Diterpenes from Calceolaria latifolia

Garbarino, Juan A.; Molinari, Aurora

doi:10.1016/0031-9422(90)87134-g

Cited by 27 publications

(40 citation statements)

References 7 publications

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“…The C-13 epimer of compound 3 was previously described in a study of cationic rearrangements and cyclizations of diterpenes [22] as well as from Phoma betae [23]. Compound 4 was identified as 8,15-isopimaradien-19-ol and shows clear differences with the ent -isopimaranes isolated from Calceolaria polifolia [24] and C. latifolia [25]. Sandaracopimaric acid ( 5 ) as well as several abietanes were isolated from the endemic species Taxus mairei occurring in Taiwan [26], Juniperus chinensis [27] and other gymnosperms [5].…”

Section: Resultsmentioning

confidence: 99%

Resin Diterpenes from Austrocedrus chilensis

2011

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Section: Resultsmentioning

confidence: 99%

Resin Diterpenes from Austrocedrus chilensis

2011

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“…The strategy adopted is that described in Scheme 13. The starting material was (−)-19-hydroxypodocarp-9-en-12-one (67), available in four steps from (+)-podocarpic acid (4). Photoaddition of allene to (−)-67 in THF at −78 °C gave quantitatively the photoadduct (+)-68 the structure of which was established by 2D NMR experiments (Scheme 15).…”

Section: Synthesis Of (+)-Stemar-13-enementioning

confidence: 99%

“…Finally, having in hand an efficient methodology for the construction of the C/D ring system of stemarane diterpenoids, we decided to apply it to the synthesis of (+)-2-deoxyoryzalexin S (66), the structure and absolute configuration of which had been established only on the basis of the corresponding 1 H-and 13 C-NMR spectra [66][67][68]. The strategy adopted is that described in Scheme 13.…”

Section: Synthesis Of (+)-Stemar-13-enementioning

confidence: 99%

(+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †

et al. 2016

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Abstract:In this review the synthetic work in the field of aphidicolane, stemodane and stemarane diterpenoids, in which readily available (+)-podocarpic acid (4) was used as chiral template for the construction of their polycyclic structures, is described as it developed along the years. In the frame of this work (+)-podocarpic acid (4) was a very useful tool in a model study leading to the syntheses of tetracyclic ketones 7 and 8, models of key intermediates 5a and 6 in the syntheses of (+)-aphidicolin (1) and (+)-stemodin (2a), respectively. (+)-Podocarpic acid (4) was also converted into (+)-2-deoxystemodinone (2d), allowing confirmation of the stemodane diterpenoids absolute configuration, into (+)-aphidicol-15-ene (36) and into Stemodia chilensis tetracyclic diterpenoid (+)-19-acetoxystemodan-12-ol (2f), allowing confirmation of its structure. (+)-Podocarpic acid (4) was then extensively used in the work which led to the synthesis of (+)-stemar-13-ene (57) and (+)-18-deoxystemarin (3b). Finally, (+)-4 was converted into (+)-2-deoxyoryzalexin S (66), which made it possible to demonstrate that the structure of (+)-66 could not be attributed to a Chilean Calceolaria isolated diterpenoid to which this structure had been assigned.

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“…Sob o ponto de vista químico, as espécies desse gênero têm sido bem estudadas sendo identifi cados diferentes diterpenos e bis-diterpenos Chamy et al, 1990;Chamy et al, 1991a) de diferentes esqueletos: pimarano Piovano et al, 1989;Chamy et al, 1990;Chamy et al, 1995a), isopimaradieno (Chamy et al, 1990;Chamy et al, 1998), pimaradieno (Chamy et al, 1991a), labdano (Garbarino et al, 2004), abietano (Chamy et al, 1987;Chamy et al, 1991b), desidroabietano (Chamy et al, 1987;Chamy et al, 1995a), estemodano (Chamy et al, 1995b), estemarano (Chamy et al, 1990;Molinari, 1990a;Molinari, 1990b;Chamy et al, 1991a;Chamy et al, 1995b) e diterpenos endoperóxidos de esqueleto abietano (Chamy et al, 1993); além de fl avonóides não glicosilados (Wollenweber;Mann;Roitman, 1989), fenilpropanóides glicosilados (verbascosídeo, calceolariosídeos A-E, forsitosídeo A e isoarenariosídeo) (Nicoletti et al, 1988;Di Fabio et al, 1995) e naftoquinonas (Khambay;Jewess, 2000). As partes aéreas de C. chelidonioides foram avaliadas quanto as atividades antioxidante, utilizando a metodologia do radical livre DPPH e antimicrobiana, frente a bactérias (Staphylococcus aureus MRSA e Staphylococcus epidermidis) e fungos (Candida albicans, Cryptococcus neoformans, Fonsecaea pedrosoi e Trychophyton rubrum).…”

Section: Introductionunclassified

Atividade antioxidante e antimicrobiana de Calceolaria chelidonioides Humb. Bonpl. & Kunth.

Falcão¹,

Costa²,

Alviano³

et al. 2006

Rev. bras. farmacogn.

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RESUMO:A espécie Calceolaria chelidonioides (Scrophulariaceae), até então inédita nas citações científi cas, foi estudada sob o ponto de vista farmacológico buscando-se identifi car possíveis atividades antimicrobiana e antioxidante em metodologia in vitro. As partes aéreas dessa espécie demonstraram atividade antioxidante em modelo usando o radical livre DPPH. As fl ores de C. chelidonioides mostraram grande potencial antibacteriano frente à bactéria Staphylococcus aureus resistente a meticilina MRSA, um dos principais responsáveis em casos de infecção hospitalar.Unitermos: Calceolaria chelidonioides, Scrophulariaceae, MRSA, DPPH.ABSTRACT: "Antioxidant and anti-microbial activity from Calceolaria chelidonioides Humb. Bonpl. & Kunth." The species Calceolaria chelidonioides (Scrophulariaceae), not scientifi c described so for, was studied in pharmacological aspects aiming to identify some anti-microbial and antioxidant activity. The aerial parts showed antioxidant activity using in vitro DPPH model. The fl owers from C. chelidonioides showed strong antibacterial potential against meticiline resistant Staphylococcus aureus (MRSA) strains the main responsible for hospital infection complications.

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Diterpenes from Calceolaria latifolia

Cited by 27 publications

References 7 publications

Resin Diterpenes from Austrocedrus chilensis

Resin Diterpenes from Austrocedrus chilensis

(+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †

Atividade antioxidante e antimicrobiana de Calceolaria chelidonioides Humb. Bonpl. & Kunth.

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