Abstract
Despite more than 400 species of Baccharis occurring worldwide, only less than 20% of the species have chemically been studied. In the Baccharis genus, within terpenes and other phenolic compounds (see Chaps. 12 and 13), flavonoids are largely accumulated as aglycone, being apigenin, genkwanin, hispidulin, kaempferol (flavones), quercetin (flavonol), naringenin, sakuranetin (flavanones), and others widely distributed. Additionally, some flavonoid glycosides such as quercitrin, rutin, and others are also found, but in minor frequency. Flavonoids are compounds with a basic skeleton of 15 carbons (C6-C3-C6) arranged in two aromatic rings linked through a three-carbon moiety. The oxidation degree of the C3 moiety is directly related to the classification of flavonoids into flavanones, flavones, isoflavones, flavanonols, and flavonols. With respect to biological activity, flavonoids from Baccharis display a significant antioxidant potential, especially for the capacity of suppression of ROS formation, ROS scavenging, and upregulation of antioxidant defenses. In this chapter, the distribution of flavonoids in Baccharis is so justified through this antioxidant effect since those species are inserted in areas with direct incidence of sunrays, such as in montane savannas. In addition, flavonoids display hepatoprotective, antimicrobial, anti-inflammatory, antitumoral, antiviral, and other activities. In this chapter, the occurrence and distribution of flavonoids in Baccharis species are discussed, as well as their biosynthesis and biological aspects.
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Keywords
- Biological activity
- Biosynthesis
- Flavonoid distribution
- Modulation of redox balance
- Structure and composition
1 Introduction
Although more than 400 Baccharis species are distributed worldwide, only a reduced number of plants belonging to this genus were chemically and/or biologically investigated. Among the chemical compounds present in these species, the occurrence of flavonoids is reported in about 15% of Baccharis species (Campos et al. 2016). Flavonoids are a class of phenolic compounds, widely distributed within the kingdom Plantae, with a basic skeleton of 15 carbons (Fig. 11.1) arranged as two aromatic rings (A and B) connected by a three-carbon moiety (C6-C3-C6).
Basic skeleton of a flavonoid
The classification of flavonoids is directly related to the degree of oxidation of the C3 portion. Flavonoids can be classified into flavanones, flavononols, flavones, isoflavones, flavonols, catechins, and anthocyanidins.
2 Biosynthesis
Secondary metabolites , also known as special metabolites, are substances from natural sources that do not participate in the essential functions of these organisms (reproduction, growth, or development). Most are substances produced in processes of interaction between plants and the environment in which they are inserted. It is important to note that the production of secondary metabolites is also associated with the various conditions to which plant species are subjected. Since these substances are produced to benefit these individuals, depending on the environment surrounding them, it acts as protection against the action of predators, coloring and volatiles agents, attracting pollinators, and also as competition agents among plants in the same habitat. Therefore, the production of these metabolites is fundamental in the maintenance of these species (Dewick 2009).
Besides being responsible for the production of substances that act with different functions in the interaction of these plant species and the environment, which are inserted, the secondary metabolism is also responsible for providing the majority of natural products with pharmacological activity. The secondary metabolism acts as substrates originating from the metabolic pathways that form the primary metabolism (photosynthesis, glycolysis, and Krebs/ citric acid cycle). These substrates are involved in different metabolic pathways, responsible for the synthesis of several classes of secondary metabolites.
Flavonoids are considered mixed pathway metabolites, being synthesized from precursors of two metabolic routes; shikimic acid (shikimate) and acetate-malonate. From the glycolysis process, the synthesis of phosphoenylpyruvate, together with erythrose-4-phosphate from the pentose-phosphate pathway, is responsible for the synthesis of shikimic acid. In glycolysis, phosphoenylpyruvate, through the enzyme pyruvate kinase, transfers the phosphate ion to a molecule of ADP, generating pyruvate and ATP. This pyruvate is responsible for the synthesis of acetyl-CoA (acetyl coenzyme A). From the shikimic acid path, p-coumaric acid (4-coumaric acid) is obtained, resulting from the ammonia elimination from L-phenylalanine side chain (precursors of the C6-C3 portions), and precursor of p-coumaric alcohol. The elimination of ammonia occurs in the presence of PAL (phenylalanine ammonia lyase) into cinnamic acid, which is converted into p-coumaric acid by direct hydroxylation, in the presence of cinnamate-4-hydroxylase (C4H), which is converted to 4-hydroxycinnamoyl-CoA by the 4-coumarate CoA ligase (4CL), by a process known as the general pathway to the formation of phenylpropanoids. The enzyme involved in the consensation process of malonyl-CoA units to form flavonoids is chalcone synthase, through the acetyl-CoA carboxylase (ACC) mediates carboxylation reaction. Therefore, the formation of flavonoids (Fig. 11.2) occurs from 4-hydroxycinnamoyl-CoA units, derived from the pathway of shikimic acid with the addition of malonyl-CoA units (for chain elongation), the route of acetate-malonate (Davies and Schwinn 2006; Dewick 2009).
Formation of the polyketide side chain, precursor of flavonoids, by acetate-malonate route
After the addition of malonyl-CoA units, two pathways could be involved in the formation of different metabolites – flavonoids or stilbenes (e.g., resveratrol). After the formation of the polyketide, different enzymes are involved in aldol or Claisen type condensations to form aromatic ring A. For the formation of flavonoids, the enzyme involved in the condensation process of malonyl-CoA units is chalcone synthase. Chalcones are the precursors of flavonoids (I), followed by enolization (II) of the polyketide (Fig. 11.3).
Steps for chalcone biosynthesis from polyketide side chain
For the synthesis of flavonoids, chalcones undergo a nucleophilic attack reaction of the OH group to the α,β-unsaturated ketone, forming a heterocyclic ring (C-ring) yielding flavanones. Acidic environments may favor the synthesis of flavanones, while alkaline environments favor the production of chalcones. However, it is worth emphasizing that in nature, these processes occur under very specific conditions, in the presence of stereospecific enzymes that prevent the formation of enantiomers. From the flavanones, a large variety of flavonoids can be synthesized, such as flavones, flavonols, and anthocyanidins (Davies and Schwinn 2006).
According to the basic skeleton of flavonoids, the variations between the different classes of flavonoids are related to the oxygenations and substituents of rings B and C. However, many flavonoids can also lose one or two hydroxyl groups in ring A, a process related to the action of chalcone reductase and chalcone synthase enzymes. The enzymatic complex involved in the biosynthesis of the different classes of flavonoids is broad and with high specificity, through this complex, the alterations of the oxygenation patterns in the aryl moiety are realized. In addition, methylation, glycosylation, and dimethylation processes are responsible for increasing the possibilities of formation of different compounds, increasing the diversity of flavonoids distributed in different plant species (Dewick 2009).
Flavanones, the first group of flavonoids synthesized from chalcones, are the precursors of the other groups of flavonoids. Flavones are synthesized from reactions in the presence of flavone synthase I, oxygen and 2-oxo-glutarate and flavone synthase IIe, oxygen and NADPH. In the presence of oxygen, 2-oxoglutarate, and flavanone 3-hydroxylase enzyme, dihydroflavonols are produced, which are the precursors of flavonols and flavandiols. Finally, flavodiols act as precursors of the catechins and anthocyanidins, through specific enzymatic processes that occur in the presence of oxygen and NADPH, and by water elimination (Davies and Schwinn 2006; Dewick 2009). Figure 11.4 briefly illustrates the biosynthesis of flavonoids.
Scheme of flavonoid biosynthesis
3 Flavonoid Composition
As described above, the main composition of Baccharis are flavonoids, diterpenes, and other phenolic compounds. From the Baccharis genus, which is composed of 441 species, only approximately 20% have been investigated in chemical aspects. The occurrence of flavonoids was reported in 86 distinct species of Baccharis; these studies lead to the identification of 129 flavonoids separated into 16 flavanones (Table 11.1), 11 flavanonols (Table 11.2), 46 flavones (Table 11.3), and 55 flavonols (Table 11.4).
4 Flavanones
The main precursor of all flavonoids, naringenin (1), was found in aerial parts of B. alaternoides (Bohlmann et al. 1979), B. conferta (Weimann et al. 2002), B. ligustrina (Moreira et al. 2003a, b; Abad and Bermejo 2007), B. polycephala (Davila et al. 2013), B. retusa (Grecco et al. 2012a, b; Campos et al. 2016), B. salzmannii (Bohlmann et al. 1981a, b), and B. varians (Bohlmann et al. 1981a). Compound 1 was also found in the flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016), leaves of B. dracunculifolia (Fukuda et al. 2006; Campos et al. 2016) and B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007). The methylation of position C-7 leads to sakuranetin (2) accumulated in the aerial parts of B. concinna (Wollenweber et al. 2006), B. marginalis (Faine et al. 1987), B. retusa (Herz et al. 1977; Grecco et al. 2012a, b, 2014a, b; Rodriguez et al. 2012; Taguchi et al. 2015a, b; Sakoda et al. 2016; Bittencourt-Mernak et al. 2017; Ueno et al. 2018), B. salicifolia (del Corral et al. 2012; Campos et al. 2016), B. serrulata (Bohlmann et al. 1981a), and B. trinervis var. rhexioides (Bohlmann et al. 1979). This compound was also found in the roots of B. leptocephala (Bohlmann et al. 1981a) and B. intermixta (Bohlmann et al. 1981a) and leaves of B. teindalensis. The methylation at position C-4′ rather than C-7 of naringenin (1) affords isosakuranetin (3) identified in aerial parts of B. alaternoides (Bohlmann et al. 1979), B. conferta (Weimann et al. 2002), B. dracuncunfolia, within its roots and vegetative gems (da Silva Filho et al. 2004, 2008; Park et al. 2004; de Alencar et al. 2005; Lemos et al. 2007; Missima et al. 2007; de Sousa et al. 2009; Guimaraes et al. 2012; Figueiredo-Rinhel et al. 2013; Campos et al. 2016) and in B. polycephala (Davila et al. 2013), in the roots of B. leptocephala (Bohlmann et al. 1981b), and in the shrub B. leptophylla. The C-6 hydroxylation of isosakuranetin (3) leads to the formation of 5,6,7-trihydroxy-4′-methoxyflavanone (4) accumulated in the leaves and aerial parts of B. conferta (Weimann et al. 2002), B. retusa (Grecco et al. 2010a, b), B. teindalensis (Vidari et al. 2003), and B. viminea (Wollenweber et al. 1997). The dimethoxy derivative of naringenin (1), 5-hydroxy-4′,7-dimethoxyflavanone (5), was identified in the aerial parts of B. conferta (Weimann et al. 2002) and B. polycephala (Davila et al. 2013) and 4′-hydroxy-5,7-dimethoxyflavanone (6) in ground parts of B. alaternoides (Bohlmann et al. 1979). The 4′-dehydroxylated derivative, pinocembrin (7), was identified in B. viminea (Wollenweber et al. 1997), in the roots of B. concinna (Bohlmann et al. 1981b), and in B. oxyodonta (Bohlmann et al. 1981b; Abad Martinez et al. 2005). Less frequently isolated 3’- and 6-monomethoxylated derivatives of pinocembrin (7): 5,7-dihydroxy-3′-methoxyflavanone (8) and 5,7-dihydroxy-6-methoxyflavanone, known as dihydrooroxylin A (9), were identified in the roots of B. truncata [27] and aerial parts of B. uncinella, respectively (Grecco et al. 2010a, b; Campos et al. 2016). Eriodictyol (10) was found in aerial parts of B. concinna (Bohlmann et al. 1981b), B. confertifolia (Wollenweber et al. 2006), B. marginalis (Faine et al. 1987), B. retusa (Campos et al. 2016; Grecco et al. 2012a, b), and B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007; Campos et al. 2016). Six eriodictyol derivatives were found in Baccharis species: eriodictyol-7-methyl ether (11) at B. concinna (Wollenweber et al. 2006), homoeriodictyol (12) and eriodictyol-3′,4′-dimethyl ether (13) at B. calliprinos (Gianello et al. 1999), eriodictyol 7,3′,4′-trimethyl ether (14) at B. confertifolia (Wollenweber et al. 2006), filifolin (15) at B. concinna (Wollenweber et al. 2006) and B. boliviensis (Campos et al. 2016), and 8-methoxyeriodictyol (16) at B. concinna (Wollenweber et al. 2006). Flavanones identified at Baccharis species are summarized in Table 11.1, followed by their respective structures in Fig. 11.5.
Structures of flavanones 1–16 identified in Baccharis species
5 Flavanonols
The 3-hydroxylation of flavanones through 3-hydroxylase enzymes leads to the biosynthesis of flavanonol derivatives. Naringenin-3-hydroxylase affords aromadendrin, also known as dihydrokaempferol (17), identified in leaves of B. dracunculifolia (Guimaraes et al. 2012), shrubs of B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007; Campos et al. 2016), leaves and flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016), and in aerial parts of B. retusa (Campos et al. 2016; Grecco et al. 2012a). Aromadendrin-7-methyl ether (18) was isolated from aerial parts of B. dracunculifolia (Campos et al. 2016) and B. illinita (Pizzolatti et al. 2006). Dihydrokaempferide (19) was identified in the aerial parts of B. conferta (Weimann et al. 2002), in leaves, roots, flowers, buds, and stems of B. dracunculifolia (Figueiredo-Rinhel et al. 2013; da Silva Filho et al. 2004, 2008; Missima et al. 2007; Lemos et al. 2007; de Sousa et al. 2009, 2011; Resende et al. 2007; Rezende et al. 2014; Cestari et al. 2011Midorikawa et al. 2003; Kumazawa et al. 2003), and from B. leptophylla (Mollinedo et al. 2001; Almanza et al. 2000). 3-Acetylated derivative such as 3-acetoxy-4′ 5 7-trihydroxyflavanone (20) was isolated from aerial parts of B. varians (Bohlmann et al. 1981a; Abad Martinez et al. 2005), while 3-acetoxy-4′,5-dihydroxy-7-methoxyflavanone (21) was obtained from leaves of B. dracunculifolia, (Fukuda et al. 2006; Campos et al. 2016). A 4′-dehydroxylated derivative of aromadendrin, pinobanksin (22), was isolated from roots of B. oxyodonta (Bohlmann et al. 1981b; Abad Martinez et al. 2005) as well as from vegetative gems and leaves of B. dracunculifolia (Park et al. 2004; de Alencar et al. 2005). Additionally, its acetylated derivative, pinobanksin-3-acetate (23), was identified in B. dracunculifolia leaf bud (Park et al. 2005) and in B. trinervis (Jakupovic et al. 1986). Taxifolin (24) was identified in B. illinita (Abad and Bermejo 2007), especially in flowers (Verdi et al. 2004; Campos et al. 2016), as well as in aerial parts of B. retusa (Grecco et al. 2012a; Campos et al. 2016). 3-hydroxyhesperetin or taxifolin-4′-methyl ether (25), together with 8-prenyltaxifolin (26), were identified in aerial parts of B. tola (Simirgiotis et al. 2016). Furthermore, an acetylated derivative, taxifolin-3-acetate (27), was identified in aerial parts of B. varians (Bohlmann et al. 1981a; Abad Martinez et al. 2005). Flavanonols identified in Baccharis species are summarized in Table 11.2, followed by their respective structures in Fig. 11.6, Flavanonols identified in Baccharis species are summarized in Table 11.3, followed by their respective structures in Fig. 11.6.
Structures of flavanonols 17–27 identified in Baccharis species
6 Flavones
The enzymatic dehydration of flavanone naringenin (1) through flavone synthase affords apigenin (28) identified in the aerial parts of B. bigelovii (Arriaga-Giner et al. 1986), B. crispa (Palacios et al. 1983), B. dentata (Campos et al. 2016), B. gaudichaudiana (Fullas et al. 1994; Guo et al. 2007; Visintini et al. 2013; Campos et al. 2016), B. notosergila (Palacios et al. 1983), B. pedicellata (Faine et al. 1987), B. retusa (Grecco et al. 2012a; Campos et al. 2016), B. salicifolia (Campos et al. 2016; Bohlmann et al. 1981b), B. salzmannii (Campos et al. 2016), as well as in the aerial and epigeous parts of B. trimera (Nakasugi 1990, 1998; Fullas et al. 1994). This compound was also identified in the flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016), leaves, and shrubs of B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007; Campos et al. 2016) and B. teindalensis (Vidari et al. 2003), and vegetative gems of B. dracunculifolia (de Alencar et al. 2005). The flavone 28 was also found in B. genistelloides (Kuroyanagi et al. 1985; Abad Martinez et al. 2005; Hennig et al. 2011), B. heterophylla (Wollenweber et al. 1986), B. pteronioides (Wollenweber et al. 1986), B. ramosissima (Bohlmann et al. 1981b), B. tola (San Martin et al. 1982, 1983; Abad Martinez et al. 2005), B. trinervis (Arriaga et al. 1982), B. vaccinioides (Wollenweber et al. 1986), and B. viminea (Wollenweber et al. 1997). Its 8-hydroxylated derivative, isoscutellarein (29), was identified only in B. pilularis var. consanguinea (Wollenweber et al. 1997), while the 4′-methylated derivative, acacetin (30), was found in aerial parts of B. articulata (Gianello and Giordano 1984; Cariddi et al. 2012), B. conferta (Weimann et al. 2002), and B. polycephala (Davila et al. 2013), in the leaf parts of B. dracunculifolia (Park et al. 2004; da Silva Filho et al. 2009) and B. rhomboidalis (Silva et al. 1971) and from B. grandicapitulata (Bohlmann et al. 1985), B. patagonica (Zdero et al. 1986; Rivera et al. 1988); B. salicifolia (Wollenweber et al. 1986), B. trinervis (Arriaga et al. 1982), B. vaccinioides (Wollenweber et al. 1986), and B. viminea (Wollenweber et al. 1997). Also other two monomethylated derivatives were found: genkwanin (31) in aerial parts of B. crispa (Palacios et al. 1983), B. notosergila (Palacios et al. 1983), B. pedicellata (Faine et al. 1987), B. trimera (Nakasugi 1990; Nakasugi and Komai 1998), in leaves of B. trinervis (Herrera et al. 1996) as well as from B. genistelloides (Abad Martinez et al. 2005; Hennig et al. 2011) and B. pilularis (Wollenweber et al. 1997). Thevetiaflavone (32) was identified in aerial parts of B. gaudichaudiana (Guo et al. 2007; Campos et al. 2016). 4′,5- and 4′,7- dimethylated derivatives (33 and 34 derivatives, respectively) were identified in some Baccharis species, 7-Hydroxy-5,4′-dimethoxyflavone (33) was isolated from aerial parts of B. articulata (de Oliveira et al. 2014) and B. usterii (Salcedo Ortiz et al. 2001), while 5-Hydroxy-4′,7-dimethoxyflavone (34), from aerial parts of B. conferta (Weimann et al. 2002), B. crispa (Bandoni et al. 1978), B. illinita (Pizzolatti et al. 2006; Campos et al. 2016), from leaves of B. rhomboidalis (Silva et al. 1971), B. teindalensis (Vidari et al. 2003), B. tola (San Martin et al. 1982), B. trinervis (Herrera et al. 1996), and from B. latifolia (Salcedo Ortiz et al. 2001). Flavones biosynthesized from phenylalanine-cinnamic acid-pinocembrin were also identified: chrysin (35) and 7-methylchrysin (36) from leaves of B. dracunculifolia (Park et al. 2004; Paula et al. 2017) and B. viminea (Wollenweber et al. 1997). Its 2′-methoxylated derivative, 2′-methoxychrysin (37), was also identified from flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016). Hispidulin (38) was identified in aerial parts of B. flabellata (Saad et al. 1988), B. gaudichaudiana (Fullas et al. 1994; Akaike et al. 2003; Campos et al. 2016), B. genistelloides (Daily et al. 1984; San Martin et al. 2012), B. grisebachii (Tapia et al. 2004; Abad and Bermejo 2007), B. halimifolia (Joshi et al. 1997; Jakupovic et al. 1990), B. ligustrina (Moreira et al. 2003a, b; Abad and Bermejo 2007; Nogueira Sobrinho et al. 2016), B. magellanica (Cordano et al. 1982), B. rhomboidalis (Labbe et al. 1986), B. trimera (Soicke and Leng-Eschlow 1987; Nakasugi 1990; Nakasugi and Komai 1998; Padua et al. 2014), and B. uncinella (Grecco et al. 2010a, b, 2014a, b; Campos et al. 2016). Flavonoid 38 was also identified in leaves and shrub of B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007; Campos et al. 2016) and nonspecified parts of B. vaccinioides (Wollenweber et al. 1986). Pectolinaringenin (39) was identified in aerial parts of B. concava (Zamorano et al. 1987), B. conferta (Weimann et al. 2002), B. decussata (Morales Mendez et al. 1984; Rojas and Morales 2000), B. grisebachii (Gianello and Giordano 1987; Feresin et al. 2003; Abad Martinez et al. 2005), and B. uncinella (Grecco et al. 2010a, b, 2014a, b; Passero et al. 2011; Zalewski et al. 2011; Campos et al. 2016). Flavonoid (39) was also detected in the leaves of B. pedunculata (Rahalison et al. 1995), branches of B. trinervis (Sharp et al. 2000; Abad Martinez et al. 2005) [44, 103], and nonspecified parts of fresh B. macraei (Faini et al. 1991) [104], B. pilularis var. consanguinea (Wollenweber et al. 1997) [41] and B. vaccinioides (Wollenweber et al. 1986). Cirsimaritin (40) was identified in the aerial parts of B. concava (Zamorano et al. 1987), B. concinna (Wollenweber et al. 2006), B. conferta (Weimann et al. 2002), B. genistelloides (Suttisri et al. 1994; Abad Martinez et al. 2005; Hennig et al. 2011), B. rhomboidalis (Labbe et al. 1986), B. rufescens var. rufescens (Simirgiotis et al. 2003; Abad and Bermejo 2007; Campos et al. 2016), B. trimera (Nakasugi 1990; Nakasugi and Komai 1998), B. elaeagnoides (Mesquita et al. 1985), B. halimifolia (Joshi et al. 1997), B. intermedia and B. macraei (Faini et al. 1991), B. pilularis var. consanguinea (Wollenweber et al. 1997), and B. tricuneata (Wagner et al. 1978). Scutellarein-7,4′-dimethyl ether (41) was identified from aerial parts of B. tucumanensis (Tonn et al. 1982), while salvigenin (42) was found in the aerial parts of B. concava (Zamorano et al. 1987), B. conferta (Weimann et al. 2002), B. rhomboidalis (Labbe et al. 1986), and B. scandens (Cabrera et al. 2016). Flavonoid 42 was identified in the branches of B. trinervis (Sharp et al. 2000; Abad Martinez et al. 2005), and in nonspecified parts of B. macraei (Faini et al. 1991) and B. pilularis var. consanguinea (Wollenweber et al. 1997). Desmethoxysudachitin (43) was identified in the aerial parts of B. grisebachii (Gianello and Giordano 1987; Tapia et al. 2004; Grecco et al. 2010a, b; Campos et al. 2016) and B. solierii (Labbe et al. 1986). Its 4′-methylated derivative, nevadensin (44), was found in the aerial parts of B. decussata (Rojas and Morales 2000), B. grisebachii (Gianello and Giordano 1987; Feresin et al. 2003; Tapia et al. 2004; Grecco et al. 2010a, b), and B. nitida (Chidiak et al. 2007; Campos et al. 2016). A methylated derivative of 43 in position C-7 afforded xantomicrol (45) found in aerial parts of B. boliviensis (Calle et al. 2012; Campos et al. 2016), B. nitida (Chidiak et al. 2007; Campos et al. 2016), B. patens (Silva et al. 1985), B. scandens (Cabrera et al. 2016), and B. tucumanensis (Tonn et al. 1982). Compound 45 was also found in the leaves of B. pentlandii (Tarqui et al. 2012) and roots of B. quitensis (Bohlmann et al. 1981b). Gardenin B (46) was identified in the aerial parts of B. grisebachii (Feresin et al. 2003; Tapia et al. 2004; Campos et al. 2016) and B. scandens (Cabrera et al. 2016). A pentamethoxylated derivative, tangeretin (47), was found in the flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016). The flavone luteolin (48), derived from dehydration of flavanone eriodictyol, was identified in aerial parts of B. articulata (Cariddi et al. 2012), B. bigelovii (Arriaga-Giner et al. 1986; Wollenweber et al. 1986), B. concinna (Wollenweber et al. 2006), B. confertifolia (Wollenweber et al. 2006), B. gaudichaudiana (Guo et al. 2007), B. genistelloides (San Martin et al. 2012), B. incarum (Zampini et al. 2009; Campos et al. 2016), B. linearis (Wollenweber et al. 2006), B. lycioides (Wollenweber et al. 2006), B. reticularia (Bohlmann et al. 1981a), B. trimera (Soicke and Leng-Eschlow 1987; da Silva et al. 2016; Menezes et al. 2016), B. trinervis (Jaramillo-Garcia et al. 2018), and B. varians (Bohlmann et al. 1981a). Furthermore, flavonoid 48 was isolated from flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016), and nonspecified parts of B. halimifolia (Wollenweber et al. 1997), B. microcephala (Bohlmann et al. 1985), B. nitida (Bohlmann et al. 1985), and B. pteronioides (Wollenweber et al. 1986). Methylated derivatives of luteolin, biosynthesized through luteolin-methyltransferase, were found in several studied Baccharis species. A monomethylated (C-3′) derivative, chrysoeriol (49), was identified in the flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016), shrub of B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007; Campos et al. 2016), and aerial parts of B. salicifolia (Warning et al. 1986). 4′,7- and 3′,7- Dimethylated derivatives of Luteolin were also found in Baccharis genus, luteolin-4′,7-dimethylether (50) in aerial parts of B. trimera (Padua et al. 2014; de Araujo et al. 2016), and leaves of B. trinervis (Herrera et al. 1996) and luteolin-3′,7-dimethylether (51) in aerial parts of B. calliprinos (Gianello et al. 1999), B. rhetinodes (Gianello et al. 1999), and B. salicifolia (Warning et al. 1986). The trimethylated derivative, 5-hydroxy-7,3′,4′-trimethoxyflavone/luteolin-3′,4′,7-trimethylether (52), was identified in the aerial parts of B. crispa (Bandoni et al. 1978) [80], B. latifolia (Salcedo et al. 2003; Campos et al. 2016), and in the leaves of B. trinervis (Herrera et al. 1996). 6-Hydroxyluteolin (53) was found only in aerial parts of B. boliviensis (Campos et al. 2016), while its methylated derivatives were identified in several Baccharis species; nepetin, also known as eupafolin (54), was identified in aerial parts of B. concinna (Wollenweber et al. 2006), B. confertifolia (Wollenweber et al. 2006), B. flabellata (Saad et al. 1988), B. gaudichaudiana (Akaike et al. 2003; Campos et al. 2016), B. genistelloides (San Martin et al. 2012), B. linearis (He 1995; He et al. 1996; Wollenweber et al. 2006), B. lycioides (Wollenweber et al. 2006), and B. trimera (Soicke and Leng-Eschlow 1987; Simões-Pires et al. 2005). Jaceosidin (55) was isolated from aerial parts of B. concinna (Wollenweber et al. 2006), B. flabellata (Saad et al. 1988), B. gaudichaudiana (Akaike et al. 2003; Campos et al. 2016), and B. grisebachii (Tapia et al. 2004). Desmethoxycentaureidin (56) was obtained from aerial parts of B. gaudichaudiana (Akaike et al. 2003; Campos et al. 2016), B. solierii (Labbe et al. 1986), and nonspecified parts of B. petiolata (Labbé et al. 1990) and B. salicina (Parodi and Fischer 1988; Quijano et al. 1998). Cirsiliol (57) was identified in the aerial parts of B. concinna (Wollenweber et al. 2006), B. confertifolia (Wollenweber et al. 2006), B. flabellata (Saad et al. 1988), B. linearis (Wollenweber et al. 2006), B. rufescens var. rufescens (Simirgiotis et al. 2003; Abad and Bermejo 2007; Campos et al. 2016), and in nonspecified parts of B. genistelloides (Kuroyanagi et al. 1985; Abad Martinez et al. 2005; Hennig et al. 2011) and B. tricuneata. Cirsilineol (58) was detected in aerial parts of B. concinna (Wollenweber et al. 2006), B. salicifolia (Warning et al. 1986), and nonspecified parts of B. genistelloides (Abad Martinez et al. 2005; Hennig et al. 2011), while 5,6-dihydroxy-3′,4′,7-trimethoxyflavone (59) from young parts of B. trimera (Borella et al. 2006). The aerial parts of B. conferta (Weimann et al. 2002) and B. gaudichaudiana (Akaike et al. 2003; Campos et al. 2016) afforded eupatilin (60), while aerial parts of B. genistelloides (Suttisri et al. 1994; Hennig et al. 2011) and leaves, stems, flowers, and fruits of B. trimera (Herz et al. 1977; de Mello and Petrovick 2000; Torres et al. 2000; da Silva et al. 2004; Silva et al. 2006; Padua et al. 2014; de Araujo et al. 2016) afforded eupatorin (61). 5-Hydroxy-3′,4′,6,7-tetramethoxyflavone (62) was identified from aerial parts of B. genistelloides (Suttisri et al. 1994) and leaves of B. trimera (Rendon and Vila 1995; Silva et al. 2006). Sideritiflavone (63) was detected in aerial parts of B. patens (Silva et al. 1985) and B. thymifolia (Saad et al. 1987) as well as from leaves of B. pentlandii (Tarqui et al. 2012; Campos et al. 2016;). 4′,5-Dihydroxy-3′,6,7,8-tetramethoxyflavone (64), known as 7-methylsudachitin or 3′-methoxyxanthomicrol, was identified from aerial parts of B. incarum (Faini et al. 1982a, b), B. salicifolia (Warning et al. 1986) and B. thymifolia (Saad et al. 1987), from leaves of B. pentlandii (Tarqui et al. 2012; Campos et al. 2016), and roots of B. oxyodonta and B. quitensis (Bohlmann et al. 1981b). Gardenin D (65) was identified in aerial parts of B. patens (Silva et al. 1985). A pentamethoxylated derivative, 5-hydroxy-3′,4′,6,7,8-pentamethoxytlavone (66), was detected only in aerial parts of B. thymifolia (Saad et al. 1987). Nobiletin was identified only in the flowers of B. illinita (67). Although in less distribution, flavone glycosides were found in Baccharis species: isoschaftoside (68) was identified in the aerial parts of B. gaudichaudiana (Akaike et al. 2003; Campos et al. 2016), while vicenin II (69), 6(8)-C-furanosyl-8(6)-C-hexosyl flavone (70), 6(8)-C-hexosyl-8(6)-C-furanosyl flavone (71), and 5,3′-dihydroxy-4′-methoxy-7-O-pyranosyl-furanosyl flavone (72) were detected in the aerial parts of B. trimera (Padua et al. 2014; de Araujo et al. 2016; Rabelo et al. 2017). Flavones identified in Baccharis species are summarized in Table 11.3, followed by their respective structures in Fig. 11.7.
Structures of flavones 28–72 identified in Baccharis species
7 Flavanols
The biosynthesis of flavanols, the main group of flavonoids of genus Baccharis, occurs after the formation of flavanonols, through flavanol synthase enzyme (FLS). Thus, naringenin (1) is converted to aromadendrin/dihydrokaempferol (17) to finally afford the flavanol kaempferol (73). Compound 73 was identified in aerial parts of B. conferta (Weimann et al. 2002), B. dentata (Sartor et al. 2013; Campos et al. 2016), B. gaudichaudiana (Campos et al. 2016), B. polycephala (Davila et al. 2013), B. trimera (da Silva et al. 2016), and B. retusa (Campos et al. 2016; Grecco et al. 2012a). This compound was also identified in the flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016), flowering tops of B. maritima (Moreira et al. 1975), leaves of B. pseudotenuifolia (Moreira et al. 2003a, b; Campos et al. 2016), and buds, stems, and vegetative gems of B. dracunculifolia (Palacios et al. 1983; Park et al. 2004, 2005; de Alencar et al. 2005) and nonspecified parts of B. genistelloides (Daily et al. 1984), and B. pilularis var. consanguinea (Wollenweber et al. 1997). The 3-methylation of kaempferol afforded isokaempferide (74) identified in the aerial parts of B. linearis (Faini et al. 1999; Wollenweber et al. 2006), B. lycioides (Wollenweber et al. 2006), and B. pedicellata (Faine et al. 1987). Furthermore, this compound was also identfiied in the leaves of B. papillosa (Escobar et al. 2009; Campos et al. 2016), and nonspecified parts of fresh B. intermedia (Faini et al. 1991), B. linearis (Faini et al. 1991), B. macraei (Faini et al. 1991), and B. pilularis var. consanguinea (Wollenweber et al. 1997). The 4′-methylation affords kaempferide (75), found in aerial parts of B. conferta (Weimann et al. 2002) and B. polycephala (Davila et al. 2013) as well as in the flowers, leaves, buds, stems, and vegetative gems of B. dracunculifolia (Midorikawa et al. 2003; Park et al. 2004, 2005; de Alencar et al. 2005; Piantino et al. 2008; Campos et al. 2016; Paula et al. 2017), in no-nspecified parts of B. leptophylla (Almanza et al. 2000; Mollinedo et al. 2001) and in B. pilularis var. consanguinea and B. viminea (Wollenweber et al. 1997). Kaempferol-7-methyleter (76) was identified only in B. pilularis var. consanguinea (Wollenweber et al. 1997). The leaves of B. papillosa (Campos et al. 2016) afforded emanin (77), also identified in buds, leaves, and stems of B. dracunculifolia (Midorikawa et al. 2003; da Silva Filho et al. 2009) and from nonspecified parts of B. pilularis var. consanguinea and from B. viminea (Wollenweber et al. 1997). Kaempferol-7,4′-dimethyl ether (78) was detected in the aerial parts of B. crispa (Bandoni et al. 1978) and B. illinita (Pizzolatti et al. 2006; Campos et al. 2016) as well as from leaves of B. teindalensis (Vidari et al. 2003). Kaempferol-3,7-dimethyl ether (79) was identified in the aerial parts of B. pedicellata (Faine et al. 1987) and B. santelicis (Zdero et al. 1991) and nonspecified parts of B. pilularis var. consanguinea (Wollenweber et al. 1997). The trimethylated derivative, kaempferol-3,4′,7-trimethylether (80), was identified in the aerial parts of B. illinita (Pizzolatti et al. 2006; Campos et al. 2016) and B. santelicis (Zdero et al. 1991). Galangin (81) was detected in the leaf bud of B. dracunculifolia (Park et al. 2005) and nonspecified parts of B. viminea (Wollenweber et al. 1997), that also afforded galangin-7-methyleter (82). 6-Hydroxylated kaempferol and its derivatives were identified in few Baccharis species, 6-hydroxykaempferol (83) in B. pilularis var. consanguinea (Wollenweber et al. 1997); 6-methoxykaempferol (84) in leaves of B. dracunculifolia (Kumazawa et al. 2003); 4′,6-dimethoxykaempferol (85) in aerial parts of B. conferta (Weimann et al. 2002); and 6,7-dimethoxykaempferol (86) in B. pilularis var. consanguinea (Wollenweber et al. 1997). Penduletin (87) was identified in leaves of B. pedunculata (Rahalison et al. 1995), branches of B. trinervis (Sharp et al. 2000; Abad Martinez et al. 2005), and nonspecified parts of B. salicifolia, B. sarothroides and B. vaccinioides (Wollenweber et al. 1986), while herbacetin-3-methylether (88) was isolated from B. pilularis var. consanguinea (Wollenweber et al. 1997). Quercetin (89) was identified in the aerial parts of B. articulata (Campos et al. 2016), B. bigelovii (Arriaga-Giner et al. 1986; Wollenweber et al. 1986), B. concinna and B. confertifolia (Wollenweber et al. 2006), B. dentata (Sartor et al. 2013; Campos et al. 2016), B. genistelloides (Daily et al. 1984; San Martin et al. 2012), B. grisebachii (Tapia et al. 2004), B. linearis (Wollenweber et al. 2006, B. lycioides (Wollenweber et al. 2006), B. pteronioides, B. retusa, B. salicifolia (Wollenweber et al. 1986), B. scandens (Cabrera et al. 2016), B. thesioides (Liu et al. 1993), B. trimera (Soicke and Leng-Eschlow 1987; Simões-Pires et al. 2005; Padua et al. 2014; da Silva et al. 2016; de Araujo et al. 2016; Menezes et al. 2016; Sabir et al. 2017), B. trinervis (Jaramillo-Garcia et al. 2018), in the leaf bud of B. dracunculifolia (Park et al. 2005), leaves and shrubs of B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007; Campos et al. 2016), leaves, stems, and flowers of B. spicata (Agudelo et al. 2016) flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016) and B. maritima (Moreira et al. 1975) as well as in the nonspecified parts of B. viminea (Wollenweber et al. 1997). Rhamnetin (90) was detected in leaves and stems of B. confertifolia (Wollenweber et al. 2006) and nonspecified parts of B. pilularis var. consanguinea (Wollenweber et al. 1997), while isorhamnetin (91) was detected in the aerial parts of B. tola, leaves and stems of B. linearis (He 1995; Wollenweber et al. 2006) and B. lycioides (Wollenweber et al. 2006), leaves and shrubs of B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007; Campos et al. 2016), and in nonspecified parts of B. viminea (Wollenweber et al. 1997). The 3-methylated derivative of quercetin, 3-methylquercetin (92), was identified in the aerial parts of B. tola (Simirgiotis et al. 2016) and B. trimera (de Mello and Petrovick 2000), in the leaves of B. linearis (Faini et al. 1999), flowers of B. illinita (Verdi et al. 2004; Abad and Bermejo 2007; Campos et al. 2016), fresh parts of B. intermedia and B. linearis (Faini et al. 1991) as well as in the nonspecified parts of B. halimifolia (Wollenweber et al. 1997). Rhamnazin (93) was found in the aerial parts of B. tola (Simirgiotis et al. 2016), leaves and stems of B. confertifolia (Wollenweber et al. 2006), and nonspecified parts of B. latifolia (Salcedo et al. 2001). Isorhamnetin 3-methylether (94) was identified in the aerial parts of B. tola (Simirgiotis et al. 2016), leaves and stems of B. linearis (Faini et al. 1999; Wollenweber et al. 2006) and B. lycioides (Wollenweber et al. 2006), and in the nonspecified parts of fresh B. intermedia and B. linearis (Faini et al. 1991). B. sarothroides afforded 3,4′-dimethoxy-3′,5,7-trihydroxyflavone (95) (Abad Martinez et al. 2005), while 3,7-dimethoxyquercetin (96) was found in aerial parts of B. triangularis (Gianello and Giordano 1989) and nonspecified parts of B. pilularis var. consanguinea (Wollenweber et al. 1997). 3,7-Dimethylisorhamnetin (97) was isolated from aerial parts of B. tola (Simirgiotis et al. 2016), while 3,7,4′-trimethylquercetin (98) was obtained from leaves and stems of B. illinita (Campos et al. 2016) and nonspecified parts of B. grisebachii (Abad and Bermejo 2007). 3,5-dihydroxy-7,3′,4′-trimethoxyflavone (99) was detected in B. latifolia. Retusin (100) was isolated from leaves and stems of B. illinita (Pizzolatti et al. 2006; Campos et al. 2016), while 3-hydroxy-5,7,3′,4’tetramethoxyflavone (101) was obtained from aerial parts of B. latifolia (Salcedo et al. 2003; Campos et al. 2016) and B. conferta (Weimann et al. 2002). Patuletin (102) was detected in leaves and stems of B. concinna and B. confertifolia (Wollenweber et al. 2006) as well as in nonspecified parts of B. halimifolia and B. pilularis var. consanguinea (Wollenweber et al. 1997). Flavonoid 3′-methylpatuletin (103) was detected in B. halimifolia (Wollenweber et al. 1997), while axillarin (104) was identified in the leaves and stems of B. incarum (Campos et al. 2016), B. linearis (Labbe et al. 1986; Wollenweber et al. 2006), and B. solierii (Labbe et al. 1986) as well as in the nonspecified parts of B. halimifolia (Wollenweber et al. 1997). Eupatolitin (105) was isolated from leaves and stems of B. confertifolia (Wollenweber et al. 2006) and aerial parts of B. gaudichaudiana (Akaike et al. 2003). Centaureidin (106) was identified in the leaves and twigs of B. sarothroides (Montes et al. 1971; Abad Martinez et al. 2005), leaves and stems of B. solierii (Labbe et al. 1986), and nonspecified parts of B. salicina (Parodi and Fischer 1988; Quijano et al. 1998). 5,7-Dihydroxy-3,6,3′,4′-tetramethoxyflavone (107) was detected in B. salicina (Quijano et al. 1998), while three gossypetin derivatives (108–110) were identified in leaves and stems of B. linearis (Wollenweber et al. 2006): 3,3′-dimethyl- (108), 3,8-dimethyl- (109) and 3,8,3′-trimethyl-(110) derivatives. 3′,4′,5,7-Tetrahydroxy-3,6,8-trimethoxyflavone (111) and 4′,5,7-trihydroxy-3,3′,6,8-tetramethoxyflavone (112) were identified in the leaves and stems of B. incarum (Campos et al. 2016); compound 112 was also identified in the leaves and stems of B. solierii (Labbe et al. 1986). 3′,5-Dihydroxy-3,4′,6,7,8-pentamethoxyflavone (113) was detected in the aerial parts of B. boliviensis (Campos et al. 2016) and 4′,5-dihydroxy3′,,3,6,7,8-pentamethoxyflavone (114) in the leaves and stems of B. incarum (Faini et al. 1982a, b; Nuño et al. 2012; Campos et al. 2016). Six myricetin derivatives (115–120) were detected in leaves and stems of B. tola (Simirgiotis et al. 2016): 3-O-acetyl- (115), 7,3′-dimethyl- (116), 7,3′,5′-trimethyl- (117), 3′,5′,7,8-tetramethyl- (118), 6-hydroxy-7,3′,5′-trimethyl – (119) and 6-hydroxy-3,7,3′,5′-tetramethyl (120) derivatives. Additionally, nine flavonol glycosides (121–129) were identified in several species of Baccharis: apigenin 3-O-β-D-glucopyranoside, also known as astragalin (121), from aerial parts of B. dracunculifolia (Nagatani et al. 2001) and from B. angustifolia (Wagner et al. 1972), kaempferol-3-O-rutinoside, also known as nicotiflorin (122), from B. antioquensis (Mejia-Giraldo et al. 2016), quercetin 3-O-[β-D-apiofuranosyl-(1 → 2) α-Lrhamnopyranosyl-(1 → 6)]-β-D-glucopyranoside (123) from B. thesioides (Liu et al. 1993), isoquercetin (124) from aerial parts of B. dracunculifolia (Nagatani et al. 2001), B. thesioides (Kakehashu et al. 2016), B. trimera (Simões-Pires et al. 2005), B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007; Campos et al. 2016), B. angustifolia (Wagner et al. 1972), and B. ochracea (Schenkel et al. 1997). Hyperoside (125) was detected in the aerial parts of B. dracunculifolia (Nagatani et al. 2001) and B. thesioides (Liu et al. 1993) [144], while quercitrin (126) was identified in B. gaudichaudiana (Akaike et al. 2003; Campos et al. 2016), B. microdonta (Toyama et al. 2014), and B. pseudotenuifolia (Moreira et al. 2003a, b; Abad and Bermejo 2007; Campos et al. 2016). Rutin (127) was identified in the aerial parts of B. gaudichaudiana (Akaike et al. 2003; Campos et al. 2016), B. thesioides (Liu et al. 1993), B. trinervis (Jaramillo-Garcia et al. 2018), and B. trimera (Gene et al. 1996; Menezes et al. 2016; Sabir et al. 2017). Furthermore, flavonoid 127 was also isolated from leaves of B. antioquensis (Mejia-Giraldo et al. 2016), leaves and stems of B. dentata (Sartor et al. 2013; Campos et al. 2016), leaves, stems, and flowers B. spicata (Agudelo et al. 2016), and nonspecified parts of B. genistelloides (Hennig et al. 2011). Finally, quercetin-3-O-(4″’-O-caffeoyl)-rhamnopyranosyl-(1 → 6)-galactopyranoside (128) was identified in the leaves of B. antioquensis (Mejia-Giraldo et al. 2016). Flavanols identified in Baccharis species are summarized in Table 11.4, followed by their respective structures in Fig. 11.8.
Structures of flavanols 73–128 identified in Baccharis species Biological activities
Flavonoids display a significant role in biological functions, especially those that depend on the modulation of redox balance. Several studies describes the antioxidant and radical scavenger activities of extracts and isolated flavonoids of Baccharis, such as the antioxidant activities of isosakuranetin (3), dihydrokaempferide (19), kaempferol (75) (Mollinedo et al. 2001), isokaempferide (74), ermanin (77), 3-methylquercetin (92) (Escobar et al. 2009), luteolin (48), axillarin (104), 3′,4′,5,7-tetrahydroxy-3,6,8-trimethoxyflavone (111), 4′,5,7-trihydroxy-3,3′,6,8-tetramethoxyflavone (112), and 4′,5-dihydroxy-3′,3,6,7,8-pentamethoxyflavone (114). Antioxidant activities were also attributed to extracts of B. spicata, B. tola, and B. trimera (Agudelo et al. 2016; Simirgiotis et al. 2016; Sabir et al. 2017), while radical scavenger activity (DPPH, ROS) was attributed to B. dentata and B. trimera extracts (Sartor et al. 2013; Agudelo et al. 2016; Sabir et al. 2017). The last extract also inhibits ROS production through PKC and downregulates p47phox phosphorylation of NADPH oxidase in SK Hep-1 cells. Hispidulin (38), desmethoxysudachitin (43), jaceosidin (55), and quercetin (89) suppress/scavenge erythrocyte lipoperoxidation, 38 and 89 superoxide anions, and 89 DPPH (Tapia et al. 2004). Eupafolin (54), quercitrin (127), and rutin (128) moderately scavenge DPPH radical (Akaike et al. 2003). Compounds 48, 104, 111, 112, and 114 also displayed antimicrobial activity against methicillin-resistant Staphylococcus aureus and Enterococcus faecalis (Zampini et al. 2009; Nuño et al. 2012). Antimicrobial activities were also attributed to some flavonoids: penduletin (87) presented antifungal activity against some human pathogenic and phytopathogenic fungi (Rahalison et al. 1995). Isosakuranetin (3) showed antifungal activities against Neurospora crassa (Almanza et al. 2000) and Cryptococcus neoformans (da Silva Filho et al. 2008); besides the antioxidant activity, previously described, compound 3 also demonstrated strong trypanocidal (da Silva Filho et al. 2004) and antiinflammatory activities (Figueiredo-Rinhel et al. 2013); both activities were also attributed to dihydrokaempferide (19). B. dentata extracts presented antibacterial activity against Staphylococcus aureus (Sartor et al. 2013), while B. crispa and B. notosergila ethanolic extracts presented antimicrobial activities against Bacillus subtilis, Micrococcus luteus, and Staphylococcus aureus, due to the presence of genkwanin (31) and apigenin (28). Sakuranetin (2) presented antifungal activity against pathogenic yeast belonging to the genus Candida (six species – C. dubliniensis, C. tropicalis, C. glabrata, C. parapsilosis, C. krusei, and C. albicans), Cryptococcus (two species/four serotypes – C. neoformans – serotypes A and D, C. gattii – serotypes B and C. neoformans), and Saccharomyces cerevisiae (Grecco et al. 2014a, b). Compound 2 demonstrated promising activities to prevent and treat several respiratory disorders, such as acute lung injury (Bittencourt-Mernak et al. 2017), chronic allergic pulmonary inflammation (Sakoda et al. 2016), emphysema, through regulation of NF-κB, oxidative stress, and metalloproteinases (Taguchi et al. 2015a, b),and reverses airway inflammation and remodelling in an asthma murine model (Toledo et al. 2013). Sakuranetin (2) displayed activity against four Leishmania species (L. amazonensis, L. braziliensis, L. major, and L. chagasi) and Trypanosoma cruzi (Davila et al. 2013) and also presented phytotoxic activities against Panicum miliaceum and Raphanus sativus, inhibiting its growth and germination (del Corral et al. 2012). Pectolinaringenin (39) and cirsimaritin (40) present spasmolytic activities (Weimann et al. 2002) and antiparasitic potential (antileishmanial and trypanocidal). This was attributed to 5,6,7-trihydroxy-4′-methoxyflavanone (4), hispidulin (38), spectolinaringenin (39), acacetin (30), and ermanin (77) (da Silva Filho et al. 2009; Passero et al. 2011; Grecco et al. 2010a, b, 2014a, b). Luteolin-3′,7-dimethylether (51) displayed anti-inflammatory activity (Gianello et al. 1999), which was also attributed to rutin (128), within its analgesic effect (Gene et al. 1996) and pectolinaringenin (39) (Zalewski et al. 2011). B. gaudichaudiana and B. spicata presented antiviral activities against poliovirus type 2 (PV2) and vesicular stomatitis virus; PV2 attributed to the presence of apigenin (28) (Visintini et al. 2013) This compound also enhances the action of nerve growth factor to stimulate neurite outgrowth from PC12D cells, that could be useful in the treatment of neurological disorders (Guo et al. 2007). B. articulata extract induced the death of human peripheral blood mononuclear cells (PBMCs) through apoptosis and exerted low mutagenic effects on mice, those could be related to the presence of luteolin (48) and acacetin (30) and other nonflavonoidic compounds (Cariddi et al. 2012). Antitumoral activities were attributed to 3,4′-dimethoxy-3′,5,7-trihydroxyflavone (95) and centaureidin (106) (Montes et al. 1971), while gardenin B (46) demonstrated cytotoxic activities against HL60 and U937 – human leukemia cell lines, leading to activation of extrinsic and the intrinsic apoptotic pathways (Cabrera et al. 2016). Kaempferol and quercetin glycosides (123, 128 and 129) from B. antioquensis displayed photoprotective potential, while quercitrin (127) displayed antivenom effect (Crotalus durissus terrificus snake) through inhibition of sPLA2 enzyme, preventing myotoxicity and edematogenic effect. Genkwanin (31), cirsimaritin (40), hispidulin (38), and apigenin (28) showed antimutagenic activity (Nakasugi and Komai 1998), while quercetin (89), luteolin (48), nepetin (54), apigenin (28), and hispidulin (38) were responsible for antihepatotoxic properties of B. trimera (Soicke and Leng-Eschlow 1987), leading to a protective effect against acute hepatic injury induced by acetaminophen (Padua et al. 2014), an effect also detected in B. dracunculifolia leaves extract (Rezende et al. 2014). B. teindalensis displayed antiulcer and antidiarrhoeic effects (Vidari et al. 2003), also observed for B. dracunculifolia extracts, with inhibition of doxorubicin-induced mutagenicity (Resende et al. 2007). Finally, stems of B. illinita presented anticoagulant activity, leading to a significant effect on platelet aggregation (Pizzolatti et al. 2006) and B. trinervis displayed cytotoxic, genotoxic, and mutagenic activities that could be related to the presence of flavonoids (Jaramillo-Garcia et al. 2018).
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dos Santos Grecco, S., Sessa, D.P., Lago, J.H.G. (2021). Flavonoids of Baccharis. In: Fernandes, G.W., Oki, Y., Barbosa, M. (eds) Baccharis. Springer, Cham. https://doi.org/10.1007/978-3-030-83511-8_11
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