Grazielia intermedia
Creators: name: de Souza, Tiago J. T.
name: S
name: Bordignon, ergio A. L.
name: Apel, Miriam A.
name: Henriques, Amelia T.
Publisher: name: Zenodo
Year: 2021
Subjects: Biodiversity
Taxonomy
Plantae
Tracheophyta
Magnoliopsida
Asterales
Asteraceae
Grazielia
Grazielia intermedia

description: Grazielia intermedia (Spreng.) R.M.King & H.Rob. and Grazielia serrata (Spreng.) R.M.King & H.Rob.
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).
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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.
description: Published as part of 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, pp. 1-23 in Phytochemistry (112734) (112734) 186 on pages 4-9, DOI: 10.1016/j.phytochem.2021.112734, http://zenodo.org/record/8258534