Skip to main content
Log in

Iridoid glucosides substitution patterns inVerbenaceae and their taxonomic implication

  • Published:
Plant Systematics and Evolution Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • Benkrief, R., Skaltsounis, A.-L., Tillequin, F., Koch, M., Pusset, J., 1991: Iridoids and an alkaloid fromOxera morieri. — Pl. Med. (Stuttgart)57: 79–80.

    Google Scholar 

  • —, 1978: Chemical examination of the fruits ofDuranta plumeri Jacq. — Indian J. Chem.6B: 844–845.

    Google Scholar 

  • Bheemasankara Rao, C., Vijayakumar, E. K. S., Vijayalakshmi, K. V., 1981: Iridoids fromPremna latifolia. — Pl. Med. (Stuttgart)41: 80–83.

    Google Scholar 

  • Boros, C. A., Stermitz, F. R., 1990: Iridoids. Un updated review. Part I. — J. Nat. Prod. (Lloydia)53: 1055–1147.

    Google Scholar 

  • Briquet, J., 1895:Verbenaceae. — InEngler, A., Prantl, K., (Eds): Die natürlichen Pflanzenfamilien,43a, pp. 132–182. — Leipzig: Engelmann.

    Google Scholar 

  • 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.

    Google Scholar 

  • —, —,Oliveira, A. L. F., Guimaräes, L. A. S., Magalhäes, H. G., Pires, F. R. S., 1990: Constituents ofPetrea racemosa andP. subserrata. — Fitoterapia61: 284.

    Google Scholar 

  • Çalis, I., Hosny, M., Yürüker, A., 1993: Inerminosides A1, C, and D: three new iridoid biglycosides fromClerodendrum inerme. — Pl. Med. (Stuttgart)59: A600-A602.

    Google Scholar 

  • —, —, —,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.

    Google Scholar 

  • 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.

    Google Scholar 

  • —, 1992b: Evidence for a polyphyletic origin of theLabiatae. — Ann. Missouri Bot. Gard.79: 361–379.

    Google Scholar 

  • —, 1992: Genera ofLabiatae: Status and classification. — InHarley, R. M., Reynolds, T., (Eds): Advances in Labiate science, pp. 511–522. — Kew: Royal Botanical Gardens.

    Google Scholar 

  • 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.

    Google Scholar 

  • Cronquist, A., 1981: An integrated system of classification of flowering plants. — New York: Columbia University Press.

    Google Scholar 

  • 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.

    Google Scholar 

  • Damtoft, S., Jensen, S. R., Nielsen, B. J., 1979: Iridoids inVerbena. — Taxon28: 525–528.

    Google Scholar 

  • —, —, —, 1983: Biosynthesis of iridoid glucosides cornin, hastatoside, and griselinoside inVerbena species. — J. Chem. Soc. Perkin Trans. I22: 1943–1948.

    Google Scholar 

  • De Luca, C., 1980: Isolation of ipolamiide fromStachytarpheta mutabilis. — Fitoterapia51: 27–280.

    Google Scholar 

  • —, 1983: 6β-hydroxyipolamiide, an iridoid glucoside fromStachytarpheta mutabilis. — Phytochemistry22: 1185–1187.

    Google Scholar 

  • Demuth, H., Jensen, S. R., Nielsen, B. H., 1989: Iridoid glucosides fromAsystasia bella. — Phytochemistry28: 3361–3364.

    Google Scholar 

  • 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.

    Google Scholar 

  • El-Gazzar, A., Watson, L., 1970: A taxonomic study ofLabiatae and related genera. — New Phytol.69: 451–486.

    Google Scholar 

  • El-Naggar, L., Beal, J., 1980: Iridoids. A review. — J. Nat. Prod. (Lloydia)43: 649–707.

    Google Scholar 

  • Erdtman, G., 1945: Pollen morphology and plant taxonomy. IV.Labiatae, Verbenaceae andAvicenniaceae. — Svensk Bot. Tidskr.39: 279–285.

    Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • Franke, A., Rimpler, H., 1987: Vebraside, an iridoid glucoside fromVerbena brasiliensis. — Phytochemistry26: 3015–3020.

    Google Scholar 

  • Ganapaty, S., Venkata Rao, D., 1983: Chemical constituents of the leaves ofCitharexylum subserratum. — Fitoterapia1: 13–15.

    Google Scholar 

  • —, 1988: Iridoid glycosides from the leaves ofCitharexylum fruticosum. — Pl. Med. (Stuttgart)54: 42–43.

    Google Scholar 

  • Garnier, J., 1977: Etude chimique de deux Verbénacées de Guyane:Stachytarpheta guyannensis Vahl etStachytarpheta mutabilis Vahl. — Pl. Méd. Phytothérap.11: 303–305.

    Google Scholar 

  • Goerler, K., Oehlke, D., Soicke, H., 1985: Iridoidführung vonVitex agnuscastus. — Pl. Med. (Stuttgart)6: 530–531.

    Google Scholar 

  • 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.

    Google Scholar 

  • Hegnauer, R., 1990: Chemotaxonomie der Pflanzen.9. — Basel: Birkhäuser.

    Google Scholar 

  • —, 1978: Die systematische Bedeutung von iridoiden Inhaltsstoffen im Rahmen vonWettstein'sTubiflorae. — Pl. Med. (Stuttgart)33: 1–33.

    Google Scholar 

  • Iwagawa, T., Nakahara, A., Nakatani, M., 1993a: Iridoids fromVitex cannabifolia. — Phytochemistry32: 453–454.

    Google Scholar 

  • —, —,Miyauchi, A., Okamura, H., Nakatani, M., 1993b: Constituents of the leaves ofVitex cannabifolia. — Kagoshima Daigaku Rigakubu Kiyo, Suguku, Butsurigaku, Kagaku26: 57–61.

    Google Scholar 

  • Jacke, G., Rimpler, H., 1983: Distribution of iridoid glycosides inClerodendrum species. — Phytochemistry22: 1729–1734.

    Google Scholar 

  • 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.

    Google Scholar 

  • —, 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.

    Google Scholar 

  • —, 1975: Iridoid compounds, their occurrence and systematic importance in the angiosperms. — Bot. Not.218: 148–180.

    Google Scholar 

  • Junell, S., 1934: Zur Gynöceummorphologie und Systematik der Verbenaceen und Labiaten. — Symb. Bot. Upsal.4: 1–219.

    Google Scholar 

  • Koenig, G., Rimpler, H., 1985: Iridoid glucosides inAvicennia marina. — Phytochemistry24: 1245–1248.

    Google Scholar 

  • —, —,Hunkler, D., 1987: Iridoid glucosides inAvicennia officinalis. — Phytochemistry26: 423–427.

    Google Scholar 

  • Kooiman, P., 1975: The occurrence of iridoid glycosides in theVerbenaceae. — Acta Bot. Neerl.24: 459–468.

    Google Scholar 

  • Kouno, I., Inoue, M., Onizuka, Y., Fujisaki, T., Kawano, N., 1988: Iridoids and phenolic glucosides fromVitex rotundifolia. — Phytochemistry27: 611–612.

    Google Scholar 

  • Kustrak, D., Antolic, A., 1992: Isolation of iridoids from leaves ofVitex agnus-castus. — Farm. Glasn.48: 305–310.

    Google Scholar 

  • Lahloub, M. F., Salama, O. M., Mansour, E. S., 1990: Phenylpropanoids and iridoid glycosides fromVerbena officinalis. — Bull. Fac. Pharm.28(2): 75–77.

    Google Scholar 

  • Lammel, G., Rimpler, H., 1981: Iridoide ausClerodendrum thomsonae Balf.,Verbenaceae. — Z. Naturf.36: 708–713.

    Google Scholar 

  • Melchior, H., 1964:A Engler's Syllabus der Pflanzenfamilien.2. 12th edn. — Berlin: Borntraeger.

    Google Scholar 

  • Milz, S., Rimpler, H., 1978a: Pulchellosid I, ein neues Iridoid ausVerbena pulchella Sweet. — Tetrahedron Lett.19: 895–898.

    Google Scholar 

  • —, —, 1978b: Pulchellosid II, ein neues Iridoid ausVerbena pulchella Sweet. — Tetrahedron Lett.19: 3549–3552.

    Google Scholar 

  • —, —, 1979: Verbreitung von Iridoiden in der GattungVerbena und einigen anderenVerbenoideae. — Z. Naturf.34: 319–329.

    Google Scholar 

  • Moldenke, H. N., 1940: Contribution to the flora of extratropical South America. — Lilloa5: 353–440.

    Google Scholar 

  • Otsuka, H., Kubo, N., Yamasaki, K., Padolina, W. G., 1989a: Two iridoid glycosid caffeoyl esters fromPremna odorata. — Phytochemistry28: 513–515.

    Google Scholar 

  • —, —, —, 1989b: Premnosides A-D: diacyl 6-O-α-L-rhamnopyranosylcatalpols fromPremna odorata. — Phytochemistry28: 3063–3067.

    Google Scholar 

  • —, 1989c: 6-O-α-L-(2″-O-and 3″-O-isoferuloyl) rhamnopyranosylcatalpols fromPremna japonica. — Phytochemistry28: 3069–3071.

    Google Scholar 

  • —, —, —, 1990a: Iridoid diglycoside monoacyl esters from the leaves ofPremna japonica. — J. Nat. Prod. (Lloydia)53: 107–111.

    Google Scholar 

  • —, —, —,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.

    Google Scholar 

  • —, 1991a: Iridoid diglycoside monoacyl esters from stems ofPremna japonica. — Phytochemistry30: 1917–1920.

    Google Scholar 

  • —, 1991b: Isolation and structure elucidation of mono and diacyl-iridoid diglycosides from leaves ofPremna japonica. — J. Nat. Prod. (Lloydia)52: 547–553.

    Google Scholar 

  • —, 1993: A verbascoside iridoid glucoside conjugate fromPremna corymbosa var.obtusifolia. — Phytochemistry32: 983–986.

    Google Scholar 

  • 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.

    Google Scholar 

  • —, 1992b: Chemical constituents of the roots ofLantana camara. — Acta Pharm. Sin.27: 515–521.

    Google Scholar 

  • Rimpler, H., 1972a: Iridoids and ecdysones fromVerbenaceae II. Iridoids and ecdysones fromVitex species — Phytochemistry11: 2653–2654.

    Google Scholar 

  • —, 1972b: Iridoids and ecdysones fromVerbenaceae. III. Iridoids fromStilbe species. — Phytochemistry11: 3096–3097.

    Google Scholar 

  • —, 1972c: Iridoids and ecdysones fromVerbenaceae. IV. Lamiide fromChascanum cernuum. — Phytochemistry11: 3094.

    Google Scholar 

  • —, 1972d: Phytoecdysone und Iridoide ausVitex megapotamica. — Arch. Pharm. (Weinheim)305: 746–751.

    Google Scholar 

  • —, 1973: Iridoide ausCaryopteris incana undCaryopteris odorata. — Pharm. Zeitung118(39): 1508.

    Google Scholar 

  • —, 1974: Iridoide und Ecdysone ausVerbenaceae. VI. Stilbericoside, ein neues C8-Iridoid ausStilbe ericoides L. — Z. Naturf.29: 368–373.

    Google Scholar 

  • —, 1986: Iridoid glucosides as taxonomic markers in the generaLantana, Lippia, Aloysia andPhyla. — Biochem. Syst. Ecol.14: 307–310.

    Google Scholar 

  • —, 1979: Hastatosid, ein neues Iridoid ausVerbena hastata L. undV. officinalis L. — Z. Naturf.34c: 311–318.

    Google Scholar 

  • —, 1974: Iridoide und Ecdysone ausVerbenaceae. V. Iridoide ausDuranta repens. — Z. Naturf. c29: 11–115.

    Google Scholar 

  • —, 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • —, —, —, 1983: 6'p-hydroxybenzoilmussaenosidic acid—an iridoid glucoside fromVitex negundo. — Phytochemistry22: 1036–1038.

    Google Scholar 

  • Sirait, M., Liemtjawanhoo, F., 1966: Isolation of agnuside from the leaves ofVitex trifolia. — Suara Pharm.9: 47–51.

    Google Scholar 

  • Stenzel, E., Rimpler, H., Hunkler, D., 1986: Iridoid glucosides fromClerodendrum incisum. — Phytochemistry25: 2557–2561.

    Google Scholar 

  • —, 1988: Phenetic relationships inClerodendron (Verbenaceae) and some phylogenetic considerations. — Pl. Syst. Evol.159: 257–271.

    Google Scholar 

  • Taguchi, H., 1976: Studies of the constituents ofVitex cannabifolia. — Chem. Pharm. Bull.24: 1668–1670.

    Google Scholar 

  • 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.

    Google Scholar 

  • Tantisewie, B., Sticher, O., 1975: Isolation of ipolamiide fromStachytarpheta indica. — Phytochemistry14: 1462–1463.

    Google Scholar 

  • Troncoso, N. S., 1974: Los géneros de verbenáceas de Sudamérica extratropical (Argentina, Chile, Bolivia, Paraguay, Uruguay y Sur de Brasil). — Darwiniana18: 295–412.

    Google Scholar 

  • 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.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01464409

Key words

Navigation