Five New Sesquiterpenoids and a New Diterpenoid from Erigeron annuus (L.) PERS., Erigeron philadelphicus L. and Erigeron sumatrensis RETZ.

Iijima, Takeyoshi; Yaoita, Yasunori; Kikuchi, Masao

doi:10.1248/cpb.51.545

Cited by 62 publications

(38 citation statements)

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“…10 A substância 4, conhecida como Carainterol, também foi isolada de plantas 11 e, recentemente, foi sintetizada, 12 enquanto a substância 5 tem sido encontrada frequentemente em óleos essenciais. 13,14 A substância 6, que possui o esqueleto pouco comum do tipo opositano, foi obtida anteriormente de plantas dos gêneros Eringeron, 11 Senecio 15 e Tephrosia. 16 No entanto, este é o primeiro registro de isolamento das substâncias 3-6 de Meliaceae.…”

Section: Resultsunclassified

Sesquiterpenos de sementes de Guarea guidonia (Meliaceae)

et al. 2012

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Recebido em 28/3/11; aceito em 1/7/11; publicado na web em 19/8/11SESQUITERPENES FROM THE SEEDS OF Guarea guidonia (MELIACEAE). Two new sesquiterpenes 6α-ethoxyeudesm-4(15)-en-1β-ol (1) and (7R*)-5-epi-opposit-4(15)-ene-1β,7-diol (7) were isolated from the seeds of a specimen of Guarea guidonia (Meliaceae). Five other known sesquiterpenes, eudesm-4(15)-ene-1β,6α-diol (2), 5-epi-eudesm-4(15)-ene-1β,6β-diol (3), eudesm-4(15)-ene-1β,5α-diol (4), eudesm-4(15),7-dien-1β-ol (5) and (7R*)-opposit-4(15)-ene-1β,7-diol (6), were also isolated in this work. Their structures were determined on the basis of spectral data (MS, IR, and NMR-1D and 2D) and subsequent comparisons with the literature. The substances 3, 4 and 6 are reported for the first time in Meliaceae and 5 for the first time in the genus Guarea.Keywords: Guarea guidonia; Meliaceae; eudesmane. INTRODUÇÃOGuarea guidonia L. Sleumer (sin. Guarea trichilioides L.), pertencente à família Meliaceae e popularmente conhecida como carrapeta-verdadeira, é uma árvore ocorrente no Brasil desde a região Amazônica até o estado do Rio Grande do Sul, 1 podendo atingir 20 m de altura. Na medicina popular é utilizada no tratamento de reumatismo, hidropsia e tumores artríticos, tendo, ainda, propriedades adstringentes, purgativas, febrífugas, abortivas, eméticas e anti-inflamatórias. 1 Estudos fitoquímicos prévios dos extratos hexânico e etanólico da casca do tronco desta espécie, além do óleo volátil de suas folhas, resultaram no isolamento de limonoides, 2-3 esteroides, 4 seco-esteroides, 5 cumarinas, 2 di-, 4,6,7 tri-4 e sesquiterpenos. 2,4,8 O presente trabalho trata do estudo fitoquímico de sementes de um espécime de G. guidonia, que levou ao isolamento de sete sesquiterpenos, sendo dois deles inéditos: 6α-etoxieudesm-4(15)-eno-1β-ol (1), eudesm-4(15)-eno-1β,6α-diol (2), 5-epi-eudesm-4(15)-eno-1β,6β-diol (3), eudesm-4(15)-eno-1β,5α-diol (4), eudesm-4(15),7-dien-1β-ol (5), (7R*)-oposit-4(15)-eno-1β,7-diol (6) e (7R*)-5-epioposit-4(15)-eno-1β,7-diol (7) (Figura 1). As substâncias 1 e 7 são inéditas na literatura, enquanto 3, 4 e 6 estão sendo descritas pela primeira vez em Meliaceae e 5 pela primeira vez no gênero Guarea. PARTE EXPERIMENTAL Instrumentação e procedimentos geraisPara cromatografia em camada fina utilizaram-se placas de gel de sílica (Whatman), com indicador de fluorescência UV 254 , em camadas de 0,25 mm de espessura, empregando-se como revelador solução saturada de sulfato de cério IV em ácido sulfúrico 36%. A separação cromatográfica em coluna foi realizada utilizando-se gel de sílica 230-400 mesh (Acros Organics). Os experimentos de RMN 1 H e 13 C (uni-e bidimensionais) foram obtidos em espectrômetro Bruker DPX-300 (300/75 MHz), utilizando-se CDCl 3 como solvente e o sinal do CHCl 3 residual como referência. Os espectros de IV foram registrados em espectrômetro Bomem-Hartmann & Braun FT, tendo sido as amostras preparadas sob a forma de filme. As medidas de rotação óptica foram determinadas em polarímetro Perkin-Elmer 341 e os espectros de massas obtidos no es...

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Section: Resultsunclassified

Sesquiterpenos de sementes de Guarea guidonia (Meliaceae)

et al. 2012

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“…3) and HMQC correlations suggested the plane structure of 4 is same as that of (7R*)-opposit-4(15)-en-1b,7-diol (5) ( Table 2). 8) In the NOESY spectrum, the cross peaks observed between H 3 -14 and H-6, and H-5 and H-1 suggested a trans junction for the two rings, and the relative configuration of the hydroxy at C-1, Me-14 and isobutyl group at C-6 should be b, b and a respectively. These observations were identical to that of compound 5.…”

Section: )mentioning

confidence: 93%

“…6) As a part of our ongoing study on the finding antibacterial and antifungal sesquiterpenoids from poisonous plants scattered in northeast China, the lesser polar constituents of S. argunensis were systematically investigated. As a result, three new sesquiterpenoids, isodauc-7(14)-en-6a,10b-diol (1), 10b-hydroxyisodauc-6-en-14-al (2), and (7S*)-opposit-4(15)-en-1b,7-diol (4), along with nine known compounds, artabotrol (3), 7) (7R*)-opposit-4(15)-en-1b,7-diol (5), 8) opposit-4(15)-en-1b, 11-diol (6), 9) loliolide (7), 10) 5a,6a-epoxy-3b-hydroxymegastigm-7-en-9-one (8), 11) chromolaevane dione (9), 12) pregn-4-en-3,20-dione (10), 13) 12b-hydroxypregn-4-en-3,20-dione (11), 14) ergost-6,22-dien-3b,5a,8a-triol (12), 15) (23Z)-cycloart-23-en-3b,25-diol (13) 16) have been isolated from the aerial parts of this plant. This paper deals with the isolation and structure determination of three new constituents.…”

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confidence: 99%

Sesquiterpenoids and Other Constituents from Senecio argunensis

et al. 2010

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Three new sesquiterpenoids, isodauc-7(14)-en-6a,10b-diol (1), 10b-hydroxyisodauc-6-en-14-al (2), and (7S*)-opposit-4(15)-en-1b,7-diol (4), along with ten known compounds have been isolated from the aerial parts of Senecio argunensis. Their structures were established by means of detailed spectroscopic analysis including IR, HR-MS, and 1D NMR and 2D NMR data. The sesquiterpenoids were assayed against Escherichia coli, Staphylococcus aureus and Bacillus subtilis. Compounds 4 exhibited weak antibacterial activity against Escherichia coli and Bacillus subtilis.

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“…Thus, the structure of 3 was established as (3R,7R,9R)-3,9-dihydroxygermacra-4(15),10(14),11(12)-triene. The structures of the other known compounds (4-11) were identified as 6β,14-epoxyeudesm-4(15)-en-1β-ol (4), 14 6a-methoxyeudesm-4(15)-en-1β-ol (5), 14 (7R*)-opposit-4(15)-ene-1β,7-diol (6), 14 7β-methoxy-4(14)-oppositen-1β-ol (7),…”

Section: Notesmentioning

confidence: 99%

Two New Sesquiterpenes from the Aerial Parts of Pimpinella brachycarpa NAKAI

Lee¹,

Shin²,

Lee³

2013

Bulletin of the Korean Chemical Society

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Pimpinella brachycarpa (Umbelliferae) is one of the most favored and increasingly popular wild vegetables grown in Asian regions.1,2 In particular, this plant has been used in Korean folk medicine for treating gastrointestinal disturbances, bronchial asthma, insomnia, and persistent cough. Terpenes, flavonoids, and essential oil components have been isolated from the herbs.3-5 Several biological activities of P. brachycarpa have been reported, including antibacterical, antioxidative, anti-proliferative, antifungal, and antithrombotic activities.6-9 We have recently reported the isolation of quinic acid derivatives with an anti-inflammatory effect from this plant.10 In continuing research on this source, two new sesquiterpenes (1 and 2) and ten known terpenes (3-12) were further isolated from the MeOH extracts. The structures were elucidated by means of spectroscopic methods and chemical evidence. Figure 2). In the HMBC spectrum of 1, long-range correlations were observed between the following protons and carbons: H-1 and C-3, C-9, C-14; H-3 and C-5, C-15; H-7 and C-9, C-12, C-13; H-9 and C-7, C-14; H-13 and C-7, C-12 (Figure 2). These spectral data led us to conclude that the planar structure of 1 is sinugibberodiol (3), which was isolated from Sinularia gibberosa.11 The optical rotation of 1 ( +8.6, CHCl 3 ) was almost the same value but of the opposite sign to that of sinugibberodiol (3) ( −5.0, CHCl 3 ), suggesting that compound 1 could be a stereoisomer of sinugibberodiol (3).11,12 The relative configurations of the hydroxyl groups at Assignments were based on 2D NMR including COSY, HMQC and HMBC (Well-resolved couplings are expressed with coupling patterns and coupling constants in Hz in parentheses).

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Five New Sesquiterpenoids and a New Diterpenoid from Erigeron annuus (L.) PERS., Erigeron philadelphicus L. and Erigeron sumatrensis RETZ.

Cited by 62 publications

References 15 publications

Sesquiterpenos de sementes de Guarea guidonia (Meliaceae)

Sesquiterpenos de sementes de Guarea guidonia (Meliaceae)

Sesquiterpenoids and Other Constituents from Senecio argunensis

Two New Sesquiterpenes from the Aerial Parts of Pimpinella brachycarpa NAKAI

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