Abstract
The familiar limits ofVerbenaceae are controversial, ranging from a sensu lato arrangement of seven subfamilies until a sharply defined sensu stricto group consisting of only some genera from subfam.Verbenoideae. Iridoid contents of genera belonging toVerbenaceae s. l. were examined through a cladistic analysis, using outgroup analysis to evaluate character polarity within the ingroup. The cladogram obtained shows the distribution of the species according to their iridoid content.
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Abdel-Baky, A. M., Makboul, M. A., Bishay, D. W., Ross, S. A., 1990: Pharmacognostical study ofAvicennia officinalis L. growing in Egypt. Part III: Terpenoids, flavonoids and iridoids. — Bull. Pharm. Sci.13: 59–64.
Akisue, G., Alvarenga, M. A. de, Barros, D. A. D., Gottlieb, O. R., 1981: Presença de ipolamiida emStachytarpheta australis Moldenke. — Anais Farm. Quim. São Paulo21: 57–60.
Benkrief, R., Skaltsounis, A.-L., Tillequin, F., Koch, M., Pusset, J., 1991: Iridoids and an alkaloid fromOxera morieri. — Pl. Med. (Stuttgart)57: 79–80.
—, 1978: Chemical examination of the fruits ofDuranta plumeri Jacq. — Indian J. Chem.6B: 844–845.
Bheemasankara Rao, C., Vijayakumar, E. K. S., Vijayalakshmi, K. V., 1981: Iridoids fromPremna latifolia. — Pl. Med. (Stuttgart)41: 80–83.
Boros, C. A., Stermitz, F. R., 1990: Iridoids. Un updated review. Part I. — J. Nat. Prod. (Lloydia)53: 1055–1147.
Briquet, J., 1895:Verbenaceae. — InEngler, A., Prantl, K., (Eds): Die natürlichen Pflanzenfamilien,43a, pp. 132–182. — Leipzig: Engelmann.
Brito, N. R. S., Lainetti, R., Guimaräes, L. A. S., Magalhäes, H. G., 1987: Ipolamiide, an iridoid glucoside fromStachytarpheta dichotoma. — Bull. Soc. Chim. Belg.96: 633.
—, —,Oliveira, A. L. F., Guimaräes, L. A. S., Magalhäes, H. G., Pires, F. R. S., 1990: Constituents ofPetrea racemosa andP. subserrata. — Fitoterapia61: 284.
Çalis, I., Hosny, M., Yürüker, A., 1993: Inerminosides A1, C, and D: three new iridoid biglycosides fromClerodendrum inerme. — Pl. Med. (Stuttgart)59: A600-A602.
—, —, —,Wright, A. D., Sticher, O., 1994: Inerminosides A and B: two novel iridoid biglycosides with an open-chain monoterpene unit fromClerodendrum inerme. — Phytochemistry37: 1083–1085.
Cantino, P. D., 1992a: Toward a phylogenetic classification of theLabiatae. — InHarley, R. M., Reynolds, T., (Eds): Advances in Labiate science, pp. 27–37. — Kew: Royal Botanical Gardens.
—, 1992b: Evidence for a polyphyletic origin of theLabiatae. — Ann. Missouri Bot. Gard.79: 361–379.
—, 1992: Genera ofLabiatae: Status and classification. — InHarley, R. M., Reynolds, T., (Eds): Advances in Labiate science, pp. 511–522. — Kew: Royal Botanical Gardens.
Castro, O., Umana, E., Herrera, M. L., 1990: Potencial biologico y quimico deVerbena litoralis, una planta medicinal usada en Costa Rica como agente antidiarreico. — Quím. Nova13: 310–311.
Cronquist, A., 1981: An integrated system of classification of flowering plants. — New York: Columbia University Press.
Dahlgren, G., 1989: The last Dahlgrenogram. System of classification of the dicotyledons. — InKit Tan, (Ed.): Plant taxonomy, phytogeography and related subjects, pp. 249–260. — Edinburgh: Edinburgh University Press.
Damtoft, S., Jensen, S. R., Nielsen, B. J., 1979: Iridoids inVerbena. — Taxon28: 525–528.
—, —, —, 1983: Biosynthesis of iridoid glucosides cornin, hastatoside, and griselinoside inVerbena species. — J. Chem. Soc. Perkin Trans. I22: 1943–1948.
De Luca, C., 1980: Isolation of ipolamiide fromStachytarpheta mutabilis. — Fitoterapia51: 27–280.
—, 1983: 6β-hydroxyipolamiide, an iridoid glucoside fromStachytarpheta mutabilis. — Phytochemistry22: 1185–1187.
Demuth, H., Jensen, S. R., Nielsen, B. H., 1989: Iridoid glucosides fromAsystasia bella. — Phytochemistry28: 3361–3364.
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 fromVitex negundo. — Tetrahedron39: 3067–3072.
El-Gazzar, A., Watson, L., 1970: A taxonomic study ofLabiatae and related genera. — New Phytol.69: 451–486.
El-Naggar, L., Beal, J., 1980: Iridoids. A review. — J. Nat. Prod. (Lloydia)43: 649–707.
Erdtman, G., 1945: Pollen morphology and plant taxonomy. IV.Labiatae, Verbenaceae andAvicenniaceae. — Svensk Bot. Tidskr.39: 279–285.
Farris, J. S., 1988: Hennig86 version 1.5. Computer program distributed by the author.
Fauvel, M.-T., Bousquet-Melou, A., Moulis, C., Gleye, J., Jensen, S. R., 1995: Iridoid glucosides fromAvicennia germinans. — Phytochemistry38: 893–894.
Ford, C. W., Bendall, M. R., 1980: Identification of the iridoid glucoside theveside inLantana camara (Verbenaceae) and determination of its structure and stereochemistry by means of NMR. — Austral. J. Chem.33: 509–518.
Franke, A., Rimpler, H., 1987: Vebraside, an iridoid glucoside fromVerbena brasiliensis. — Phytochemistry26: 3015–3020.
Ganapaty, S., Venkata Rao, D., 1983: Chemical constituents of the leaves ofCitharexylum subserratum. — Fitoterapia1: 13–15.
—, 1988: Iridoid glycosides from the leaves ofCitharexylum fruticosum. — Pl. Med. (Stuttgart)54: 42–43.
Garnier, J., 1977: Etude chimique de deux Verbénacées de Guyane:Stachytarpheta guyannensis Vahl etStachytarpheta mutabilis Vahl. — Pl. Méd. Phytothérap.11: 303–305.
Goerler, K., Oehlke, D., Soicke, H., 1985: Iridoidführung vonVitex agnuscastus. — Pl. Med. (Stuttgart)6: 530–531.
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.
Hänsel, R. C., Leuckert, H., Rimpler, H., Schaaf, K. D., 1965: Chemotaxonomische Untersuchungen in der GattungVitex L. — Phytochemistry4: 19–27.
Hegnauer, R., 1990: Chemotaxonomie der Pflanzen.9. — Basel: Birkhäuser.
—, 1978: Die systematische Bedeutung von iridoiden Inhaltsstoffen im Rahmen vonWettstein'sTubiflorae. — Pl. Med. (Stuttgart)33: 1–33.
Iwagawa, T., Nakahara, A., Nakatani, M., 1993a: Iridoids fromVitex cannabifolia. — Phytochemistry32: 453–454.
—, —,Miyauchi, A., Okamura, H., Nakatani, M., 1993b: Constituents of the leaves ofVitex cannabifolia. — Kagoshima Daigaku Rigakubu Kiyo, Suguku, Butsurigaku, Kagaku26: 57–61.
Jacke, G., Rimpler, H., 1983: Distribution of iridoid glycosides inClerodendrum species. — Phytochemistry22: 1729–1734.
Jensen, S. R., 1991: Plant iridoids, their biosynthesis and distribution in angiosperms. — InHarborne, J. B., Tomas-Barberan, F. A., (Eds): Ecological chemistry and biochemistry of plant terpenoids, pp. 133–158. — Oxford: Clarendon Press.
—, 1992: Systematic implications of the distribution of iridoids and other chemical compounds in theLoganiaceae and other families of theAsteridae. — Ann. Missouri Bot. Gard.79: 284–302.
—, 1975: Iridoid compounds, their occurrence and systematic importance in the angiosperms. — Bot. Not.218: 148–180.
Junell, S., 1934: Zur Gynöceummorphologie und Systematik der Verbenaceen und Labiaten. — Symb. Bot. Upsal.4: 1–219.
Koenig, G., Rimpler, H., 1985: Iridoid glucosides inAvicennia marina. — Phytochemistry24: 1245–1248.
—, —,Hunkler, D., 1987: Iridoid glucosides inAvicennia officinalis. — Phytochemistry26: 423–427.
Kooiman, P., 1975: The occurrence of iridoid glycosides in theVerbenaceae. — Acta Bot. Neerl.24: 459–468.
Kouno, I., Inoue, M., Onizuka, Y., Fujisaki, T., Kawano, N., 1988: Iridoids and phenolic glucosides fromVitex rotundifolia. — Phytochemistry27: 611–612.
Kustrak, D., Antolic, A., 1992: Isolation of iridoids from leaves ofVitex agnus-castus. — Farm. Glasn.48: 305–310.
Lahloub, M. F., Salama, O. M., Mansour, E. S., 1990: Phenylpropanoids and iridoid glycosides fromVerbena officinalis. — Bull. Fac. Pharm.28(2): 75–77.
Lammel, G., Rimpler, H., 1981: Iridoide ausClerodendrum thomsonae Balf.,Verbenaceae. — Z. Naturf.36: 708–713.
Melchior, H., 1964:A Engler's Syllabus der Pflanzenfamilien.2. 12th edn. — Berlin: Borntraeger.
Milz, S., Rimpler, H., 1978a: Pulchellosid I, ein neues Iridoid ausVerbena pulchella Sweet. — Tetrahedron Lett.19: 895–898.
—, —, 1978b: Pulchellosid II, ein neues Iridoid ausVerbena pulchella Sweet. — Tetrahedron Lett.19: 3549–3552.
—, —, 1979: Verbreitung von Iridoiden in der GattungVerbena und einigen anderenVerbenoideae. — Z. Naturf.34: 319–329.
Moldenke, H. N., 1940: Contribution to the flora of extratropical South America. — Lilloa5: 353–440.
Otsuka, H., Kubo, N., Yamasaki, K., Padolina, W. G., 1989a: Two iridoid glycosid caffeoyl esters fromPremna odorata. — Phytochemistry28: 513–515.
—, —, —, 1989b: Premnosides A-D: diacyl 6-O-α-L-rhamnopyranosylcatalpols fromPremna odorata. — Phytochemistry28: 3063–3067.
—, 1989c: 6-O-α-L-(2″-O-and 3″-O-isoferuloyl) rhamnopyranosylcatalpols fromPremna japonica. — Phytochemistry28: 3069–3071.
—, —, —, 1990a: Iridoid diglycoside monoacyl esters from the leaves ofPremna japonica. — J. Nat. Prod. (Lloydia)53: 107–111.
—, —, —,Takeda, Y., Seki, T., 1990b: Isolation and characterization of new diacyl 6-O-α-L-rhamnopyranosylcatalpol from the leaves ofPremna japonica Miq. — Chem. Pharm. Bull.38: 426–429.
—, 1991a: Iridoid diglycoside monoacyl esters from stems ofPremna japonica. — Phytochemistry30: 1917–1920.
—, 1991b: Isolation and structure elucidation of mono and diacyl-iridoid diglycosides from leaves ofPremna japonica. — J. Nat. Prod. (Lloydia)52: 547–553.
—, 1993: A verbascoside iridoid glucoside conjugate fromPremna corymbosa var.obtusifolia. — Phytochemistry32: 983–986.
Pan, W. D., Langtian, M., Li, Y. J., Ohtani, K., Kasai, R., Tanaka, D., 1992a: Iridoid glucosides from common lantana (Lantana camara). — Zong cao yao23: 12–25.
—, 1992b: Chemical constituents of the roots ofLantana camara. — Acta Pharm. Sin.27: 515–521.
Rimpler, H., 1972a: Iridoids and ecdysones fromVerbenaceae II. Iridoids and ecdysones fromVitex species — Phytochemistry11: 2653–2654.
—, 1972b: Iridoids and ecdysones fromVerbenaceae. III. Iridoids fromStilbe species. — Phytochemistry11: 3096–3097.
—, 1972c: Iridoids and ecdysones fromVerbenaceae. IV. Lamiide fromChascanum cernuum. — Phytochemistry11: 3094.
—, 1972d: Phytoecdysone und Iridoide ausVitex megapotamica. — Arch. Pharm. (Weinheim)305: 746–751.
—, 1973: Iridoide ausCaryopteris incana undCaryopteris odorata. — Pharm. Zeitung118(39): 1508.
—, 1974: Iridoide und Ecdysone ausVerbenaceae. VI. Stilbericoside, ein neues C8-Iridoid ausStilbe ericoides L. — Z. Naturf.29: 368–373.
—, 1986: Iridoid glucosides as taxonomic markers in the generaLantana, Lippia, Aloysia andPhyla. — Biochem. Syst. Ecol.14: 307–310.
—, 1979: Hastatosid, ein neues Iridoid ausVerbena hastata L. undV. officinalis L. — Z. Naturf.34c: 311–318.
—, 1974: Iridoide und Ecdysone ausVerbenaceae. V. Iridoide ausDuranta repens. — Z. Naturf. c29: 11–115.
—, 1992: Cladistic analysis of the subfamilyCaryopteridoideae Briq. and related taxa ofVerbenaceae andLamiaceae using morphological and chemical characters. — InHarley, R. M., Reynolds, T., (Eds): Advances in Labiate science, pp. 39–54. — Kew: Royal Botanical Gardens.
Salama, O. M., Amer, M. A., Lahloub, M. F., Spengel, S., 1992: Repenoside, a new iridoid glucoside fromDuranta repens. — Mansoura J. Pharm. Sci.8: 212–221.
Sehgal, C. K., Taneja, S. C., Dhar, K. L., Atal, C. K., 1982: 2'-p-hydroxybenzoyl mussaenosidic acid, a new iridoid glucoside fromVitex negundo. — Phytochemistry21: 363–366.
—, —, —, 1983: 6'p-hydroxybenzoilmussaenosidic acid—an iridoid glucoside fromVitex negundo. — Phytochemistry22: 1036–1038.
Sirait, M., Liemtjawanhoo, F., 1966: Isolation of agnuside from the leaves ofVitex trifolia. — Suara Pharm.9: 47–51.
Stenzel, E., Rimpler, H., Hunkler, D., 1986: Iridoid glucosides fromClerodendrum incisum. — Phytochemistry25: 2557–2561.
—, 1988: Phenetic relationships inClerodendron (Verbenaceae) and some phylogenetic considerations. — Pl. Syst. Evol.159: 257–271.
Taguchi, H., 1976: Studies of the constituents ofVitex cannabifolia. — Chem. Pharm. Bull.24: 1668–1670.
Takeda, Y., Morimoto, Y., Natsumoto, T., Ogimi, C., Hirata, E., Takushi, A., Otsuka, H., 1995: Iridoid glucosides from the leaves and stems ofDuranta erecta. — Phytochemistry39: 829–833.
Tantisewie, B., Sticher, O., 1975: Isolation of ipolamiide fromStachytarpheta indica. — Phytochemistry14: 1462–1463.
Troncoso, N. S., 1974: Los géneros de verbenáceas de Sudamérica extratropical (Argentina, Chile, Bolivia, Paraguay, Uruguay y Sur de Brasil). — Darwiniana18: 295–412.
Von Poser, G. L., Moulis, C., Sobral, M., Henriques, A. T., 1995: Chemotaxonomic features of iridoids occurring inVerbenoxylum reitzii (Verbenaceae). — Pl. Syst. Evol.198: 287–290.
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von Poser, G.L., Toffoli, M.E., Sobral, M. et al. Iridoid glucosides substitution patterns inVerbenaceae and their taxonomic implication. Pl Syst Evol 205, 265–287 (1997). https://doi.org/10.1007/BF01464409
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DOI: https://doi.org/10.1007/BF01464409