Spectaline and iso-6 cassine, two new piperidin 3-ol alkaloids from the leaves of cassia spectabilis

CHRISTOFIDIS, I.; Welter, A.; Jadot, J.

doi:10.1016/0040-4020(77)80211-1

Cited by 59 publications

(37 citation statements)

References 15 publications

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“…As a result, pure compound was isolated from fraction 1 (CS-EA-CC1-F8-CC2-F4-CC3-F1) and was designated as compound 1 which possessed the highest activity in decreasing intracellular amastigotes (EC 50 = 20.58 ± 1.65 µg/mL). Compound 1 was identified as (+)-spectaline, a known piperidine alkaloid (Figure 1) that agrees in every respect (IR, NMR and MS) with those in literature [32] which the comparison of NMR data are summarised in Table 2 and 3. With an EC 50 value of 20.58 ± 1.65 µg/mL, compound 1 decreased the parasite burden or, it has the activity in macrophage clearance. This value seems to be more potent than activity of Amp-B against L.donovani infection on THP-1 which is around 231.02 µg/mL (0.25 µM) [33].…”

Section: Resultssupporting

confidence: 53%

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(+)-Spectaline, a Piperidine Alkaloid from Senna spectabilis DC. Effective in Reducing the In Vitro Infection of Leishmania major

Sain

Amanah

Zahari

et al. 2016

IJPPE

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Senna spectabilis is known to have antimicrobial, laxative, antiulcerogenic, analgesic, and anti-inflammatory properties in folk medicine. Piperidine alkaloids extracted from various parts of this plant have been shown to have anticonvulsant (iso-6-spectaline), antinociceptive [(-)-spectaline] and lipid peroxidation [(+)-3-O-feruloylcassine, (-)-spectaline and (-)-3-O-acetylspectaline] activities. In our study, the ethyl acetate extract from S. spectabilis exhibited antileishmanial activity via intracellular promastigote assay or leishmanicidal assay and was further fractionated by using bioassay-guided isolation approach. The antiprotozoal principle was isolated from the ethyl acetate portion through solvent fractionation and a few series of chromatographic processes. The isolated active compound 1 was identified as (+)-spectaline on the basis of its spectral analysis (MS, 1D & 2D NMR) with EC50 value of 0.063 ± 0.005 µM for antileishmanial activity and selectivity index of 3.76.

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Section: Resultssupporting

confidence: 53%

“…(+)-spectaline has been successfully isolated from the leaves of S. spectabilis [32]. However, no antileishmanial studies being done on this compound thus far.…”

Section: Resultsmentioning

confidence: 99%

(+)-Spectaline, a Piperidine Alkaloid from Senna spectabilis DC. Effective in Reducing the In Vitro Infection of Leishmania major

Sain

Amanah

Zahari

et al. 2016

IJPPE

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“…Nestas espécies, as substâncias de maior interesse são os alcaloides 2,6-dialquil-piperidin-3-óis, dos quais a (-)-cassina (1), isolada originalmente de Cassia excelsa, teve sua estrutura e estereoquímica discutidas em diferentes publicações. [22][23][24] Investigações adicionais mostraram a coocorrência de (-)-cassina (1) e (-)-espectalina (7) nos extratos de S. spectabilis, além de outros componentes de uma série homóloga, através de técnicas de espectrometria de massas com ionização por electrospray sequencial (ESI-MS e ESI-MS/MS), contribuindo para o estabelecimento do perfil metabolômico desta espécie com destacada importância farmacológica. Foi ainda demonstrada a atividade potencialmente antitumoral dos alcaloides − -3-O-acetil-espectalina (11), − -7-hidróxi-espectalina, iso-6-espectalina (3 , − -espectalina (7), obtidos das flores e de frutos verdes de Senna spectabilis, por meio do bioensaio usando linhagens mutantes de Saccharomyces cerevisae com deficiência para atuar no reparo do DNA.…”

Section: Alcaloides Piperidínicos Bioativos De Senna Spectabilisunclassified

Spectaline, cassine and semi-synthetic analogues as potential candidate drugs for the treatment of Alzheimer disease

Silva¹,

Viegas²,

Santos³

et al. 2010

Revista Virtual De Química

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Spectaline, Cassine and Semi-Synthetic Analogues as Potential Candidate Drugs for the Treatment of Alzheimer DiseaseAbstract: This paper describes the main steps in the study of Senna spectabilis, as part of our bioprospection studies, with the isolation of spectaline, cassine and other piperidine alkaloids, as well as the preparation of semi-synthetic analogues, and the studies of their pharmacological and toxicological properties, which led to the establishment of two candidate drugs for the treatment of Alzheimer disease.Keywords: spectaline; cassine; Senna spectabilis; acetylcholinesterase inhibitor; bioprospection. ResumoEste artigo descreve o estudo fitoquímico de Senna spectabilis que conduziu ao isolamento de espectalina, cassina e outros alcaloides piperidínicos, a obtenção de análogos semi-sintéticos da espectalina e cassina, e a avaliação de suas propriedades farmacológicas e toxicológicas que resultaram no estabelecimento de dois candidatos a fármacos para o tratamento da doença de Alzheimer (DA).

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“…[10][11][12][13][14][15][16] Piperidine alkaloids were extensively studied through the years, being (−)-cassine (1) the first alkaloid discovered on leaves of S. spectabilis. This secondary metabolite was isolated in 1976 by Christofidis et al, 17 along with two new alkaloids, (+)-spectaline (2) and (−)-iso-6-cassine (3).…”

Section: Phytochemistrymentioning

confidence: 99%

“…14 isolated three new piperidine alkaloids (−)-3-O-acetylspectaline (15), (−)-7-hydroxyspectaline (16) and 6-iso-spectaline (17) from the flowers and immature fruits of S. spectabilis.…”

Section: Phytochemistrymentioning

confidence: 99%

Update: Biological and Chemical Aspects of Senna spectabilis

Selegato¹,

Monteiro²,

Vieira³

et al. 2016

J. Braz. Chem. Soc.

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Senna spectabilis (syn Cassia spectabilis) is one of the most important species within the Fabaceae family, natively found in Central and South America, as well as parts of Asia and Africa. Due to the extensive geographical distribution, this fast-growing tree produces a wide variety of bioactive secondary metabolites, being of special interest for chemical and pharmacological studies. Phytochemical investigations have shown that S. spectabilis produces over 40 constituents from different biosynthetic pathways, including piperidine alkaloids, pentacyclic terpenoids and anthraquinones, displaying antiproliferative, antitumoral and antifungal activities. Moreover, studies have also been conducted to identify endophytic and rizhospheric microorganisms associated to S. spectabilis and their chemical composition, enabling further elucidation of cadinane sesquiterpenoids, cytochalasins, depsipeptides and dibenzopirones. This review aims to provide an updated summary of the main features of S. spectabilis, compiling all currently available information on the chemical and pharmacological composition of its parts and its associated microorganisms.

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Spectaline and iso-6 cassine, two new piperidin 3-ol alkaloids from the leaves of cassia spectabilis

Cited by 59 publications

References 15 publications

(+)-Spectaline, a Piperidine Alkaloid from <i>Senna spectabilis</i> DC. Effective in Reducing the <i>In Vitro</i> Infection of <i>Leishmania major</i>

(+)-Spectaline, a Piperidine Alkaloid from <i>Senna spectabilis</i> DC. Effective in Reducing the <i>In Vitro</i> Infection of <i>Leishmania major</i>

Spectaline, cassine and semi-synthetic analogues as potential candidate drugs for the treatment of Alzheimer disease

Update: Biological and Chemical Aspects of Senna spectabilis

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