Three quinicine derived alkaloids from Guettarda trimera

Kan-Fan, Christiane; Brillanceau, M.H.; Pussett, J.; Chauvière, G.; Husson, Henri‐Philippe

doi:10.1016/s0031-9422(00)80726-8

Cited by 14 publications

(6 citation statements)

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“…Importantly, the occurrence of quinicine in cinchona has been questioned since the substance has been reported to occur naturally only in trace amounts, prompting the suggestion that such occurrence may be an artifact of the inadvertent chemical conversion of small amounts of quinine and/or quinidine to quinicine during the isolation of the alkaloids. [65,66] Throughout his career Pasteur considered practical applications of his fundamental discoveries to have great importance (he insisted, however, that there is no such thing as 'applied science', only 'applications of science' [67] ). Malaria was endemic in many parts of Europe in the 19 th century, and with the isolation of quinine from cinchona by Pelletier and Caventou, the substance came into wide use as the only effective treatment for the disease.…”

Section: Quinicine and Cinchonicine: Additional Workmentioning

confidence: 99%

“…[74] Nevertheless, 'quinotoxin(e)' has continued to be widely used, [14,28,[75][76][77][78][79] although some authors have 'remained faithful' to 'quinicine'. [62,65,74,80] The next episode in the nomenclature story is connected to the above-mentioned introduction of quinicine as a cerebral-vasodilating agent. [70] Understandably, 'quinotoxine' was not adopted as the name of the new pharmaceutical, but neither was Pasteur's 'quinicine' -the new drug was assigned the nonproprietary appellation 'viquidil', undoubtedly further complicating the identification of the substance.…”

Section: Quinicine and Cinchonicine: Additional Workmentioning

confidence: 99%

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Louis Pasteur, Chemist: An Account of His Studies of Cinchona Alkaloids

Gál

2019

Helvetica Chimica Acta

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Pasteur carried out pioneering work on cinchona alkaloids and their derivatives and his studies led to important discoveries. He examined crystals of cinchona alkaloids for his correlation of crystal hemihedrism with molecular chirality, studies that led Pasteur to the discovery of physicochemical differences between diastereoisomeric salts of tartaric acids with optically active cinchona bases, an important insight into fundamentals of molecular chirality. These physicochemical differences also led to Pasteur’s invention of the vital method of racemate resolution through diastereoisomeric derivatives. Pasteur clarified the confusion around the cinchona alkaloids by elucidating their identities and relations. He discovered the conversion of the major cinchona alkaloids to quinicine and cinchonicine, a finding subsequently of considerable importance in studies of the structure and synthesis of the major cinchona alkaloids. The reaction producing quinicine and cinchonicine led Pasteur to the discovery of the racemization of tartaric acid and the finding of meso‐tartaric acid, fundamental breakthroughs in the development of stereochemistry.

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Section: Quinicine and Cinchonicine: Additional Workmentioning

confidence: 99%

Section: Quinicine and Cinchonicine: Additional Workmentioning

confidence: 99%

Louis Pasteur, Chemist: An Account of His Studies of Cinchona Alkaloids

Gál

2019

Helvetica Chimica Acta

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“…Toxicity may have been related to alkaloids in the chloroform fraction (Duarte, 2012). Alkaloids have also been described in other Guettarda species (Husson et al, 1977;Kan-Fan and Husson, 1979;Brillanceau et al, 1984;Kan-Fan et al, 1985;Ferrari et al, 1986;Montagnac et al, 1997;Capasso et al, 1998). In the wake of such results, an alkaloid extract was assessed to verify whether toxicity could be reproduced.…”

Section: Brine Shrimp Lethality Bioassaymentioning

confidence: 99%

Evaluation of antioxidant capacity, phenolic content, antimicrobial and cytotoxic properties of Guettarda uruguensis flowers and fruits

Duarte¹,

Szabo²,

Duarte³

et al. 2016

Afr. J. Pharm. Pharmacol.

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Antioxidant capacity, phenolic content, antimicrobial and cytotoxic properties of extracts and fractions from flowers and fruits of G. uruguensis were evaluated. Total phenolic content ranged between 406.8 ± 20.47 and 57.98 ± 1.734 gallic acid equivalent in mg g-1 (mg GAE g-1) samples. Ethyl acetate and butanol fractions from flowers had the greatest rates in phenolic content and antioxidant activity in 1,1diphenyl-2-picrylhydrazyl (DPPH) and thiobarbituric acid reactive substances (TBARS) assays. Pearson´s coefficient showed a strong association between total phenolic compounds in DPPH (r =-0.83, p < 0.01) and TBARS (r = 0.85, p < 0.01). Eleven out of the 12 samples tested were toxic in the brine shrimp assay (LC50 < 100 µg mL-1). Antimicrobial susceptibility profile revealed flower remaining fraction and fruit extract with moderate activity against Enterococcus faecalis. Results indicate that G. uruguensis is a good source of compounds with antioxidant and cytotoxic activities. Further studies to identify compounds causing these activities are recommended.

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“…Arg. , G. speciosa L. (Kan-Fan et al, 1985;Yaga & Kazuhiko, 1985;Inouye et al, 1988;Montagnac et al, 1997) e G. trimera (Less.) DC.…”

Section: Introductionmentioning

confidence: 99%

“…DC. (Kan-Fan et al, 1985;Montagnac et al, 1997)] e alcalóides (Kan-Fan et al, 1985;Ferrari et al, 1986;Matos et al, 1986;Jiang et al, 1994;Montagnac et al, 1997;Capasso et al, 1998), iridóides (Kan-Fan et al, 1985Aquino et al, 1988;Inouye et al, 1988), secoiridóides (Ferrari et al, 1986;Aquino et al, 1988;Inouye et al, 1988), derivados dos ácidos quínico e chiquímico (Capasso et al, 1998; e triterpenos (Bhattacharyya & Almeida, 1985;Ferrari et al, 1986;Matos et al, 1986;Aquino et al, 1988;Capasso et al, 1998; têm sido isolados. Triterpenos têm sido encontrado somente em quatro delas [G. acreana (Capasso et al, 1998), G. angelica (Sousa et al, 1984;Matos et al, 1986), G. platypoda (Bhattacharyya & Almeida, 1985;Ferrari et al, 1986;Aquino et al, 1988;1989) e G. pohliana .…”

Section: Introductionunclassified

Triterpenos de Guettarda grazielae M: R.V. Barbosa (Rubiaceae)

Lima¹,

Moura²,

Lemos³

et al. 2009

Rev. bras. farmacogn.

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RESUMO:O presente trabalho descreve o isolamento e a identificação estrutural de seis triterpenos (acetato de a-amirina, cicloartenona, 3b,19a,23-triidroxi-urs-12-eno e os ácidos ursólico, 6b,19a,23-tetraidroxi-urs-12-en-28-óico), além de um fitoesteróide (sitostenona) de extratos das folhas, cascas do caule e caule de Guettarda grazielae M.R.V. Barbosa (Rubiaceae). Os compostos isolados, exceto o ácido 3-b-O-b-D-glicopiranosilquinóvico, estão sendo descritos pela primeira vez no gênero Guettarda e foram identificados com base na análise de dados espectrais de RMN, incluindo APT e DEPT, bem como pela comparação com dados da literatura.Unitermos: Guettarda grazielae, Rubiaceae, triterpenos.ABSTRACT: "Triterpenes from Guettarda grazielae M.R.V. Barbosa (Rubiaceae)". This work describes the isolation and structural identification of six triterpenes (a-amyrin acetate, cycloartenone, 3b,19a,23-trihydroxyurs-12-ene, and ursolic, 3-b-O-b-D-glucopyranosylquinovic, 3b,6b,19a,23-tetrahydroxyurs-12-en-28-oic acids), beside a phytosteroid (sitostenone) from leaves, stem barks and stems of Guettarda grazielae (Rubiaceae). All isolated compounds, except 3-b-O-b-D-glucopyranosylquinovic acid, are being described for the first time in the genus Guettarda and were identified on basis of the spectral NMR data, including APT and DEPT, as well as by comparison with data of the literature.

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Three quinicine derived alkaloids from Guettarda trimera

Cited by 14 publications

References 1 publication

Louis Pasteur, Chemist: An Account of His Studies of Cinchona Alkaloids

Louis Pasteur, Chemist: An Account of His Studies of Cinchona Alkaloids

Evaluation of antioxidant capacity, phenolic content, antimicrobial and cytotoxic properties of Guettarda uruguensis flowers and fruits

Triterpenos de Guettarda grazielae M: R.V. Barbosa (Rubiaceae)

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