Sesquiterpenes, diterpenes, alkenyl p-coumarates, and flavonoid from the aerial parts of Baccharis retusa (Asteraceae)

Chemical Constituents from Aerial Parts of Baccharis sphenophylla and Effects against Intracellular Forms of Trypanosoma cruzi

“…NMR and ESI‐HR‐MS spectral data analysis followed by comparison with reports in literature allowed the identification of ent ‐kaur‐16‐en‐19‐oic acid ( 2 ), [15] grandifloric acid ( 3 ), [16] 15β‐tiglinoyloxy‐ ent ‐kaur‐16‐en‐19‐oic acid ( 4 ), [17] spathulenol ( 5 ), [18] oplopanone ( 6 ), [19] and hexacosyl p‐ coumarate ( 7 ) [20] . Compounds 2 , 3 and 5 have previously been isolated from B. concinna , [21] B. minutiflora , [22] B. potosina , [23] B. pylicoides , [24] B. quitensis , [21] B. retusa , [15] B. salzmannii , [25] and B. truncata , [21] whereas this is the first occurrence of 4 , 6 and 7 in the Baccharis genus. Diterpenes, especially those with ent ‐kaurane, labdane and isopimarane skeleton, are commonly found in the genus, but the presence of sesquiterpenes is more restrict, having been previously described only in essential oils studies, [26–28] including one from B. sphenophylla [29] .…”

“…Chemical investigation of the bioactive extract provided seven compounds ( 1 – 7 ) as shown in Figure 1. NMR and ESI‐HR‐MS spectral data analysis followed by comparison with reports in literature allowed the identification of ent ‐kaur‐16‐en‐19‐oic acid ( 2 ), [15] grandifloric acid ( 3 ), [16] 15β‐tiglinoyloxy‐ ent ‐kaur‐16‐en‐19‐oic acid ( 4 ), [17] spathulenol ( 5 ), [18] oplopanone ( 6 ), [19] and hexacosyl p‐ coumarate ( 7 ) [20] . Compounds 2 , 3 and 5 have previously been isolated from B. concinna , [21] B. minutiflora , [22] B. potosina , [23] B. pylicoides , [24] B. quitensis , [21] B. retusa , [15] B. salzmannii , [25] and B. truncata , [21] whereas this is the first occurrence of 4 , 6 and 7 in the Baccharis genus.…”

“…Diterpenes, especially those with ent ‐kaurane, labdane and isopimarane skeleton, are commonly found in the genus, but the presence of sesquiterpenes is more restrict, having been previously described only in essential oils studies, [26–28] including one from B. sphenophylla [29] . Concerning the C 6 C 3 derivatives such as compound 7 , the occurrence of alkyl p‐ coumarates containing unsaturated side chains were previously reported in B. retusa [15] . Compound 1 was isolated as a white amorphous solid with [α] D 24 =−12.5 ( c =0.1, CHCl 3 ).…”

“…[29] Concerning the C 6 C 3 derivatives such as compound 7, the occurrence of alkyl p-coumarates containing unsaturated side chains were previously reported in B. retusa. [15] Compound 1 was isolated as a white amorphous solid with [α] D 24 = À 12.5 (c = 0.1, CHCl 3 ). The IR spectrum showed absorption peaks at υ max 3412, 1730 and 1660 cm À 1 of hydroxy group, carbonyl group (lactone), and double bonds, respectively.…”

Two New Flavonoids from the Leaves of Baccharis oblongifolia (Ruiz and Pav.) Pers. (Asteraceae)

“…Some Baccharis species are used in folk medicine, including for spasmolytic, diuretic, and analgesic purposes and for the treatment of ulcers, fever, gastrointestinal illnesses, diabetes, and microbial infections [4,5,6]. Previous phytochemical studies of this genus have reported several classes of natural products, such as chlorogenic acid derivatives [4,7,8,9,10], terpenoids [11,12,13,14,15,16,17,18,19,20,21,22], especially diterpenes with dozens of isolated compounds from Baccharis [4,5,17,18,19,20,21,22], and flavonoids from flavone, flavanone, and flavonol types [4,5,21,22,23,24,25,26]. Furthermore, it has also been described as having diverse biological activities including antimicrobial [4,5,6,14,15], antiviral [4,5,6], antiprotozoal [9,24,25], anti-inflammatory [10,13], cytotoxic [4,5,6,23], and antioxidant [7,13,14,15,22,…”