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Composition of essential oils and secretory structures of Baccharis anomala, B. megapotamica and B. ochracea

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Márcia R. Duarte
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Patrícia Mathias Döll-Boscardin at State University of Ponta Grossa
Patrícia Mathias Döll-Boscardin
Paulo Vitor Farago at State University of Ponta Grossa
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Abstract and Figures

The chemical composition of the essential oils and the anatomical structures of the aerial parts from Baccharis anomala, B. megapotamica and B. ochracea growing in Brazil were studied. The volatile constituents isolated by hydrodistillation were analyzed by gas chromatograph coupled to a mass spectrometer detector (GC-MSD) and gas chromatograph coupled to a flame ionization detector (GC-FID). The botanical material was fixed, sectioned and prepared according to light and scanning microtechniques. The essential oil from B. anomala yielded 0.18% and showed α-acorenol (16.0%), spathulenol (13.3%) and caryophyllene oxide (12.1%) as the main components. Spathulenol (28.0% and 37.1%) and caryophyllene oxide (20.4% and 30.8%) represented the major constituents of the essential oils from B. megapotamica (yield = 0.17%) and B. ochracea (yield = 0.18%), respectively. The leaves and stems of these Baccharis species showed non-glandular trichomes and secretory ducts. Glandular trichomes were also found on the vegetative aerial parts of B. megapotamica
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Composition of essential oils and secretory structures
of Baccharis anomala, B. megapotamica and B.
ochracea
Jane M. Budel a , Márcia R. Duarte a , Patrícia M. Döll-Boscardin a , Paulo V. Farago b ,
Nelson I. Matzenbacher c , Adilson Sartoratto d & Beatriz H. L. N. Sales Maia e
a Postgraduate Program of Pharmaceutical Sciences, Federal University of Paraná, Curitiba,
Brazil
b Department of Pharmaceutical Sciences, State University of Ponta Grossa, Ponta Grossa,
Brazil
c Postgraduate Program of Botany, Federal University of Rio Grande do Sul, Porto Alegre,
Brazil
d Research Center for Chemistry, Biology and Agriculture, University of Campinas,
Campinas, Brazil
e Department of Chemistry, Federal University of Paraná, Curitiba, Brazil
Available online: 03 Feb 2012
To cite this article: Jane M. Budel, Márcia R. Duarte, Patrícia M. Döll-Boscardin, Paulo V. Farago, Nelson I. Matzenbacher,
Adilson Sartoratto & Beatriz H. L. N. Sales Maia (2012): Composition of essential oils and secretory structures of Baccharis
anomala, B. megapotamica and B. ochracea , Journal of Essential Oil Research, 24:1, 19-24
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Composition of essential oils and secretory structures of Baccharis anomala,
B. megapotamica and B. ochracea
Jane M. Budel
a
, Márcia R. Duarte
a
, Patrícia M. Döll-Boscardin
a
, Paulo V. Farago
b
*, Nelson I. Matzenbacher
c
,
Adilson Sartoratto
d
and Beatriz H. L. N. Sales Maia
e
a
Postgraduate Program of Pharmaceutical Sciences, Federal University of Paraná, Curitiba, Brazil;
b
Department of Pharmaceuti-
cal Sciences, State University of Ponta Grossa, Ponta Grossa, Brazil;
c
Postgraduate Program of Botany, Federal University of
Rio Grande do Sul, Porto Alegre, Brazil;
d
Research Center for Chemistry, Biology and Agriculture, University of Campinas, Cam-
pinas, Brazil;
e
Department of Chemistry, Federal University of Paraná, Curitiba, Brazil
(Received 10 December 2010; final form 29 July 2011)
The chemical composition of the essential oils and the anatomical structures of the aerial parts from Baccharis
anomala,B. megapotamica and B. ochracea growing in Brazil were studied. The volatile constituents isolated by
hydrodistillation were analyzed by gas chromatograph coupled to a mass spectrometer detector (GC-MSD) and gas
chromatograph coupled to a flame ionization detector (GC-FID). The botanical material was fixed, sectioned and pre-
pared according to light and scanning microtechniques. The essential oil from B. anomala yielded 0.18% and showed
a-acorenol (16.0%), spathulenol (13.3%) and caryophyllene oxide (12.1%) as the main components. Spathulenol
(28.0% and 37.1%) and caryophyllene oxide (20.4% and 30.8%) represented the major constituents of the essential
oils from B. megapotamica (yield = 0.17%) and B. ochracea (yield = 0.18%), respectively. The leaves and stems of
these Baccharis species showed non-glandular trichomes and secretory ducts. Glandular trichomes were also found
on the vegetative aerial parts of B. megapotamica
Keywords: Asteraceae; Baccharis spp.; essential oil; secretory ducts; trichomes
Introduction
The genus Baccharis L. belongs to Asteraceae and
comprises herbs and shrubs native to tropical and sub-
tropical regions of America, from United States to
Argentina (1, 2). Baccharis taxa have been investigated
as an economically important group of plants used for
the pharmaceutical, flavor and perfumery industries (3,
4). Chemical composition of the essential oils from a
limited number of Baccharis species (around 10%)
have been reported due to their pharmacological prop-
erties, for example, as antifungal, antibacterial and anti-
ulcer medicines and as a mosquito repellent (3, 5–15).
However, more restricted data are available from other
widely distributed and popularly used Baccharis spe-
cies, particularly B.anomala DC., B.megapotamica
Spreng. and B.ochracea Spreng. Baccharis anomala,
known as uva-do-mato and cambará-de-cipó, is a popu-
lar Brazilian diuretic medicine due to its tannin and
saponin composition (16). Baccharis megapotamica
(commonly known as vassoura) has been of medical
interest due to the macrocyclic trichothecenes (17). In
spite of the potential toxicity, these trichothecenes have
demonstrated antileukemic and antiviral activities (18,
19). Baccharis ochracea showed aromatic and bitter
properties and revealed an antiproliferative activity
against tumor cells that support the popular name of
erva-santa in Brazil (20–22). Nevertheless, a lack of
reports concerned with the essential oils from these
species has been established. Due to the confirmed
pharmacological properties and the use as traditional
medicines, the aim of this paper was to study the
chemical composition of the essential oils from B.ano-
mala,B.megapotamica and B.ochracea. A compre-
hensive discussion on secretory elements is also given.
Experimental
Plant material
The botanical materials were collected at the Fazenda
São Maximiano in Guaíba, Rio Grande do Sul, Brazil
(altitude: 27 m, latitude: 30°10’S and longitude: 51°20’
W), in December 2008. Baccharis anomala,B.megapot-
amica and B.ochracea were identified by the vouchers
ICN 53478, ICN 49056 and ICN 59562, respectively,
and lodged in the herbarium at the Instituto de Ci^
encias
Naturais, at the Federal University of Rio Grande do Sul.
Essential oils were extracted by steam distillation of
the dried aerial parts in a commercial Clevenger appa-
ratus (23). After 6 hours of distillation, essential oils
were obtained from 50 g of crude drug. The essential
*Corresponding author. Email: pvfarago@uepg.br
The Journal of Essential Oil Research
Vol. 24, No. 1, February 2012, 19–24
ISSN 1041-2905 print/ISSN 2163-8152 online
Ó2012 Taylor & Francis
http://dx.doi.org/10.1080/10412905.2012.645634
http://www.tandfonline.com
Downloaded by [Paulo Farago] at 11:14 03 February 2012
Figure 1. (A–C) Baccharis anomala: A –Leaf surface view of the adaxial epidermis, showing flagelliform non-glandular trichomes
(SEM); B –Leaf surface view of the abaxial epidermis, with conical non-glandular trichomes (SEM); C –Cross-section of the midrib,
indicating a secretory duct (
⁄
). (D–G) Baccharis megapotamica: D –Leaf surface view with a flagelliform non-glandular trichome; E –
Leaf surface view of the adaxial epidermis, displaying a non-capitate glandular trichome (SEM); F –Leaf surface view, adaxial
epidermis with a non-capitate glandular trichome; G –Leaf cross-section, showing non-capitate glandular trichomes. (H–J) Baccharis
ochracea: H –Cross-section of the midrib, indicating a secretory duct (
⁄
); I –Leaf surface view of the adaxial epidermis with
flagelliform non-glandular trichomes (SEM); J –Detail of a secretory duct (
⁄
) in the mesophyll. Bars in C, D, F–H, J = 20 lm.
20 J.M. Budel et al.
Downloaded by [Paulo Farago] at 11:14 03 February 2012
oil content was determined on a volume to dry weight
basis. The values for essential oil content of the three
replications were averaged. The essential oil samples
were stored in glass vials with Teflon-sealed caps at 4
± 0.5
o
C in the absence of light.
Analysis of the essential oils
The identification of volatile constituents was per-
formed using a Hewlett-Packard 6890 gas chromato-
graph, equipped with a Hewlett-Packard 5975 mass
selective detector and capillary column HP-5 (30 m x
0.25 mm x 0.25 lm). The GC-MS was carried out
using split/splitless injection, with the injector set at
220°C, the column set at 60°C, with a heating ramp of
3°C min
–1
,afinal temperature of 240°C and the detec-
tor set at 250°C. Helium was used as the carrier gas at
1 mL min
–1
. The GC-MS electron ionization system
was set at 70 eV. Quantitative analysis was performed
using a Hewlett-Packard 5890 gas chromatograph
equipped with a flame ionization detector under the
same conditions previously described. A sample of
essential oil was dissolved in ethyl acetate (20
mgmL
–1
) for the analyses. Retention indices (RI) were
determined by injection of hydrocarbon standards and
essential oil samples under the same conditions. The oil
components were identified by comparison with data
from literature (24) and the profiles from the mass
spectral libraries (Wiley 139, 275 and 7 and Nist 127).
The GC-FID quantification was obtained using a
GC-FID chromatogram and was expressed as mean ±
standard deviation for three samples of each extracted
essential oil.
Botanical assays
Leaf and stem fragments of B.anomala,B.megapot-
amica and B.ochracea were fixed in formalin-acetic
acid-alcohol (FAA) and kept in 70% and kept in 70%
ethanol solution (25, 26). Transverse and longitudinal
freehand sections were stained either with toluidine
blue or astra blue and basic fuchsine (27, 28). As addi-
tional data, the histochemical test of Sudan III was
used for lipophilic substances (29). Photographs were
taken using an Olympus BX40 light microscope
attached to the control unit PM20. For scanning elec-
tron microscopy (SEM) analysis (30), leaves and stem
fixed in FAA 70 were dehydrated in a graded ethanolic
series and critical point dried in a Bal-Tec CPD-030,
coated with gold in a Balzers SCD-030 and examined
by Jeol JSM-6360LV microscope.
Results and discussion
Secretory structures
The leaves and stems of B.megapotamica have shown
glandular trichomes usually inserted in small epidermal
depressions. These trichomes are non-capitate, multicel-
lular (4–10 cells), uniseriate and rounded at the apex
(Figures 1E–G). Non-glandular trichomes are also
Table 1. Chemical composition of the essential oils from the three studied Baccharis species.
N°Constituents RIa RIb B. anomala (%) B. megapotamica (%) B. ochracea (%)
1a-Pinene 932 939 0.8±0.09
2a-Terpineol 1186 1189 0.20±0.01
3b-Elemene 1389 1390 1.6±0.05
4Trans-Caryophyllene 1417 1416 2.4±0.03
5a-Humulene 1452 1450 1.0±0.15
6c-Muurolene 1478 1478 9.5±0.10
7 Bicyclogermacrene 1500 1494 3.0±0.12
8a-Bisabolene 1506 1502 1.3±0.08
9d-Cadinene 1522 1521 1.1±0.06
10 Spathulenol 1577 1575 13.3±0.10 28.0±0.11 37.1±0.21
11 Caryophyllene oxide 1582 1580 12.1±0.14 20.4±0.23 30.8±0.14
12 Humulene 1,2-epoxide 1608 1605 1.7±0.02 3.6±0.15 4.1±0.08
13 1-epi-Cubenol 1627 1627 3.0±0.07
14 a-Acorenol 1632 1631 16.0±0.19 2.5±0.02 5.0±0.06
15 epi-a-Muurolol 1640 1639 2.1±0.03 2.0±0.05
16 Selin-11-en-4-a-ol 1658 1651 2.7±0.02 3.7±0.09 4.4±0.10
17 Cadalene 1675 1672 1.0±0.01
18 Curcuphenol 1717 1717 2.6±0.07
Compounds identified 74.4 61.2 81.4
Monoterpene hydrocarbon 0.8
Oxygenated monoterpene 0.2
Sesquiterpene hydrocarbons 19.9 1.0
Oxygenated sesquiterpenes 53.5 60.2 81.4
Notes:
a
Tabulated Retention Index available in literature (24).
b
Calculated Retention Index.
The Journal of Essential Oil Research 21
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Major identified peaks: (3)
β
-Elemene; (4) Trans-Caryophyllene; (5)
α
-Humulene; (6)
γ
-Muurolene; (7) Bicyclogermacrene; (8)
α
-
Bisabolene; (9)
δ
-Cadinene; (10) Spathulenol; (11) Caryophyllene oxide; (12) Humulene 1, 2-epoxide; (13) 1-epi-Cubenol; (14)
α
-
Acorenol; (15) epi-
α
-Muurolol; (16) Selin-11-en-4-
α
-ol; (17) Cadalene; (18) Curcuphenol.
3
4
5
6
10
11
14
7
8912
13
15
16 18
10
10
11
11
12
12
14
14
15
16
16
17
A
B
C
Figure 2. GC-MS chromatograms in expanded view of the essential oils from aerial parts of (A) Baccharis anomala, (B) B.
megapotamica and (C) B. ochracea.
22 J.M. Budel et al.
Downloaded by [Paulo Farago] at 11:14 03 February 2012
encountered on the vegetative aerial parts of B. ano-
mala,B.megapotamica and B.ochracea. Regarding B.
anomala, two particular types of trichomes are
observed, conical (Figure 1B) and flagelliform (Figures
1A, D, I). Conical non-glandular trichomes are uniseri-
ate, 5-celled with a structure gradually narrowed to a
pointed apex (Figure 1B). The flagelliform non-glandu-
lar trichomes are composed by a flagellum-like apical
cell and another 3–5 cells (Figures 1A, D, I). These fla-
gelliform trichomes are also present in B.megapotami-
ca and B.ochracea. Comparing with B.anomala,
shorter and more elongated apical cells are found at
these trichome structures of B.megapotamica and B.
ochracea. Dense contents occur in the basal cells of
these trichomes which probably have a secretory func-
tion.
The three studied Baccharis species have shown
one or more secretory ducts whose epithelium has 6 –
12 cells in a single layer. These secretory elements are
located next to the parenchymatic sheath leading to the
phloem (Figures 1C, H, J) and are formed by dense
cytoplasm, evident nucleus and lipophilic content.
The essential oils can be considered as signals of
chemical communication with other flora species and
as chemical protection against animals. In Asteraceae
family, the essential oils are located in anatomical
structures that have developed from idioblast oil cells,
cavities and secretory ducts to glandular trichomes
(31). The secretory ducts are generally reported in the
Baccharis genus (32–34). Considering the reported ana-
tomical details, the secretory structures can also be use-
ful to differentiate the three analyzed species as well as
the chemical composition. Moreover these anatomical
structures have a further particular feature of releasing
other chemical components such as tannin and resins
besides essential oils (35).
Essential oil content and chemical composition
Table 1 shows the essential oil compositions
determined by the combined GC-MS analysis from
aerial parts of B. anomala,B.megapotamica and
B.ochracea. A high fraction of sesquiterpenes has been
achieved for the three evaluated volatile oils (Figure 2).
The essential oil from B.anomala has yielded 0.18%
and showed a-acorenol (16.0%), spathulenol (13.3%)
and caryophyllene oxide (12.1%) as the main compo-
nents. Spathulenol (28.0%) and caryophyllene oxide
(20.4%) have represented the major constituents of the
essential oil from B. megapotamica (yield = 0.17%).
The volatile oil of B. ochracea (yield = 0.18%) also
shows spathulenol (37.1%) and caryophyllene oxide
(30.8%) as main compounds.
The essential oil from B.anomala has shown a
minor composition of monoterpenes, represented by
a-pinene (0.8%) and a-terpineol (0.2%). Sesquiterpene
hydrocarbons have been observed in B.anomala
(19.9%) and B.megapotamica (1.0%). Besides, a high
amount of oxygenated sesquiterpenes (more than 50%)
have been verified in the chemical composition of the
essential oil from the three analyzed Baccharis species.
Non-identified compounds have also revealed typical
mass spectra of oxygenated sesquiterpenes with molec-
ular ions in m/z 218, 220, 222, 234, 236 and 250.
Previous studies about essential oils of Baccharis
taxa with pharmacological properties reported some
remarkable differences in their terpene compositions,
including variations attributed to the edapho-climatic
conditions (5–15, 36). Nevertheless, from these papers, it
can be observed that sesquiterpenes have been archived
as the main related compounds. Baccharis dracunculifo-
lia from the Atlantic Forest of Brazil showed only 0.30%
of monoterpenes (b-pinene, camphenilone and a-terpin-
eol) with a high content of sesquiterpenes (71.97%) (36).
In addition, the essential oils from B.regnelli,B.schultzii
and B.uncinella achieved a higher monoterpene fraction,
respectively, of 35.79%, 34.93% and 21.34%. However,
despite these values, sesquiterpene compounds also cor-
responded to the more representative fraction for these
taxa (36). Therefore, the obtained results for B. anomala,
B.megapotamica and B.ochracea can corroborate the
notable tendency of Baccharis plants to biosynthesize
sesquiterpenes. Furthermore, sesquiterpenes are usually
associated with a bitter taste in Baccharis (13). Due to
the high content of sesquiterpenes, the composition of
the studied essential oils could also be used as a chemical
standard to evaluate quality in bitters from these species.
From the 18 identified compounds, spathulenol,
caryophyllene oxide, humulene 1, 2-epoxide,
a-acorenol and selin-11-en-4-a-ol were oxygenated
sesquiterpenes detected in all three evaluated volatile
oils. These data support additional information about
the chemical composition of the essential oils from
Baccharis plants. No other report available in the litera-
ture has been devoted to the elucidation of the essential
oil composition from B. anomala,B.megapotamica
and B.ochracea.
Acknowledgements
The authors are thankful to the CME/UFPR for the scanning
electron micrographs.
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24 J.M. Budel et al.
Downloaded by [Paulo Farago] at 11:14 03 February 2012
... In the case of B. ochracea aerial parts' EO from the Rio Grande do Sul Brazilian State, Budel et al. (2012) [28] reported a composition with spathulenol and caryophyllene oxide (37.1 and 30.8 %, respectively) as the main components, also supporting the results of the present investigation. Similarly, [20] reported a similar profile for a volatile extract (employed technique: simultaneous distillationextraction, SDE) obtained from B. ochracea aerial parts collected in Uruguay. ...
... In the case of B. ochracea aerial parts' EO from the Rio Grande do Sul Brazilian State, Budel et al. (2012) [28] reported a composition with spathulenol and caryophyllene oxide (37.1 and 30.8 %, respectively) as the main components, also supporting the results of the present investigation. Similarly, [20] reported a similar profile for a volatile extract (employed technique: simultaneous distillationextraction, SDE) obtained from B. ochracea aerial parts collected in Uruguay. ...
... The identification of the individual compounds was based on the comparison of their GC linear retention index (LRI) in the named non-polar column and on the mass spectra match of the components with dedicated libraries [31,32,[44][45][46] and with previously published data from our research group. [14,[20][21][22]28] The abundances of each component were obtained as the raw percentage peak area of each compound from the full scan GC/MS chromatograms. Additional standardization was not performed since the focus of this research was to identify EO volatile compounds for the differentiation of the species. ...
Chemical Profiles and Cytotoxic Activities of Essential Oils from Six Species of Baccharis Subgenus Coridifoliae (Asteraceae)
Article
  • Aug 2023
  • CHEM BIODIVERS
Several Baccharis species are popularly known in traditional medicine as "carquejas", "vassouras", "ervas-santas" and "mio-mios", and are used as anti-inflammatories, digestives, and diuretics. Therefore, this study aimed to investigate the chemical compositions, performing graphical analysis of multivariate data and test cytotoxic activities of essential oils (EOs) of six Baccharis species belonging to subgenus Coridifoliae, namely B. albilanosa, B. coridifolia, B. erigeroides, B. napaea, B. ochracea and B. pluricapitulata. GC-MS analyses of the EOs showed that the oxygenated sesquiterpenes spathulenol (7.32-38.22%) and caryophyllene oxide (10.83-16.75%) were the major components for all the species. The EOs of almost all species were cytotoxic against cancer (BT-549, KB, SK-MEL and SK-OV-3) and normal kidney (VERO and LLC-PK1) cell lines, whereas B. erigeroides EO showed cytotoxicity only against LLC-PK1. This paper augments the current knowledge about the chemical-biological properties of Baccharis subgenus Coridifoliae and discusses the therapeutic potentials of these economically unexploited plants.
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... Flagelliform glandular trichomes have some variations, including simple flagelliform with straight body (Fig. 9.5b, e, f, g, i), as seen in B. microdonta (Budel et al. 2018a), B. pentaptera (Budel et al. 2015), B. ochracea (Budel et al. 2012), B. singularis (Souza et al. 2011), B. spicata (Oliveira et al. 2011), B. trilobata (Bobek et al. 2016), B. aracatubaensis, and B. organensis (Zuccolotto et al. 2019); branched with straight body (Fig. 9.3c, e), as observed in B. coridifolia (Budel and 2007), B. uncinella ( Fig. 9.5c), and B. erioclada (Fig. 9.5e); aseptate simple flagellate in B. artemisioides Hook. & Arn. ...
... & Arn. (Freire et al. 2007) and B. caprariifolia DC. (Bobek et al. 2015a); filiform flagellate with pointed terminal cell in B. multiflora Kunth or pearlike and rounded at the apex ( Fig. 9.5d) in B. megapotamica (Budel et al. 2012); and flagellate with C-shaped curved body ( Fig. 9.5h), as observed in B. punctulata (Budel et al. 2018a). The body in these trichomes is secretory, voluminous, and made up of 3-9 cells. ...
Book Chapter: Morpho-anatomical Characteristics of Species of Baccharis
Chapter
  • Feb 2022
Baccharis L. is one of the largest and most diversified genera of Asteraceae. Two groups of species, namely, “vassouras” and “carquejas,” are generally recognized based on their habit and branching pattern. “Vassouras” plants possess regular stems and leaves and are often broom-like in appearance, whereas “carquejas” have stems that are modified as cladodes and are devoid of leaves or have diminutive, scalelike leaves. Despite these major differences in their growth forms, stems, and leaves, the species within these groups show close resemblances in their morphologies. This chapter provides a comprehensive review of the morphology and anatomy of the genus and discusses the main morpho-anatomical features helpful in the identification of various Baccharis species. Further research involving comparative morpho-anatomical studies are required to better understand the species diversity as well as to develop a more accurate classification of Baccharis as well as of Asteraceae.
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... The genus Baccharis (Asteraceae) comprises about 440 species [27] of subshrubs, shrubs and trees and show a wide range of morphological diversity [27]. Many of the species are commonly used in traditional medicine due to the presence of essential oils with medicinal properties [28][29][30]. Several important biological activities attributed to these essential oils include anti-inflammatory [31], antibacterial, antifungal, antiprotozoal, antiviral [32,33], schistosomicidal [34], antimalarial, antitrypanosomal and insecticidal [35]. ...
Baccharis Species Essential Oils: Repellency and Toxicity against Yellow Fever Mosquitoes and Imported Fire Ants
Article
Full-text available
  • Oct 2023
Essential oils from five Baccharis species were screened for their toxicity and biting deterrence/repellency against yellow fever mosquito, Aedes aegypti (L.), and imported fire ants, including Solenopsis invicta Buren (RIFA), Solenopsis richteri Forel (BIFA) and their hybrids (HIFA). Baccharis microdonta DC. and B. punctulata DC. at 10 µg/cm 2 showed biting deterrence similar to DEET, N,N-diethyl-meta-toluamide at 25 nmol/cm 2 , whereas the repellency of B. pauciflosculosa DC., B. spheno-phylla Dusén ex Malme and B. reticularioides Deble & A.S. Oliveira essential oils was significantly lower than DEET against mosquitoes. Two major compounds from the active essential oils, kongol and spathulenol, also exhibited biting deterrence similar to DEET against mosquitoes. The highest toxicity exhibited against mosquitoes was by Baccharis punctulata essential oil (LC 50 = 20.4 ppm), followed by B. pauciflosculosa (LC 50 = 31.9 ppm), B. sphenophylla (LC 50 = 30.8 ppm), B. microdonta (LC 50 = 28.6 ppm), kongol (LC 50 = 32.3 ppm), spathulenol (LC 50 = 48.7 ppm) and B. reticularioides essential oil (LC 50 = 84.4 ppm). Baccharis microdonta essential oil showed repellency against RIFA, BIFA and HIFA at 4.9, 4.9 and 39 µg/g, respectively. Baccharis microdonta essential oil also showed toxicity with LC 50 of 78.9, 97.5 and 136.5 µg/g against RIFA, BIFA and HIFA, respectively, at 24 h post treatment.
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... Por outro lado, em B. ochracea os componentes β-pineno, viridiflorol, di-epi-1,10-cubenol e β-eudesmol são detectados, enquanto em B. albilanosa não são observados. Budel et al. (2012) Montanha et al. (2004), em que o extrato aquoso e hidroetanólico de B. erigeroides não foi citotóxico contra células normais VERO. Cabe salientar que os resultados obtidos para B. ochracea foram promissores uma vez que os valores de IC50 para células cancerígenas SK-MEL, SK-OV-3 e BT-549 foram menores quando comparados aos valores de IC50 obtidos para células normais VERO e LLC-PK1, sugerindo maior seletividade contra células cancerosas (Tabela 2). ...
Study of volatile polyacetylenes and terpenoids of Baccharis palustris Heering through GC/MS, GC/HRMS-TOF and GCxGC/HRMS-TOF
Conference Paper
Full-text available
  • Oct 2022
Polyacetylenes, a group of specialized bioactive metabolites potentially useful in therapy as antitumorals, are present in plants mostly from the Asteraceae family. Baccharis L. is a known source of C10 and C17-polyacetylenes, despite so far, their presence in essential oils is extremely rare. Previously we studied the unusual composition of B. palustris hydrodistilled essential oil (BPEO) from Southern Uruguay identifying a series of volatile C9-polyacetylenes. In this work, we re-analyze BPEO conducting GC/MS (ISO standard), GC/HRMS-TOF and GCxGC/HRMS-TOF analyses with the aim to find new components. In full, 42 compounds were identified or tentatively identified, most of them monoterpenoids and sesquiterpenoids. Ten minor oxygenated terpenoids were detected for the first time in BPEO (α-pinene epoxide, trans-β-ocimene epoxide, epicubebol, cubebol, germacrene D-4-ol, junenol, epi-α-cadinol, epi-α-muurolol, germacra- 4(15),5,10(14)-trien-1-β-ol and oplopanone), several of them co-eluting with major components. The C9-polyacetylenes baccharisdyine and the 7-dehydro-baccharisdyine geometric isomers were the main BPEO components, while 1-nonen-3-yne and 3-ethylidene-2-methyl-1-hexen-4-yne (two isomers) were tentatively identified. Finally, applying GCxGC/HRMS-TOF it was possible to identify the lachnophyllum lactone (undefined stereochemistry) in the second chromatographic dimension through deconvolution of the cis -lachnophyllum acid methyl ester peak. Being B. palustris a highly endangered species, our results might contribute to its preservation as a valuable source of polyacetylenes whose bioactivities need to be studied further.
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... Diterpenoids are the most prominent chemicals in Baccharis, while other biologically active elements, such as essential oils and phenolic compounds, were discovered in recent years [80]. Sabinene, myrcene, pinene, cadinene, limonene, nerolidol, cadinol, muurolol, and vivid floral are the major ingredients of essential oil [82,83]. The neo-clerodane-type diterpenes are characteristic diterpenic elements of the Baccharis genus, while kaurane and labdane derivatives have also been identified. ...
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... The principal class of compounds represented was the sesquiterpenoids, comprising oxygenated sesquiterpenoids (62.52%) and sesquiterpenoid hydrocarbons (8.01%). These are also the principal compounds of the EOs of several Baccharis species (Lago et al., 2008;Budel et al., 2012;Bogo et al., 2016;Campos et al., 2016;Pereira et al., 2016). However, Agostini et al. (2005) observed a predominance of monoterpenoids in the EO of Baccharis uncinella. ...
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... Budel et al. (2012) B. paniculata α-Pinene, β-pinene, α-phellandrene, limonene, Z-β-ocimene, β-caryophyllene, germacrene-D, γ-cadineneConcha et al. (2014) B. papilosa β-Pinene, δ-amorphene Dávila et al. (2008) B. parvidentata Sabinene, β-pinene, δ-3-carene, terpinen-4-ol, himachalol Perera et al. (2017) B. platypoda Diterpene clerodane, platypodiol, octahydronaftalen-1-ol., α-terpineol, spathulenol, α-cadinol Moreira (2014) and Ferracini et al. (1996) B. polycephala α-Pinene, β-pinene, limonene, bicyclogermacrene, α-muurolene Dávila et al. (2008) B. prunifolia Myrcene, limonene, trans-β-ocimene, β-caryophyllene Rojas et al. (2007) B. racemose α-Pinene, sabinene, limonene, δ-cadinene, (E)-nerolidol, α-muurolol Malizia et al. (2005) B. regnelli δ-Car-3-eno, β-elemene, biciclogermacrene, δ-cadinene Lago et al. (2008) B. reticularia α-Pinene, β-pinene, β-myrcen, d-limonene, (E)-caryophyllene, bicyclogermacrene, spathulenol Botas et al. (2017) B. retusa Synonym B. salzmannii Cadinene, caryophyllene oxide, humulene oxide, diterpenes, kaurenoic acid, 15-β-senecioyloxy acid, flavonoid sakuranetin, C6C3 derivatives substances named trans hexacos-18-enyl cumarate and cis hexacos-18-enyl cumarate flavonoids 5,7,4′-trihydroxy-flavone (apigenin) and 5,7,4′-trihydroxy-flavanone (narigenina) Vasconcelos Ribeiro et al. (2013) and Ueno et al. (2018)B. rhomboidalis Scopoletin, hispidulin, circimaritin, salvigenin, erythrodiolLabbe et al. (1986) ...
The potential of the genus Baccharis spp. as an insecticide for mosquitoes and non-biting flies of veterinary importance
Chapter
Full-text available
  • May 2022
Mosquitoes and non-biting flies are a group of insects that have great importance in livestock, agriculture and human health. These insects in the order Diptera are vectors of many species' pathogens such as salmonella, bots, mycosis, filariasis, and others (Carvalho et al., 2009). The mosquitoes are vectorsbearing anthropophilic and zoonotic disease that restrict rural and urban development by causing damage to economies (World Health Organization, 2014, 2016), while other flies are synanthropic and are related to the handling and care of domestic animals (Brito et al., 2008). Mosquitoes are a large arthropod group with 3563 species occurring in the world and about a hundred of them carry vector-borne diseases (World Health Organization, 1997; Harbach, 2018). These insects are divided into two subfamilies: Anophelinae, including the most critical mosquito genus Anopheles that is responsible for transmitting malaria and Culicinae where the genera Aedes, Culex, and Mansonia are most important. Several diseases are transmitted by these insects, such as arbovirus and filariasis (World Health Organization, 1997; Harbach, 2018). These insects have life cycles that consist of four stages: eggs, larvae, pupae, which require an aquatic environment, and adults living in air and land environments (European Commission, 2020). Mosquitoes lay their eggs separately over the surface of the water; after 2 or 3 days in contact with water, the larva is born, and it is about 1.5mm long when newly hatched and about l0mm long when fully grown. During growth, the larvae pass through four instars. After this phase, the larvae transform into pupae, which are a non-feeding stage that provides the morphological and physiological changes required for the transformation of the larva to the adult. Adults emerge from the pupae and are winged, with long legs and antennae, and the vast majority of them are bloodsucking (World Health Organization, 1982). Another critical group of flies that are vectors of human disease is the non-biting flies, which have developed a close relationship with human habitation. Non-biting flies are adapted to the different human population habitats, which permit them to feed, grow and reproduce around human environments. These features enable commensal flies to be mechanical vectors of disease to humans. Nonbiting flies are a group of insects from order Diptera, composed explicitly of species from sub-order Brachycera and infra-order Muscomorpha (old sub-order Cyclorrapha). Among the various species in this infra-order are Musca domestica (housefly), Musca sorbens (face fly), and Chrysomya spp. (blowfly) (European Commission, 2020). The females of these flies lay about 100 to 150 eggs in moist organic material, which larvae usually hatch from after 8 to 48 h. Larvae grow by feeding on organic matter, including animal or human excrement. Depending on the temperature, quantity of food, and the species, after a few days, the larvae dig in soil or substrate, where they become pupae. After this period, the adults will emerge from the pupae. Adults have a lifespan of 1 to 2 months, depending on species and life conditions (Moon et al., 2002). Recently, bioprospecting for natural products able to control mosquitoes and flies has been received increased attention especially that for pest control (Rajashekar et al., 2012). Botanical insecticides includes natural products obtained from plant extracts and used to protect farmer production against insects plague and vectors (Stevenson and Belmain, 2016; Isman, 2000, 2008). Bio-pesticides present a significant advantage over synthetic insecticides because they do not affect non-target species, they break down rapidly, and they have reduced risk to produce insect resistance since they have multiple modes of action (Amoabeng et al., 2013; Dubey et al., 2010; Isman, 2006; Koul, 2008; Tembo et al., 2018). Plants represent an essential source of secondary metabolism products, such as alkaloids, phenols, and terpenoids. These products are part of an evolutionary defense against predator attacks that have developed over millions of years (Amoabeng et al., 2019). Thus, some plants have demonstrated a potential insecticidal agent. Among them is genus Baccharis, in the Asteraceae family. This genus is composed of 433 species classified into seven subgenera and 47 sections (Heiden et al., 2017). It is considered the largest group, and it predominantly occurs in the Neotropical American megadiverse region (Heiden, 2014). Heiden (2014) present seven main lineages that are recognized and treated as subgenera, all of which re-circumscribed as monophyletic lineages. Baccharis spp. plants could occur from the Columbian Andes to the middle of Chile and Argentina, through Brazilian mountain regions in the south and southern, Uruguay, and up to the east of Paraguay. In Brazil, this genus has around 177 species (Heiden, 2014). Baccharis spp. are dioecious species, which means that there are male and female individuals (Ferracini et al., 1994). Many species of Baccharis spp. are known in scientific and in folk knowledge to produce important secondary compounds for medicinal use. Thus, this chapter aims to review the literature on the potential of Baccharis spp. as insecticides to control the overpopulation of mosquitos and non-biting flies in breeding sites. This discussion of natural products from Baccharis spp. plants could lead to promissory and effective products to control mosquitoes and flies of importance agriculture and livestock.
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Morphoanatomy and histochemistry of Baccharis palustris: insights into a highly endangered endemic species from Southeastern America
Article
Full-text available
  • Apr 2024
Morphoanatomy and histochemistry of Baccharis palustris: insights into a highly endangered endemic species from Southeastern America. The phenotypic plasticity of the Baccharis genus makes species identification difficult, even at the flowering stage. In this context, morphoanatomical studies are a powerful tool for botanical authentication, mainly emphasizing the recognition of diagnostic characteristics that may be useful for distinguishing similar species. Given the limited knowledge available about the endemic species B. palustris, this work aimed to characterize the morphoanatomy and histochemistry of its vegetative aerial parts to identify characters with diagnostic value and to elucidate the sites of synthesis and accumulation of metabolites of medicinal importance. B. palustris leaf showed pinnate, camptodrome-brochidodrome venation patterns. Blade with dorsiventral mesophyll, aerenchymatous spongy parenchyma, collateral vascular bundles, and different types of stomata and trichomes, including glandular trichomes with a multi-layered base evidenced and described for the first time in the genus. The petiole was winged, with three collateral vascular bundles. The stem showed a penta-lobulated contour with unusual growth, starch, and crystals in the pith. The presence of secretory ducts and glandular trichomes, which synthesized lipids, terpenes/polyacetylenes, and phenolic compounds, was observed. The morphological/histochemical characteristics described in this work contribute to the knowledge of the species, highlighting the importance of its preservation as a valuable resource.
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Fitoquímica de Baccharis spp L. (Asteraceae): Metabolitos secundarios, Semi-síntesis y Bioactividad
Thesis
Full-text available
  • Oct 2019
Las plantas medicinales y aromáticas (PAMs) han sido empleadas por las sociedades humanas desde sus inicios, y son el punto de partida para la investigación en productos naturales. En ésta tesis se trabajó sobre la fitoquímica del género Baccharis L. (Asteraceae) como modelo de PAMs, colectando in natura 19 especies nativas de Uruguay, del sur de Brasil y del nordeste de Argentina: B. articulata, B. crispa, B. cultrata, B. dentata, B. dracunculifolia, B. genistifolia, B. gibertii, B. gnaphalioides, B. linearifolia, B. microdonta, B. milleflora, B. ochracea, B. palustris, B. phyteumoides, B. punctulata, B. spicata, B. tridentata, B. trimera y B. uncinella. Para todas ellas se describió su composición química volátil (volatiloma) y se identificaron los principales metabolitos producidos por cromatografía gaseosa convencional y acoplada a espectrometría de masa (GC-FID y GC-MS). Para el estudio, se tomaron en cuenta diferentes variables que inciden directamente sobre la composición como: metodología de extracción (B. uncinella), origen geográfico de las poblaciones vegetales (B. trimera), estacionalidad (B. dracunculifolia y B. microdonta) y género de las plantas (masculino/femenino; B. articulata, B. crispa, B. dracunculifolia, B. linearifolia, B. spicata y B. tridentata). En particular, sobre éste último aspecto se trabajó en caracterizar el perfil de emisión volátil de ambos sexos empleando para ello cromatografía gaseosa/olfatometría (GC-O) y cromatografía gaseosa enantioselectiva (eGC). Para la especie B. trimera (―carqueja‖) se realizó un detallado estudio de la composición del aceite esencial, fraccionando el mismo por cromatografía en columna (CC) y estudiando la composición de cada una de las fracciones por GC-MS. Adicionalmente, se realizó un estudio de las características morfoanatómicas e histoquímicas de una población de referencia de B. trimera, lo que permitió su caracterización biotípica. Desde el aceite esencial de ésta especie fue aislado por CC su compuesto mayoritario acetato de carquejilo, y mediante reacciones químicas específicas fueron obtenidos sus derivados semi-sintéticos: carquejol, carquejifenol, carquejona, iso-carquejona y óxido de carquejol (los últimos tres no reportados anteriormente en la bibliografía). En todos los casos los productos fueron caracterizados por medio de técnicas espectroscópicas de resonancia magnética nuclear (RMN), infrarrojo (IR), ultravioleta (UV), dicroísmo circular (DC), Raman y espectrometría de masa (MS). También fue realizado un estudio de química computacional para predecir las propiedades moleculares del acetato de carquejilo, carquejol y carquejifenol, empleando la teoría del funcional de densidad (DFT). Para la especie B. palustris fue determinado por diferentes técnicas espectroscópicas la presencia de poliacetilenos en su volatiloma. Consecuentemente, fueron identificados los siguientes compuestos 1-nonen-3,5-diino, 1,7(Z)-nonadien-3,5-diino, 1,7(E)-nonadien-3,5-diino y 3,5-nonadiino; así como los (E)/(Z) ésteres de lachnophyllum. Para los tres primeros compuestos es su primer reporte en la literatura como productos naturales. Finalmente, se estudió la bioactividad de extractos y compuestos semi-sintéticos mediante técnicas in-vitro: antiradicalaria (metodología del DPPH) y neutralizante del veneno de serpientes del género Bothrops sp. (―yaras‖) (actividad alexitérica). Los extractos de B. dracunculifolia, B. punctulata y B. trimera demostraron la mejor actividad de captura del DPPH, en tanto la carquejona y el (Z)-éster de lachnophyllum exhibieron los mejores resultados de neutralización de los venenos. Los resultados de ésta tesis y sus correspondientes publicaciones demuestran la importancia del enfoque desarrollado en la búsqueda de metabolitos bioactivos provenientes de PAMs.
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Leaf and stem morpho-anatomy of Baccharis dracunculifolia DC., Asteraceae
Article
Full-text available
  • Oct 2004
Baccharis dracunculifolia DC. belongs to Spicata group and Discolores section, and is known in the traditional medicine as "carqueja", "chilca", "vassourinha". It is commonly employed for treating dyspepsia, anorexia, fatigue and mild fever. The aim of this work was to study the leaf and stem morpho-anatomy of B. dracunculifolia, in order to contribute for the drug identification and group taxonomy. Usual optical and scanning microtechniques were applied to the botanical material. The leaves are simple, entire, alternate, lanceolate and measure 1-2 cm long and 3-4 mm wide. They have uniseriate epidermis coated by striated cuticle, anomocytic stomata on both surfaces, pluricellular glandular trichomes united at the base, isobilateral mesophyll and secretory canals associated to collateral bundles. The stem has lignified aspect and approximately 2 m height and 5 mm of diameter. It shows circular transection, epidermis similar to the leaf one, secretory canals near the starch sheath which encircles the vascular system, and calcium oxalate crystals in the outer layers of the pith.
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Antiviral activity of Brazilian plant extracts
Article
Full-text available
  • Apr 2004
Ethanolic and aqueous extracts of fifty one plant species collected in Southern Brazil were tested for antiviral activity against herpes simplex virus type 1 (HSV-1) on Vero cell line. Nine of the species tested, namely Aloysia gratissima (Gill. & Hook.), Baccharis erioclada DC., Baccharis megapotamica Hook & Arn., Baccharis uncinella DC., Glechon marifolia Benth., Glechon spathulata Benth., Ilex brevicuspis Reiss., Ilex theezans Mart, and Maytenus ilicifolia Mart, ex Reiss. exhibited antiherpetic activity.
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Essential oil of Baccharis cordobensis Heering
Article
  • May 2000
The essential oil of the aerial parts of Baccharis cordobensis was examined by GC and GC-MS. The major constituents were trans-nerolidol (15.8%), T-cadinol (14.7%) and cubenol (8.8%). Copyright (C) 2000 John Wiley & Sons, Ltd.
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Morpho-anatomical characters of Baccharis gaudichaudiana DC., Asteraceae
Article
  • Oct 2003
Baccharis gaudichaudiana DC., Asteraceae, popularly known as "carqueja" and "chilca melosa", is employed in the traditional medicine as stomachic, diuretic and hypoglycemic agent. The aim of this work was to study the winged stem morpho-anatomy, in order to supply information to the pharmacognostical identification of this medicinal plant and to the taxonomy of the Trimera group. The botanical material was prepared according to the usual optical and electronic microtechniques. The species is 70 cm height and has got a three-winged stem. The epidermis is uniseriate and coated by a slightly striated cuticle, and it has got anomocytic stomata and pluricellular glandular trichomes. In the caulinar expansions, the clorenchyma consists of palisade parenchyma on both sides of the epidermis and spongy parenchyma in the middle. In the caulinar axis, the clorenchyma and the angular collenchyma distribute alternately, the vascular cylinder is formed with phloem, centrifugally and xylem, centripetally, and in the perimedular zone prismatic crystals are found. Secretory ducts, with uniseriate epithelium, are observed in the stem.
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Volatile constituents of leaf oils from the genus Baccharis. Part II: Baccharis obovata Hooker et Arnott and B. sallcifolla (Ruiz et Pav.) Pers. species from Argentina
Article
  • Mar 2005
Volatile compounds from Baccharis obovata Hooker et Arnott and B. salicifolia (Ruiz et Pav.) Pers. leaves collected in the Argentinean Patagonia were isolated by steam distillation. Yields on the essential oils were 2.81% for B. obovata and 1.50% for B. salicifolia. The oils were analyzed by GC and GC/MS. The main constituents of each oil were: (i) B. obovata oil: α-thujene (5.8%), α-pinene (9.2%), sabinene (23.2%), β-pinene (9.9%), myrcene (3.7%), limonene (10.7%), terpinen-4-ol (5.9%); and (ii) B. salicifolia oil: α-thujene (2.1%), α-pinene (4.4%), sabinene (2.9%), β-pinene (5.5%), myrcene (2.2%), α-phellandrene (3.2%), limonene (8.1%), (Z)-β-ocimene (4.6%), terpinen-4-ol (5.9%), δ-cadinene (2.3%), elemol (2.7%), cis-α-copaen-8-ol (2.3%), α-muurolol (5.5%), α-eudesmol (2.7%), verboccidentafuran (2.8%), chromolaenin (3.1%) and dihydroisochromolaenin (2.9%).
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Baccharis (compositae): A review update
Article
  • Jan 2007
The Baccharis genus is an important source of natural medicinal products. The information collected here is an attempt to cover the most recent developments in the ethnopharmacology, pharmacology and phytochemistry of this genus. This review describes its traditional and folkloric uses, phyto-constituents and pharmacological and toxicological reports of the prominent species of the genus Baccharis. Flavonoids and other phenolic compounds, diterpenoids and volatile constituents have been reported as the major phyto-constituents of the Baccharis species. Pharmacological studies are mainly based on the anti-inflammatory, antioxidant, antimicrobial and antifungal properties. The potential for development of leads from Baccharis genus continues to grow. The information summarized here is intended to serve as a reference tool to practitioners in the fields of ethnopharmacology and chemistry of natural products.
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