Secondary Metabolites from an Infusion of Lippia gracilis Schauer Using the LC‑DAD-SPE/NMR Hyphenation Technique

Abstract

The genus Lippia comprises approximately 200 species of herbs, shrubs and small trees, distributed throughout the South and Central America and tropical Africa. The species Lippia gracilis Schauer is an endemic aromatic plant of the Brazilian Northeast normally found in the states of Bahia, Sergipe and Piauí. The traditional communities of Caatinga, a semi-arid region of the Brazilian Northeast, use its leaves to treat throat and mouth infections, cutaneous diseases, ulcers, vagina disorders, acne, Pityriasis alba, dandruff, burns, wounds, sinusitis, bronchitis, nasal congestion, headache, jaundice and paralysis. Considering that the main investigations into the L. gracilis Schauer species are focused on its volatile constituents, in this report, we describe the isolation, by liquid chromatography with diode array detector-solid phase extraction/nuclear magnetic resonance (LC-DAD-SPE/NMR), of five flavonoids besides free and glycosidically bound carvacrol from an infusion of the leaves of a genotype of this species. Keywords: Lippia gracilis Schauer, infusion, LC-DAD-SPE/NMR, flavonoids, carvacrol IntroductionBrazilian plants have a great potential to be explored because, for many of them, there is little or no knowledge of their chemical compositions.1 Lippia gracilis Schauer (Verbenaceae) is a species that is included in this group once, to our knowledge, there is only one report about its non-volatile constituents, 2 while most reports are focused on studies on the composition of essential oils and their biological activities. 3-21The genus Lippia comprises approximately 200 species of herbs, shrubs and small trees, distributed throughout the South and Central America countries and tropical Africa. 22The species L. gracilis Schauer is an endemic aromatic plant to the Brazilian Northeast normally found in the states of Bahia, Sergipe and Piauí. The traditional communities of Caatinga, a semi-arid region of the Brazilian Northeast, use its leaves to treat throat and mouth infections, cutaneous diseases, ulcers, vagina disorders, acne, Pityriasis alba, dandruff, burns, wounds, sinusitis, bronchitis, nasal congestion, headache, jaundice and paralysis. [23][24][25] Although there is little knowledge about the non-volatile constituents of L. gracilis, there are several phytochemical studies describing the isolation of various compounds from other species of this genus, including iridoid glucosides, phenylethanoid glucosides, phenylpropanoids, triterpenes saponins, flavonoids, naphthoquinones, flavonoids glucosides, lignans, sesquiterpenes and triterpenes. Previous chemical investigations into the L. gracilis Schauer species are focused on its volatile constituents where thymol and carvacrol, which showed strong antimicrobial activity against fungi and bacteria, are the main components. 12 The chemical composition of the volatile compounds shows quantitative variations of the The literature only reports one study on the isolation of fixed constituents from the methanolic extract from the leaves of L. gracilis Schau...

The Role of High-Resolution Analytical Techniques in the Development of Functional Foods

“…For example, numerous studies use LC-NMR for the characterization of phenolic compounds. These examples include the identification of gallic acid, protocatechuic acids and anthocyanins from Hibiscus sabdariffa calyces [ 82 , 84 ], flavonoids from Lippia gracilis [ 85 ], procyanidins from cacao beans [ 86 ], epicatechin vanillate from grape seed and red wine [ 87 ], terpenoid glycosides from Rosmarinus officinalis L . [ 88 ], and flavonols and phenolic acids from red onion peels [ 89 ].…”

Investigation of Antioxidant Activity, Acute Toxicity and Anticholinesterasic Potential of Lippia hirta (Verbenaceae)

“…12 The genus Lippia has cataloged about 200 species among herbs, shrubs and small trees, which can be found mainly in South and Central America, and in tropical areas of Africa. 13 Extracts and essential oils obtained from Lippia spp. have been extensively scientifically tested because of the potential of bioactive principles.…”

“…respectively. One-bond and long-range 1 H- 13 C correlation from HMQC and HMBC NMR experiments were optimized for an average coupling constant 1 J(C,H) and LR J(C,H) of 140 and 8 Hz, respectively. All 1 H and 13 C NMR chemical shifts (δ) are given in ppm related to the TMS signal at 0.00 ppm as an internal reference, and the coupling constants (J) in Hz.…”

“…173-175 o C. IR (ATR) ν / cm -1 3410 (OH),3258 (NH), 1452 (NH), 1622 (C-C sp 2 ), 740 (disubstituted 1,2-aromatic ring) 1. H NMR (400 MHz): δ 7.96 (NH), 7.50 (d, J = 7.5 Hz, H9) and 7.31 (d, J = 7.5 Hz, H12), 7.10 (dd, J = 7.5 and 1.5 Hz, H10 ) 7.14 (dd, J = 7.5 and 1.5 Hz, H11) 13. C NMR (100 MHz) δ 10.9 (C18), 21.6 (C6), 23.4(19), 35.2 (C14), 35.4 (C16), 37.2 (C15), 41.6 (C20), 53.0 (C5), 59.8 (C3), 60.1 (C21), 60.3 (C17), 107.7 (C7), 110.8 (C12), 118.0 (C9), 119.2 (C10), 121.1 (C11), 127.3 (C8), 135.0 (C2), 136.1 (C13).…”

Impact of Colored Shade Nets on Biomass Production, Essential Oil Composition and Orientin and Isoorientin Content in Lippia gracilis Schauer

“…However, analgesic and anti‐inflammatory activities have also been demonstrated in rodents using the methanolic extract of L. gracilis , which is rich in phenolic compounds [11] . Among some phenolic compounds already isolated from L. gracilis are the flavone derivatives orientin, isoorientin, luteolin and apigenin and the flavanone naringenin from the leaves [17] …”