Alkaloids from cassia carnaval speg.: Cassine and carnavaline

Lythgoe, David J.; Vernengo, Marcelo J.

doi:10.1016/s0040-4039(00)90651-8

Cited by 27 publications

(16 citation statements)

References 6 publications

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“…23 Three years later, in 1995, Bolzani et al 10 isolated four new piperidine alkaloids (−)-spectaline (8), leptophyllin A (9), 3-O-acetylleptophyllin A (10) and leptophyllin B (11), along with previously described carnavaline (12), found for the first time by Lythgoe and Vernenge, 24 from the leaves of Cassia carnaval. Both leptophyllin A and 3-O-acetylleptophyllin A show a selective cytotoxic activity against a DNA-reparing mutant S. cerevisiae.…”

Section: Phytochemistrymentioning

confidence: 99%

“…Both leptophyllin A and 3-O-acetylleptophyllin A show a selective cytotoxic activity against a DNA-reparing mutant S. cerevisiae. 24,25 In 2003, Kamo et al 11 isolated two derivatives of (+)-6-iso-cassine from S. spectabilis named spectamine A (O-benzoyl) (13) and B (O-acetyl) (14). Compound 13 displays significant anti-inflammatory activities, acting on the inhibition of superoxide anion of macrophages.…”

Section: Phytochemistrymentioning

confidence: 99%

“…[29][30][31] These secondary metabolites, isolated from leaves, flowers and green fruits of S. spectabilis, were found in both mixture (α-amyrin (22), β-amyrin (23), ursolic acid (24) and oleanolic acid (25)) and pure forms (betulinic acid (26), lupeol (27), cycloeucalenol (28), friedelin (29)), showing biological activity in animal and human models ( Figure 2). 31 Lupeol (27), also called lup-20-(29)-en-3β-ol, is widely found in fruits and vegetables as well as in a variety of medicinal plants such as Tamarindus indica, Emblica officinalis and Celastrus paniculatus.…”

Section: Pentacyclic Triterpenesmentioning

confidence: 99%

“…[47][48][49][50] Isomers α-amyrin ((3β)-urs-12-en-3-ol) (22) and β-amyrin ((3β)-olean-12-en-3-ol) (23) have been isolated from several plants and algae species, 51,52 exhibiting anti- Figure 2. Chemical structure of pentacyclic triterpenes isolated from S. spectabilis (22)(23)(24)(25)(26)(27)(28)(29). Vol.…”

Section: Pentacyclic Triterpenesmentioning

confidence: 99%

“…Betulinic (26), ursolic (24) and oleanolic (25) acids are found in several species of the kingdom Plantae, including medicinal herbs and fruits from the human diet. 31,61,62 Betulinic acid, isolated from leaves, fruits and flowers of Senna, is a highly bioactive triterpene, displaying anti-HIV, antibacterial, antimalarial and anti-inflammatory effects.…”

Section: Pentacyclic Triterpenesmentioning

confidence: 99%

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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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Section: Phytochemistrymentioning

confidence: 99%

Section: Phytochemistrymentioning

confidence: 99%

Section: Pentacyclic Triterpenesmentioning

confidence: 99%

Section: Pentacyclic Triterpenesmentioning

confidence: 99%

Section: Pentacyclic Triterpenesmentioning

confidence: 99%

See 3 more Smart Citations

Update: Biological and Chemical Aspects of Senna spectabilis

Selegato¹,

Monteiro²,

Vieira³

et al. 2016

J. Braz. Chem. Soc.

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Alcaloïdes Pipéridiniques III. Nouveaux Alcaloïdes du Prosopis Africana (Guill. et Perr.) Taub.: Isoprosopinines A et B, Prosophylline, Prosafrine Et Prosafrinine [1]

Khuong-Huu

Monseur

et al. 1972

Bulletin des Soc Chimique

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The structures of five new alkaloids have been established: the isoprosopinines A and B, 1 and 2 are homogeneous mixture: isoprosopinine A is (2R, 3S, 6R) 2‐hydroxymethyl 3‐hydroxy 6‐dodecyl 7°‐keto piperidine and isoprosopinine B is (2R, 3S, 6R) 2‐hydroxymethyl 3‐hydroxy 6‐dodecyl 8°‐keto piperidine. Prosophylline 4 is d 2‐hydroxymethyl 3‐hydroxyl 6‐dodecyl 10°‐keto piperidine, prosafrine 9 is (2R, 3R, 6S) 2‐methyl 3‐hydroxy 6‐dodecyl 10°‐hydroxy piperidine and prosafrinine 11, is (2R, 3R, 6S) 2‐methyl 3‐hydroxy 6‐dodecyl 10°‐keto piperidine.

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