Chemical profiling of the fruits of Styrax officinalis L. from Monti Lucretili (Latium region, Central Italy): Chemotaxonomy and nutraceutical potential

Subject Areas : Phytochemistry: Isolation, Purification, Characterization

Alessandro Venditti ¹ , Claudio Frezza ² , Ilaria Serafini ³ , Sabina Pulone ⁴ , Giorgina Scardelletti ⁵ , Fabio Sciubba ⁶ , Armandodoriano Bianco ⁷ , Mauro Serafini ⁸

1 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185, Rome, Italy
2 - Dipartimento di Biologia Ambientale, 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 - Parco Naturale Regionale dei Monti Lucretili, Via A. Petrocchi 11, 00018 Palombara Sabina (Italy)
6 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185, Rome, Italy
7 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185, Rome, Italy
8 - Dipartimento di Biologia Ambientale, Università di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185, Rome, Italy

Received: 2017-11-07 Accepted : 2018-01-28 Published : 2018-03-01

Keywords:

References:

Akgul, Y.Y., Alankuş-Çalışkan, Ö., Anil, H., Bates, R.B., Stessman, C.C., Kanec, V.V., 2002. Saponins from Styrax officinalis. Fitoterapia 73(4), 320-326.

Akgul, Y.Y., Anil H., 2003a. Benzofuran from seeds of Styrax officinalis. Fitoterapia 74(7-8), 743-745.

Akgul, Y.Y., Anil, H., 2003b. Benzofurans and another constituent from seeds of Styrax officinalis. Phytochemistry 63, 939-943.

Akhlaghi, H., 2017. Chemical composition of the essential oil, total phenolic contents and antioxidant activity of Vitex pseudo-negundo seeds collected from northeastern Iran. Trends Phytochem. Res. 1(1), 27-32.

Anil, H., 1977. Isolation of styracitol and sucrose from fruit peels of Styrax officinalis L. Doga 1, 326-328, Chemical Abstracts 90, 36298.

Anil, H., 1980. Four benzofuran glycosides from Styrax officinalis. Phytochemistry 19(12), 2784-2786.

Asahina, Y., 1912. Zur Chemie des Styracits. I. Ber. Dtsch. Chem. Ges. 45, 2363-2369.

Baciocchi, R., Zenoni, G., Valentini, M., Mazzotti, M., Morbidelli, M., 2002. Measurement of the dimerization equilibrium constants of enantiomers. J. Phys. Chem.A. 106, 10461-10469.

Balbani, A.P., Stelzer, L.B., Montovani, J.C., 2006. Pharmaceutical excipients and the information on drug labels. Braz. J. Otorhinolaryngol. 72, 400-406.

Bancroft, W.D., Davis, H.L., 1930. The optical rotation of malic acid. J. Phys. Chem. 34, 897-928.

Bankeu, J.J.K., Dawé, A., Mbiantcha, M., Feuya, G.R.T., Ali, I., Tchuenmogne, M.A.T., Mehreen, L., Lenta, B., Ali, M.S., Ngouela, A.S., 2017. Characterization of bioactive compounds from Ficus vallis-choudae Delile (Moraceae). Trends Phytochem. Res. 1(4), 235-242.

Bertanha, C.S., Braguine, C.G., Moraes, A.C.G., Gimenez V.M., Groppo M., Silva, M.L., Cunha, W.R.,  Januário, A.H., Pauletti, P.M., 2012. Cyclooxygenase inhibitory properties of nor-neolignans from Styrax pohlii. Nat. Prod. Res. 26(24), 2323-2329.

Bertanha, C.S., Soares, E., Gonçalves, U.O., de Oliveira, P.F., Magalhães, L.G., Rodrigues, V., Crispim Tavares, D., Andrade e Silva M.L., Cunha W.R., Januário, A.H., Pauletti, P.M., 2014. In vitro antischistosomal and cytotoxic activities of norneolignans from Styrax pohlii A. DC. J. Herbs Spices Med. Plants., 20(4), 394-401.

Bock K., Pedersen C., Thøgersen H., 1981. Acid catalyzed dehydration of alditols. Part I. D-glucitol and D-mannitol. Acta Chem. Scand. 35b. 441-449.

Camilo, C.J., Alves Nonato, C.d.F., Galvão-Rodrigues, F.F., Costa, W.D., Clemente, G.G., Sobreira Macedo, M.A.C., Galvão Rodrigues, F.F., da Costa, J.G.M., 2017. Acaricidal activity of essential oils: a review. Trends Phytochem. Res. 1(4), 183-198.

Cao, T.Q., Tran, M.H., Kim, J.A., Tran, P.T., Lee, J.H., Woo, M.H., Lee, H.-K., Min, B.S., 2015. Inhibitory effects of compounds from Styrax obassia on NO production. Bioorg. Med. Chem. Lett. 25(22), 5087-5091.

Cardile, V., Graziano, A. C. E., Venditti, A., 2015. Clinical evaluation of Moro (Citrus sinensis (L.) Osbeck) orange juice supplementation for the weight management. Nat. Prod. Res. 29(23), 2256-2260.

Coffey, S., 1967. In “Rodd’s Chemistry of Carbon Compounds”. (Second Ed.). Elsevier Publishing Company, Amsterdam, London, New York., Vol 1, part F, pp.49.

Consiglio, G., Pino, P., Flowers, L.I., Pittman, C.U., 1983. Asymmetric hydroformylation of styrene by chiral platinum catalysts: A re-evaluation of the optical yields. J. Chem. Soc. Chem. Commun. 612-613.

D'Alonzo, D., Guaragna, A., Van Aerschot, A., Herdewijn, P., Palumbo, G., 2008. De novo approach to l-anhydrohexitol nucleosides as building blocks for the synthesis of l-hexitol nucleic acids (l-HNA). Tetrahedron Lett. 49(42), 6068-6070.

de Oliveira, P.F., Damasceno, J.L., Bertanha, C.S., Araújo AR, Pauletti, P.M., Tavares, D.C., 2016a. Study of the cytotoxic activity of Styrax camporum extract and its chemical markers, egonol and homoegonol. Cytotech. 68(4), 1597-1602.

de Oliveira, P.F., Damasceno, J.L., Nicolella, H.D., Bertanha CS, Pauletti, P.M., Tavares, D.C., (2016b). Influence of Styrax camporum and of chemical markers (egonol and homoegonol) on DNA damage induced by mutagens with different mechanisms of action. Biol. Pharm. Bull. 39(11), 1839-1845

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. Pathog. Dis. 68(3), 116-124.

Fletcher, H.G., JR., Diehl, H.W., 1952. The Preparation of 1,5-anhydro-d-mannitol (styracitol) from D-mannitol. J. Am. Chem. Soc. 74, 3175-3176.

Freudenberg, W., Rogers, E.F., 1937. The chemistry of naturally occurring monohydrohexitols. J. Am. Chem. Soc. 59(9), 1602-1605.

Freudenberg, W., Sheehan, J.T., 1940. The chemistry of naturally occurring monoanhydrohexitols. II. Synthetic tetramethylstyracitol. J. Am. Chem. Soc. 62(3), 558-560.

Frezza, C., Venditti, A., Matrone, G., Serafini, I., Foddai, S., Bianco, A., Serafini, M., 2017a. Iridoid glycosides and polyphenolic compounds from Teucrium chamaedrys L. Nat. Prod. Res. 23, 1-7, doi: 10.1080/14786419.2017.1392948.

Frezza, C., Venditti, A., Serafini, I., Carassiti, A., Foddai, S., Bianco, A., Serafini, M., 2017b. Phytochemical characteristics of Galeopsis ladanum subsp. angustifolia (Ehrh. ex Hoffm.) Gaudin collected in Abruzzo region (Central Italy) with chemotaxonomic and ethnopharmacological implications. Trends Phytochem. Res. 1(2):  61-68.

Fried, J., Walz, D.E., 1949. Ethyl thioglycosides of D-mannose and D-galactose and a new synthesis of styracitol. J. Am. Chem. Soc. 71(1), 140-143.

Ganesan, K., Xu, B., 2017. Ethnobotanical studies on folkloric medicinal plants in Nainamalai, Namakkal District, Tamil Nadu, India. Trends Phytochem. Res. 1(3), 153-168.

Giesbrecht, A.M., Alvarenga, M.A., Silva, J.J., Panizza, S., 1985. Presença de homoegonol em Styrax camporum. An. Farm. Quím. 25, 55-57.

Girard, C., Kagan, H.B., 2000. On diastereomeric perturbations. Can. J. Chem. 78, 816-828.

Gray, G.R., Barker, R., 1967. The platinum-catalyzed hydrogenation and hydrogenolysis of acylated pyranosyl halides, tetra-O-acetyl-2-hydroxy-D-glucal and tri-O-acetyl-D-glucal. J. Org. Chem. 32(9), 2764-2768.

Harada, H., Yamashita, U., Kurihara, H., Fukushi, E., Kawabata, J., Kamei, Y., 2002. Antitumor activity of palmitic acid found as a selective cytotoxic substance in a marine red alga. Anticancer Res. 22(5), 2587-2590.

Hirano, T., Gotoh, M., Oka, K., 1994. Natural flavonoids and lignans are potent cytostatic agents against human leukemic HL-60 cells. Life Sci. 55(13), 1061-1069.

Hisaku, S., Fujisue, M., Abe, J.I., 2004. Prophylactic for tooth disease and method for producing food containing the same. Japan Patent Application (JP) nr. 2004123604.

Hockett, R.C., Dienes, M.T., Ramsden, H.E., 1943. Lead tetraacetate oxidations in the sugar group. IV.1 The rates of oxidation of trehalose, levoglucosan, α-methyl-l-sorbopyranoside, polygalitol and styracitol in glacial acetic acid. J. Am. Chem. Soc. 65(8), 1474-1477.

Ikeda, K., 2002. New seasonings. Chem. Senses. 27(9), 847-849.

Ipek, Y., Ozen, T., Demirtas, I., 2017. Extraction, purification, characterization and antioxidant activities of heat-resistance phenolic compounds from lemon pulp. Trends Phytochem. Res. 1(4), 199-206.

Kim, M.R., Moon, H.T., Lee, D.G., Woo, E.R., 2007. A new lignan glycoside from the stem bark of Styrax japonica S. et Z. Arch. Pharm. Res. 30(4), 425-430.

Kobayashi, H., Yokoyama, H., Feng, B.,  Fukuoka, A., 2015. Dehydration of sorbitol to isosorbide over H-beta zeolites with high Si/Al ratios. Green Chem. 17, 2732-2735.

Kocienski, P., Pant, C., 1982. A convenient preparation of some 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-hexitols. Carbohydr. Res. 110, 330-332.

Lambertucci, C., Schepers, G., Cristalli, G., Herdewijn, P., Aerschot, A.V., 2007. Synthesis and evaluation of hexitol nucleoside congeners as ambiguous nucleosides. Tetrahedron Lett. 48(12), 2143-2145.

Lee, H., Park, S.Y., Lee, O., Jo, H., Kang, H., Choi, D., Paik, K., Khan, M., 2008. Benzofurans and sterol from the seeds of Styrax obassia. Chem. Nat. Comp., 44(4), 435-439.

Les, F., Venditti, A., Cásedas, G., Frezza, C., Guiso, M., Sciubba, F., Serafini, M., Bianco, A., Valero, M.S., López, V., 2017. Everlasting flower (Helichrysum stoechas Moench) as a potential source of bioactive molecules with antiproliferative, antioxidant, antidiabetic and neuroprotective properties. Ind. Crops Prod. 108, 295-302.

Li, J., Jiang, Y., Tu, P., 2005b. Tricornoses A-L, oligosaccharide multi-esters from the roots of Polygala tricornis. J. Nat. Prod. 68(5), 739-744

Li, Q.L., Li, B.G., Qi, H.Y., Gao, X.P., Zhang, G.L., 2005a. Four new benzofurans from seeds of Styrax Perkinsiae. Planta Med. 71(9), 847-851.

Liang, G., Wu, C., He, L., Ming, J., Cheng, H., Zhuo, L., Zhao, F., 2011. Selective conversion of concentrated microcrystalline cellulose to isosorbide over Ru/C catalyst. Green Chem. 13, 839.

Luo, Y., He, Z., Li, H., 2007. 2-Aryl benzofurans and their derivatives from seeds of Styrax macranthus. Fitoterapia 78(3), 211-214.

Meng, X.J., Kawahara, K.I., Matsushita, K., Nawa, Y., Shrestha, B., Kikuchi, K., Sameshima, H., Hashiguchi, T., Maruyama, I., 2009b. Attenuation of LPS-induced iNOS expression by 1,5-anhydro-D-fructose. Biochem. Biophys. Res. Commun. 387, 42-46.

Meng, X.J., Kawahara, K.I., Nawa, Y., Miura, N., Shrestha, B., Tancharoen, S., Sameshima, H., Hashiguchi, T., Maruyama, I., 2009a. 1,5-Anhydro-D-fructose attenuates lipopolysaccharide-induced cytokine release via suppression of NF-κB p 65 phosphorylation. Biochem. Biophys. Res. Commun.   380, 343-348

Min, B., Oh, S., Ahn, K., Kim, J., Lee, J., Kim, F., Kim, E., Lee, H., 2004. Anti-complement activity of norlignans and terpenes from the stem bark of Styrax japonica. Planta Med. 70, 1210-1215.

Miyase, T., Noguchi, H., Chen, X.M., 1999. Sucrose esters and xanthone C-glycosides from the roots of Polygala sibirica. J. Nat. Prod. 62(7), 993-996.

Miyase, T., Ueno, A., 1993. Sucrose derivatives from the Roots of Polygala tenuifolia. Shoyakugaku Zasshi (The Japanese Journal of Pharmacognosy) 47(3), 267-278.

Mohammadhosseini, M., 2017. The ethnobotanical, phytochemical and pharmacological properties and medicinal applications of essential oils and extracts of different Ziziphora species. Ind. Crops Prod. 105, 164-192.

Mohammadhosseini, M., Sarker, S.D., Akbarzadeh, A., 2017. Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review. J. Ethnopharmacol. 199, 257-315.

Montelucci, G., 1946. Investigazioni botaniche nel Lazio. I - lo Styrax officinalis nei dintorni di Tivoli. N. Giorn. Bot. Ital. n.s. 53, 230-268.

Moraes, A.C., Bertanha, C.S., Gimenez, V.M., Groppo, M., Silva, M.L., Cunha, W.R., Januário, A.H., Pauletti, P.M., 2012. Development and validation of a high-performance liquid chromatography method for quantification of egonol and homoegonol in Styrax species. Biomed. Chromatogr. 26, 869-874.

Nat. Prod. Res. 29(15), 1466-1468.

Nunes, H.S., Miguel, M.G., 2017. Rosa damascena essential oils: a brief review about chemical composition and biological properties. Trends Phytochem. Res. 1(3), 111-128.

Ostrowski, T., Wroblowski, B., Busson, R., Rozenski, J., De Clercq, E., Bennett, M.S., Champness, J.N., Summers, W.C.,  Sanderson, M.R., Herdewijn, P., 1998. 5-substituted pyrimidines with a 1,5-anhydro-2,3-dideoxy-D-arabino- hexitol moiety at N-1: Synthesis, antiviral activity, conformational analysis, and interaction with viral thymidine kinase. J. Med. Chem. 41(22), 4343-4353.

Öztürk, S.E., Akgül, Y., Anıl, H., 2008. Synthesis and antibacterial activity of egonol derivatives. Bioorg. Med. Chem. 16, 4431-4437.

Pan, A., Chen, M., Chowdhury, R., Wu, J.H., Sun, Q., Campos, H., Mozaffarian, D., Hu, F.B., 2012. α-Linolenic acid and risk of cardiovascular disease: a systematic review and meta-analysis". Am. J. Clin. Nutr. (Systematic review). 96(6), 1262-1273.

Parenti, C., Aricò, G., Pennisi, M., Venditti, A., & Scoto, G.M., 2016. Harpagophytum procumbens extract potentiates morphine antinociception in neuropathic rats. Nat. Prod. Res. 30(11), 1248-1255.

Pauletti, P.M., Araújo, A.R., Young, M.C., Giesbrecht, A.M., Bolzani, V.D., 2000. Nor-lignans from the leaves of Styrax ferrugineus (Styracaceae) with antibacterial and antifungal activity. Phytochemistry 55(6), 597-601.

Pavunraj, M., Ramasubbu, G., Baskar, K., 2017. Leucas aspera (Willd.) L.: Antibacterial, antifungal and mosquitocidal activities Trends Phytochem. Res. 1(3), 135-142.

Pazar, E., Akgül, Y., 2015. Chemical composition of the endocarps of fruits of Styrax officinalis L.

Pérez-Pérez, M., De Clercq, E., Herdewijn, P., 1996. Synthesis and antiviral activity of 2-deoxy-1,5-anhydro-D-mannitol nucleosides containing a pyrimidine base moiety. Bioorg. Med. Chem. Lett. 6(13), 1457-1460.

Pignatti, S., 1982. "Flora d'Italia". Edagricole, Bologna (Italy), vol. 2, pp. 320.

Que, L., Gray, G.R., 1974. ¹³C nuclear magnetic resonance spectra and the tautomeric equilibria of ketohexoses in solution. Biochemistry 13(1), 146-53.

Richtmyer, N.K., Hudson, C.S., 1943. The ring structure of polygalitol. J. Am. Chem. Soc. 65(1), 64-67.

Rikli, M., 1942. Das Pflanzenkleid der Mittelmeerlämder. II Lieferung. Bern, Huber., pp. 195.

Sciubba, F., Capuani, G., Di Cocco, M.E., Avanzato, D., Delfini, M., 2014a. Nuclear magnetic resonance analysis of water soluble metabolites allows the geographic discrimination of pistachios (Pistacia vera). Food Res. Int. 62, 66-73.

Sciubba, F., Di Cocco, M.E., Gianferri, R., Impellizzeri, D., Mannina, L., De Salvador, F.R., Venditti, A., Delfini. M., 2014b. Metabolic profile of different Italian cultivars of hazelnut (Corylus avellana) by nuclear magnetic resonance spectroscopy. Nat. Prod. Res. 28(14), 1075-1081.

Shin, I., Ahn, K., Shin, N., Jeon, C.M., Kwon, O.K., Chin, Y.W., Lee, K., Oh, S., 2014. Homoegonol attenuates the asthmatic responses induced by ovalbumin challenge. Arch. Pharmacol. Res.37(9), 1201-1210.

Soltzberg, S., 1970. Alditol anhydrides. Adv. Carbohydr. Chem. Biochem. 25, 229-283.

Soltzberg, S., Goepp, R.M., Freudenberg, W., 1946. Hexitol anhydrides. Synthesis and structure of arlitan, the 1,4-monoanhydride of sorbitol. J. Am. Chem. Soc. 68, 919.

Sowden, J.C., Oftedahl, M.L., 1961. Anhydridization of 1-deoxy-1-nitrohexitols. J. Org. Chem. 26(6), 1974-1977.

Spada, F., 1988. Il paesaggio vegetale dei Monti Lucretili. In: De Angelis G.(a cura di), Monti Lucretili. Provincia di Roma, Roma.

Takanashi, M., Takizawa, Y., 1988. New benzofurans related to egonol from immature seeds of Styrax obassia. Phytochemistry 27, 1224-1226

Tayoub, G., Schwob, I., Bessière, J., Masotti, V., Rabier, J., Ruzzier, M., Viano, J. (2006). Composition of volatile oils of Styrax (Styrax officinalis L.) leaves at different phenological stages. Biochem. Syst. Ecol. 34, 705-709.

Teles, H.L., Hemerly, J.P., Pauletti, P.M., Pandolfi, J.R., Araujot, A.R., Valentini, S.R., Young, M.C., Bolzani, V.D.S., Silva, D.H.S., 2005. Cytotoxic lignans from the stems of Styrax camporum (Styracaceae). Nat. Prod. Res. 19(4), 319-323.

Timmers, M.A., Guerrero-Medina, J.L., Esposito, D., Grace, M.H., Paredes-López, O., García-Saucedo, P.A., Lila, M.A., 2015. Characterization of phenolic compounds and antioxidant and anti-inflammatory activities from Mamuyo (Styrax ramirezii Greenm.) Fruit. J. Agric. Food Chem. 63(48), 10459-10465.

Toniolo, C., Nicoletti, M., Maggi, F., Venditti, A., 2014. HPTLC determination of chemical composition variability in raw materials used in botanicals. Nat. Prod. Res. 28(2), 119-126.

Ulubelen, A., Saiki, Y., Lotter, H., Chari, V.M., Wagne, H., 1978. Chemical components of Styrax officinalis L. - IV¹ - The structure of a new lignan styraxin. Planta Med. 34(8), 403-407.

Van Aerschot, A., Schepers, G., Busson, R., Rozenski J., Neyts, J., De Clercq, E., Herdewijn, P., 2003. Ribavirin derivatives with a hexitol moiety: Synthesis and antiviral evaluation. Antiviral Chem. Chemother. 14(1), 23-30.

Vardar V., Oflas S., 1973. Preliminary studies on the Styrax oil. S.Qual. Plant. Mater. Veg. 22, 145-148.

Venditti, A., Bianco, A., Muscolo, C., Zorzetto, C., Sánchez-Mateo, C.C., Rabanal, R.M., Quassinti, L., Bramucci, M., Damiano, S., Iannarelli, R., Lupidi, G., Papa, F., Petrelli, D., Vitali, L. A., Vittori, S., Maggi, F., 2016b. Bioactive secondary metabolites from Schizogyne sericea (Asteraceae) endemic to Canary Islands. Chem. Biodivers. 13(7), 826-836.

Venditti, A., Frezza, C., Caretti, F., Gentili, A., Serafini, M., Bianco, A., 2016c. Constituents of Melittis melissophyllum subsp. albida. Nat. Prod. Commun. 11(11), 1631-1634.

Venditti, A., Frezza, C., Celona, D., Sciubba, F., Foddai, S., Delfini, M., Serafini, M., Bianco, A., 2017e. Phytochemical comparison with quantitative analysis between two flower phenotypes of Mentha aquatica L.: pink-violet and white. AIMS Mol. Sci. 4(3), 288-300.

Venditti, A., Frezza, C., Foddai, S., Serafini, M., Bianco, A., 2016g. A rare bis-rhamnopyranosyl-aromadendrin derivative and other flavonoids from the flowers of Genista cilentina Vals. an endemic species of Southern Italy. Arab. J. Chem., DOI:10.1016/j.arabjc.2016.02.012.

Venditti, A., Frezza, C., Foddai, S., Serafini, M., Nicoletti, M., Bianco, A., 2017d. Chemical traits of hemiparasitism in Odontites luteus. Chem. Biodiversity, 14, 1-7, DOI:10.1002/cbdv.201600416.

Venditti, A., Frezza, C., Gatto Agostinelli, V., Di Cecco, M., Ciaschetti, G., Serafini, M., Bianco, A., 2016d. Study on the molecular composition of an indigenous Italian species: Coristospermum cuneifolium (Guss.) Bertol. Int. J. Indigen. Med. Plants, 48(2), 1930-1938.

Venditti, A., Frezza, C., Guarcini, L., Foddai, S., Serafini, M., Bianco, A., 2016a. Phytochemical study of a species with ethnopharmacological interest: Sideritis romana L. Eur. J. Med. Plants, 12, 1-9.

Venditti, A., Frezza, C., Maggi, F., Lupidi, G., Bramucci, M., Quassinti, L., Giuliani, C., Cianfaglione, K., Papa, F., Serafini, M., Bianco, A., 2016f. 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., Majd Zadeh, M., Foddai, S., Serafini, M., Bianco, A., 2017a. Secondary metabolites from Teucrium polium L. collected in Southern Iran. Arab. J. Med. Aromat. Plant. 3(2), 108-123.

Venditti, A., Frezza, C., Rai, R., Sciubba, F., Di Cecco, M., Ciaschetti, G., Serafini, M., Bianco, A., 2017f. Isoflavones and other compounds from the roots of Iris marsica I. Ricci E Colas. collected from Majella National Park, Italy. Med. Chem. (Los Angeles). 7, 787-794.

Venditti, A., Frezza, C., Rossi, G., Di Cecco, M., Ciaschetti, G., Serafini, M., Bianco, A., 2016h. Secondary metabolites with ecologic and medicinal implications in Anthemis cretica subsp. petraea from Majella National Park. AIMS Mol. Sci., 3(4), 648-660.

Venditti, A., Frezza, C., Sciubba, F., Foddai, S., Serafini, M., Bianco A., 2016e. Terpenoids and more polar compounds from the male cones of Wollemia nobilis. Chem. Biodivers. 14, 1-7.

Venditti, A., Frezza, C., Trancanella, E., Zadeh, S.M.M., Foddai, S., Sciubba, F., Delfini, M., Serafini, M., Bianco, A., 2017b. A new natural neo-clerodane from Teucrium polium L. collected in Northern Iran. Ind. Crops Prod. 97, 632-638.

Venditti, A., Sanna, C., Lorenzetti, L.M., Ballero, M., Bianco, A., 2017c. New coumarinyl ethers in Daphne oleoides Schreb. collected from Sardinia Island. Chem. Biodivesity, 14, DOI: 10.1002/cbdv.201700072.

Verheggen, I., Van Aerschot, A., Rozenski, J., Wiebe, L., Snoeck, R., Andrei, G., Balzarini, J., Claes, P., De Clercq, E., Herdewijn, P., 1995. Synthesis, biological evaluation, and structure analysis of a series of new 1,5-anhydrohexitol nucleosides. J. Med. Chem. 38(5), 826-835.

Verheggen, I., Van Aerschot, A., Toppet, S., Snoeck, R., Janssen, G., Balzarini, J., De Clercq, E., Herdewijn, P., (1993). Synthesis and antiherpes virus activity of 1,5-anhydrohexitol nucleosides. J. Med. Chem. 36(14), 2033-2040.

Wei, Y., Su, H., Zhang, Y., Liao, J., Guo, L., 2002. Jingxi Huagong, 19, 208-210.

Yabuuchi, M., Masuda, M., Katoh, K., Nakamura, T., Akanuma, H., 1989. Simple enzymatic method for determining 1,5-anhydro-D-glucitol in plasma for diagnosis of diabetes mellitus. Clin. Chem. 35, 2039-2043.

Yamanouchi, T., Inoue, T., Ichiyanagi, K., Sakai, T., Ogata, N., 2003. 1,5-Anhydroglucitol stimulates insulin release in insulinoma cell lines. Biochim. Biophys. Acta. 1623, 82-87.

Yamanouchi, T., Tachibana, Y., Akanuma, H., Minoda, S., Shinohara, T., Moromizato, H., Miyashita, H., Akaoka, I., 1992. Origin and disposal of 1,5-anhydroglucitol, a major polyol in the human body. Am. J. Physiol. 263, 268-273.

Yayla, Y., Alankuş-Calişkan, O., Anil, H., Bates, R.B., Stessman, C.C., Kane, V.V., 2002. Saponins from Styrax officinalis. Fitoterapia 73(4), 320-6.

Yu, S., 2008. The anhydrofructose pathway. IUBMB Life. 60, 798-809.

Zebib, B., Merah, O., 2017. Satureja myrtifolia (Boiss. & Hohen.) Lebanese wild plant, as a resource of natural antioxidants. Trends Phytochem. Res. 1(2), 103-108.

Zehavi, U., Levy, M., Segal, R., 1986. Fungistatic activity of saponin a from Styrax officinalis L. on plant pathogens. J. Phytopathol. 116(4), 338-343.

Zeikus, J.G., Jain, M.K., Elankovan, P., 1999. Biotechnology of succinic acid production and markets for derived industrial products. Appl. Microbiol. Biotechnol. 51(5), 545.

Zhang, D., Miyase, T., Kuroyanagi, M., Umehara, K., Noguchi, H., 1998. Oligosaccharide polyesters from roots of Polygala glomerata. Phytochemistry 47(1), 45-52.

Zhang, Y., Hoon, M.A., Chandrashekar, J., Mueller, K.L., Cook, B., Wu, D., Zuker, C.S., Ryba, N.J.P., 2003. Coding of sweet, bitter, and umami tastes different receptor cells sharing similar signaling pathways. Cell. 112, 293-301.