Phytochemical characteristics of Galeopsis ladanum subsp. angustifolia (Ehrh. ex Hoffm.) Gaudin collected in Abruzzo region (Central Italy) with chemotaxonomic and ethnopharmacological implications
الموضوعات :Claudio Frezza 1 , Alessandro Venditti 2 , Ilaria Serafini 3 , Alessandra Carassiti 4 , Sebastiano Foddai 5 , Armandodoriano Bianco 6 , Mauro Serafini 7
1 - Dipartimento di Biologia Ambientale, Università di Roma “La Sapienza”, Piazzale Aldo Moro, 5 – 00185 Rome, Italy
2 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro, 5 – 00185 Rome, Italy
3 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro, 5 – 00185 Rome, Italy
4 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro, 5 – 00185 Rome, Italy
5 - Dipartimento di Biologia Ambientale, Università di Roma “La Sapienza”, Piazzale Aldo Moro, 5 – 00185 Rome, Italy
6 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro, 5 – 00185 Rome, Italy
7 - Dipartimento di Biologia Ambientale, Università di Roma “La Sapienza”, Piazzale Aldo Moro, 5 – 00185 Rome, Italy
الکلمات المفتاحية: Phytochemistry, NMR spectroscopy, Chemotaxonomy, Ethnopharmacology, Abruzzo region, <i>Galeopsis ladanum</i> subsp. <i>angustifolia</i> (Ehrh. ex Hoffm.) Gaudin,
ملخص المقالة :
In this work, a phytochemical analysis on the total aerial parts of Galeopsis ladanum subsp. angustifolia (Ehrh. ex Hoffm.) Gaudin collected in Abruzzo region (Central Italy) has been reported. Nine compounds were identified belonging to five different classes of natural compounds. Additional chemotaxonomic markers were recognized than our previous study, as well. Their presence is perfectly in accordance with the current botanical classification of the species and shows the possibility of a pronounced metabolic variability. The observed phytochemical composition may also suggest the possible use of this species in the ethnopharmacological field just like most Galeopsis species since they are endowed with several medicinal properties. Furthermore, no potential toxic component was identified in the studied accession.
Ahmad, M., Rizwani, G.H., Aftab, K., Ahmad, V.U., Gilani, A.H., Ahmad, S.P., 1995. Acteoside: a new antihypertensive drug. Phytother. Res. 9, 525-527.
Avila, G., De Liverant, J., Martínez, A., Martínez, G., Muñoz, J., Arciniegas, A., Romo, A., 1999. Vivar Mode of action of Buddleja cordata verbascoside against Staphylococcus aureus. J. Ethnopharmacol. 3, 36-39.
Belkaid, A., Currie, J.C., Desgagnés, J., Annabi, B., 2006. The chemopreventive properties of chlorogenic acid reveal a potential new role for the microsomal glucose-6-phosphate translocase in brain tumor progression. Cancer Cell Int. 6(7), 1-12.
Binyu, W., Rong, H., Pengyue, L., Qihua, X., Yanli, L., Bo, P., Jianrong, L., 2013. Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens Thunb extract in rats. J. Ethnopharmacol. 147, 503-508.
Calis, I., Lahloub, M.F., Rogenmoser, E., Sticher, O., 1984. Isomartynoside, a phenyl-propanoid glycoside from Galeopsis pubescens. Phytochemistry. 23(10), 2313-2315.
Caprioli, G., Alunno, A., Beghelli, D., Bianco, A., Bramucci, M., Frezza, C., Iannarelli, R., Papa, F., Quassinti, L., Sagratini, G., Tirillini, B., Venditti, A., Vittori, S., Maggi, F., 2016. Polar Constituents and Biological Activity of the Berry-Like Fruits from Hypericum androsaemum L. Front. Pl. Sci. 7(232), 1-12.
Cho, A., Jeon, S., Kim, M., Yeo, J., Seo, K., Choi, M., Lee, M., 2010. Chlorogenic acid exhibits anti-obesity property and improves lipid metabolism in high-fat diet-induced-obese
mice. Food Chem. Toxicol. 48(3), 937-943.
Chung, H.J., Kim, W.K., Park, H.J., Cho, L., Kim, M., Kim, M.J., Shin, J., Lee, J.H., Ha, I., Lee, S.K., 2016. Anti-osteoporotic activity of harpagide by regulation of bone formation in osteoblast cell culture and ovariectomy-induced bone loss mouse models. J. Ethnopharmacol. 179, 66-75.
Conti, F., Abbate, G., Alessandrini, A., Blasi, C., 2005. An annotated checklist of the Italian vascular flora. Palombi Editore, Rome (Italy).
Czarnecki, R., Librowski, T., Zebala, K., Kohlmünzer, S., 1993. Pharmacological properties of a lyophilizate from Galeopsis ladanum on the Central Nervous System of Rodents. Phytother. Res. 7, 9-12.
Esposito, F., Sanna, C., Del Vecchio, C., Cannas, V., Venditti, A., Corona, A., Bianco, A., Serrilli, A.M., Guarcini, L., Parolin, C., Ballero, M., Tramontano, E., 2013. Hypericum hircinum L. components as new single-molecule inhibitors of both HIV-1 reverse transcriptase-associated DNA polymerase and ribonuclease H activities. J. Pathol. Dis. Biol. 68(3), 116-124.
Frezza, C., Venditti, A., Di Cecco, M., Ciaschetti, G., Serafini, M., Bianco, A., 2017. Iridoids and phenylethanoid glycosides from the aerial parts of Ajuga tenorei, an endemic Italian species. Nat. Prod. Res. 31(2), 218-223.
Gibson, R.H., Nelson, I.L., Hopkins, G.W., Hamlett, B.J., Memmott, J., 2006. Pollinator webs, plant communities and the conservation of rare plants: arable weeds as a case study. J. Appl. Ecol. 46(2), 246-257.
Guarino, C., De Simone, L., Santoro, S., 2008. Ethnobotanical study of the Sannio area, Campania, southern Italy. Ethnobot. Res. Applicat. 6, 255-317.
Jensen, S.R., 1992. Systematic implications of the distribution of iridoids and other chemical compounds in the loganiaceae and other families of the asteridae. Ann. Miss. Bot. Gard. 79, 284-302.
Komarov, V.L., 1934. Flora of the USSR. Smithsonian Libraries, Springfield, Virginia (USA).
Konoshima, T., Takasakia, M., Tokuda, H., Nishino, H., 2000. Cancer chemopreventive activity of an iridoid glycoside, 8-acetylharpagide, from Ajuga decumbens. Cancer Lett. 157 87-92.
Lenherr, A., Mabry, T.J., 1987. Acetylated allose-containing flavonoid glucosides from Stachys anisochila. Phytochemistry. 26(4), 1185-1188.
Mandrone, M., Lorenzi, B., Venditti, A., Guarcini, L., Bianco, A., Sanna, C., Ballero, M., Poli, F., Antognoni, F., 2015. Antioxidant and anti-collagenase activity of Hypericum hircinum L. Ind. Crops Prod. 76, 402-408.
Matkowski, A., Tasarz, P., Szypuła, E., 2008. Antioxidant activity of herb extracts from five medicinal plants from Lamiaceae, subfamily Lamioideae. J. Med. Pl. Res. 2(11), 321-330.
Mazza, F., 2000. Itinerari alla scoperta delle erbe officinali del Monte Amiata. Stampa, Siena, Italy.
Nardini, M., Aquino, M.D., Tomassi, G., Gentili, V., Di Felice, M., Scaccini, C., 1995. Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Rad. Biol. Med. 19, 542-552.
Papoutsi, Z., Kassi, E., Mitakou, S., Aligiannis, N., Tsiapara, A., Chrousos, G.P., Moutsatsou, P., 2006. Acteoside and martynoside exhibit estrogenic/antiestrogenic properties. J. Steroid Biochem. Mol. Biol. 98, 63-71.
Pauli, G.F., Poetsch, F., Nahrstedt, A., 1988. Structure assignment of natural quinic acid derivatives using proton nuclear magnetic resonance techniques. Phytochem. Anal. 9, 177-185.
Pérez-Sirvent, L., Rodríguez, B., Savona, G., Servetta, O., 1983. Rearranged labdane diterpenoids from Galeopsis angustifolia. Phytochemistry. 22(2), 527-530.
Pero, R.W., Lund, H., Leanderson, T., 2009. Antioxidant metabolism induced by quinic acid. Phytother. Res. 23, 335-346.
Pignatti, S., 1982. Flora d’Italia. Edagricole, Bologna (Italy), vol 2, pag. 454.
Rodriguez, B., Savona, G., 1980. Diterpenoids from galeopsis angustifolia. Phytochemistry. 19(8), 1805-1807.
Saracoglu, I., Inoue, M., Calis, I., Ogihara, Y., 1995. Studies on constituents with cytotoxic and cytostatic activity of two Turkish medicinal plants Phlomis armeniaca and Scutellaria salvifolia. Biol. Pharm. Bull. 18, 1396-1400.
Sato, Y., Itagaki, S., Kurokawa, T., Ogura, J., Kobayashi, M., Hirano, T., Sugawara, M., Iseki, K., 2011. In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid. Int. J. Pharm. 403, 136-138.
Speranza, L., Franceschelli, S., Pesce, M., Reale, M., Menghini, L., Vinciguerra, I., De Lutiis, M.A., Felaco, M., Grilli, A., 2010. Antiinflammatory effects in THP-1 cells treated with verbascoside. Phytother. Res. 24, 1398-1404.
Sticher, O., Rogenmoser, E., Weisflog, A., 1975. New iridoid glucosides from Galeopsis tetrahit and Galeopsis pubescens. Tetrahedron Lett. 16, 291-294.
Sticher, O., Weisflog, A., 1975. Determination and isolation of iridoid glucosides from Galeopsis tetrahit (Labiatae) and the structure elucidation of gluroside. Pharm. Acta Helv. 50, 394-403.
Tomàs-Barberàn, F.A., Gil, M.I., Ferreres, F., Tomàs-Lorente, F., 1991. Correlations between flavonoid composition and infrageneric taxonomy of some European Galeopsis species. Phytochemistry. 30(10), 3311-3314.
Tomàs-Barberàn, F.A., Gil, M.I., Ferreres, F., Tomàs-Lorente, F., 1992. Flavonoid p-coumarylglucosides and 8-hydroxyflavone allosylglucosides in some Labiatae. Phytochemistry. 31(9), 3097-3102.
Townsend, C.C., 1962. Some notes on Galeopsis ladanum L. and G. angustifolia Ehrh. ex Hoffm. Watsonia, 5(3), 143-149.
Uriarte-Pueyo, P., Calvo, M.I., 2009. Phytochemical Study and Evaluation of Antioxidant, Neuroprotective and Acetylcholinesterase Inhibitor Activities of Galeopsis ladanum L. extracts. Pharmacogn. Mag. 5, 287-290.
Uriarte-Pueyo, I., Calvo, M.I., 2010. Structure–activity relationships of acetylated flavone glycosides from Galeopsis ladanum L. (Lamiaceae). Food Chem. 120, 679-683.
Venditti, A., Serrilli, A.M., Bianco, A., 2013a. A new flavonoid and other polar compounds from Galeopsis angustifolia Ehrh. ex Hoffm. Nat. Prod. Res. 27(4-5), 412-416.
Venditti, A., Bianco, A., Maggi, F., Nicoletti, M., 2013b. Polar constituents composition of endemic Sideritis italica (MILL.) Greuter et Burter from Central Italy. Nat. Prod. Res. 27, 1408-1412.
Venditti, A., Bianco, A., Nicoletti, M., Quassinti, L., Bramucci, M., Lupidi, G., Vitali, L.A., Petrelli, D., Papa, F., Vittori, S., Lucarini, D., Maleci Bini, L., Giuliani, C., Maggi, F., 2013c. Phytochemical analysis, biological evaluation and micromorphological study of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande endemic to central Apennines, Italy. Fitoterapia. 90, 94-103.
Venditti, A., Bianco, A., Nicoletti, M., Quassinti, L., Bramucci, M., Lupidi, G., Vitali, L.A., Papa, F., Vittori, S., Petrelli, D., Maleci Bini, L., Giuliani, C., Maggi, F., 2014. Characterization of Secondary Metabolites, Biological Activity and Glandular Trichomes of Stachys tymphaea Hausskn. from the Monti Sibillini National Park (Central Apennines, Italy). Chem. Biodivers. 11(2), 245-261.
Venditti, A., Bianco, A., Frezza, C., Conti, F., Maleci Bini, L., Giuliani, C., Bramucci, M., Quassinti, L., Damiano, S., Lupidi, G., Beghelli, D., Caterbi, S., Petrelli, D., Vitali, L.A., Papa, F., Caprioli, G., Maggi, F., 2015. Essential oil composition, polar compounds, glandular trichomes andbiological activity of Hyssopus officinalis subsp. aristatus (Godr.) Nyman from central Italy. Ind. Crops Prod. 77, 353-363.
Venditti, A., Frezza, C., Serafini, M., Bianco, A., 2016a. Iridoids and phenylethanoid from Pedicularis kerneri Dalla Torre growing in Dolomites, Italy. Nat. Prod. Res. 30(3), 327-331.
Venditti, A., Frezza, C., Guarcini, L., Maggi, F., Bianco, A., Serafini, M., 2016b. Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction. Nat. Prod. Res. 30(2), 218-222.
Venditti, A., Frezza, C., Guarcini, L., Foddai, S., Serafini, M., Bianco, A., 2016c. Phytochemical study of a species with ethnopharmacological interest: Sideritis romana L. Eur. J. Med. Pl. 12(3), 1-9.
Venditti, A., Bianco, A., Frezza, C., Serafini, M., Giacomello, G., Giuliani, C., Bramucci, M., Quassinti, L., Lupidi, G., Lucarini, D., Papa, F., Maggi, F., 2016d. Secondary Metabolites, Glandular Trichomes and Biological Activity of Sideritis montana L. subsp. montana from Central Italy. Chem. Biodivers. 13, 1380-1390.
Venditti, A., Frezza, C., Maggi, F., Lupidi, G., Bramucci, M., Quassinti, L., Giuliani, C., Cianfaglione, K., Papa, F., Serafini, M., Bianco, A., 2016e. Phytochemistry, micromorphology and bioactivities of Ajuga chamaepitys (L.) Schreb. (Lamiaceae, Ajugoideae): two new harpagide derivatives and an unusual iridoid glycosides pattern. Fitoterapia. 113, 35-43.
Venditti, A., Frezza, C., Caretti, F., Gentili, A., Serafini, M., Bianco, A., 2016f. Constituents of Melittis melissophyllum subsp. albida. Nat. Prod. Comm. 11(11), 1631-1634.
Venditti, A., Frezza, C., Gatto Agostinelli, V., Di Cecco, M., Ciaschetti, G., Serafini, M., Bianco, A., 2016g. Study on the molecular composition of an indigenous Italian species: Coristospermum cuneifolium (Guss.) Bertol. Int. J. Indig. Med. Pl. 48(2), 1930-1938.
Venditti, A., Frezza, C., Celona, D., Bianco, A., Serafini, M., Cianfaglione, K., Fiorini, D., Ferraro, S., Maggi, F., Lizzi, A.R., Celenza, G., 2017a. Polar constituents, protection against reactive oxygen species, and nutritional value of Chinese artichoke (Stachys affinis Bunge). Food Chem. 221, 473-481.
Venditti, A., Frezza, C., Bianco, A., Serafini, M., Cianfaglione, K., Nagy, D.U., Iannarelli, R., Caprioli, G., Maggi, F., 2017b. Polar Constituents, Essential Oil and Antioxidant Activity of Marsh Woundwort (Stachys palustris L.). Chem. Biodivers. 14(3), 1-8.
Xiang, Z., Ning, Z., 2008. Scavenging and antioxidant properties of compound derived from chlorogenic acid in South-China honeysuckle. Food Sci. Technol. 41, 1189-1203.
Xie, Z.Y,, Qin, M.Z., Fang, Y.L., 2005. The pharmacological activity of 8-O-acetylharpagide. World Notes Planta. Med. 20, 56-58.
Yalcin, F.N., Ersöz, T., Akbay, P., Çaliş, I., Dönmez, A.A., 2003. Iridoid and Phenylpropanoid Glycosides from Phlomis samia, P. monocephala and P. carica. Turk. J. Chem. 27, 295-305.