Iridoid glucosides substitution patterns in Verbenaceae and their taxonomic implication

Plant Systematics and Evolution

Volumn 205, Issue 3-4, 1997, Pages 265-287

  Von Poser, Gilsane Lino ^a   Toffoli, Maria Elisa ^a   Sobral, Marcos ^a   Henriques, Amélia T ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

Cladistic analysis; Lamiaceae. Iridoid glucosides; Taxonomy; Verbenaceae

Indexed keywords

LAMIACEAE; MAGNOLIOPHYTA; VERBENACEAE;

EID: 0031007851     PISSN: 03782697     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF01464409     Document Type: Article

References (88)

1. ABDEL-BAKY, A. M., MAKBOUL, M. A., BISHAY, D. W., Ross, S. A., 1990: Pharmacognostical study of Avicennia officinalis L. growing in Egypt. Part III: Terpenoids, flavonoids and iridoids. - Bull. Pharm. Sci. 13: 59-64.
2. AKISUE, G., ALVARENGA, M. A. DE, BARROS, D. A. D., GOTTLIEB, O. R., 1981: Presença de ipolamiida em Stachytarpheta australis MOLDENKE. - Anais Farm. Quim. São Paulo 21: 57-60.
3. BENKRIEF, R., SKALTSOUNIS, A.-L., TILLEQUIN, F., KOCH, M., PUSSET, J., 1991: Iridoids and an alkaloid from Oxera morieri. - Pl. Med. (Stuttgart) 57: 79-80.
4. _ BHEEMASANKARA RAO, C., NAMOSIVA RAO, T., VIJAYAKUMAR, E. K. S., 1978: Chemical examination of the fruits of Duranta plumeri JACQ. - Indian J. Chem. 6B: 844-845.
5. BHEEMASANKARA RAO, C, VIJAYAKUMAR, E. K. S., VIJAYALAKSHMI, K. V., 1981: Iridoids from Premna latifolia. - Pl. Med. (Stuttgart) 41: 80-83.
6. BOROS, C. A., STERMITZ, F. R., 1990: Iridoids. Un updated review. Part I.-J. Nat. Prod. (Lloydia)53: 1055-1147.
7. BRIQUET, J., 1895: Verbenaceae. - In ENGLER, A., PRANTL, K., (Eds): Die natürlichen Pflanzenfamilien, 43a, pp. 132-182. - Leipzig: Engelmann.
8. BRITO, N. R. S., LAINETTI, R., GUIMARÄES, L. A. S., MAGALHÄES, H. G., 1987: Ipolamiide, an iridoid glucoside from Stachytarpheta dichotoma. - Bull. Soc. Chim. Belg. 96: 633.
9. _ OLIVEIRA, A. L. F., GUIMARÄES, L. A. S., MAGALHÄES, H, G., PIRES, F. R. S., 1990: Constituents of Petrea racemosa and P. subserrata. - Fitoterapia 61: 284.
10. ÇALIS, I., HOSNY, M., YÜRÜKER, A., 1993: Inerminosides A1, C, and D: three new iridoid biglycosides from Clerodendrum inerme. - Pl. Med. (Stuttgart) 59: A600-A602.
11. _ WRIGHT, A. D., STICHER, O., 1994: Inerminosides A and B: two novel iridoid biglycosides with an open-chain monoterpene unit from Clerodendrum inerme. - Phytochemistry 37: 1083-1085.
12. CANTINO, P. D., 1992a: Toward a phylogenetic classification of the Labiatae. - In HARLEY, R. M., REYNOLDS, T., (Eds): Advances in Labiate science, pp. 27-37. - Kew: Royal Botanical Gardens.
13. _ 1992b: Evidence for a polyphyletic origin of the Labiatae. - Ann. Missouri Bot. Gard. 79: 361-379.
14. _ HARLEY, R. M., WAGSTAFF, S. J., 1992: Genera of Labiatae: Status and classification. - In HARLEY, R. M., REYNOLDS, T., (Eds): Advances in Labiate science, pp. 511-522. - Kew: Royal Botanical Gardens.
15. CASTRO, O., UMAN̈A, E., HERRERA, M. L., 1990: Potencial biologico y quimico de Verbena litoralis, una planta medicinal usada en Costa Rica como agente antidiarreico. - Quim. Nova 13: 310-311.
16. CRONQUIST, A., 1981: An integrated system of classification of flowering plants. - New York: Columbia University Press.
17. DAHLGREN, G., 1989: The last Dahlgrenogram. System of classification of the dicotyledons. -In KIT TAN, (Ed.): Plant taxonomy, phytogeography and related subjects, pp. 249-260. -Edinburgh: Edinburgh University Press.
18. DAMTOFT, S., JENSEN, S. R., NIELSEN, B. J., 1979: Iridoids in Verbena. - Taxon 28: 525-528.
19. _ 1983: Biosynthesis of iridoid glucosides cornin, hastatoside, and griselinoside in Verbena species. - J. Chem. Soc. Perkin Trans. I 22: 1943-1948.
20. DE LUCA, C., 1980: Isolation of ipolamiide from Stachytarpheta mutabilis. - Fitoterapia 51: 27-280.
21. _ GUIZO, M., MARTINO, C., 1983:6ß-hydroxyipolamiide,an iridoid glucoside from Stachytarpheta mutabilis. - Phytochemistry 22: 1185-1187.
22. DEMUTH, H., JENSEN, S. R., NIELSEN, B. H., 1989: Iridoid glucosides from Asystasia bella. -Phytochemistry 28: 3361-3364.
23. DUTTA, P. K., CHOWDHURY, U. S., CHAKRAVARTY, A. K., ACHARI, B., PAKRASHI, S. C., 1983: Studies on Indian medicinal plants. Part LXXV. Nishindaside, a novel iridoid glycoside from Vitex negundo. - Tetrahedron 39: 3067-3072.
24. EL-GAZZAR, A., WATSON, L., 1970: A taxonomic study of Labiatae and related genera. - New Phytol. 69: 451-486.
25. EL-NAGGAR, L., BEAL, J., 1980: Iridoids. A review. - J. Nat. Prod. (Lloydia) 43: 649-707.
26. ERDTMAN, G., 1945: Pollen morphology and plant taxonomy. IV. Labiatae, Verbenaceae and Avicenniaceae. - Svensk Bot. Tidskr. 39: 279-285.
27. FARRIS, J. S., 1988: Hennig86 version 1.5. Computer program distributed by the author.
28. FAUVEL, M.-T., BOUSQUET-MELOU, A., MOULIS, C., GLEYE, J., JENSEN, S. R., 1995: Iridoid glucosides from Avicennia germinans. - Phytochemistry 38: 893-894.
29. FORD, C. W., BENDALL, M. R., 1980: Identification of the iridoid glucoside theveside in Lantana camara (Verbenaceae) and determination of its structure and stereochemistry by means of NMR. - Austral. J. Chem. 33: 509-518.
30. FRANKE, A., RIMPLER, H., 1987: Vebraside, an iridoid glucoside from Verbena brasiliensis. -Phytochemistry 26: 3015-3020.
31. GANAPATY, S., VENKATA RAO, D., 1983: Chemical constituents of the leaves of Citharexylum subserralum. - Fitoterapia 1: 13-15.
32. _ HENI, J., VENKATA RAO, D., RIMPLER, H., 1988: Iridoid glycosides from the leaves of Citharexylum fruticosum. - Pl. Med. (Stuttgart) 54: 42-43.
33. GARNIER, J., 1977: Etude chimique de deux Verbénacées de Guyane: Stachytarpheta guyannensis VAHL et Stachytarpheta mutabilis VAHL. - Pl. Méd. Phytothérap. 11: 303-305.
34. GOERLER, K., OEHLKE, D., SOICKE, H., 1985: Iridoidführung von Vitex agnuscastus. - Pl. Med. (Stuttgart) 6: 530-531.
35. GUNN, C. R., WIERSEMA, J. H., RITCHIE, C. A., KIRKBRIDE, J. Jr., 1992: Families and genera of spermatophytes recognized by the Agricultural Research Service. - Techn. Bull. U.S.D.A. 1796 & 4999.
36. HÄNSEL, R. C., LEUCKERT, H., RIMPLER, H., SCHAAF, K. D., 1965: Chemotaxonomische Untersuchungen in der Gattung Vitex L. - Phytochemistry 4: 19-27.
37. HEGNAUER, R., 1990: Chemotaxonomie der Pflanzen. 9. - Basel: Birkhäuser.
38. _ KOOIMAN, P., 1978: Die systematische Bedeutung von iridoiden Inhaltsstoffen im Rahmen von WETTSTEIN'S Tubiflorae. - Pl. Med. (Stuttgart) 33: 1-33.
39. IWAGAWA, T., NAKAHARA, A., NAKATANI, M., 1993a: Iridoids from Vitex cannabifolia. -Phytochemistry 32: 453-454.
40. _ MIYAUCHI, A., OKAMURA, H., NAKATANI, M., 1993b: Constituents of the leaves of Vitex cannabifolia. - Kagoshima Daigaku Rigakubu Kiyo, Suguku, Butsurigaku, Kagaku 26: 57-61.
41. JACKE, G., RIMPLER, H., 1983: Distribution of iridoid glycosides in Clerodendrum species. -Phytochemistry 22: 1729-1734.
42. JENSEN, S. R., 1991: Plant iridoids, their biosynthesis and distribution in angiosperms. - In HARBORNE, J. B., TOMAS-BARBERAN, F. A., (Eds): Ecological chemistry and biochemistry of plant terpenoids, pp. 133-158. - Oxford: Clarendon Press.
43. _ 1992: Systematic implications of the distribution of iridoids and other chemical compounds in the Loganiaceae and other families of the Asteridae. - Ann. Missouri Bot. Gard. 79: 284-302.
44. _ NIELSEN, B. J., DAHLGREN, R., 1975: Iridoid compounds, their occurrence and systematic importance in the angiosperms. - Bot. Not. 218: 148-180.
45. JUNELL, S., 1934: Zur Gynöceummorphologie und Systematik der Verbenaceen und Labiaten. - Symb. Bot. Üpsal. 4: 1-219.
46. KOENIG, G., RIMPLER, H., 1985: Iridoid glucosides in Avicennia marina. - Phytochemistry 24: 1245-1248.
47. _ HUNKLER, D., 1987: Iridoid glucosides in Avicennia officinalis. - Phytochemistry 26: 423-427.
48. KOOIMAN, P., 1975: The occurrence of iridoid glycosides in the Verbenaceae. - Acta Bot. Neerl. 24: 459-468.
49. KOUNO, I., INOUE, M., ONIZUKA, Y., FUJISAKI, T., KAWANO, N., 1988: Iridoids and phenolic glucosides from Vitex rotundifolia. - Phytochemistry 27: 611-612.
50. KUSTRAK, D., ANTOLIC, A., 1992: Isolation of iridoids from leaves of Vitex agnus-castus. -Farm. Glasn. 48: 305-310.
51. LAHLOUB, M. F., SALAMA, O. M., MANSOUR, E. S., 1990: Phenylpropanoids and iridoid glycosides from Verbena officinalis. - Bull. Fac. Pharm. 28(2): 75-77.
52. LAMMEL, G., RIMPLER, H., 1981: Iridoide aus Clerodendrum thomsonae BALF., Verbenaceae. -Z. Naturf. 36: 708-713.
53. MELCHIOR, H., 1964: A ENGLER'S Syllabus der Pflanzenfamilien. 2. 12th edn. - Berlin: Borntraeger.
54. MILZ, S., RIMPLER, H., 1978a: Pulchellosid I, ein neues Iridoid aus Verbena pulchella SWEET. - Tetrahedron Lett. 19: 895-898.
55. _ 1978b: Pulchellosid II, ein neues Iridoid aus Verbena pulchella SWEET. - Tetrahedron Lett. 19: 3549-3552.
56. _ 1979: Verbreitung von Iridoiden in der Gattung Verbena und einigen anderen Verbenoideae. - Z. Naturf. 34: 319-329.
57. MOLDENKE, H. N., 1940: Contribution to the flora of extratropical South America. - Lilloa 5: 353-440.
58. OTSUKA, H., KUBO, N., YAMASAKI, K., PADOLINA, W. G., 1989a: Two iridoid glycosid caffeoyl esters from Premna odorata. - Phytochemistry 28: 513-515.
59. _ 1989b: Premnosides A-D: diacyl 6-O-α-L-rhamnopyranosylcatalpols from Premna odorata. - Phytochemistry 28: 3063-3067.
60. _ SASAKI, Y., YAMASAKI, K., TAKEDA, Y., SEKI, T., 1989c: 6-O-α-L-(2″-O-and 3″-O-isoferuloyl) rhamnopyranosylcatalpols from Premna japonica. - Phytochemistry 28: 3069-3071.
61. _ 1990a: Iridoid diglycosidemonoacyl esters from the leaves of Premna japonica. - J. Nat. Prod. (Lloydia) 53: 107-111.
62. _ TAKEDA, Y., SEKI, T., 1990b: Isolation and characterization of new diacyl 6-O-α-L-rhamnopyranosylcatalpol from the leaves of Premna japonica MIQ. - Chem. Pharm. Bull. 38: 426-429.
63. _ KUBO, N., SASAKI, Y., TAKEDA, Y., SEKI, T., 1991a: Iridoid diglycoside monoacyl esters from stems of Premna japonica. - Phytochemistry 30: 1917-1920.
64. _ SASAKI, Y., KUBO, N., YAMASAKI, K., 1991b: Isolation and structure elucidation of mono and diacyl-iridoid diglycosides from leaves of Premna japonica. - J. Nat. Prod. (Lloydia) 52: 547-553.
65. _ WATANABE, E., YUASA, K., OGINI, C., TAKUSHI, A., TAKEDA, Y., 1993: A verbascoside iridoid glucoside conjugate from Premna corymbosa var. obtusifolia. - Phytochemistry 32: 983-986.
66. PAN, W. D., LANGTIAN, M., LI, Y. J., OHTANT, K., KASAI, R., TANAKA, D., 1992a: Iridoid glucosides from common lantana (Lantana camara). - Zong cao yao 23: 12-25.
67. _ LI, Y. J., OHTANI, K., KASAI, R., TANAKA, D., 1992b: Chemical constituents of the roots of Lantana camara. - Acta Pharm. Sin. 27: 515-521.
68. RIMPLER, H., 1972a: Iridoids and ecdysones from Verbenaceae II. Iridoids and ecdysones from Vitex species - Phytochemistry 11: 2653-2654.
69. _ 1972b: Iridoids and ecdysones from Verbenaceae. III. Iridoids from Stilbe species. -Phytochemistry 11: 3096-3097.
70. _ 1972c: Iridoids and ecdysones from Verbenaceae. IV. Lamiide from Chascanum cernuum. -Phytochemistry 11: 3094.
71. _ 1972d: Phytoecdysone und Iridoide aus Vitex megapotamica. - Arch. Pharm. (Weinheim) 305: 746-751.
72. _ 1973: Iridoide aus Caryopteris incana und Caryopteris odorata. - Pharm. Zeitung 118(39): 1508.
73. _ PISTOR, H., 1974: Iridoide und Ecdysone aus Verbenaceae. VI. Stilbericoside, ein neues C8-Iridoid aus Stilbe ericoides L. - Z. Naturf. 29: 368-373.
74. _ SAUERBIER, H., 1986: Iridoid glucosides as taxonomic markers in the genera Lantana, Lippia, Aloysia and Phyla. - Biochem. Syst. Ecol. 14: 307-310.
75. _ SCHÄFER, B., 1979: Hastatosid, ein neues Iridoid aus Verbena hastata L. und V. officinalis L. - Z. Naturf. 34c: 311-318.
76. _ TIMM, H., 1974: Iridoide und Ecdysone aus Verbenaceae. V. Iridoide aus Duranta repens. -Z. Naturf. c29: 11-115.
77. _ WINTERHALTER, C., FALK, U., 1992: Cladistic analysis of the subfamily Caryopteridoideae BRIQ. and related taxa of Verbenaceae and Lamiaceae using morphological and chemical characters. - In HARLEY, R. M., REYNOLDS, T., (Eds): Advances in Labiate science, pp. 39-54. - Kew: Royal Botanical Gardens.
78. SALAMA, O. M., AMER, M. A., LAHLOUB, M. F., SPENGEL, S., 1992: Repenoside, a new iridoid glucoside from Duranta repens. - Mansoura J. Pharm. Sci. 8: 212-221.
79. SEHGAL, C. K., TANEJA, S. C., DHAR, K. L., ATAL, C. K., 1982: 2'-p-hydroxybenzoyl mussaenosidic acid, a new iridoid glucoside from Vitex negundo. - Phytochemistry 21: 363-366.
80. _ 1983: 6'p-hydroxybenzoilmussaenosidic acid - an iridoid glucoside from Vitex negundo. - Phytochemistry 22: 1036-1038.
81. SIRAIT, M., LIEMTJAWANHOO, F., 1966: Isolation of agnuside from the leaves of Vitex trifolia. - Suara Pharm. 9: 47-51.
82. STENZEL, E., RIMPLER, H., HUNKLER, D., 1986: Iridoid glucosides from Clerodendrum incisum. - Phytochemistry 25: 2557-2561.
83. _ HENI, J., RIMPLER, H., VOGELLEHNER, D., 1988: Phenetic relationships in Clerodendron (Verbenaceae) and some phylogenetic considerations. - Pl. Syst. Evol. 159: 257-271.
84. TAGUCHI, H., 1976: Studies of the constituents of Vitex cannabifolia. - Chem. Pharm. Bull. 24: 1668-1670.
85. TAKEDA, Y., MORIMOTO, Y., NATSUMOTO, T., OGIMI, C., HIRATA, E., TAKUSHI, A., OTSUKA, H., 1995: Iridoid glucosides from the leaves and stems of Duranta erecta. - Phytochemistry 39: 829-833.
86. TANTISEWIE, B., STICHER, O., 1975: Isolation of ipolamiide from Stachytarpheta indica. -Phytochemistry 14: 1462-1463.
87. TRONCOSO, N. S., 1974: Los géneros de verbenáceas de Sudamérica extratropical (Argentina, Chile, Bolivia, Paraguay, Uruguay y Sur de Brasil). - Darwiniana 18: 295-412.
88. VON POSER, G. L., MOULIS, C., SOBRAL, M., HENRIQUES, A. T., 1995: Chemotaxonomic features of iridoids occurring in Verbenoxylum reitzii (Verbenaceae). - Pl. Syst. Evol. 198: 287-290.