Clerodane diterpenes from the stems of Casearia grewiifolia var. gelonioides (Flacourtiaceae/Salicaceae sensu lato)

Mosaddik, Ashik; Forster, Paul I.; Booth, Ron; Waterman, Peter G.

doi:10.1016/j.bse.2007.03.003

Cited by 14 publications

(8 citation statements)

References 4 publications

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“…The 13 C NMR chemical shifts and 1 H NMR coupling constants allowed the inference to be made that the configuration of 2 is similar to that of 1, apart from C-2. The α-ester group at C-2 correlated with a 13 C NMR chemical shift at δ C 66.1− 67.5 [3][4][5][7][8][9]11,13,14,17,19,23,24 and a β-ester group at δ C 70.3− 72.1; [3][4][5]11,12,16,20,21,24,25 The 1 H and 13 C NMR data for compound 3 were very similar to those of 1, except that the cinnamoyl was replaced by a 3-hydroxydodecanoyl (=3-hydroxylaureate) group (see Tables 1 and 2). The 1 H and 13 13 C NMR data for the clerodane skeleton were very similar to those of 1, but the signals for the 2-substituted butadiene unit were missing and replaced by signals indicating a 3,6-dihydro-1,2dioxin unit.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The 13 C NMR chemical shifts and 1 H NMR coupling constants allowed the inference to be made that the configuration of 2 is similar to that of 1 , apart from C-2. The α-ester group at C-2 corre-lated with a 13 C NMR chemical shift at δ C 66.1–67.5 − ,− ,,,,,,, and a β-ester group at δ C 70.3–72.1; − ,,,,,,, consequently, the cinnamoyl moiety was assigned as being attached to the C-2-OH in a β-orientation [δ C 71.0 (C-2)]. Therefore, zuelaguidin B ( 2 ) was assigned as rel -(2 S ,5 S ,6 S ,8 R ,9 R ,10 S ,18 R ,19 S )-18,19-diacetoxy-18,19-epoxy-2-cinnamoyloxy-6-hydroxyclero-3,13(16),14-triene.…”

Section: Resultsmentioning

confidence: 99%

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Cytotoxic Clerodane Diterpenes from Zuelania guidonia

et al. 2014

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The leaves of Zuelania guidonia yielded eight new clerodane diterpenes, namely, zuelaguidins A-H (1-8), and the known clerodane diterpene esculentin A (9). Some of these structures contained a 3,6-dihydro-1,2-dioxin moiety. The new compounds were isolated and identified using 1D- and 2D-NMR experiments. All compounds were evaluated for cytotoxicity against the CCRF-CEM (human acute lymphocytic leukemia), CEM-ADR5000 (human acute lymphocytic leukemia resistant to doxorubicin), and MIA-PaCa-2 (human pancreatic carcinoma) cell lines as well as for their selectivity against peripheral blood mononuclear cells from healthy human subjects. Zuelaguidins B, C, and E were the most potent compounds against the CCRF-CEM cell line, with IC50 values ranging from 1.6 to 2.5 μM.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…The 13 C NMR chemical shifts and 1 H NMR coupling constants allowed the inference to be made that the configuration of 2 is similar to that of 1 , apart from C-2. The α-ester group at C-2 corre-lated with a 13 C NMR chemical shift at δ C 66.1–67.5 − ,− ,,,,,,, and a β-ester group at δ C 70.3–72.1; − ,,,,,,, consequently, the cinnamoyl moiety was assigned as being attached to the C-2-OH in a β-orientation [δ C 71.0 (C-2)]. Therefore, zuelaguidin B ( 2 ) was assigned as rel -(2 S ,5 S ,6 S ,8 R ,9 R ,10 S ,18 R ,19 S )-18,19-diacetoxy-18,19-epoxy-2-cinnamoyloxy-6-hydroxyclero-3,13(16),14-triene.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Clerodane Diterpenes from Zuelania guidonia

et al. 2014

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“…Compounds 1 and 2 were obtained as an inseparable mixture of two isomers in a ratio of approximately 1.3:1, as determined by (16),14-dien-18,19-oxolane, 23 except for the absence of the acetoxy groups at C- and H-4 (3.4 Hz) in 1 was in agreement with a β-orientation of OH-18, in which case the dihedral angle of H-18 relative to H-4 was 29.9°in the MM2 energy minimized model and the vicinal coupling constant would be relatively small (Figure 1). Therefore, the structure of 1 was determined to be rel-(2S,4S,5R,8S,9S,10R,18R,19S)-2,19:18,19-diepoxycleroda-13-( 16),14-dien-18-ol, named caseabalansin A.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Cytotoxic Clerodane Diterpenoids from the Leaves and Twigs of Casearia balansae

Wang

et al. 2013

J. Nat. Prod.

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Ten new clerodane diterpenoids (1-10), caseabalansins A-G, 18-epicaseabalansin A, 2-epicaseabalansin B, and 2-epicaseabalansin C, one new triterpenoid, balansinone (11), and seven known diterpenoids (12-18) were obtained from the leaves and twigs of Casearia balansae. Compounds 1 and 2 are the first examples of clerodane diterpenoids with an oxygen bridge between C-2 and C-19, and compounds 5-7 are three new diterpenoid artifacts presumably formed during the extraction process. The structures of the new compounds were established on the basis of extensive spectroscopic data, and that of 11 was verified by single-crystal X-ray crystallographic analysis. Compound 15 showed cytotoxic activity against the tumor cell lines PC3, DU145, SKOV3, and A549 with IC₅₀ values of 4.5, 4.3, 5.1, and 5.7 μM, respectively. Compounds 1a, 2a, and 4 showed selective activity against PC3 tumor cells.

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“…Pode-se acrescentar também que possui outras indicações como a neutralização de venenos e a coagulação de sangramentos (Borges, 1997;Borges et al, 2000;Tropical plant database., 2006). Dessas espécies vários metabólitos secundários já foram isolados como: flavonóides (Shaari;Waterman., 1994;Raslan et al, 2002), taninos (Weniger et al, 1978), cumarinas (Talapatra et al, 1982), compostos fenólicos (Raslan et al, 2002;Mosaddik et al, 2007) e terpenóides (Wang et al, 2009;Shaari;Waterman., 1994;Gunasekera et al, 1977), se destacando diterpenos clerodânicos (Vieira junior et al, 2010).…”

Section: Resultsunclassified

Potencial antileishmania, antimalárico e antitrypanossoma de espécies de Casearia: Uma revisão integrativa

Oliveira

Silva

Cardoso

et al. 2021

RSD

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O tratamento de doenças parasitárias tem como um de seus maiores desafios a resistência desenvolvida pelos parasitos contra os medicamentos disponíveis. Portanto, a busca por alternativas terapêuticas é urgente. Este estudo realizou uma revisão integrativa da literatura que avaliou o potencial antileishmania, antimalárico e antitrypanossoma de plantas do gênero Casearia. A busca dos artigos científicos foi realizada no Portal de Periódicos da CAPES (PPC), Biblioteca Virtual em Saúde (BVS), PUBMED e SCIELO, utilizando-se os seguintes descritores: Casearia e antileishmania; Casearia e antimalárico; e Casearia e antitrypanossoma. Um total de 122 publicações foram coletadas para triagem, destes, 11 foram incluídos na revisão integrativa. Na atividade antileishmania, a Casearia sylvestris se destacou, com extrato hexano da madeira e casca do caule e o extrato etanólico da casca da raiz apresentando atividade contra diferentes espécies de Leishmania (CI50<100 µg/mL), porém com elevada toxicidade (CC50<100 µg/mL). Dentre as substâncias isoladas, o flavonoide Tricina se mostrou ativo contra Leishmania e não citotóxico. Quanto a atividade antimalárica, 11 extratos de 3 espécies, C. elliptica, C. coriaceae e C. sylvestris mostraram-se ativos (CI50<100 µg/mL), no entanto, apresentaram toxicidade. Na atividade antitrypanossoma, as casearinas isoladas das folhas de C. sylvestris, apresentaram grande potencial contra a forma tripomastigota de T. cruzi (CI50<3,0 µg/mL), porém, apresentaram elevada toxicidade. As espécies de Casearia são, portanto, promissoras quanto à sua atividade antiparasitária, mas sua toxicidade é um problema. No entanto, os flavonoides da espécie apresentam bom índice de seletividade e, alterações moleculares e/ou formulações adequadas podem reduzir a toxicidade dos outros componentes.

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Clerodane diterpenes from the stems of Casearia grewiifolia var. gelonioides (Flacourtiaceae/Salicaceae sensu lato)

Cited by 14 publications

References 4 publications

Cytotoxic Clerodane Diterpenes from Zuelania guidonia

Cytotoxic Clerodane Diterpenes from Zuelania guidonia

Cytotoxic Clerodane Diterpenoids from the Leaves and Twigs of Casearia balansae

Potencial antileishmania, antimalárico e antitrypanossoma de espécies de Casearia: Uma revisão integrativa

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