Biological activity of Hyptis Jacq. (Lamiaceae) is determined by the environment

Ángel, 1999, Plantas que contienen polifenoles Antioxidantes dentro del estilo de vida, Rev. Cuba. Investig. Biomed., 18, 12 Agra, 2008, Survey of medicinal plants used in the region Northeast of Brazil, Revista Brasileira de Farmacognosia, 18, 472, 10.1590/S0102-695X2008000300023 Agrawal, 2007, Macroevolution of plant defense strategies, Trends Ecol. Evol., 22, 103, 10.1016/j.tree.2006.10.012 Alimi, 2011, Evaluation of antioxidant and antiulcerogenic activities of Opuntia ficus indica f. inermis flowers extract in rats, Environ. Toxicol. Pharmacol., 32, 406, 10.1016/j.etap.2011.08.007 Arrigoni-Blank, 2008, Antinociceptive activity of the volatile oils of Hyptis pectinata L. Poit. (Lamiaceae) genotypes, Phytomedicine, 15, 334, 10.1016/j.phymed.2007.09.009 Atkinson, 1982, Seasonal occurence of na antimicrobial flavanone, sakuranetin, associated with glands on leaves of Ribes nigrum, New Phytol., 92, 63, 10.1111/j.1469-8137.1982.tb03363.x Awaad, 2013, Antiulcerogenic activities of the extracts and isolated flavonoids of Euphorbia cuneata Vahl, Phyther. Res., 27, 126, 10.1002/ptr.4872 Bispo, 2001, Antinociceptive and antiedematogenic effects of the aqueous extract of Hyptis pectinata leaves in experimental animals, J. Ethnopharmacol., 76, 81, 10.1016/S0378-8741(01)00172-6 Bowlers, 1994, Caffeic acid activity against clostridium botulinum spores, J. Food Sci., 59, 905, 10.1111/j.1365-2621.1994.tb08154.x Brand-Williams, 1995, Use of a free radical method to evaluate antioxidant activity, LWT − Food Sci. Technol., 28, 25, 10.1016/S0023-6438(95)80008-5 Brenna, 2001, Multivariate analysis of antioxidant power and polyphenolic composition in red wines, J. Agric. Food Chem., 49, 4841, 10.1021/jf0104376 Brooks, 2004, Seasonal variation in Daucus carota leaf-surface and leaf-tissue chemical profiles, Biochem. Syst. Ecol., 32, 769, 10.1016/j.bse.2004.01.004 Cavalcanti, 2008, Genotoxic effects of tanshinones from Hyptis martiusii in V79 cell line, Food Chem. Toxicol., 46, 388, 10.1016/j.fct.2007.08.009 Chen, 2016, Modifications of dietary flavonoids towards improved bioactivity: an update on structure?activity relationship, Crit. Rev. Food Sci. Nutr., 8398, 1 Chukwujekwu, 2005, Antiplasmodial diterpenoid from the leaves of Hyptis suaveolens, J. Ethnopharmacol., 102, 295, 10.1016/j.jep.2005.08.018 Clark, 1990, Seasonal variation in leaf exudate flavonoids of Isocoma acradenia (Asteraceae), Biochem. Syst. Ecol., 18, 145, 10.1016/0305-1978(90)90049-L Clifford, 2003, Hierarchical scheme for LC-MS in identification of chlorogenic acids, J. Agric. Food Chem., 51, 2900, 10.1021/jf026187q Cooper-Driver, 1977, Seasonal variation in secondary plant compounds in relation to the palatability of Pteridium aquilinum, Biochem. Syst. Ecol., 5, 177, 10.1016/0305-1978(77)90002-3 Coutinho, 2008, In vitro anti-staphylococcal activity of Hyptis martiusii Benth against methicillin-resistant Staphylococcus aureus: MRSA strains, Rev. Bras. Farmacogn., 18, 670, 10.1590/S0102-695X2008000500005 Cunha, 2012 Dai, 2010, Plant Phenolics: extraction, analysis and their antioxidant and anticancer properties, Molecules, 15, 7313, 10.3390/molecules15107313 De Lira Mota, 2009, Flavonoids with gastroprotective activity, Molecules, 14, 979, 10.3390/molecules14030979 Dement, 1974, Seasonal variation in the production of tannins and cyanogenic glucosides in the chaparral shrub, Heteromeles arbutifolia, Oecologia, 15, 65, 10.1007/BF00345228 Deng, 2009, Bioactive 5, 6-dihydro-α-pyrone derivatives from Hyptis brevipes, J. Nat. Prod., 72, 1165, 10.1021/np9001724 Dudt, 1994, The influence of light and nutrients on foliar phenolics and insect herbivory, Ecology, 75, 86, 10.2307/1939385 Dustin, 1992, Changes in phenolic production in the hay-scented fern (Dennstaedtia punctilobula) in relation to resource availability, Biochem. Syst. Ecol., 20, 99, 10.1016/0305-1978(92)90096-V Falcão, 2003, Revisão etnofarmacológica, farmacológica e química do gênero Hyptis: the Hyptis genus: an ethnopharmacological and chemical review, Rev. Bras. Farmacogn., 84, 69 Farhoosh, 2016, Structure-antioxidant activity relationships of o-hydroxyl, o-methoxy, and alkyl ester derivatives of p-hydroxybenzoic acid, Food Chem., 194, 128, 10.1016/j.foodchem.2015.08.003 Fresco, 2006, New insights on the anticancer properties of dietary polyphenols, Med. Res. Rev., 26, 747, 10.1002/med.20060 Furlan, 2015, Flavonoids and antioxidant potential of nine Argentinian species of Croton (Euphorbiaceae), Brazilian J. Bot., 38, 693, 10.1007/s40415-014-0115-9 Gershenzon, 1984, Changes in the levels of plant secondary metabolites under water and nutrient stress, 273 Gobbo-neto, 2007, Plantas medicinais: fatores de influência no conteúdo de metabólitos secundários, Quim. Nova, 30, 374, 10.1590/S0100-40422007000200026 Grace, 1998, Seasonal differences in foliar content of chlorogenic acid, a phenylpropanoid antioxidant, in Mahonia repens, Plant, Cell Environ., 21, 513, 10.1046/j.1365-3040.1998.00282.x Grayer, 2003, The chemotaxonomic significance of two bioactive caffeic acid esters, nepetoidins A and B, in the Lamiaceae, Phytochemistry, 64, 519, 10.1016/S0031-9422(03)00192-4 Guinn, 1982, Catechin and condensed tannin contents of leaves and bolls of cotton in relation to irrigation and boll load, Crop Sci., 22, 614, 10.2135/cropsci1982.0011183X002200030044x Harborne, 2000, Advances in flavonoid research since 1992, Phytochemistry, 55, 481, 10.1016/S0031-9422(00)00235-1 Harley, 2012, A generic revision and new combinations in the Hyptidinae (Lamiaceae), based on molecular and morphological evidence, Phytotaxa, 58, 1, 10.11646/phytotaxa.58.1.1 Harley, R., França, F., Santos, É.P., Santos, J.S. dos, 2010. Lamiaceae, in: Catálogo de Plantas E Fungos Do Brasil. Volume 2. Jardim Botânico do Rio de Janeiro, Rio de Janeiro, pp. 1130–1146. Harley, 2012, Checklist and key of genera and species of the Lamiaceae of the Brazilian Amazon, Rodriguésia, 63, 129, 10.1590/S2175-78602012000100010 Harley, R., França, F., Santos, E.P., Santos, J.S., Pastore, J.F., 2015a. Lamiaceae in Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro. Disponivel em: <http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB133004>. BFG. Growing knowledge: an overview of Seed Plant diversity in Brazil. Rodriguésia, v.66, n.4, p.1085–1113. 2015. https://dx.doi.org/10.1590/2175-7860201566411. Harley, R., França, F., Santos, E.P., Santos, J.S., Pastore, J.F., 2015b. Lamiaceae in Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro. Disponivel em: <http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB133011>. BFG. Growing knowledge: an overview of Seed Plant diversity in Brazil. Rodriguésia, v.66, n.4, p.1085–1113. 2015. https://dx.doi.org/10.1590/2175-7860201566411. Harley, R., França, F., Santos, E.P., Santos, J.S., Pastore, J.F. 2015c. Lamiaceae in Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro. Disponivel em: <http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB133007>. BFG. Growing knowledge: an overview of Seed Plant diversity in Brazil. Rodriguésia, v.66, n.4, p.1085–1113. 2015. https://dx.doi.org/10.1590/2175-7860201566411. Harley, R., França, F., Santos, E.P., Santos, J.S., Pastore, J.F. 2015d. Lamiaceae in Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro. Disponivel em: <http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB133002>. BFG. Growing knowledge: an overview of Seed Plant diversity in Brazil. Rodriguésia, v.66, n.4, p.1085–1113. 2015. https://dx.doi.org/10.1590/2175-7860201566411. Harley, R., França, F., Santos, E.P., Santos, J.S.,Pastore, J.F. 2015e. Lamiaceae in Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro. Disponivel em: <http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB8216>. BFG. Growing knowledge: an overview of Seed Plant diversity in Brazil. Rodriguésia, v.66, n.4, p.1085–1113. 2015. https://dx.doi.org/10.1590/2175-7860201566411. Harley, R., França, F., Santos, E.P., Santos, J.S., Pastore, J.F. 2015f. Lamiaceae in Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro. Disponivel em: <http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB8219>. BFG. Growing knowledge: an overview of Seed Plant diversity in Brazil. Rodriguésia, v.66, n.4, p.1085–1113. 2015. https://dx.doi.org/10.1590/2175-7860201566411. Harley, R., França, F.,Santos, E.P.,Santos, J.S., Pastore, J.F. 2015g. Lamiaceae in Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro. Disponivel em: <http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB8232>. BFG. Growing knowledge: an overview of Seed Plant diversity in Brazil. Rodriguésia, v.66, n.4, p.1085–1113. 2015. https://dx.doi.org/10.1590/2175-7860201566411. Holst, 2008, Nutrients and phytochemicals: from bioavailability to bioefficacy beyond antioxidants, Curr. Opin. Biotechnol., 19, 73, 10.1016/j.copbio.2008.03.003 Horner, 1990, Nonlinear effects of water deficits on foliar tannin concentration, Biochem. Syst. Ecol., 18, 211, 10.1016/0305-1978(90)90062-K Hrazdina, 1970, Studies on the stability of the anthocyanidin-3,5diglucosides, Am. J. Enol. Vitic., 21, 201, 10.5344/ajev.1970.21.4.201 Hsieh, 2005, Antioxidant activities of phenolic acids on ultraviolet radiation-induced erythrocyte and low density lipoprotein oxidation, J. Agric. Food Chem., 53, 6151, 10.1021/jf050707a Ito, 1998, Antiallergic activities of rabdosiin and its related compounds: chemical and biochemical evaluations, Bioorg. Med. Chem., 6, 1051, 10.1016/S0968-0896(98)00063-7 Izzo, 2007, Herbal medicines to treat Alzheimer’s disease, Pharmacol. Sci., 28, 47 Jalal, 1982, Phenolic composition and its seasonal variation in Calluna vulgaris, Phytochemistry, 21, 1397, 10.1016/0031-9422(82)80150-7 Jassim, 2003, Novel antiviral agents: a medicinal plant perspective, J. Appl. Microbiol., 95, 412, 10.1046/j.1365-2672.2003.02026.x Jeong, 2004, Effects of plant hormones and shading on the accumulation of anthocyanins and the expression of anthocyanin biosynthetic genes in grape berry skins, Plant Sci., 167, 247, 10.1016/j.plantsci.2004.03.021 Ji, 2008, Multipotent natural agents to combat Alzheimer’s disease. Functional spectrum and structural features, Acta Pharmacol. Sin., 29, 143, 10.1111/j.1745-7254.2008.00752.x Judd, 2002 Kapravelou, 2015, Improvement of the antioxidant and hypolipidaemic effects of cowpea flours (Vigna unguiculata) by fermentation: results of in vitro and in vivo experiments, J. Sci. Food Agric., 95, 1207, 10.1002/jsfa.6809 Karthikesan, 2010, Protective effect of tetrahydrocurcumin and chlorogenic acid against streptozotocin-nicotinamide generated oxidative stress induced diabetes, J. Funct. Foods, 2, 134, 10.1016/j.jff.2010.04.001 Kini, 1993, Chemical composition of the essential oil of Hyptis spicigera Lam. from Burkina Faso, J. Essent. Oil Res., 5, 219, 10.1080/10412905.1993.9698206 Klink, 2005, Conservation of the Brazilian Cerrado, Conserv. Biol., 19, 707, 10.1111/j.1523-1739.2005.00702.x Kutchan, 2001, Ecological arsenal and developmental dispatcher. the paradigm of secondary metabolism, Plant Physiol., 125, 58, 10.1104/pp.125.1.58 Larrosa, 2010, Ellagitannins, ellagic acid and vascular health, Mol. Aspects Med., 31, 513, 10.1016/j.mam.2010.09.005 Li, 2008, Antioxidant properties in vitro and total phenolic contents in methanol extracts from medicinal plants, LWT − Food Sci. Technol., 41, 385, 10.1016/j.lwt.2007.03.011 Li, 2008, Neuroprotective effects of chlorogenic acid against apoptosis of PC12 cells induced by methylmercury, Environ. Toxicol. Pharmacol., 26, 13, 10.1016/j.etap.2007.12.008 Lisboa, 2006, Antinociceptive effect of Hyptis pectinata leaves extracts, Fitoterapia, 77, 439, 10.1016/j.fitote.2006.06.001 Lobstein, 1991, Seasonal variations of the flavonoid content from Ginkgo biloba leaves, Planta Med., 57, 430, 10.1055/s-2006-960142 Ma, 2007, Synthesis of chlorogenic acid derivatives with promising antifungal activity, Bioorg. Med. Chem., 15, 6830, 10.1016/j.bmc.2007.07.038 Markham, 1998, Possible protective role for 3’, 4’ − dihydroxyflavones Induced by enhanced UV-B in a UV-tolerant rice cultivar, Phytochemistry, 49, 1913, 10.1016/S0031-9422(98)00438-5 Markham, 1982 Martins, 2016, In vivo antioxidant activity of phenolic compounds: facts and gaps, Trends Food Sci. Technol., 48, 1, 10.1016/j.tifs.2015.11.008 Mattson, 1987, The role of drought stress in provoking outbreaks of phytophagous insects, Insect Outbreaks, 365, 10.1016/B978-0-12-078148-5.50019-1 Medina, 1984, Water stress and light intensity effects on growth and nocturnal acid accumulation in a terrestrial CAM bromelias (Bromelia humilis Jacq.) under natural conditions, Oecologia, 70, 441, 10.1007/BF00379509 Menezes, 2007, Antinociceptive effect and acute toxicity of the essential oil of Hyptis fruticosa in mice, Fitoterapia, 78, 192, 10.1016/j.fitote.2006.11.020 Menkovic, 2000, Chemical composition and seasonal variations in the amount of secondary compounds in Gentiana lutea leaves and flowers, Planta Med., 66, 178, 10.1055/s-0029-1243126 Messana, 1990, (−)-Salzol, an isopimarane diterpene, and a chalcone from Hyptis salzmanii, Phytochemistry, 29, 329, 10.1016/0031-9422(90)89065-H Miranda, 2013, Atividade antibacteriana in vitro de quatro espécies vegetais em diferentes graduações alcoólicas, Rev. Bras. Pl. Med., 15, 104, 10.1590/S1516-05722013000100015 Moon, 2009, Antioxidant assays for plant and food components antioxidant assays for plant and food componentes, J. Agric. Food Chem., 57, 1655, 10.1021/jf803537k Myers, 2000, Biodiversity hotspots for conservation priorities, Nature, 403, 853, 10.1038/35002501 Nacif de Abreu, 2005, Effect of water and temperature stress on the content of active constituents of Hypericum brasiliense Choisy, Plant Physiol. Biochem., 43, 241, 10.1016/j.plaphy.2005.01.020 Nayak, 1952, Essential oil from Hyptis suaveolens, J. Indian Chem. Soc., 29, 183 Ohsaki, 2005, New labdane diterpenoids from Hyptis fasciculata, Chem. Pharm. Bull. (Tokyo)., 53, 1577, 10.1248/cpb.53.1577 Pastore, 2011, Phylogeny of the subtribe Hyptidinae (Lamiaceae tribe Ocimeae) as inferred from nuclear and plastid DNA, Taxon, 60, 1317, 10.1002/tax.605008 Paynter, 2005, Coffee and sweetened beverage consumption and the risk of type 2 Diabetes mellitus, Am. J. Epidemiol., 164, 1075, 10.1093/aje/kwj323 Pedersen, 2000, Distribution and taxonomic implications of some phenolics in the family Lamiaceae determined by ESR spectroscopy, Biochem. Syst. Ecol., 28, 229, 10.1016/S0305-1978(99)00058-7 Pereda-Miranda, 1990, Triterpenoids and flavonoids from Hyptis albida, J. Nat. Prod., 53, 182, 10.1021/np50067a028 Pereda-Miranda, 1993, Structure and stereochemistry of pectinolides A-C, novel antimicrobial and cytotoxic 5, 6-Dihydro-α-pyrones from Hyptis pectinata, J. Nat. Prod., 56, 583, 10.1021/np50094a019 Pereira, 2006 Petersen, 2003, Rosmarinic acid, Phytochemistry, 62, 121, 10.1016/S0031-9422(02)00513-7 Pietta, 2000, Flavonoids as antioxidants, J. Nat. Prod., 63, 1035, 10.1021/np9904509 Quideau, 2011, Plant polyphenols: chemical properties, biological activities, and synthesis, Angew. Chemie − Int. Ed., 50, 586, 10.1002/anie.201000044 Razzaghi-Asl, 2013, Antioxidant properties of hydroxycinnamic acids: a review of structure-activity relationships, Curr. Med. Chem., 20, 4436, 10.2174/09298673113209990141 Rice-Evans, 1996, Structure-antioxidant activity relationships of flavonoids and phenolic acids, Free Radic. Biol. Med., 20, 933, 10.1016/0891-5849(95)02227-9 Rodriguez de Sotillo, 2002, Chlorogenic acid modifies plasma and liver concentrations of: cholesterol, triacylglycerol, and minerals in Zucker rats, J. Nutr. Biochem., 13, 717, 10.1016/S0955-2863(02)00231-0 Rubió, 2013, Recent advances in biologically active compounds in herbs and spices: a review of the most effective antioxidant and anti-inflammatory active principles, Crit. Rev. Food Sci. Nutr., 53, 943, 10.1080/10408398.2011.574802 Santos, 2014 Santos, 2007, Antinociceptive effect and acute toxicity of the Hyptis suaveolens leaves aqueous extract on mice, Fitoterapia, 78, 333, 10.1016/j.fitote.2007.01.006 Santos, 2016, Antioxidant activity of flavonoids from Croton sphaerogynus Baill, Brazilian J. Bot., 39, 1021, 10.1007/s40415-016-0302-y Santos, 2004, Metabolismo básico e origem dos metabólitos secundários Sevgi, 2015, Antioxidant and DNA damage protection potentials of selected phenolic acids, Food Chem. Toxicol., 77, 12, 10.1016/j.fct.2014.12.006 Shahidi, 1992, Phenolic antioxidants, Crit. Rev. Food Sci. Nutr., 32, 67, 10.1080/10408399209527581 Silva, 2002, Structure-antioxidant activity relationships of flavonoids: a re-examination, Free Radic. Res., 36, 1219, 10.1080/198-1071576021000016472 Simões, 2001 Soares, 2002 Southwell, 2001, Seasonal variation in hypericin content of Hypericum perforatum L. (St. john’s wort), Phytochemistry, 56, 437, 10.1016/S0031-9422(00)00411-8 Souza, 2003, Antimicrobial activity of Hyptis ovalifolia towards dermatophytes, Mem. Inst. Oswaldo Cruz, 98, 963, 10.1590/S0074-02762003000700018 Takeda, 2002, Identification of rosmarinic acid as a novel antidepressive substance in the leaves of Perilla frutescens Britton var. acuta Kudo (Perillae Herba), Nihon Shinkei Seishin Yakurigaku Zasshi, 22, 15 Tattini M., Galardi C., Pinelli P., Massai R., Remorini D., Agati G., 2004. Differential accumulation of flavonoids and hydroxycinnamates in leaves of 547–561. Teixeira, 2013, Hydroxycinnamic acid antioxidants: an electrochemical overview, Biomed Res. Int., 2013, 1 Tripathi, 2007, Modulation of oxidative damage by natural products, Food Chem., 100, 81, 10.1016/j.foodchem.2005.09.012 Urones, 1998, Tricyclic diterpenes from Hyptis dilatata, Phytochemistry, 48, 1035, 10.1016/S0031-9422(97)00997-7 Valko, 2007, Free radicals and antioxidants in normal physiological functions and human disease, Int. J. Biochem. Cell Biol., 39, 44, 10.1016/j.biocel.2006.07.001 Wang, 2009, Anti-hepatitis B virus activity of chlorogenic acid, quinic acid and caffeic acid in vivo and in vitro, Antiviral Res., 83, 186, 10.1016/j.antiviral.2009.05.002 Waterman, 1989, 1 Waterman, 1994 Wilt, 1992, Seasonal variation of coumarin and flavonoid concentrations in persistent leaves of wyoming big sagebrush (Artemisia tridentata ssp. wyomingensis: Asteraceae), Biochem. Syst. Ecol., 20, 53, 10.1016/0305-1978(92)90072-L Wren, 1988 Yeh, 2006, Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats, J. Nutr. Biochem., 17, 561, 10.1016/j.jnutbio.2005.10.008 Yesilada, 2014, Anti-ulcerogenic activity and isolation of the active principles from Sambucus ebulus L. leaves, J. Ethnopharmacol., 153, 478, 10.1016/j.jep.2014.03.004 Yildirim, 2001, Determination of antioxidant and antimicrobial activities of Rumex crispus L. extracts, J. Agric. Food Chem., 49, 4083, 10.1021/jf0103572 Zheng, 2001, Antioxidant activity and phenolic compounds in selected herbs, J. Agric. Food Chem., 49, 5165, 10.1021/jf010697n Zidorn, 2001, Evaluation of chemosystematic characters in the genus Leontodon (Asteraceae), Taxon, 50, 115, 10.2307/1224515 al-Sereiti, 1999, Pharmacology of rosemary (Rosmarinus officinalis Linn.) and its therapeutic potentials, Indian J. Exp. Biol., 37, 124 da Cruz Araújo, 2004, Spectral assignments of new diterpenes from Hyptis martiusii Benth, Magn. Reson. Chem., 42, 1049, 10.1002/mrc.1489