra, P. J. May and F. Thudium: Long Range Effects in Alicyclic Systems. Part III. The Relative Rates of Condensation of Some Steroid and Triterpenoid Ketones with Benzaldehyde. J. Chem. Soc. (London) 1960, 1297; and other papers in the series.
Barton, D. H. R. and C. R. Narayanan: Sesquiterpenoids. Part X. The Constitution of Lactucin. J. Chem. Soc. (London) 1958, 963 (there connected references).
Bauer, S., L. Masler, S. Orszagh, J. Mokry and J. Tomko: Alkaloids from Fritillaria meleagris. Chem. zvesti 12 584 (1958) [Chem. Abstr. 53, 5591 (1959)].
Beaton, J. M., J. I. Shaw, F. S. Spring, R. Stevenson, W. S. Strachan and J. L. Stewart: Triterpenoids. Part XXXVIII. Ursa-9(11) : 13(18)-dien-3β-yl Acetate. J. Chem. Soc. (London) 1955, 2606.
Bellamy, L. J.: The Infra-red Spectra of Complex Molecules. London: Methuen and Co. Ltd. 1958.
Blount, B. K.: The Veratrine Alkaloids. Parts I and II. The Constitution of Veratridine and Cevine. J. Chem. Soc. (London) 1935, 122.
Blount, B. K. and D. Crowfoot: The Veratrine Alkaloids. Part III. The Preparation of Cevanthrol and the X-Ray Crystallographic Examination of Cevanthrol and Cevanthridine. J. Chem. Soc. (London) 1936, 424.
Boit, H. G.: Über Imperialin. I. Mitt. Chem. Ber. 87, 472 (1954).
Boit, H. G. und L. Paul: Über Imperialin. II. Mitt. Chem. Ber. 90, 723 (1957).
Bruice, T. C. and T. H. Fife: The Nature of Neighbouring Hydroxyl Group Assistance in the Alkaline Hydrolysis of the Ester Bond. Tetrahedron Letters 1961 No. 8, 263.
Burn, D. and W. Rigby: The Skeleton of Isorubijervine. J. Chem. Soc. (London) 1953, 963.
Chapman, J. H., J. Elks, G. H. Phillipps and L. J. Wyman: Studies in the Synthesis of Cortisone. Part XVI. A New Method of Preparing 11-Oxotigogenin. J. Chem. Soc. (London) 1956, 4344.
Chi, Y., Y. S. Kao and K. J. Chang: The Alkaloids of Fritillaria roylei. I. Isolation of Peimine. J. Amer. Chem. Soc. 58, 1306 (1936).
Chou, T. Q. and T. T. Chu: The Preparation and Properties of Peimine and Peiminine. J. Amer. Chem. Soc. 63, 2936 (1941).
Chu, T. T. and T. Q. Chou: Conversion of Peimine into Peiminine and vice versa. J. Amer. Chem. Soc. 69, 1257 (1947).
Chu, T. T., W. K. Hwang and J. Y. Lox: Fritillaria Alkaloids. III. The Skeleton of Peimine and Peiminine by Zinc Dust Distillation and Selenium Dehydrogenation. Acta Chim Sinicia 21 232 (1955) [Chem. Abstr. 51, 444 (1957)].
Chu, T. T. and J. Y. Lox : Fritillaria Alkaloids. II. Peimine and Peiminine. IV. Isolation of a New Alkaloid from Si-pei-mu. Acta Chim. Sinicia 21 227, 241 (1955) [Chem. Abstr. 51, 444 (1957)].
Chu, T. T., J. Y. Lox and W. K. Hwang: Fritillaria Alkaloids. V. Dehydrogenation of Sipeimine and the Relationship between Sipeimine, Peimine and Peiminine. VI. The Oxidation and Reduction of Sipeimine. VII. Selenium Dehydrogenation of Sipeimine and the Relationship between Fritillaria and Veratrum Alkaloids. VIII Alkali Fusion and Acid and Alkali Treatment of Sipeimine. IX. Isolation of Several New Alkaloids from Commercial Fritillaria Species “Szechuan pei-mu”. Acta Chim. Sinicia 21 401 (1955) 22 205, 210, 356, 361 (1956) [Chem. Abstr. 51, 445 (1957)]
Chu, T. T., J. Y. Lox and W. K. Hwang: A Study of Fritillaria Alkaloids. X. New Alkaloids from pei-mu, a Fritillaria Species from Min Hsien. K’O Hsueh T’ung Pao No. 1, 13 (1957) [Chem. Abstr. 53, 647 (1959)1.
Chu, T. T., J. Y. Lox and W. K. Hwang: Fritillaria Alkaloids. XI. Proof of the Identity of Sipeimine with Imperialine. K’O Hsueh T’ung Pao 207 (1957) [Chem. Abstr. 53, 7503 (1959)].
Cookson, R. C. and S. H. Dandegaonker: Absorption Spectra of Ketones. Part II. The Configuration of Some Bromo-derivatives of 6-Oxocholestanyl Acetate. Absorption Spectra of a-Ketols. J. Chem. Soc. (London) 1955, 352.
Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. V. The Selenium Dehydrogenation of Cevine. J. Biol. Chem. 129, 79 (1939).
Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. VI. The Oxidation of Cevine. J. Amer. Chem. Soc. 61, 2252 (1939).
Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. VII. On Decevinic Acid. J. Biol. Chem. 134, 123 (1940).
Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. VIII. Further Studies on the Selenium Dehydrogenation of Cevine. X. The Structure of Cevanthridine. J. Biol. Chem. 139, 263, 293 (1941).
Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. XII. Further Studies on the Oxidation of Cevine. J. Biol. Chem. 141, 253 (1941).
Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. XIII. The Dehydrogenation of Protoveratrine. J.Biol. Chem. 143, 427 (1942).
Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. XVII. On Germine. Its Formulation and Degradation. J. Biol. Chem. 148, 57 (1943).
Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. XX. Further Correlations in the Veratrine Group. The Relationship between the Veratrine Bases and Solanidine. J. Biol. Chem. 149, 451 (1943).
Craig, L. C., W. A. Jacoss and G. I. Lavin: The Veratrine Alkaloids. IX. The Nature of the Hydrocarbon from the Dehydrogenation of Cevine. J. Biol. Chem. 139, 277 (1941).
Criegee, R., E. Büchner und W. Walther: Die Geschwindigkeit der Glykolspaltung mit Blei IV-acetat in Abhängigkeit von der Konstitution des Glykols. Ber. dtsch. chem. Ges. 73, 571 (1940).
Edwards, O. E., F. H. Clarke and B. Douglas: 17-Hydroxylupanine and 17-Oxylupanine Canad. J. Chem. 32, 235 (1954).
Eeles, W. T.: An X-ray Study of the Configuration of Cevine. Tetrahedron Letters 1960 No. 7, 24.
Elming, N., C. Vogel, O. Jeger und V. Prelog: Veratrum-Alkaloide. 2. Mitt. Über die Konstitution der Hexan-tetracarbonsäure aus Cevin und Germin. Helv. Chim. Acta 35, 2541 (1952).
Elming, N., C. Vogel, O. Jeger und V. Prelog: Veratrum-Alkaloide. 3. Mitt. Zur Konstitution der Hexantetracarbonsäure aus Cevin und Germin. II. Helv. Chim. Acta 36, 2022 (1953).
Erskine, R. L. and E. S. Waight: Stereochemistry and Infrared Spectra of a,ß-Unsaturated Ketones. J. Chem. Soc. (London) 1960, 3425.
Fieser, L. F. and M. Fieser: Steroids. New York: Reinhold Publ. Corp. 1959.
Fragner, K.: Ein neues Alkaloid Imperialin. Ber. dtsch. chem. Ges. 21, 3284 (1888).
Freund, M. : Beitrag zur Kenntnis des Cevadins. Ber. dtsch. them. Ges. 37, 1946 (1904).
Freund, M. und H. P. Schwarz: Beitrag zur Kenntnis des Cevadins. Ber. dtsch. chem. Ges. 32, 800 (1899).
Freund, M. und A. Schwarz: Cevadin. III. J. prakt. Chem. 96, 237 (1918).
Fried, J. and A. Klingsberg: The Structure of Jervine. III. Degradation to Nitrogen Free Derivatives. J. Amer. Chem. Soc. 75, 4929 (1953).
Fried, J., P. Numerof and N. H. Coy: Neogermitrine, A New Ester Alkaloid from Veratrum viride. J. Amer. Chem. Soc. 74, 3045 (1952).
Fried, J., H. L. White and O. Wintersteiner: The Hypotensive Principles of Veratrum viride. J. Amer. Chem. Soc. 72, 4621 (1950).
Fried, J., O. Wintersteiner, M. Moore, B. M. Iselin and A. Klingsberg: The Structure of Jervine. II. Degradation to Perhydrobenzfluorene Derivatives. J. Amer. Chem. Soc. 73, 2970 (1951).
Gautschi, F., O. Jeger, V. Prelog und R. B. Woodward: Veratrum-Alkaloide. 5. Mitt. Über die Konstitution der Decevinsäure. Heiv. Chim. Acta 37, 2280 (1954).
Gautschi, F., O. Jeger, V. Prelog und R. B. Woodward: Veratrum-Alkaloide. 9. Mitt. Absolute Konfiguration des Kohlenstoffatoms ro in Cevin und verwandten Alkaloiden. Heiv. Chim. Acta 38, 296 (1955).
Gillam, A. E. and E. S. Stern: An Introduction to Electronic Absorption Spectroscopy in Organic Chemistry. London: E. Arnold, Ltd. 1957.
Goodman, L. S. and A. Gilman: The Pharmacological Basis of Therapeutics, 2nd ed., pp. 747–754. New York: Macmillan Co. 1955.
Henbest, H. B. and B. J. Lovell: Aspects of Stereochemistry. Part II. Intramolecular Electrophilic Assistance in Displacement Reactions. J. Chem. Soc. (London) 1957, 1965.
Hennig, A. J., T. Higuchi and L. M. Parks: Sabadilla Alkaloids. III. Chromatographic Separation of the Water Soluble Fraction. Isolation of a New Crystalline Alkaloid Sabatine. J. Amer. Pharmaceut. Assoc. 40, 168 (1951).
Herz, J. E. and J. Fried: Jervine. VII. 3,5-Cyclo Derivatives of Jervine Degradation Products. J. Amer. Chem. Soc. 76, 5621 (1954).
Hess, K. und H. Mohr: Über das Cevin und Sabadinin. Ber. dtsch. chem. Ges. 52, 1984 (1919).
Heyl, F. W., F. E. Hepner and S. K. Loy: Zygadenine. The Crystalline Alkaloid of Zygadenus intermedius. J. Amer. Chem. Soc. 35, 258 (1913).
Heyl, F. W. and M. E. Herr: The Formula of Zygadenine. J. Amer. Chem. Soc. 71, 1751 (1949).
Heymann, H. and L. F. Fieser: A New Route to II-Ketosteroids by Fission of a 49(11)-Ethylene Oxide. J. Amer. Chem. Soc. 73, 5252 (1951).
Hirschmann, R., C. S. Snoddy, Jr., C. F. Hiskey and N. L. Wendler: The Rearrangement of the Steroid CID Rings. J. Amer. Chem. Soc. 76, 4013 (1954).
Hosansky, N. L. and O. Wintersteiner: 8,9-Seto Derivatives of Triacetyl Dihydro Veratramine. J. Amer. Chem. Soc. 78, 3126 (1956).
Huebner, C. F. and W. A. Jacobs: The Veratrine Alkaloids. XXVI. On the Hexanetetracarboxylic Acid from Cevine and Germine. J. Biol. Chem. 170, 181 (1947).
Iselin, B. M., M. Moore and O. Jervine, IX. Miscellaneous New Derivatives. J. Amer. Chem. Soc. 78, 403 (1956).
Iselin, B. M. and O. Wintersteiner: Jervine. VI. The Sulfuric Acid-catalyzed Acetolysis of N-Acetyl-3-desoxy-3(a)-chlorotetrahydrojervine. J. Amer. Chem. Soc. 76, 5616 (1854).
Iselin, B. M. and O. Wintersteiner: Jervine. VIII. z113-Jervine, a New Double Bond Isomer of Jervine. J. Amer. Chem. Soc. 77, 5318 (1955).
Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. I. The Degradation of Cevine. II. Further Study of the Basic Degradation Products of Cevine. III. Further Studies on the Degradation of Cevine, the Question of Coniine. IV. The Degradation of Cevine Methiodide. J. Biol. Chem. 119, 141 (1937) 120, 447 (1937); 124, 659 (1938); 125, 625 (1938).
Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XV. On Rubijervine and Isorubijervine. J. Biol. Chem. 148, 41 (1943).
Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XVI. The Formulation of Jervine. J. Biol. Chem. 148, 51 (1943).
Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XIX. On Protoveratrine and its Alkamine Protoverine. J. Biol. Chem. 149, 271 (1943).
Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XXI. The Conversion of Rubijervine to Allorubijervine. The Sterol Ring System of Rubijervine. J. Biol. Chem. 152, 641 (1944).
Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XXII. On Pseudojervine and Veratrosine, a Companion Glycoside in Veratrum viride. J. Biol. Chem. 155, 565 (1944).
Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XXIII. The Ring System of Rubijervine and Isorubijervine. J. Biol. Chem. 159, 617 (1945).
Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XXV. The Alkaloids of Veratrum wide. J. Biol. Chem. 160, 555 (1945).
Jacobs, W. A., L. C. Craig and G. I. Lavin: The Veratrine Alkaloids. XI. The Dehydrogenation of Jervine. J. Biol. Chem. 141, 51 (1941).
Jacobs, W. A. and C. F. Huebner: The Veratrine Alkaloids. XXVII. Further Studies with Jervine. J. Biol. Chem. 170, 635 (1947).
Jacoss, W. A. and S. W. Pelletier: The Veratrine Alkaloids. XXXVI. A Possible Skeletal Structure for Veracevine, Cevine, Germine and Protoverine. J. Organ. Chem. (USA) 18, 765 (1953).
Jacobs, W. A. and Y. Sato: The Veratrine Alkaloids. XXVIII. The Structure of Jervine. J. Biol. Chem. 175, 57 (1948).
Jacobs, W. A. and Y. Sato: The Veratrine Alkaloids. XXX. A Further Study of the Structure of Veratramine and Jervine. J. Biol. Chem. 181, 55 (1949).
Jacobs, W. A. and Y. Sato: The Veratrine Alkaloids. XXXII. The Structure of Veratramine. J. Biol. Chem. 191, 71 (1951).
Jaffe, H. and W. A. Jacoss: The Veratrine Alkaloids. XXXIII. The Isomeric Forms of Cevine, Germine and Protoverine. J. Biol. Chem. 193, 325 (1951).
Jeger, O., R. Mirza, V. Prelog, C. Vogel und R. B. Woodward: VeratrumAlkaloide. 6. Mitt. Die Konstitution der Hexan-tetracarbonsäure aus Cevin und Germin. Rely. Chim. Acta 37, 2295 (1954).
Jeger, O. and V. Prelog: Steroid Alkaloids. Veratrum Group. In: R. H. F. Manske, The Alkaloids, Chemistry and Physiology, Vol. 7, P. 363. New York: Academic Press. 1960.
Jeger, O., V. Prelog, E. Sundt und R. B. Woodward: Veratrum-Alkaloide. 7. Mitt. Die Konstitution des Ringes F und die absolute Konfiguration des Kohlenstoffatoms 25 des Cevins. Rely. Chim. Acta 37, 2302 (1954).
Keller, L., CH. Tamm und T. Reichstein: Synthese des 7-Athyl-I,2-benzofluorens und des 7-Äthyl-8-methyl-I,2-benzofluorens und Identifizierung des letzteren mit dem Jacobs’schen Kohlenwasserstoff. Glykoside und Aglykone, 192. Mitt. Hely. Chim. Acta 41 1633 (1958).
Kerstan, W. : Veratrum Alkaloide. Pharm. Zentralhalle 96, 251 (1957).
Kimishjma, K. and T. Kanno: Certain Pharmacological Actions of Veratramine. Yonago Igku Zasshi 8, 429 (1957) [Chem. Abstr. 53, 573 (1959)].
Klohs, M. W., R. Arons, M. D. Draper, F. Keller, S. Koster, W. Malesh and F. J. Petracek : The Isolation of Neoprotoveratrine and Protoveratrine from Veratrum viride AIT. J. Amer. Chem. Soc. 74, 5107 (1952).
Klohs, M. W., M. D. Draper, F. Keller, S. Koster, W. Malesh and F. J. Petracek: The Alkaloids of Veratrum fimbriatum GRAY. J. Amer. Chem. Soc. 75, 4925 (1953).
Klohs, M. W., M. D. Draper, F. Keller, S. Koster, W. Malesh and F. J. Petracek: Alkaloids of Veratrum eschscholtzii GRAY. II. The Ester Alkaloids. J. Amer. Chem. Soc. 76, 1152 (1954).
Klohs, M. W., M. D. Draper, F. Keller, W. Malesh and F. J. Petracek: Alkaloids of Veratrum eschscholtzii GRAY. I. The Glycosides. J. Amer. Chem. Soc. 75, 2133 (1953).
Klohs, M. W., M. D. Draper, F. Keller, W. Malesh and F. J. Petracek: The Isolation of Desacetylneoprotoveratrine from Veratrum viride AIT. J. Amer. Chem. Soc. 75, 3595 (1953).
Krayer, O.: Veratrum Alkaloids. In: V. A. DRILL, Pharmacology in Medicine, 2nd ed., pp. 515–524. New York: McGraw Hill Book Co. 1958.
Kupchan, S. M.: Hypotensive Veratrum Ester Alkaloids. J. Pharmaceut. Sci. (USA) 50, 273 (1961).
Kupchan, S. M.: Schoenocaulon Alkaloids. IV. The Isomeric Cevagenine Orthoacetates. J. Amer. Chem. Soc. 77, 686 (1955).
Kupchan, S. M.: Veratrum Alkaloids. XXIX. The Structures of Germitrine, Neogermitrine and Several Related Hypotensive Ester Alkaloids. J. Amer. Chem. Soc. 81, 1921 (1959).
Kupchan, S. M.: Veratrum Alkaloids. XXX. The Structure and Configuration of Zygadenine. J. Amer. Chem. Soc. 81, 1935 (1959).
Kupchan, S. M. and A. Afonso: Veratrum Alkaloids. XXXVII. The Structure of Germanitrine, a Hypotensive Ester Alkaloid. J. Amer. Pharmaceut. Assoc. 48, 731 (1959).
Kupchan, S. M. and A. Afonso: Veratrum Alkaloids. XLIII. The Structure of Cevadine. J. Amer. Pharmaceut. Assoc. 49, 242 (1960).
Kupchan, S. M. and C. I. Ayres: Veratrum Alkaloids. XXXII. The Structures of Germitetrine and Some Related Hypotensive Ester Alkaloids. J. Amer. Pharmaceut. Assoc. 48, 440 (1959).
Kupchan, S. M. and C. I. Ayres: Veratrum Alkaloids. XXXIX. The Structures of Protoveratrine A and Protoveratrine B. J. Amer. Chem. Soc. 82 2252 (1960).
Kupchan, S. M. and C. I. Ayres: Veratrum Alkaloids. XL. The Structure of Escholerine, a Hypotensive Ester Alkaloid. J. Amer. Pharnaceut. Assoc. 48, 735 (1959).
Kupchan, S. M., C. I. Ayres and R. H. Hensler: Veratrum Alkaloids. XLII. The Structures of Desacetylprotoveratrine A and Desacetylprotoveratrine B. J. Amer. Chem. Soc. 82, 2616 (1960).
Kupchan, S. M., C. I. Ayres, M. Neeman, R. H. Hensler, T. Masamune and S. Rajagopalan: Veratrum Alkaloids. XXXVIII. The Structure and Configuration of Protoverine. J. Amer. Chem. Soc. 82 2242 (1960).
Kupchan, S. M. and C. V. Deliwala: Zygadenus Alkaloids. III. Active Principles of Zygadenus venenosus. Veratroylzygadenine and Vanilloylzygadenine. IV. Germine Esters. J. Amer. Chem. Soc. 75, 1025 (1953); 76, 5545 (1954).
Kupchan, S. M. and C. V. Deliwala: The Isolation of Crystalline Hypotensive Veratrum Ester Alkaloids by Chromatography. J. Amer. Chem. Soc. 75, 4671 (1953).
Kupchan, S. M., C. V. Deliwala and R. D. Zoxls: Zygadenus Alkaloids. VI. Active Principles of Zygadenus paniculatus. J. Amer. Chem. Soc. 77, 755 (1955).
Kupchan, S. M., M. Fieser, C. R. Narayanan, L. F. Fieser and J. Fried: The Germine-Isogermine-Pseudogermine Isomerizations. J. Amer. Chem. Soc. 77, 5896 (1955).
Kupchan, S. M., J. C. Grivas, C. I. Ayres, L. J. Pandya and L. C. Weaver: Veratrum Alkaloids. XLVI. Structure Activity Relationship in a Series of Analogs of the Protoveratrines. J. Pharmaceut. Sci. (USA) 50, 396 (1961).
Kupchan, S. M. and N. Gruenfeld: Veratrum Alkaloids. XLI. The Structure of Germbudine, A Hypotensive Ester Alkaloid. J. Amer. Pharmaceut. Assoc. 48, 737 (1959).
Kupchan, S. M., R. H. Hensler and L. C. Weaver: Veratrum Alkaloids. XLIV. Structure Activity Relationships in a Series of Synthetic Hypotensive Esters of Protoverine. J. Med. Pharmaceut. Chem. (USA) 3, 129 (1961).
Kupchan, S. M., W. S. Johnson and S. Rajagopalan: The Configuration of Cevine. Tetrahedron 7, 47 (1959).
Kupchan, S. M. and D. Lavie: Schoenocaulon Alkaloids. III. The Bismuth Oxide Oxidation of Veracevine, Cevagenine and Cevine. J. Amer. Chem. Soc. 77, 683 (1955).
Kupchan, S. M., D. Lavie, C. V. Deliwala and B. Y. A. Andoh: Schoenocaulon Alkaloids. I. Active Principles of Schoenocaulon officinale. Cevacine and Protocevine. J. Amer. Chem. Soc. 75, 5519 (1953).
Kupchan, S. M., D. Lavie and R. D. Zonis: Zygadenus Alkaloids. V. Active Principles of Zygadenus venenosus. Zygacine. J. Amer. Chem. Soc. 77, 689 (1955).
Kupchan, S. M. and T. Masamune: Structure of the Presumed Hofmann Elimination Product of Cevine Methiodide. Chem. and Ind. 1959, 632.
Kupchan, S. M. and C. R. Narayanan: The Structure of Germine and Some Related Hypotensive Ester Alkaloids. Chem. and Ind. 1956, 1093.
Kupchan, S. M. and C. R. Narayanan: Veratrum Alkaloids. XVIII. The Structure and Configuration of Germine. J. Amer. Chem. Soc. 81, 1913 (1959).
Kupchan, S. M., P. Slade and R. J. Young: Intramolecular Catalysis. Facilitation of Alkaline Hydrolysis of Alicyclic 1,2-Diol Monoesters. Tetrahedron Letters 1960 No. 24, 22.
Kupchan, S. M., L. C. Weaver, C. I. Ayres and R. H. Hensler: Veratrum Alkaloids. XLV. Structure Activity Relationship in a Series of Protoverine Derivatives. J. Pharmaceut. Sci. (USA) 50, 52 (1961).
Leonard, N. J. and M. A. Rebenstorf: Lead Tetraacetate Oxidation of Amino Alcohols. J. Amer. Chem. Soc. 67, 49 (1945).
Macbeth, A. K. and R. Robinson: Cevadine. Part I. J. Chem. Soc. (London) 121 1571 (1922).
Macek, K., S. Vanécek, V. Pelcovil und Z. J. Vejdélek: Veratrum-Alkaloide. IV. Analyse des Veratrins mit Hilfe der Papierchromatographie. Collect. Czech. Chem. Commun. 21, 1182 (1956).
Macek, K., S. Vanmek und Z. J. Vejdélek: Veratrum-Alkaloide. II. Über die Papierchromatographie der Alkaloide aus Schoenocaulon officinale und einiger Strukturanaloga. Collect. Czech. Chem. Commun. 21, 987 (1956).
Macek, K., S. Vanmek und Z. J. Vejdélek: Veratrum-Alkaloide. VI. Beitrag der Papierchromatographie zur Lösung von Strukturfragen. Collect. Czech. Chem. Commun. 22, 253 (1957).
Maison, G. L., E. Gotz and J. W. Stutzman: Relative Hypotensive Activity of Certain Veratrum Alkaloids. J. Pharmacol. exp. Therapeut. 103, 74 (1951).
Mckenna, J.: Steroidal Alkaloids. Quart. Rev. (Chem. Soc. London) 7, 231 (1953).
Mijovié, M. V., E. Sundt, E. Kyburz, O. Jeger und V. Prelog: VeratrumAlkaloide. 8. Mitt. Über die Konstitution der Ringe C und D des Cevadins und verwandter Alkaloide. Rely. Chim. Acta 38, 231 (1955).
Mitchner, H. and L. M. Parks: Sabadilla Alkaloids. VI. Separation of Veratridine and Cevadine by Countercurrent Distribution; pH vs. Partition Coefficients. J. Amer. Pharmaceut. Assoc., Sci. Ed. 45, 549 (1956).
Mitchner, H. and L. M. Parks: Sabadilla Alkaloids. VII. Sabatine and its Alkamine Sabine. J. Amer. Pharmaceut. Assoc. 48, 303 (1959).
Mitsuhashi, H. and Y. Shimizu: Synthesis of a Nitrogen-free Derivative of Jervine. Tetrahedron Letters 1961, No. 21, 777.
Möhrle, H. und H. Auterhoff: Die Konstitution des Sabadins. to. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 292 337 (1959).
Möhrle, H. und H. Auterhoff: Zur Kenntnis der Reaktion von Sabadilla-Alkaminen mit Perjodat. LI. Mitt. Sabadilla-und Veratrum-Alkaloide. Arch. Pharmaz. 293 813 (1960).
Morgan, K. J.: Thesis, Oxford Univ. (1952) [cf. Ref. 146].
Morgan, K. J. and J. A. Barltrop: Veratrum Alkaloids. Quart. Rev. (Chem. Soc. London) 12 34 (1958).
Myers, G. S., W. L. Glen, P. Morozovitch, R. Barber, G. Papineau-Couture and G. A. Grant: Some Hypotensive Alkaloids from Veratrum album. J. Amer. Chem. Soc. 78, 1621 (1956).
Myers, G. S., P. Morozovitch, W. L. Glen, R. Barber, G. Papineau-Couture and G. A. Grant: Some New Hypotensive Ester Alkaloids from Veratrum viride. J. Amer. Chem. Soc. 77, 3348 (1955).
Nash, H. A. and R. M. Brooker: Hypotensive Alkaloids from Veratrum album. Protoveratrine A, Protoveratrine B and Germitetrine B. J. Amer. Chem. Soc. 75, 1942 (1953).
Neuss, N.: A New Alkaloid from Amianthium Muscaetoxicum GRAY. J. Amer. Chem. Soc. 75, 2772 (1953).
Okuda, S., K. Tsuda and H. Kataoka: Absolute Configuration at C(25) in Jervine and Veratramine. Chem. and Ind. 1961, 512.
Paul, L. und H. G. Boit: Nebenalkaloide von Fritillaria imperialis. III. Mitt. über Fritillaria-Alkaloide. Chem. Ber. 91, 1968 (1958).
Pelletier, P. J., J. B. Caventou: Examen chimique de plusieurs végétaux de la famille des colchicées, et du principe actif qu’ils renferment [Cévadille (veratrum sabadilla) ; hellébore blanc (veratrum album) ; colchique commun (colchicum autumnale)]. Ann. Chim. [2], 14, 69 (1820).
Pelletier, S. W. and W. A. Jacobs: The Veratrine Alkaloids. XXXV. Veracevine, the Alkanolamine of Cevadine and Veratridine. J. Amer. Chem. Soc. 75, 3248 (1953).
Pelletier, S. W. and W. A. Jacobs: The Veratrine Alkaloids. XXXVII. The Structure of Isorubijervine. Conversion to Solanidine. J. Amer. Chem. Soc. 75, 4442 (1953).
Pelletier, S. W. and W. A. Jacobs: The Veratrine Alkaloids. XXXIX. A Study of Certain Selenium Dehydrogenation Products of Cevine. J. Amer. Chem. Soc. 78, 1914 (1956).
Pelletier, S. W. and D. M. Locxe: The Veratrum Alkaloids. XLI. The Position of the Second Hydroxyl in Rubijervine and the Identity of Certain Dehydrogenation Products. J. Amer. Chem. Soc. 79, 4531 (1957).
Poethee, W.: Die Alkaloide von Veratrum album. 1. Mitt.: Darstellung der Alkaloide und ihre Verteilung in Rhizomen, Wurzeln und Blattbasen. — Germerin, ein neues Alkaloid von Vevatrum album. — z. Mitt.: Die einzelnen Alkaloide und ihre Beziehungen zueinander. Protoveratridin, Germerin, Protoveratrin. Arch. Pharmaz. 275, 357, 571 (1937).
Poethke, W. : Die Alkaloide von Veratrum album. 3. Mitt. : Jervin, Pseudojervin, Rubijervin. Einteilung der Alkaloide. Arch. Pharmaz. 276, 170 (1938).
Preininger, V. and F. Santavÿ: Polarography of Alkaloids. XXII. A Polarographic Study of Veratrum Alkaloids. Collect. Czech. Chem. Commun. 23, 1153 (1958).
Prelog, V. and O. Jeger: The Chemistry of Veratrum Alkaloids. In: R. H. F. Manske and H. L. Holmes, The Alkaloids, Chemistry and Physiology, Vol. 3, p. 243. New York: Academic Press Inc. 1953.
Rosenfelder, W. J.: The Methanolysis of Some Acetyl Derivatives of Cevine. J. Chem. Soc. (London) 1954, 2638.
Saito, K.: Veratramine, a New Alkaloid of White Hellebore (Veratrum grandiflorum LoES fil.). Bull. Chem. Soc. Japan 15, 22 (1940).
Saito, K., H. Suginome and M. Takaoka: The Alkaloids of White Hellebore. t. Isolation of Constituent Alkaloids. Bull. Chem. Soc. Japan 9, 15 (1934).
Salzberger, G.: Über die Alkaloide der weißen Nieswurz (Veratrum album). Arch. Pharmaz. 228, 462 (1890).
Sato, Y. and W. A. Jacoss: The Veratrine Alkaloids. XXIX. The Structure of Rubijervine. J. Biol. Chem. 179, 623 (1949).
Sato, Y. and W. A. Jacoss: The Veratrine Alkaloids. XXXI. The Structure of Isorubijervine. J. Biol. Chem. 191, 63 (1951).
Shaligram, A. M.: Studies in Essential Oils. Ph. D. Thesis, Poona Univ., 1961. — A. M. SHALIGRAM, A. S. RAO and S. C. BHATTACHARYYA: Absolute Configuration of Junenol and Laevojunenol and Synthesis of Junenol from Costunolide. Tetrahedron (in press) (1962).
Sheehan, J. C., R. L. Young and P. A. Cruickshank: C16-C18 Rearrangements of Steroid Alkaloids. J. Amer. Chem. Soc. 82, 6147 (1960).
Sicher, J. and M. Tichy: The Relative Configuration at C22 and C23 in Veratramine and Jervine. Tetrahedron Letters 1959, No. 12, 6.
Stoll, A.: Les alcaloïdes du Vératrum. Gazz. chim. ital. 84, 1190 (1954).
Stoll, A. und E. Seebeck: Die Spaltprodukte von Cevadin und Veratridin bei alkalischer Hydrolyse. 2. Mitt. über Veratrum-Alkaloide. Hely. Chim. Acta 35, 1270 (1952).
Stoll, A. und E. Seebeck: Derivate des Cevadins und des Cevagenins und über die Eigenschaften und die vermutliche Lage der Sauerstoffatome im Cevagenin. 4. Mitt über Veratrum-Alkaloide. Heiv. Chim. Acta 35, 1942 (1952).
Stoll, A. und E. Seebeck: Über zwei Isomere des a-Cevins. 5. Mitt. über Veratrum-Alkaloide. Rely. Chim. Acta 36, 189 (1953).
Stoll, A. und E. Seebeck: Über Protoveratrin A und Protoveratrin B. 6. Mitt. über VeratrumAlkaloide. Rely. Chim Acta 36, 718 (1953).
Stoll, A. und E. Seebeck: Veratroyl-zygadenin aus Veratrum album. 7. Mitt. über VeratrumAlkaloide. Hely. Chim. Acta 36, 1570 (1953).
Stoll, A. und E. Seebeck: Über eine Orthoessigsäureester-Gruppierung in den Acetylierungsprodukten von Cevadin und Cevagenin. 9. Mitt. über Veratrum-Alkaloide. Hely. Chim. Acta 37, 824 (1954).
Stoll, A. und E. Seebeck: Veratrobasine and Geralbine, two New Alkaloids Isolated from Veratrum album. J. Amer. Chem. Soc. 74, 4728 (1952).
Stoll, A., D. Stauffacher und E. Seebeck: Nachweis einer a-Ketol-Gruppierung im Cevagenin. 8. Mitt. über Veratrum-Alkaloide. Hely. Chim. Acta 36, 2027 (1953).
Stoll, A., D. Stauffacher und E. Seebeck: Über Veratrobasin. 10. Mitt. über Veratrum-Alkaloide. Helv. Chim. Acta 38, 1964 (1955).
Stuart, D. M. and L. M. Parks : Sabadilla Alkaloids. V. Vanilloylcevine. J. Amer. Pharmaceut. Assoc. 45, 252 (1956).
Sundt, E., O. Jeger and V. Prelog: Conversion of Cevagenin into a Diosphenol. Chem. and Ind. 1953, 1365.
Suzuki, M., Y. Murase, R. Hayashi and N. Sandei: Constituent of Veratrum album. J. pharmac. Soc. Japan 79, 619 (1959) [Chem. Abstr. 53, 22050 (1959)].
Swiss, E. D.: Emetic Properties of Veratrum Derivatives. J. Pharmacol. exp. Therapeut. 104, 76 (1952).
Swiss, E. D. and G. L. Maison: New Alkaloids of Veratrum. Federat. Proc. (Amer. Soc. exp. Biol.) 11, 395 (1952).
Tamm, CH. and O. Wintersteiner: The Structure of Veratramine. J. Amer. Chem. Soc. 74, 3842 (1952).
Uffer, A.: Holarrhenin aus Holarrhena congolensis STAPF. Helv. Chim Acta 39, 1834 (1956).
Uhle, F. and W. A. Jacobs: The Veratrine Alkaloids. XXIV. The Octahydropyrrocoline Ring System of the Tertiary Bases. Conversion of Sarasapogenin to a Solanidine Derivative. J. Biol. Chem. 160, 243 (1945).
Uhle, F. C., J. E. Krueger and F. Sallmann: N-Alkyl Derivatives of Veratramine. J. Amer. Chem. Soc. 82, 489 (1960).
Vansheidt, A. A.: Fluorene and Triphenylmethane Hydrocarbons. XIII. Alcoholic Alkali as a Reagent for Fluorene Hydrocarbons with a Mobile Hydrogen. J. Gen. Chem. (USSR) 4, 875 (1934) [Chem. Abstr. 29, 2160 (1935)].
Vejdělek, Z. J., K. Macek und B. Buděšínský: Veratrum-Alkaloide. V. Über Synthese und Struktur einiger neuer Ester des Veracevins, Cevagenins und Cevins. Partialsynthese des Cevacins und Veratridins. Collect. Czech. Chem. Commun. 22, 98 (1957).
Vejdělek, Z. J., K. Macek und B. Kakáč: Veratrum-Alkaloide. III. Über die Inhaltsstoffe des Veratrins. Collect. Czech. Chem. Commun. 21 995 (1956).
>Vejdělek, Z. J., K. Macek und V. Trčka: Veratrum-Alkaloide. VII. Gemischte Veracevinester. Collect. Czech. Chem. Commun. 22 816 (1957).
Vejdělek, Z. J. und V. Trčka: Veratrum-Alkaloide. I. Über einige Ester des Cevins und die Zusammensetzung des „Cevindikaliums“. Collect. Czech. Chem. Commun. 21 743 (1956).
Weisenborn, F. L. and J. W. Bolger: The Synthesis of Monoacetylneogermitrine and Germidine from Germine. J. Amer. Chem. Soc. 76, 5543 (1954).
Weisenborn, F. L., J. W. Bolger, D. B. Rosen, L. T. Mann, Jr., L. Johnson and H. L. Holmes: Synthetic Hypotensive Esters from Germine. J. Amer. Chem. Soc. 76, 1792 (1954).
Wfisenborn, F. L. and D. Burn : The Structure of Isorubijervine. — Conversion to Solanidine and Solanidane-3ß-ol. J. Amer. Chem. Soc. 75, 259 (1953).
White, H. L.: Some Synthetic Esters of Germine. J. Amer. Chem. Soc. 73, 492 (1951).
Wintersteiner, O.: Some Aspects of the Chemistry of Jervine and Veratramine In: Festschrift Arthur Stoll, pp. 166–176. Basel: Birkhäuser. 1957.
Wintersteiner, O.: Chemistry of the Veratrum Alkaloids. Record Chem. Progr. 14, 19 (1953).
Wintersteiner, O. and N. Hosansky: The Structural Correlation of Jervine and Veratramine. J. Amer. Chem. Soc. 74, 4474 (1952).
Wintersteiner, O. and M. Moore: The Structure of Jervine. IV. The Sulfuric Acid-catalyzed Acetolysis of O,N-Diacetyljervine. J. Amer. Chem. Soc. 75, 4938 (1953).
Wintersteiner, O. and M. Moore: Jervine. X. Quaternary Dihydrometoxazine Salts as Intermediates in the Jervisine Rearrangement. J. Amer. Chem. Soc. 78, 6193 (1956).
Wintersteiner, O., M. Moore, J. Fried and B. Iselin: On the Structure of Jervine. Diacetyl-7-keto-jervine. Proc. Nat. Acad. Sci. (USA) 37, 333 (1951).
Wintersteiner, O., M. Moore and N. Hosansxy: Degradation of Veratramine to Benzene-x,2,3,4-tetracarboxylic Acid. J. Amer. Chem. Soc. 75, 2781 (1953).
Wintersteiner, O., M. Moore and B. M. Iselin; Jervine. V. Sulfuric Acid-catalyzed Acetolysis of Diacetyltetrahydrojervine. J. Amer. Chem. Soc. 76, 5609 (1954).
Wolfrom, M. L. and J. M. Bobbitt: Periodate Oxidation of Cyclic 1,3Diketones. J. Amer. Chem. Soc. 78, 2489 (1956).
Woodward, R. B.: Lectures on the Chemistry of Natural Products — Veratrum Alkaloids. Harvard University, 1953 (see also Ref. 120).
Wright, C. R. A. and A. P. Luff: The Veratrum Alkaloids. J. Chem. Soc. (London) 33, 338 (1878).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1962 Springer-Verlag in Vienna
About this chapter
Cite this chapter
Narayanan, C.R. (1962). Newer Developments in the Field of Veratrum Alkaloids. In: Zechmeister, L. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles, vol 20. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7153-0_8
Download citation
DOI: https://doi.org/10.1007/978-3-7091-7153-0_8
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-7155-4
Online ISBN: 978-3-7091-7153-0
eBook Packages: Springer Book Archive