taxonID	type	description	language	source
03F88786C314FFD2FE6A4B66FA97F977.taxon	discussion	Four species of Grazielia were sampled and analyzed in this study. 68 compounds were identified in the VOs obtained from the species in this genus, amounting to 87.6 – 99.9 % of the VOs. All the VOs obtained from the leaves and / or inflorescences of the species in this genus were characterized by the predominance of hydrocarbon monoterpenes (63.8 – 80.1 %) with the same compounds being identified among the major constituents of all the samples. In the VOs obtained from the branches of G. nummularia (Hook. & Arn.) R. M. King & H. Rob a lower percentage of monoterpenes was present. Two samples of the 0.3 – 1.5 m tall, low-branched, white-flowered sub-shrub native to Southern Brazil (from Minas Gerais to Rio Grande do Sul) (King and Robinson, 1987; Matzenbacher, 1979)	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C314FFD1F81448FCFA42FAA8.taxon	discussion	were collected in Canela and Paraíso do Sul, which exhibited VOs with very similar chemical compositions in terms of the monoterpene fraction. The major compounds in this fraction were α- pinene (12.4 – 15.5 %), β- pinene (9.2 – 28.9 %), and limonene (18.3 – 37.2 %). The sample from Canela / 05 also showed a large percentage of α- thujene (10.1 %). In the sesquiterpene fraction, the VOs presented large quantitative differences. The VOs obtained from a region of higher altitude (Canela) were characterized by the presence of sesquiterpene hydrocarbon compounds with a germacrane nucleus, namely germacrene D and bicyclogermacrene (11.3 and 7.6 %), these compounds did not reach 2 % of the VOs obtained from the Paraíso do Sul / 06 sample. In the VOs from the samples obtained from the lower central region, this fraction was characterized by the predominance of an oxygenated compound with an aromadendrane nucleus, spathulenol (20.5 and 9.4 % in the leaves and inflorescences, respectively). The transformation of bicyclogermacrene and germacrene D into spathulenol has already been reported (Toyota et al., 1996; Venturi et al., 2015). Previously, several diterpenes bearing an ent-caurane nucleus have been isolated from this species collected in S ˜ ao Paulo state (Taleb et al., 1999) and from a sample collected in Parana´state, a cytotoxic 18 - nor-ent-labdane furan was isolated together with sterols, triterpenes, and flavonols (Balbinot et al., 2019). The yield of the VOs has already been reported to be 1.09 – 1.29 % (in dry and fresh inflorescences, respectively), which was in the same range as our samples, but the chemical composition has not been previously reported (Souza, 2015). In Southeastern Brazil, this species has been reported to be associated with Cecidomyiidae stem gall inducers (Coelho et al., 2013) and an unknown lepidopteran leaf gall inducer whose galls were occupied by coleopterans (Maia and Mascarenhas, 2017). In addition, its flower heads have been reported to be a feeding site for adults of the very endangered endemic Nymphalidae butterfly Actinote zikani (Francini et al., 2005), the threatened Pierideae butterfly Charonias theano (Freitas et al., 2011), and the Ithomiiniae Placidula euryanassa (which also feeds on other Eupatorieae, such as Chromolaena laevigata and Barrosoa betoniciiformis) (Freitas, 1993). The role of VOs in the interactions between plants and insects, gall inducers, leaf-suckers, and leaf-eaters has been previously studied (Jiang et al., 2018; Rost´as et al., 2013; Tooker et al., 2008; Tooker and De Moraes, 2008). For instance, Malacosoma disstria caterpillars induce a germacrene D synthase in Populus trichocarpa × deltoides by feeding on that species, possibly implying a role for this compound in attracting the caterpillar’ s natural enemies in a tri-trophic interaction (Arimura et al., 2004). On the other hand, the moth Heliothis virescens (Noctuidae) is attracted by () - germacrene D in tobacco, enhancing oviposition in the plant (Mozuraitis et al., 2002; Røstelien et al., 2000). Limonene exhibits insect repellent activity (Hebeish et al., 2008; Tripathi et al., 2003), while β- pinene has also been shown to be neurotoxic to the coleopteran Tribolium castaneum by inducing the overexpression of the histamine-gated chloride channel 2 (Hiscl 2), GABA-gated ion channel (Grd), and acetylcholinesterase (Ace 1) Ace 1 genes (Pajaro-Castro et al., 2017). The role of the VOs produced by G. gaudichaudieana during the interaction of this species with insects remains to be established.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C317FFD0FE094B36FEF3FB68.taxon	discussion	a 0.3 – 0.9 m tall, low-branched, white-flowered sub-shrub native to Southern Brazil (Parana´and Rio Grande do Sul), which is anatomically very similar and exhibits the same geographical distribution as G. gaudichaudieana (King and Robinson, 1987; Matzenbacher, 1979), was collected in Sapiranga (2006). The VOs in its leaves / inflorescences are also qualitatively and quantitatively very similar to those obtained from G. gaudichaudieana. Hydrocarbon monoterpenes are the main fraction (78.9 %) and are composed of the same substances that make up the VOs in G. gaudichaudieana (α- pinene, 8.5 %; β- pinene, 20.5 %; and limonene, 36.5 %). The sesquiterpene fraction is very similar to that of the G. gaudichaudieana sample obtained from Canela / 05 with 10.1 vs 11.3 % germacrene D. The VOs obtained from the branches of G. nummularia present some quantitative differences when compared to the plant’ s leaves: A lower percentage of pinenes (α- pinene, 2.8 %; β- pinene, 10.0 %) and a higher percentage of para-cymene (5.5 % vs 1.8 % in the leaves / inflorescences), the percentage of limonene was similar in both subsamples (31.5 vs 36.5 %), and the hydrocarbon sesquiterpene germacrene D was higher in the branches (26.3 % vs. 10.1 %). This is the first piece of evidence showing that the lesser-known G. nummularia is not only botanically and geographically, but also chemically similar to G. gaudichaudieana, suggesting that the bouquet of volatile terpenes is likely to exert similar functions in the biological interactions of both species with insects.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C316FFDBFDDC4AF6FC66FCA5.taxon	discussion	are anatomically similar sympatric species. In the same way as other species in this genus, their VOs are mainly composed of hydrocarbon monoterpenes, specifically α- pinene, β- pinene, and limonene. G. intermedia (syn. Eupatorium intermedium, Dimorpholepis intermedia) is a 1 – 1.5 m tall, white-flowered, twiggy shrub native from Minas Gerais to Rio Grande do Sul States, Brazil and Uruguay (King and Robinson, 1987; Matzenbacher, 1979). The VOs in the two samples have similar compositions in the monoterpene fraction, where α- pinene (15.1 – 19.9 %), β- pinene (17.3 – 24.2 %), and limonene (19.7 – 25.2 %) are predominant. However, a compound bearing a caryophyllane nucleus was predominant in the sesquiterpene fractions of both samples (β- caryophyllene, 7.2 – 8.1 %) with higher amounts of bicyclogermacrene (9.4 %) among the main compounds in one sample, while in the other, the percentage of this compound was lower (2.3 – 4.7 %). Similar to another Disynaphiinae, Acanthostyles buniifolius, G. intermedia is a host species for Actinote sp. butterflies (Freitas et al., 2018; Paluch et al., 1999) and bees (Gonçalves and Melo, 2005), and has been reported to be associated with several other butterfly taxa in the Southern Brazilian Atlantic Rainforest, namely Hesperiidae, Nymphalidae, Papilionidae, Pieridae, and Riodinidae (Cruz et al., 2012), as well as the native bee Megachile (Pseudocentron) nudiventris (Krug et al., 2010). This species is also important in the reproductive biology of a Long-tailed Reed-Finch Donacospiza albifrons (as is Raulinoreitzia crenulata) (Maurício et al., 2013). Tridecapentaynene, germacrene D, bicyclogermacrene, ent-kaurenic acid, spathulenol, and sesquiterpene lactones (germacranolides, melampolides, and guaianolides) have been previously isolated from a Northeastern Brazilian sample (Ferdinand Bohlmann et al., 1981). The chemical composition of the VOs has been reported for inflorescences collected in Parana´State, Southern Brazil with spathulenol, caryophyllene oxide, (E) - β- caryophyllene, germacrene D, bicyclogermacrene, and carotol identified as the major compounds in the supercritical CO 2 or compressed propane extracted oils, while α- pinene (22.6 %), β- pinene (14.4 %), spathulenol (11.1 %), and limonene (7.0 %) were the major compounds in the gram-positive antimicrobial hydrodistilled oil (Czaikoski et al, 2015, 2017). Another sample, collected from the same Parana´area, was composed of α- pinene (22.3 %), spathulenol (11.1 %), khusimol (10.9 %), vetivenic acid (9.2 %), β- pinene (5.5 %), and limonene (5.7 %) (do Amaral et al., 2018). In contrast to the samples collected in Parana´State, no vetivenic acid, khusimol, or carotol were detected in our samples. The sample of G. serrata, a 1 – 1.5 m white-flowered shrub native to Southern Brazil (from Minas Gerais to Rio Grande do Sul), Uruguay, Paraguay, and Northeast Argentina (King and Robinson, 1987; Matzenbacher, 1979), collected in Gravataí in 2005 also presented VOs similar to others in this genus. The VOs in its leaves and inflorescences were very similar with 76.1 and 77.7 % hydrocarbon monoterpenes, respectively. The major compounds were α- pinene (30.2 and 31.5 %), β- pinene (17.0 and 13.8 %), and limonene (19.4 and 20.9 %). The only sesquiterpene among the main compounds in the VOs, as well as in the VOs of G. intermedia, was β- caryophyllene (4.8 and 5.5 %). The flower heads of G. serrata have been reported to be associated with Xanthaciura biocellata (Tephritidae), a fruit fly species associated also with Barrosoa betoniciiformis and Chromolaena congesta, and Xanthaciura chrysura, a species associated with Barrosoa betoniciiformis, Chromolaena hirsuta, and C. laevigata (Savaris et al., 2015). The association of this species with Megachile (Moureapis) maculata and Apis mellifera has also been reported (Weiss, 2008). Southeastern Brazilian butterfly Actinote alalia larvae have also been reported to be associated with this species (Freitas et al., 2018). Tridecapentaynene, α- pinene, germacrene D, bicyclogermacrene, ent-kaurenic acid, and germacranolides have been previously isolated from a Northeastern Brazilian population (Bohlmann et al., 1983; Ferdinand Bohlmann et al., 1981). 6 8 The volatile chemistry of the genus Grazielia is a neglected topic. Previously, from 10 species in this genus, only the volatiles in G. intermedia from Parana´State, Brazil have been described (Czaikoski et al., 2015). In addition, a report on the isolation of volatiles, mainly germacranes, together with other non-volatile compounds in G. serrata have also been published in 1980 (Ferdinand Bohlmann et al., 1981). Herein, we thoroughly described the volatiles in G. serrata, reported a different composition for G. intermedia, and also described the VOs from G. gaudichaudieana and G. nummularia for the first time. None of the samples collected in RS contained compounds bearing either a zizaane or carotane nucleus, as reported for the Parana´sample of G. intermedia. It is noteworthy that all four samples were characterized having very similar compositions, likely reflecting their adaptation to a similar environment.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31DFFDEFE6A4D54FA1FFCF1.taxon	discussion	Raulinoreitzia tremula (Hook. & Arn.) R. M. King & H. Rob. and Raulinoreitzia crenulata (Sprengel) R. M. King & H. Rob. (sampled in this study) are, together with R. leptophlebia, the only three species recognized in the genus Raulinoreitzia (Koiti and Hattori, 2013). The chemical composition of VOs obtained from both the leaves and inflorescences of R. tremula (syn. Eupatorium tremulum - common name: “ chirca ”, “ vassour ˜ ao-do-brejo ”), a 2 – 3 m tall, densely branched shrub, native to southern Brazil, Uruguay, and Northeastern Argentina (King and Robinson, 1987; Matzenbacher, 1979) are quite similar with the predominance of sesquiterpenes (97.2 and 84.0 %). Among the hydrocarbon sesquiterpenes (46.0 and 49.7 %), compounds bearing a bisabolane nucleus were predominant: β- bisabolene (15.5 and 17.1 %), β- sesquiphellandrene (7.9 and 7.1 %); alongside the cadinane amorpha- 4,7 (11) - diene (11.7 and 10.5 %). Among the oxygenated sesquiterpenes, furanocadinanes verboccidentafuran (16.1 and 11.6 %) and 3 - oxo-verboccidentafuran (3.6 and 14.7 %), and alcohols epi-α- bisabolol (9.6 and 10.7 %) and amorpha- 4 - en- 7 - ol (7.5 and 6.6 %) were the most abundant. The presence of sesquiterpene compounds with a bisabolane nucleus is not common in this subtribe, nor are furan compounds. However, other samples of R. tremula collected from different populations in RS have been reported to have qualitatively similar compositions (de Souza et al., 2017). This species occurs in swampy humid fields and edges of floodable galleries (Koiti and Hattori, 2013). Together with Hatschbachiella tweediena (Eupatoriinae subtribe), it is important in the reproductive biology of the rusty-collared seedeater Sporophila collaris (Rosoni, 2017; Rosoni et al., 2019). This species has been implicated in cattle intoxication (Lucioli et al., 2007) and its extracts exhibit cytotoxicity in vitro against tumor cells (Monks et al., 2002). A direct link between these activities and a particular chemical compound has not been established to date, but the participation of their characteristic furanocadinenes cannot be ruled out. The chemical composition of VOs obtained from R. crenulata, a 2 m tall, white-flowered shrub native to Central, Southern, and Northeastern Brazil, Peru, Bolivia, and Northern Argentina (King and Robinson, 1987; Matzenbacher, 1979) was quite similar to another sample of this species reported by our group and collected from the same area (Souza et al., 2007), with a slight predominance of hydrocarbon monoterpenes over sesquiterpenes: β- pinene (19.1 %) and α- pinene (14.6 %) were the main monoterpenes, and β- caryophyllene (7.3 %), germacrene D (11.4 %), and Table 2 (continued) Legend a Retention Index in a DB 5 column b inflorescences c aerial parts d leaves e Aliphatics f Hydrocarbon Monoterpenes g Oxygenated Monoterpenes h Hydrocarbon Sesquiterpenes i Oxygenated Sesquiterpenes j traces. Table 3 (continued) bicyclogermacrene (9.7 %), the main sesquiterpenes. In the previously reported sample, there were higher amounts of β- myrcene (15.3 %) and limonene (22.8 %), while the percentage of α- pinene (14.6 %) and α- thujene (7.1 %) were higher. This is an important species in the reproductive biology of black-bellied seedeaters (Sporophila melanogaster) (in the same way as Gyptidinae Barrosoa betoniciiformis) (Rovedder, 2011; Rovedder and Fontana, 2012), red-eyed Vireo (Vireo olivaceus), and Long-tailed Reed-Finch (Donacospiza albifrons) (similarly to Grazielia intermedia) (Maurício et al., 2013). The VOs were previously analyzed, yielding 0.54 – 0.68 % (dry and fresh inflorescences, respectively), but the chemical composition was not reported (Souza, 2015). Another report from Paran´a, Brazil, described limonene (39 %) and δ- cadinene (8 %) as the major compounds and their activity against the strawberry aphid Aphis forbesi (Maleski et al., 2019). Despite sharing the same origin, the chemical composition reported here shows qualitative differences regarding our previous report on this species, reflecting the known variability of volatile chemistry. The composition described for the Parana´samples was even more deviant in their values for limonene, to which the anti-aphid activity of R. crenulata oil was credited (Maleski et al., 2019). To the best of our knowledge, the only known reports on the VOs of R. tremula are from RS (de Souza et al., 2017) and no description has ever been given for the chemical composition of the other species in the genus R. leptophlebia. To date, the volatile chemistry of the genus Raulinoreitzia is very basal for R. crenulata in both Parana´and RS, and extremely atypical for R. tremula in RS. In this way, more samples of R. tremula and R. leptophlebia are needed to better describe this genus.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C318FFDDFE094DC1FF11FBB2.taxon	vernacular_names	– common name: “ chilca ” or “ chirca ”)	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C318FFDDFE094DC1FF11FBB2.taxon	discussion	is currently the only species recognized in the genus Acanthostyles (Grossi et al., 2011; King and Robinson, 1987; Matzenbacher, 1979). It is a 0.60 – 1.80 m tall shrub native to southern Bolivia and Southern Brazil, Paraguay, Uruguay, and Northern and Central Argentina. There is abundant literature on this species. VOs obtained from our sample of A. buniifolius contained 9.8 % α- pinene, the major compound in the monoterpene fraction. The main compounds in the sesquiterpene fraction were β- caryophyllene (7.1 %) and germacrene D (22.4 %), which are common to many other species of Eupatorieae analyzed by our group. In addition to these substances, germacrene A (8.3 %) and its Cope rearrangement product, β- elemene (4.7 %), were found. A compound with a guaiane nucleus, trans - β- guaiene (22.0 %), was also found in large amounts. VOs obtained from other samples from Argentina have been reported, whose major compounds were α- pinene (39.1 %), sabinene (6.42 %), limonene (8.02 %), and (E) - β- ocimene (10.42 %) (Cecati et al., 2018). A very similar composition has been reported for other samples collected from Argentina containing α- pinene (41.48 – 51.81 %), sabinene (5.37 – 8.44 %), (E) - β- ocimene (8.09 – 11.09 %), and limonene (6.95 – 9.53 %) (Guerreiro et al., 2018), which were tested against the coleopteran Tribolium castaneum, exerting repellence and lethality against this species of beetle (Lancelle and Giordano, 2009). Another sample dominated by α- pinene (68.8 %), δ- 2 - carene (5.3 %), and limonene (5.1 %), was assayed on bees against Varroa desctructor (Ruffinengo et al., 2005). In Uruguay, a different composition was reported, which was more similar to our samples with and α- pinene (14.7 %) and sesquiterpenes β- elemene (12.2 %) and germacrene D (11.5 %) as main compounds (Lorenzo et al., 2005). In a different report from the same country, samples composed of β- guaiene (10 %), germacrene D (7.8 %), β- elemene (6.7 %), and α- pinene (22 %) exhibited insecticidal and fungicidal activities toward tomato pests (Umpi´errez et al, 2012, 2013, 2017). In RS, Brazil, a different sample was previously reported with α- thujene (26.01 – 28.1 %), γ- muurolene (15.2 – 1.17 %), sabinene (8.54 – 9.42 %), α- humulene (0.6 – 7.8 %), and limonene (5.34 – 6.8 %) observed in the summer and winter samples, respectively (Stüker, 2007). The presence of either β- elemene or germacrene A in the sample could be an artifact of the injection temperature of the GC – MS analysis, resulting in the presence of β- elemene in the samples injected at high temperature or germacrene A in the samples injected at low temperature. Considering this, the samples reported with either germacrene A or β- elemene may belong to the same chemotype. This way the Uruguayan samples were more similar to ours. This species has been reported to be a host plant for the butterfly Actinote surima, similar to other closely related Eupatorieae (Grazielia intermedia, Symphyopappus reticulatus, and S. casarettoi) (Penz and Francini, 1996), A. carycina, A. pyrrha, Rothschildia jacobaeae (Saturniidae), and Pericopis sacrifica (Pericopidae) in Uruguay (Biezanko et al., 1974). It is also a host for the vineyard Basidiomycota pathogen Arambarria sp. (Pildain et al., 2017) and the aphid Uroleucon garnicai (Delfino, 1991). From plants collected in Argentina, ent-labdane diterpenes have been previously isolated (Carreras et al., 1998), as well as two flavones and one coumarin with anti-inflammatory activity (Muschietti et al., 2001). Its extracts were evaluated for antiviral (Varicellovirus pseudorabies virus strain RC / 79) (Zanon et al., 1999), antifungal (Mino ˜ et al., 2005), and trypanocidal (Trypanosoma cruzi) (Sülsen et al., 2006) activity. Inhibition of the neutrophil function (Paya´ et al., 1996), antinociception in acetic acid-induced pain test (Mino ˜ et al., 2005), in vivo CNS-depression (Mino ˜ et al., 2007), in vitro anticholinesterasic (Carpinella et al., 2010), and anti-arsenite-induced peroxidation (Soria et al., 2008) activities were also demonstrated. The antipoliovirus benzofuran euparin was isolated from the extracts of aerial parts and characterized (Visintini Jaime et al., 2013). Legend a Retention Index in a DB 5 column b aerial parts c leaves d inflorescences e twigs f Aliphatics g Hydrocarbon Monoterpenes h Oxygenated Monoterpenes i Hydrocarbon Sesquiterpenes j Oxygenated Sesquiterpenes k traces. Despite the abundance of literature data for this species reflecting its geographical dispersion in Southern South America, popular use, and several biological activities, only tests against Varroa destructor, Tribolium castaneum, Trialeurodes spp., Botrytis cinerea, Alternaria spp., and Fusarium spp. were directly performed using the VOs. Some of them were reported from the Uruguayan samples similar to the samples described herein, which were characterized by higher amounts of trans - β- guaiene.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31BFFDDFD3C4A7DFD06FB40.taxon	discussion	Campovassouria cruciata (DC) R. M. King & H. Rob. and C. barbosae are the only two species recognized in the genus (Silva et al., 2018).	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31BFFDDFF814AA1FA80FC81.taxon	vernacular_names	- common name: “ vassoura-do-campo ”), a	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31BFFDDFF814AA1FA80FC81.taxon	discussion	1.0 – 2.5 m tall branchy shrub, native to the humid fields of Southern Brazil, Bolivia, Paraguay, Northern Argentina, and Uruguay were obtained in Sao ˜ Francisco de Paula and Morro Reuter, RS, in 2005, during the flowering season (Table S 1). The VO content varied from 0.2 to 0.4 %. Sixty components were identified in the oils obtained from the leaves and inflorescences from two samples (91.1 – 97.9 % of the total). VOs in the inflorescences and leaves of the first sample were characterized by the predominance of oxygenated sesquiterpenes (74.6 and 64.1 %), including caryophyllene oxide (25.2 and 28.2 %), globulol (14.8 and 20.1 %), and epiglobulol (15.4 and 14.1 %). The second sample showed similar percentages for the monoterpenes and sesquiterpenes in the leaves (49.6 % and 47.5 %) with the predominance of sesquiterpenes in the inflorescences (68.4 %). The monoterpene fraction was composed of almost exclusively hydrocarbon compounds, mainly α- pinene (12.1 and 15.5 %), sabinene (5.1 and 8.9 %), β- pinene (4.8 and 7.2 %), and limonene (3.4 and 8.1 %). In the sesquiterpene fraction, both hydrocarbon and oxygenated compounds occurred (37.1 % and 31.3 % in inflorescences and 27.2 % and 20.3 % in leaves, respectively). The major compounds in the sesquiterpene fraction of the VOs in the second sample were β- caryophyllene (12.6 and 13.4 %) and germacrene D (10.2 and 6.4 %). The VOs obtained from both the leaves and inflorescences of both samples showed qualitatively similar chemical compositions, except for the absence of D germacrene and bicyclogermacrene in the sample from S ˜ ao Francisco de Paula. These two hydrocarbon compounds can undergo different chemical and enzymatic rearrangements and oxidations, resulting in several different sesquiterpenes and sesquiterpenoids (Bülow and K ¨ onig, 2000; Toyota et al., 1996; Venturi et al., 2015). Thus, compounds in the sesquiterpene fraction of the VOs from both samples of C. cruciata mainly originate from the caryophyllane and germacrane biogenetic pathways. This melliferous species is widely visited by bees (Gonçalves and Melo, 2005) Apis mellifera and Bombus (Fervidobombus) pauloensis (Apidae) in Southeastern Brazil (Gonçalves et al., 2009) and Pseudagapostemon sp. (Krug et al., 2010) and Plebeia remota (Halictidae) in Southern Brazil (Steiner et al., 2010). It is an important species in the reproductive biology of black-bellied seedeaters (Sporophila melanogaster) (Rovedder and Fontana, 2012). It has also been reported to have medicinal use in Argentina (Hilgert and Gil, 2006). Guaiagrazielolide-type sesquiterpene lactones were isolated from the extracts of this plant (Bohlmann et al., 1983). VO production was reported to be 1.40 – 1.77 % (dry and fresh inflorescences, respectively), but the chemical composition has not been previously reported (Souza, 2015). The absence of reports on C. barbosae and on C. cruciata from other locations prevent further discussion on the volatile chemistry of this genus. However, it is noteworthy that the composition described herein for C. cruciata is qualitatively similar to that described for Raulinoreitzia crenulata and Grazielia spp. in the hydrocarbon fraction, differing in the proportion of oxygenated sesquiterpenes, which are qualitatively different from those in Raulinoreitzia tremula.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31BFFDDFE6A4D28FA42FB84.taxon	discussion	Disynaphia, as currently circumscribed, is composed of 17 species, four of which are reported to occur in Rio Grande do Sul State (Matzenbacher, 1979), from which only D. multicrenulata (syn. E. multicrenulatum) was not sampled in this study. In phylogenetic analyses, the genus forms a clade with Campovassouria, and both genera should be merged according to some authors (Silva et al., 2018).	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31BFFDDFE094A09FAABFA45.taxon	discussion	a 0.5 – 1.5 m tall sub-shrub native to southern Brazil (King and Robinson, 1987; Matzenbacher, 1979) differ quantitatively from one another. The inflorescences contain a higher percentage of hydrocarbon sesquiterpenes (51.5 %), mainly germacrene D (18.8 %) and bicyclogermacrene (11.6 %), and oxygenated sesquiterpenes, τ- cadinol / τ- muurolol (7.9 %) and α- cadinol (14.6 %); in the VOs obtained from the leaves, in addition to the cadinanes, τ- cadinol / τ- muurolol (13.3 %) and α- cadinol (23.9 %), the guaianes spathulenol (11.8 %) and epi-globulol (8.8 %) were found, which are known to be formed via the oxidation of germacrene D and bicyclogermacrene (Bülow and K ¨ onig, 2000; Toyota et al., 1996; Venturi et al., 2015), identified in trace amounts or not detected at all in the leaf samples. This species was previously reported to be associated with wasps Mischocyttarus rotundicolis and Polybia ignobilis (Vespidae), and bees Trigona spinipes and Apis mellifera (Apidae) (Klein, 2018).	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31BFFDDFE094BCAFA58F82F.taxon	vernacular_names	common name: “ macelinha ”) (King and Robinson, 1987; Matzenbacher, 1979),	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31BFFDDFE094BCAFA58F82F.taxon	discussion	a sub-shrub up to 1.5 m tall, were obtained from the municipality of Canela, RS. The VO yields for the two samplings were similar despite their different vegetative stages (Table 1 and Table S 1). In regard the chemical composition of the VOs of this species, the inflorescences and leaves of the first sample (Canela / 05, April) showed very similar chemical compositions with a predominance of hydrocarbon monoterpenes (56.8 – 58.9 %), especially α- pinene (7.0 – 11.6 %), β- pinene (14.9 – 24.1 %), limonene (12.2 – 13.1 %), and (E) - β- ocimene (13.3 – 2.3 %). In the sesquiterpene fraction, three main compounds were identified in the flowering period: The hydrocarbon sesquiterpenes β- caryophyllene, germacrene D, and bicyclogermacrene. However, the second sampling in the vegetative stage (Viamao / 05, October) presented a very different quantitative pattern, in which oxygenated sesquiterpenes (64.1 %), spathulenol (22.6 %), caryophyllene oxide (7.0 %), and α- cadinol (12.0 %) were observed.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31BFFDCFE0949B0FDFBFE57.taxon	discussion	were similar to those obtained from Acanthostyles buniifolius, especially due to the levels of germacrene A (5.4 %) and β- elemene (9.0 %). In addition to these two compounds, the VOs contained β- caryophyllene (21.3 %), germacrene D (8.6 %), bicyclogermacrene (15.1 %), and spathulenol (8.5 %). No species from the Disynaphia genus, the type genus of this subtribe, have had its VO chemical composition previously described. The VOs obtained from D. ligulifolia, D. spathulata, and D. ericoides were similar to those in C. cruciata with a higher degree of oxidation when compared to Grazielia spp. and qualitatively different from R. tremula. The VOs from 13 species of Disynaphia remain to be described.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31AFFDCFD3C4C1BFF49FD0E.taxon	discussion	Four out of 14 species currently recognized in Symphyopappus have been reported in the area of study and three of them were sampled in this study.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31AFFDCFDFA4C6BFD67FA1D.taxon	vernacular_names	- common name: “ vassoura-do-campo ”, “ vassoura-bichada ”, due to its frequent infestation by lepidopteran larvae (Cabrera and Klein, 1989; Gandolfo and Hanazaki, 2014 )),	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31AFFDCFDFA4C6BFD67FA1D.taxon	discussion	a 1 – 2 m tall, branchy shrub, exhibit VO yields quite different from each other (0.15 and 0.4 %, respectively); the main compounds were the same for the oils obtained from the two organs, however, with only quantitative differences. While the VOs obtained from the leaves of this species are characterized by the predominance of hydrocarbon monoterpenes (71.5 %), whose main components are pinenes (54.0 %), those obtained from its inflorescences were characterized by even amounts of mono and sesquiterpene hydrocarbons (43.6 and 45.5 %, respectively). None of the components of the VOs obtained from the inflorescences of S. casarettoi were found in large amounts; the six major compounds, (E) - β- ocimene, β- pinene, limonene, germacrene D, bicyclogermacrene, α- pinene, and β- caryophyllene, were found in the range of 7.2 – 14.6 %. In contrast, in the leaf VOs, monoterpenes α- pinene and β- pinene were found in the range of 26.0 – 28.0 %. The VO profile of this species was very similar to that of the genus Grazielia. S. casarettoi, which has been reported to be part of the interaction networks of treehoppers Bocydium globuliferum (Stegaspidinae) and Bolbonota melaena (Membracinae) with Chromolaena laevigata (Praxeliinae) and other Asteraceae species (Gadelha et al., 2017). It is a frequent host for the butterfly Actinote surima (Nymphalidae) (Paluch et al., 1999) and bees Dialictus sp. (Halictinae) (Patricio et al., 2014), Ceratina (Ceratinula) sp., Ceratina (Crewella) sp., Augochlora sp., Megachile (Leptorachis) sp., and Megachile (Pseudocentron) nudiventris (Steiner et al., 2010). The antioxidant activity and cytotoxicity of its extracts have also been reported (Benetti, 2007; Monks et al., 2002; Netto Benetti et al., 2007).	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31AFFDCFDDC4B82FCBBF994.taxon	conservation	The leaves of critically endangered, densely branched, leafy, opposite-leaved, and up to 1 m tall shrub	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
03F88786C31AFFDCFDDC4B82FCBBF994.taxon	discussion	(April / 2005) showed a VO yield comparable to that of leaves of S. casarettoi (0.5 %). However, while the latter was characterized by the predominance of hydrocarbon monoterpenes, the former is mainly composed of hydrocarbon sesquiterpenes (63.1 %), germacrene D (34.4 %), and β- caryophyllene (15.2 %) as the major components with 33.9 % hydrocarbon monoterpenes, mainly limonene (15.8 %), which were found at much lower concentrations on the leaves and inflorescence of S. casarettoi (5.2 and 7.4 %, respectively). The VOs obtained from the leaves of the second sample of S. reticulatus (flowering stage, October / 2005) were quite similar to those obtained from its leaves during the vegetative period with limonene the only monoterpene observed in a large proportion (12.5 %). Hydrogenated sesquiterpenes were predominant in the VOs (63.3 %), which were the same major compounds found in the vegetative stage: Germacrene D (23.5 %), β- caryophyllene (21.6 %), bicyclogermacrene (7.8 %), and α- humulene (7.4 %). On the other hand, the VOs obtained from the inflorescences of this second sample differed from those obtained from the leaves in the two samples of this species and from the inflorescences of S. casarettoi because it was characterized by a large proportion of oxygenated sesquiterpenes including caryophyllene oxide (16.2 %) and spathulenol (14.7 %). Among the hydrocarbon sesquiterpenes, the biogenetic-related cluster of β- caryophyllene (29.0 %) and α- humulene (9.4 %), which usually occur simultaneously, were the major compounds. Monoterpenes were found in very low concentrations (8.6 %). The VOs obtained from leaves of S. reticulatus in the two samples did not present large qualitative and quantitative variations, even in the case of different locations and times of sampling, and different vegetative periods, suggesting that it was not significantly affected by edaphoclimatic variations. A comparison of the VOs obtained from the leaves of S. casarettoi revealed a large quantitative variation, mainly in the monoterpene fraction. Likewise, the VOs obtained from the inflorescences of these two species also showed larger variability. The VO profile of this species was similar to that of the genus Campovassouria. This plant has been reported to be a foraging species for the bee Melipona quinquefasciata (Apidae) (Umpi´errez et al., 2013). A very complex network of interactions between S. reticulatus, other plants, and ants in the subfamilies Myrmicinae, Dolichoderinae, and Formicinae has been described (Costa et al., 2016). Covalane-type diterpenes, as well as from tremetone derivatives, were isolated from the aerial parts of this species (F. Bohlmann et al., 1981). S. reticulatus, together with S. angustifolius, has been recently synonymized under S. braziliensis (Koiti and Hattori, 2013). The VOs obtained from the 2 – 6 m tall shrub Symphyopappus itatiayensis (Hieron.) R. M. King & H. Rob. (syn. Eupatorium itatiayense, common name: “ vassoura-braba ”) (Cabrera and Klein, 1989; King and Robinson, 1987) observed from Minas Gerais to Rio Grande do Sul, Brazil, are surprisingly similar to the VOs obtained from R. tremula with bicyclogermacrene, amorpha- 4,7 (11) - diene, verboccidentafuran, 3 - oxo-verboccidentafuran, and bisabolanes as main components. This plant has been reported to be a host species for bees Apis mellifera, Melissoptila aureocincta, Cephalotrigona capitata, Paratrigona subnuda, Schwarziana quadripunctata, Doeringiella cingillata, Paratetrapedia (Lophopedia) pygmaea (Apidae), Augochlora (Augochlora) amphitrite, A. (A.) caerulior, A. (A.) cydippe, A. (A.) esox, A. (A.) tantilla (Halictidae), and Coelioxys (Acrocoelioxys) tolteca, C. (Rhinocoelioxys) excise, Megachile (Acentron) eburnipes, M. (Austromegachile) trigonaspis, M. (Moureapis) maculate, and M. (Pseudocentron) curvipes (Megachilidae) (Imperatriz-Fonseca et al., 2011; Santos et al., 2017; Weiss, 2008). From the genus Symphyopappus, only the volatiles from a sample of S. compressus from Parana´State were chemically characterized. They only differed qualitatively from those reported for other species in the genus in the presence of the oxygenated sesquiterpenes mustakone (14 %) and cyperotundone (5.5 %) (do Amaral et al., 2018), which have copaane and patchoulane nuclei, respectively, while most of the other compounds were similar to those in our samples of S. reticulatus and S. casarettoi. The uniqueness of the chemistry of S. itatiayensis in the genus and its similarity to R. tremula is described for the first time in this study.	en	de Souza, Tiago J. T., S, Bordignon, ergio A. L., Apel, Miriam A., Henriques, Amelia T. (2021): Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae. Phytochemistry (112734) 186: 1-23, DOI: 10.1016/j.phytochem.2021.112734, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112734
