Chemical composition of teas from two cultivated chemotypes of Egletes viscosa ("Macela-da-terra")

Vieira, Gizelle A.B.; Lima, Mary Anne Sousa; Bezerra, Antônio Marcos Esmeraldo; Silveira, Edilberto R.

doi:10.1590/s0103-50532006000100006

Cited by 17 publications

(10 citation statements)

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“…Our data suggest that "macela" chemotypes A and B are indeed genetically distinct, which is in agreement with their striking morphological and chemical differences already pointed out in previous studies. 9,33 Thus, the hypothesis that these E. viscosa chemotypes may represent distinct botanical varieties or even different species should be further evaluated in future studies.…”

Section: Discussionmentioning

confidence: 99%

“…These chemotypes have been designated as "macela" A and "macela" B, whose essential oils are characterized by trans-pinocarveyl acetate and cis-isopinocarveyl acetate as their major constituents, respectively. 9 Furthermore, lyophilized teas from flower buds of both chemotypes also showed different chemical profiles. The trans-pinocarveyl chemotype ("macela" A) gave ternatin, centipedic acid, 12-acetoxy-hawtriwaic lactone and the new diterpene 12-acetoxy-7-hydroxy-3,13(14)-clerodandien-18,19:15,16-diolide.…”

Section: Introductionmentioning

confidence: 99%

“…From the cis-isopinocarveyl chemotype ("macela" B) the same diterpene, 12-epi-bacchotricuneatin and scopoletin were isolated, in addition to ternatin. 9 These two E. viscosa chemotypes also have distinct morphological features. 10 "Macela" A presents pinnatifid and broad leaves with a less distinct petiole, while "macela" B leaves are much more jagged, resembling secondary leaves, with a prominent petiole, which is a very characteristic feature of the Asteraceae family.…”

Section: Introductionmentioning

confidence: 99%

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Molecular identification and phylogenetic analysis of Egletes viscosa (L.) Less., a traditional medicinal plant from Northeastern Brazil

Batista¹,

Torres²,

Jorge³

et al. 2012

J. Braz. Chem. Soc.

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Macela (Egletes viscosa (L.) Less.) é uma erva medicinal utilizada para tratar distúrbios digestivos e intestinais. Estudos prévios revelaram a existência de dois quimiotipos de macela, cujos óleos essenciais são caracterizados pela presença de acetato de trans-pinocarveíla (quimiotipo A) ou acetato de cis-isopinocarveíla (quimiotipo B). A análise de sequências de DNA do espaçador transcrito interno (ITS/5,8S) revelou oito polimorfismos de base única (SNPs) e um sítio inserção/ deleção que diferenciam os dois quimiotipos. Além disso, foi possível identificar espécimes selvagens de E. viscosa pertencendo a ambos quimiotipos e amostras comerciais, obtidas em mercados locais, pertencendo somente ao quimiotipo A. A análise filogenética confirmou a posição taxonômica desses dois quimiotipos na tribo Astereae. Portanto, a análise de seqüências de DNA da região ITS/5,8S proporciona uma efetiva e acurada estratégia para identificar os quimiotipos A e B de E. viscosa."Macela" (Egletes viscosa (L.) Less.) is a medicinal herb used to treat digestive and intestinal problems. Previous studies revealed the existence of two chemotypes of "macela", whose essential oils are characterized by the presence of trans-pinocarveyl acetate (chemotype A) or cisisopinocarveyl acetate (chemotype B). Herein, DNA sequence analysis of the internal transcribed spacer region (ITS/5.8S) showed eight single nucleotide polymorphisms (SNPs) and one insertion/ deletion site that clearly distinguished the chemotypes of E. viscosa. Moreover, it was possible to identify wild specimens of E. viscosa belonging to both chemotypes and commercial samples, purchased at local markets, belonging only to chemotype A. The phylogenetic analysis confirmed their taxonomic position within the tribe Astereae. Therefore, analysis of ITS/5.8S DNA sequences provides an effective and accurate strategy for identifying the chemotypes A and B from E. viscosa.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Molecular identification and phylogenetic analysis of Egletes viscosa (L.) Less., a traditional medicinal plant from Northeastern Brazil

Batista¹,

Torres²,

Jorge³

et al. 2012

J. Braz. Chem. Soc.

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“…2 Previous studies with E. viscosa have reported the isolation of biologically active flavonoids and diterpenoids. [3][4][5][6][7][8][9][10][11][12][13][14] Recently, Lee et al reported the isolation of labdane diterpene glycosides and flavonoids from the entire plant native from Peru. 15 In continuation of the work with this species, we report now the isolation of the new labdane glycoside 8α-hydroxylabd-14(15)-ene-13(S)-O-β-D-ribopyranoside 1 in addition to 13-epi-sclareol, 16 barbatol, 17 tarapacol, 18 spinasterol, 19 ternatin, 7,[20][21][22][23] and triacontane from the aerial parts of E. viscosa.…”

Section: Introductionmentioning

confidence: 99%

“…15 In continuation of the work with this species, we report now the isolation of the new labdane glycoside 8α-hydroxylabd-14(15)-ene-13(S)-O-β-D-ribopyranoside 1 in addition to 13-epi-sclareol, 16 barbatol, 17 tarapacol, 18 spinasterol, 19 ternatin, 7,[20][21][22][23] and triacontane from the aerial parts of E. viscosa. The complete proton and carbon assignments of the known compounds and of the new diterpene 1, including the unpublished 13 C and 1 H NMR data of the new derivatives 2-4 were accomplished by the use of a series of 2D NMR experiments such as 1 H-1 H COSY, HMQC and HMBC.…”

Section: Introductionmentioning

confidence: 99%

A Labdane diterpene from the aerial parts of Egletes viscosa less

Silva-Filho

Lima

Bezerra

et al. 2007

J. Braz. Chem. Soc.

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Um novo labdano glicosilado, 8α-hidroxilabd-14(15)-eno-13(S)-O-β-D-ribopiranosídeo, foi isolado das partes aéreas de Egletes viscosa Less, juntamente com o 13-epi-esclareol, barbatol, tarapacol, espinasterol, ternatina e triacontano. As estruturas dos compostos isolados foram elucidadas pelo uso de métodos espectrométricos e preparação de derivados químicos.A new labdane glycoside, 8α-hydroxylabd-14(15)-ene-13(S)-O-β-D-ribopyranoside, was isolated from the aerial parts of Egletes viscosa Less, along with 13-epi-sclareol, barbatol, tarapacol, spinasterol, ternatin and triacontane. The structures of the isolated compounds were elucidated by the use of spectrometric methods and preparation of chemical derivatives. Keywords: Asteraceae, Egletes viscosa, diterpene glycoside, 8α-hydroxylabd-14(15)-ene-13(S)-O-β-D-ribopyranoside IntroductionEgletes viscosa Less (Asteraceae) is an annual herb mostly native to intertropical Americas. It is known in the Northeast of Brazil as "macela" or "macela-da-terra" and grows throughout the margins of river and lakes as soon as the raining season ends. The flower buds are largely sold in the herbal stores and used in the folk medicine as emmenagogue, diaphoretic, 1 stomachic and antidiarrhoeal. 2 Previous studies with E. viscosa have reported the isolation of biologically active flavonoids and diterpenoids. [3][4][5][6][7][8][9][10][11][12][13][14] Recently, Lee et al reported the isolation of labdane diterpene glycosides and flavonoids from the entire plant native from Peru. 15 In continuation of the work with this species, we report now the isolation of the new labdane glycoside 8α-hydroxylabd-14(15)-ene-13(S)-O-β-D-ribopyranoside 1 in addition to 13-epi-sclareol, 16 barbatol, 17 tarapacol, 18 spinasterol, 19 ternatin, 7, 20-23 and triacontane from the aerial parts of E. viscosa. The complete proton and carbon assignments of the known compounds and of the new diterpene 1, including the unpublished 13 C and 1 H NMR data of the new derivatives 2-4 were accomplished by the use of a series of 2D NMR experiments such as 1 H-1 H COSY, HMQC and HMBC. Results and DiscussionCompound 1 was isolated as a white solid. Its molecular formula was determined as C 25 H 44 O 6 from the NMR and EImass spectroscopy measurements (m/z = 440). The absorption band in the IR spectrum at 3400 cm -1 was consistent with hydroxyl groups. Inspection of the 1 H NMR spectrum indicated the presence of three angular methyl groups at δ 0.81 (s, H-19 and H-20) and 0.88 (s, H-18), two methyls attached to oxygenated tertiary carbons at δ 1.11 (s, H-17) and 1.35 (s, H-16), and an anomeric hydrogen at δ 4.32 (d, J 6.4 Hz,. Moreover, the presence of a vinyl moiety was suggested by the signals at δ 5.92 (dd, J 17.8, 10.9, H-14); 5.22 (dd, J 17.8, 1.2, H-15a) and 5.17 (dd, J 10.9, 1.2, H-15b). The 13 C NMR spectral data of 1 confirmed 1375 Silva-Filho et al. Vol. 18, No. 7, 2007 the β-ribopyranosyl unit by the signals at δ 98.6 (C-1´), 73.1 (C-3´), 71.3 (C-2´), 68.2 (C-4´) and 65.1 (C-5´); 24 together with 20 carbon ...

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