The secondary metabolite chemistry of the subtribe Gochnatiinae (tribe Mutisieae, family Compositae)

Biochemical Systematics and Ecology

Volumn 24, Issue 7-8, 1996, Pages 659-718

  Catalan C A N ^a   Borkosky, S A ^a   Joseph Nathan, P ^b  

^a UNIVERSIDAD NACIONAL DE TUCUMÁN   (Argentina)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

5 methylcoumarins; Acetylenes; Compositae; Diterpenes; Flavonoids; Gochnatiinae; Secondary metabolites; Sesquiterpene lactones; Sesquiterpenes; Triterpenes

Indexed keywords

ASTERACEAE; MUTISIEAE;

EID: 0043263935     PISSN: 03051978     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0305-1978(96)00063-4     Document Type: Article

References (100)

1. Adegawa, S., Miyase, T. and Ueno, A. (1987) Sesquiterpene lactones from Diaspananthus uniflorus (Sch. Bip.). Kitam, Chem. Pharm. Bull. 35, 1479-1485.
2. Baker, P. M., Fortes, C. C., Fortes, E. G., Gazzinelli, G., Gilbert, B., Lopes, J. N. C., Pellegrino, J., Tomassini, T. B. C. and Vichnewski, W. (1972) Chemoprophylactic agents in schistosomiasis: eremanthine, costunolide, α-cyclocostunolide and bisabolol. J. Pharm. Pharmacol. 24, 853-857.
3. Bentham, G. (1873) Notes on the classification, history and geographical distribution of the Compositae, J. Linn. Soc. (Bot.) 13, 335-577.
4. Bittner, M., Jakupovic, J., Bohlmann, F. and Silva, M. (1989) Onoseriolide derivatives from Leuceria species. Phytochemistry 28, 271-273.
5. Bittner, M., Silva, M., Rozas, Z., Papastergiou, F. and Jakupovic, J. (1994) Sesquiterpene and other constituents from chilean Mutisieae. Phytochemistry 36, 695-698.
6. Bohlmann, F. and Chen, Z. L. (1982) Guaianolides from Ainsliaea fragrans. Phytochemistry 21, 2120-2122.
7. Bohlmann, F. and Jakupovic, J. (1990) Progress in the chemistry of the Vernonieae (Compositae), Pl. Syst. Evol. [Suppl. 4], 3-43.
8. Bohlmann, F. and Le Van, N. (1978) New germacranolides from Dicoma anomale. Phytochemistry 17, 570-571.
9. Bohlmann, F. and Suwita, S. (1979) Ein neues Bisabolen-derivat und ein neues Dihydrokaffeesäure-derivat aus Tarchonantus trilobus. Phytochemistry 18, 677-678.
10. Bohlmann, F. and Zdero, C. (1977) Über Inhaltsstoffe der tribus Mutisieae. Phytochemistry 16, 239-242.
11. Bohlmann, F. and Zdero, C. (1979) Neue Germacranolide und andere Inhalsstoffe aus Vertretern der subtribus Gochnatiinae. Phytochemistry 18, 95-98.
12. Bohlmann, F. and Zdero, C. (1982a) Chemotaxonomy of the genus Pleiotaxis. Phytochemistry 21, 1434-1435.
13. Bohlmann, F. and Zdero, C. (1982b) Sesquiterpene lactones from Brachylaena species. Phytochemistry 21, 647-651.
14. Bohlmann, F., Rode, K. M. and Grenz, M. (1967) Über die Inhaltsstoffe von Dicoma zeyheri. Chem. Ber. 100, 3201-3203.
15. Bohlmann, F., Zdero, C., King, R. and Robinson, H. (1980) Onoseriolid, ein neues Sesquiterpenlacton aus Onoseris albicans. Phytochemistry 19, 689-691.
16. Bohlmann, F., Jakupovic, J., Robinson, H. and King, R. M. (1981a) Five germacranolides from Gochnatia discoidea. Phytochemistry 20, 109-112.
17. Bohlmann, F., Suwita, A., Jakupovic, J., King, R. M. and Robinson, H. (1981b) Trixikingolides and germacrene derivatives from Trixis species. Phytochemistry 20, 1649-1655.
18. Bohlmann, F., Zdero, C., Robinson, H. and King, R. M. (1981c) Modified eudesmanolides and other sesquiterpene lactones from Wunderlichia mirabilis and Actinoseris polymorpha. Phytochemistry 20, 1631-1634.
19. Bohlmann, F., Singh, P. and Jakupovic, J. (1982a) New germacranolides and other sesquiterpenes lactones from Dicoma species. Phytochemistry 21, 2029-2033.
20. Bohlmann, F., Singh, P. and Jakupovic, J. (1982b) Germacranolides from Dicoma tomentosa. Phytochemistry 21, 2122-2124.
21. Bohlmann, F., Singh, P., King, R. M. and Robinson, H. (1982c) New guaianolides from Pseudostifftia kingii. Phytochemistry 21, 1171-1172.
22. Bohlmann, F., Ahmed, M., Jakupovic, J., King, R. M. and Robinson, H. (1983) Dimeric sesquiterpene lactones and kolavane derivatives from Gochnatia paniculata. Phytochemistry 22, 191-195.
23. Bohlmann, F., Ludwig, G. W., Jakupovic, J., King, R. M. and Robinson, H. (1984a) Neue Spirosesquiterpenlactone, Germacranolide und Eudesmanolide aus Wunderlichia mirabilis, Liebigs. Ann. Chem., 228-239.
24. Bohlmann, F., Schmeda-Hirschmann, G., Jakupovic, J., King, R. M. and Robinson, H. (1984b) Germacranolides from Gochnatia vernonioides. Phytochemistry 23, 1989-1993.
25. Bohlmann, F., Grenz, M., Zdero, C., Jakupovic, J., King, R. M. and Robinson, H. (1985a) Onognaphalin, a further 5-methylcoumarin from Onoseris gnaphalioides. Phytochemistry 24, 1392-1393.
26. Bohlmann, F., Jakupovic, J., Misra, L. N. and Castro, V. (1985b) 5-Methylcumarin-derivate aus Lycoseris latifolia, Liebigs Ann. Chem., 1367-1376.
27. Bohlmann, F., Zdero, C., Schmeda-Hirschmann, G., Jakupovic, J., Domínguez, X. A., King, R. M. and Robinson, H. (1986) Dimeric guaianolides and other constituents from Gochnatia species. Phytochemistry 25, 1175-1178.
28. Boulter, D., Gleaves, J. T., Haslett, B. G., Peacock, D. and Jensen, U. (1978) The relationships of 8 tribes of the Compositae as suggested by plastocyanin amino acid sequence data. Phytochemistry 17, 1585-1589.
29. Bremer, K. (1987) Tribal interrelationships of the Asteraceae. Cladistics 3, 210-253.
30. Bremer, K. (1994) Subfamily Barnadesioideae. In Asteraceae. Cladistics and Classification (Bremer, K. ed.), pp. 49-60. Timber Press, Portland, and references cited therein.
31. Bremer, K. and Jansen, R. K. (1992) A new subfamily of the Asteraceae. Ann. Missouri Bot. Garden 79, 414-415.
32. Brooks, C. J. W. and Campbell, M. M. (1969) Brachylaenalones A and B: tricyclic sesquiterpenoid ketoaldehydes from heartwood of Brachylaena hutchinsii Hutch. (Compositae). J. Chem. Soc., Chem. Commun., 630-631.
33. Cabrera, A. L (1977) Mutisieae - Systematic Review. In The Biology and Chemistry of the Compositae (Heywood, V. H., Harborne, J. B. and Turner, B. I., eds), Vol. 2, pp. 1039-1066. Academic Press, London.
34. Cabrera, A. L. (1978) Flora de la Provincia de Jujuy. Colección científica del INTA. Tomo XIII, Parte X. Republica Argentina.
35. Carlquist, S. (1976) Tribal interrelationships and phylogeny of the Asteraceae. Aliso 8, 465-492.
36. Crisci, J. V. (1974) A numerical - taxonomic study of the subtribe Nassauviinae (Compositae Mutisieae). J. Arnold Arboretum 55, 568-610.
37. Crisci, J. V. (1980) Evolution in the subtribe Nassauviinae (Compositae Mutisieae): a phylogenetic reconstruction. Taxon 29, 213-224.
38. Cronquist, A. (1955) Phylogeny and taxonomy of the Compositae. Am. Midl. Naturalist 53, 478-511.
39. Cronquist, A. (1977) The Compositae revisited. Brittonia 29, 137-153.
40. Cronquist A. (1981) An Integrated System of Classification of Flowering Plants. Columbia University Press, New York.
41. Domínguez, X. A., Franco, R., Cano, G. and Wolzak, A. (1978) Triterpenes from the roots of Gochnatia hypoleuca. Rev. Latinoamer. Quim. 9, 214-216.
42. Faini, F., Torres, R. and Castillo, M. (1984) Costunolide and flavonols from Gochnatia foliosa var. fascicularis. J. Nat Prod. 47, 552-562.
43. Gamerro, J. C. (1990) Identidad de Pseudostifftia con Moquinia (Compositae) y consideraciones sobre la ubicación tribal del taxon. Darwiniana 30, 123-136.
44. García, E. and Guerreiro, E. (1988) Sesquiterpene lactones from Gochnatia palosanto and coumarins from G. argentina. Phytochemistry 27, 288-290.
45. García, E. E., Guerreiro, E. and Joseph-Nathan, P. (1985) ent-Pimaradiene diterpenes from Gochnatia glutinosa. Phytochemistry 24, 3059-3060.
46. Grau, J. (1980) Die Testa der Mutisieae und ihre Systematische Bedeutung. Mitteilungen der Botanischen Staatssammlung München 16, 269-332.
47. Hansen, H. V. (1991) Phylogenetic studies in Compositae, tribe Mutisieae. Opera Botanica 109, 1-50.
48. Heywood, V. H., Harborne, J. B. and Turner, B. L (eds) (1977) The Biology and Chemistry of the Compositae. Academic Press, London.
49. Hoeneisen, M. and Becker, H. (1986) New germacranolide from Gochnatia foliolosa var. foliolosa. J. Nat. Prod. 49, 360-361.
50. Hoffmann, O. (1890) Compositae. In Die Natürlichen Pflanzenfamilien (Engler, A. and Prantl, K., eds), Vol. 4(5), pp. 87-391. Verlag von Wilhelm Englemann, Leipzig.
51. Jansen, R. K. and Palmer, J. D. (1987) A chloroplast DNA inversion marks an ancient evolutionary split in the sunflower family (Asteraceae). Proc. Natl. Acad. Sci. USA 84, 5818-5822.
52. Jansen, R. K. and Palmer, J. D. (1988) Phylogenetic implications of chloroplast DNA restriction site variation in the Mutisieae (Asteraceae) Am. J. Bot. 75, 753-766 and references cited therein.
53. Jeffrey, C. (1978) Compositae. In Flowering Plants of the World, (Heywood, V. H., ed.), pp. 263-268. Mayflower Books, New York.
54. Jin, H. (1982) Studies on the constituents of Ainsliaea acerifolia Sch Bip., var. subapoda Nakai. Yakugaku Zasshi 102, 911-922.
55. Karis, P. O., Källersjö, M. and Bremer, K. (1992) Phylogenetic analysis of the Cichorioideae (Asteraceae), with emphasis on the Mutisieae. Ann. Missouri Bot. Garden 79, 416-427.
56. Karrer, W. (1958) Konstitution und Vorkommen von Organischen Pflanzenstoffen. Birkhauser, Basel.
57. Klein, E. and Schmidt, W. (1973) Main constituents of muhuhu oil. Dragoco Rep. (Ger. ed.) 20, 3-7. Chemical Abstract 78, 128337t.
58. Klein, E. and Schmidt, W. (1973) Main constituents of muhuhu oil. Dragoco Rep. (Ger. ed.) 20, 3-7. Chemical Abstract 78, 128337t.
59. Leins, P. (1971) Pollensystematische studien an Inuleen, 1: Tarchonanthinae, Plucheinae, Inulinae, Buphthalminae Botanische Jahrbücher für Systematik. Pflanzengeschichte und Pflanzengeographie 91, 91-146.
60. Maldonado, E., Flores, A. M. and Ortega, A. (1988) A germacranolide from Gochnatia hypoleuca and its transformation into a melampolide. Phytochemistry 27, 861-863.
61. Maldonado, Z., Hoeneisen, M. and Silva, M. (1988) A dithiophene from Aphyllocladus denticulatus. Phytochemistry 27, 2993-2994.
62. Mehta, R., Arora, P. O. and Menta, M. (1981) Chemical investigation of some Rajasthan desert plants. Indian J. Chem. 20B, 834.
63. Merxmüller, H., Leins, P. and Roessler, H. (1977) Inuleae - systematic review. In The Biology and Chemistry of the Compositae (Heywood, V. H., Harborne, J. B. and Turner, B. L., eds), Vol. 1, pp. 577-602. Academic Press, London.
64. Miyase, T. and Fukushima, S. (1984) Sesquiterpene lactones from Ainsliaea acerifolia Sch. Bip. and A. dissecta Franch. et Sav. Chem. Pharm. Bull. 32, 3043-3046.
65. Miyase, T., Yamaki, K. and Fukushima, S. (1984) Studies on sesquiterpenes from Macroclinidium trilobum Makino I. Chem. Pharm. Bull. 32, 3912-3917.
66. Miyase, T., Ozaki, H. and Uneo, A. (1991) Sesquiterpene glycosides from Ainsliaea cordifolia Franch. et Sav. Chem. Pharm. Bull. 39, 937-938.
67. Monteiro de Farías, A. C., Da Silva, A. J. R. and Tomassini, T. C. B. (1984) Constituents of Mochinea polymorpha, J. Nat. Prod. 47, 363-364. In this paper the genus was misspelt as Moquinia, the current designation of the plant material being Gochnatia polymorpha (Less.) Cabrera.
68. Muller, J. (1981) Fossil pollen records of extant Angiosperms. Bot. Rev. 47, 1-142.
69. 33 triterpene methyl ether. Tetrahedr. Lett. 3655-3656.
70. Nagumo, S., Izawa, K. and Nagai, M. (1978) New tetracyclic triterpenoids from Pertya robusta (Maxim) Beauv. and triterpene components of its related plants. Yakugaku Zasshi 98, 1327-1332.
71. Nagumo, S., Izawa, K., Higashiyama, K. and Nagai, M. (1980) A bitter principle of Pertya robusta (Maxim.) Beauv.: Glucozaluzanin C. Yakugaku Zasshi 100, 427-433.
72. Nagumo, S., Nagai, M. and Inoue, T. (1982) New sesquiterpene dilactone from Pertya glabrescens. Chem. Pharm. Bull. 30, 586-592.
73. Nagumo, S., Nagai, M. and Inoue, T. (1983) Bitter principles of Pertya glabrescens: Two sesquiterpene glucosides. Chem. Pharm. Bull. 31, 2302-2307.
74. Nagumo, S., Kawai, K., Nagase, H., Inoue, T. and Nagai, M. (1984) Sesquiterpenoids and (Z)-3-hexenylglucoside from Pertya glabrescens and a glucosidic sesquiterpene from P. scandens. Yakugaku Zasshi 104, 1223-1231.
75. Ortega, A. and Maldonado, E. (1984) Guaianolides from Gochnatia smithii. Phytochemistry 23, 1507-1509.
76. Palmer, J. D., Jansen, R. K., Michaels, H. J., Chase, M. W. and Manhart, J. R. (1988) Chloroplast DNA variation and plant phylogeny. Ann. Missouri Bot. Garden. 75, 1180-1206.
77. Pruski, J. F. (1989a) Notes on the Compositae of the Guayana highland - I. A new species of Stomatochaeta and the reduction of Guaicaia to Glossarion (Compositae: Mutisieae). Brittonia 41, 35-40.
78. Pruski, J. F. (1989b) Compositae of the Guayana highland - II. Novelties in Gongylolepis and Stenopadus (Mutisieae). Ann. Missouri Bot. Garden. 76, 993-1003.
79. Raven, P. H. (1975) The bases of Angiosperm phylogeny: Cytology. Ann. Missouri Bot. Garden 62, 724-764.
80. Raven, P. H. and Axelroad, D. I. (1974) Angiosperm biogeography and past continental movements. Ann. Missouri Bot. Garden 61, 539-673.
81. Robinson, H. (1979) Two new genera of Vernonieae (Asteraceae) from Brasil, Heterocypsela and Pseudostifftia. Phytologia 44, 422-450.
82. Robinson, H. (1991) Two new species of Stifftia with notes on relationships of the genus (Asteraceae: Mutisieae). Syst. Bot. 16, 685-692.
83. Robinson, H., Bohlmann, F. and King, R. M. (1980) Chemosystematic notes on the Asteraceae - III. Natural subdivisions of the Vernonieae. Phytologia 46, 421-436.
84. Skvarla, J. J., Turner, B. L., Patel, V. C. and Tomb, A. S. (1977) Pollen morphology in the Compositae and in morphologically related families. In The Biology and Chemistry of the Compositae (Heywood, V. H., Harborne, J. B. and Turner, B. L., eds), Vol. 1, pp. 141-248. Academic Press, London.
85. Solbrig, O. T. (1977) Chromosomeal cytology and evolution in the Family Compositae. In The Biology and Chemistry of the Compositae (Heywood, V. H., Harborne, J. B. and Turner, B. L., eds), Vol. 1, pp. 267-281. Academic Press, London.
86. Thorne, R. F. (1983) Proposed new realignments in the Angiosperms. Nord. J. Bot. 3, 85-117.
87. Tomassini, T. C. B. and Gilbert, B. (1972) α-Cyclocostunolide and dihydro-β-cyclocostunolide from Moquinia velutina. Phytochemistry, 11, 1177-1179. The current designation of the plant material is Gochnatia vetulina (Bong.) Cabrera.
88. Turner, B. L. (1977) Fossil history and geography. In The Biology and Chemistry of the Compositae (Heywood, V. H., Harborne, J. B. and Turner, B. L., eds), Vol. 1, pp. 20-39. Academic Press, London.
89. Vichnewski, W., Herz, W. and Kumar, N. (1979) A lactone analogue of germacrone. J. Org. Chem. 44, 2575-2578.
90. Wagenitz, G. (1976) Systematics and phylogeny of the Compositae (Asteraceae). Pl. Syst. Evol. 125, 29-46.
91. Ybarra, M. I., Catalán, C. A. N., Guerreiro, E., Gutíerrez, A. B. and Herz, W. (1990) Deoxyelephantopin and 2-epideoxyelephantopin analogs from Gochnatia palosanto. Phytochemistry 29, 2020-2024.
92. Ybarra, M. I., Catalán, C. A. N., Díaz, J. G. and Herz, W. (1992) A cyperane and trixanes from Jungia polita. Phytochemistry 31, 3627-3629 and references therein.
93. Ybarra, M. I., Catalán, C. A. N., Díaz, J. G. and Herz, W. (1994) Two homofarnesane derivatives and other constituents from Gochnatia glutinosa. Phytochemistry 35, 1585-1587.
94. Zdero, C. and Bohlmann, F. (1987) Sesquiterpene lactones from the genus Brachylaena. Phytochemistry 26, 2597-2601.
95. Zdero, C. and Bohlmann, F. (1989) Sesquiterpene lactones from Oldenburgia arbuscula and Pleiotaxis rugosa. Phytochemistry 28, 3345-3346.
96. Zdero, C. and Bohlmann, F. (1990) Sesquiterpene lactones from Dicoma species. Phytochemistry 29, 183-187.
97. Zdero, C., Bohlmann, F., King, R. M. and Robinson, H. (1986) α-Isocedrene derivatives, 5-methyl coumarins and other constituents from the subtribe Nassauviinae of the Compositae. Phytochemistry 25, 2873-2882.
98. Zdero, C., Bohlmann, F. and Niemeyer, H. M. (1988a) 5-Methylcoumarin derivatives from Aphyllocladus denticulatus. Phytochemistry 27, 1821-1825.
99. Zdero, C., Bohlmann, F. and Niemeyer, H. M. (1988b) Diterpenes and 5-methyl coumarin derivatives from Gypothamnium pinifolium and Plazia daphnoides. Phytochemistry 27, 2953-2959.
100. Zdero, C., Bohlmann, F. and Wasshausen, D. C. (1991) Guaianolides from Brachylaena species. Phytochemistry 30, 3810-3811.