The stereochemistry of ledol from Renealmia chrysotrycha : an NMR study

Kaplan, Maria Auxiliadora Coelho; Pugialli, Helena Regina Lima; Lopes, Daniel Simões; Gottlieb, Hugo E.

doi:10.1016/s0031-9422(00)00291-0

Cited by 32 publications

(32 citation statements)

References 12 publications

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“…a Table 3 or Section 4. c Proton spectrum recorded in CD 3 OD. and viridiflorol can be differentiated by their characteristic melting points or, more easily, by the chemical shifts of the cyclopropyl protons (Kaplan et al, 2000). On the basis of known 1 H NMR data (Fletcher et al, 2000;Jakupovic et al, 1988;Pizza and De Tommasi, 1988) and ours, this latter criterion seems to be also applicable to viridiflorol glycosides; thus, all the Calendula species biosynthesize (10S)-viridiflorol ( Fig.…”

Section: Structural Elucidation Of Compounds 2a-2f Andmentioning

confidence: 71%

“…The most stable conformation of (10R)-ledol was calculated by a molecular mechanic (MM) software thus establishing that the cycloheptane ring adopts a boat like conformation (Freeman et al, 2008) with the 3H-14 in an equatorial orientation (Kaplan et al, 2000). Similarly, we undertook the MM calculation of the lowest energy conformer of (10S)-viridiflorol.…”

Section: Calculation Of Compound 3fmentioning

confidence: 99%

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Structure and cytotoxic activity of sesquiterpene glycoside esters from Calendula officinalis L.: Studies on the conformation of viridiflorol

et al. 2015

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Topic applications of Calendula officinalis L. lipophilic extracts are used in phytotherapy to relieve skin inflammatory conditions whereas infusions are used as a remedy for gastric complaints. Such a different usage might be explained by some cytotoxicity of lipophilic extracts at gastric level but little is known about this. Therefore, we screened the CH2Cl2 extract from the flowers of C. officinalis by MTT and LDH assays in human epithelial gastric cells AGS. This bioassay-oriented approach led to the isolation of several sesquiterpene glycosides which were structurally characterized by spectroscopic measurements, chemical reactions and MM calculations. The conformational preferences of viridiflorol fucoside were established and a previously assigned stereochemistry was revised. The compounds 1a, 2a and 3f showed comparably high cytotoxicity in the MTT assays, whereas the effect on LDH release was lower. Our study provides new insights on the composition of C. officinalis extracts of medium polarity and identifies the main compounds that could be responsible for cytotoxic effects at gastric level.

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Section: Structural Elucidation Of Compounds 2a-2f Andmentioning

confidence: 71%

Section: Calculation Of Compound 3fmentioning

confidence: 99%

Structure and cytotoxic activity of sesquiterpene glycoside esters from Calendula officinalis L.: Studies on the conformation of viridiflorol

et al. 2015

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“…A partir da análise das folhas de R. chrysotrycha, Kaplan et al (2000) reportam o isolamento do álcool sesquiterpênico identificado como ledol conjuntamente com três outros compostos (aromadendreno, cis-calameneno e palustrol).…”

Section: R Chrysotrychaunclassified

Renealmia L.f.: aspectos botânicos, ecológicos, farmacológicos e agronômicos

Negrelle

2015

Rev. bras. plantas med.

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e alimentício. Visando ressaltar a importância deste gênero como potencial fonte de recursos agroeconômicos apresenta-se esta revisão sobre aspectos botânicos, ecológicos, farmacológicos, e agronômicos. De um universo de 87 espécies formalmente inseridas em Renealmia, registrou-se indicação de uso popular para 18 destas. Em sua maior parte as indicações de uso estiveram associadas a R. alpinia, R. exaltata e R. guianensis englobando, principalmente, os usos ornamental, alimentício e medicinal. Dentre as 14 espécies com indicação de uso popular medicinal, registram-se pesquisas farmacológicas para apenas quatro: R. alpinia, R. exaltata, R. nicolaioides e R. thyrsoidea. Entretanto, estas pesquisas evidenciam um amplo espectro de bioatividade, com ênfase na ação anticancerígena e antiofídica, especialmente de R. alpinia. Apenas seis espécies foram avaliadas quanto a composição química (R. floribunda, R. guianensis, R. alpinia, R. chrysotricha, R. exaltata e R. nicolaioides), identificando-se perfil químico que corrobora a potencialidade anticancerígena e antiofídica para os representantes deste gênero. Evidenciou-se grande lacuna no que se refere ao conhecimento científico ou técnico para o cultivo de espécies de Renealmia. Isto pode se configurar num impedimento importante na utilização destas espécies como recurso econômico.Palavras-chave: pacová, planta alimentícia, planta medicinal, planta ornamental, Zingiberaceae.ABSTRACT: Renealmia L..f.: botanical, pharmacological and agronomical aspects. The Renealmia L.f. is a genus that belongs to the Zingiberaceae with several applications, including the ornamental, medicinal and food ones. Aiming to emphasize the importance of this genus as a potential agro-economic resource, a review of its botanical, pharmacological and agronomic aspects is presented. From 87 species formally inserted in the Renealmia, 20 were registered with popular uses. In general, these popular uses were associated with R. alpinia, R. exaltata and R. guianensis, mainly including the ornamental, nourishing and medicinal uses. Among 14 species with indication of popular medicinal use, pharmacological studies were registered for only four: R. alpinia, R. exaltata, R. nicolaioides and R. Thyrsoidea. However, these studies show a large bioactivity range, with emphasis in the anti-carcinogenic and antiophidic action, especially for R. alpinia. Only six species were analyzed in terms of chemical composition (R. floribunda, R. guianensis, R. alpinia, R. chrysotricha, R. exaltata and R. nicolaioides). Their chemical profiles corroborate the anti-carcinogenic potential for the representatives of this genus. There is a great scientific or technical gap on the cultivation of Renealmia species. This can be an important limiting factor in the use of these species as economical resource.

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“…Thus, compound 3 was determined as 3b,13-dihydroxyledol. (Table 2) indicated that 4 had the same relative configuration as that of ledol [7], and both HOÀC(2) and HOÀC(3) were b-oriented [8]. Consequently, compound 4 was established as 2b,3b,13-trihydroxyledol.…”

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confidence: 99%

Novel Sesquiterpenes from the Mycelial Cultures of Dichomitus squalens

Xie

Yang

et al. 2011

Helvetica Chimica Acta

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Four novel sesquiterpenes, 5-hydroxydichomitol (1), dichomilludol (2), 3b,13-dihydroxyledol (3), and 2b,3b,13-trihydroxyledol (4), were isolated along with 2b,13-dihydroxyledol (5) from the AcOEtsoluble fraction of the mycelial solid cultures of Dichomitus squalens. Their structures were determined on the basis of spectroscopic analyses. The previously assigned structure of dichomitol was revised.Introduction. -Dichomitus squalens is a commonly found white-rot Basidiomycetous fungus with the capability to degrade both natural and synthetic lignins and lignin derivatives [1] [2]. In search for bioactive natural compounds from Basidiomycetes growing in South China, the EtOH extract of the mycelial cultures of this fungus was found to be nematicidal against a catastrophic pine wilt nematode (Bursaphelenchus xylophilus). Subsequent screening of the petroleum ether-, CHCl 3 -, and AcOEtsoluble fractions from this extract showed that the CHCl 3 -soluble fraction was more potent than the others. Our previous investigation on the CHCl 3 -soluble fraction led to the isolation of three new sesquiterpenes, dichomitol, 2b,13-dihydroxyledol, and dichomitone, of which the second one was found to be nematicidal [3]. In continuation of our studies on this fungus, the AcOEt-soluble fraction was investigated, and four new sesquiterpenes, 5-hydroxydichomitol (1), dichomilludol (2), 3b,13-dihydroxyledol (3), and 2b,3b,13-trihydroxyledol (4), were isolated along with a previously isolated sesquiterpene, 2b,13-dihydroxyledol (5). Furthermore, the previously assigned structure of dichomitol was revised. Here, we describe the isolation and structure elucidation of these compounds and the structure revision of dichomitol.

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The stereochemistry of ledol from Renealmia chrysotrycha : an NMR study

Cited by 32 publications

References 12 publications

Structure and cytotoxic activity of sesquiterpene glycoside esters from Calendula officinalis L.: Studies on the conformation of viridiflorol

Structure and cytotoxic activity of sesquiterpene glycoside esters from Calendula officinalis L.: Studies on the conformation of viridiflorol

Renealmia L.f.: aspectos botânicos, ecológicos, farmacológicos e agronômicos

Novel Sesquiterpenes from the Mycelial Cultures of Dichomitus squalens

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