The configuration of venoterpine

Ravao, Thérèse; Richard, Bernard; Zèches, Monique; Massiot, Georges; Men‐Olivier, L. Le

doi:10.1016/s0040-4039(00)61942-1

Cited by 14 publications

(5 citation statements)

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“…Eleven known indole monoterpenoid alkaloids, koumine ( 10 ), (19 R )-hydroxydihydrokoumine, (19 S )-hydroxydihydrokoumine, (4 R )-koumine N -oxide, (4 S )-koumine N -oxide, N -demethoxyhumantenine, 11-methoxy-(19 R )-hydroxygelselegine, sempervirine ( 11 ), koumidine, epi -koumidine, and gelsemine, and a monoterpenoid alkaloid, venoterpine, were also isolated. Their structures were determined by comparison of their experimental and reported NMR and MS data.…”

Section: Resultsmentioning

confidence: 99%

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Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans

Yang

Liao

et al. 2015

J. Nat. Prod.

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Nine new alkaloids of the koumine (1-4), humantenine (5-7), and yohimbane (8, 9) types as well as 12 known analogues were isolated from the leaves and vine stems of Gelsemium elegans. Compound 1 is the first N-4-demethyl alkaloid of the koumine type, compound 7 is the first nor-humantenine alkaloid, and compounds 8 and 9 are the first N-1-oxide and the first seco-E-ring alkaloids, respectively, of the yohimbane type. Compounds 1 and 7 exhibited moderate cytotoxicity against five human tumor cell lines with IC50 values in the range 4.6-9.3 μM.

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Section: Resultsmentioning

confidence: 99%

“…[8][9][10][11][12][13][14][15][16]; δ H 2.88 (2H), t, J = 7.5 Hz, δ C 35.3 (CH 2 -17)]. These observations suggested that ring E in 11 was opened in 9/9a.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans

Yang

Liao

et al. 2015

J. Nat. Prod.

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“…The anticholinesterase and vasorelaxant activities of some isolated compounds were also evaluated. In addition, the NMR data of rescidine (15) and sarpagine (22) are reported here for the first time. -1 ) and an aromatic functionality (1625, 1607 cm -1 ).…”

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confidence: 93%

“…Structures of isolated compounds from R. serpentina. stigmasterol (3)[9], reserpinine (4)[10], tetrahydroalstonine (5)[11,12], reserpine(6) [12,13], venoterpine (7)[14,15], yohimbine (8) [16], 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (9) [6], isoajmaline (10) [7], 3-epi--yohimbine (11) [17], methyl 3,4,5trimethoxy-trans-cinnamate (12) [18], a mixture of -sitosterol 3-O--D-glucopyranoside (13) and stigmasterol 3-O--D-glucopyranoside (14) [19], rescidine (15) [12], 7-deoxyloganic acid (16) [20], ajmaline (17) [7], suaveoline (18) [21], (+)-tetraphyllicine (19) [22], loganic acid (20) [23], 3-hydroxysarpagine (21) [6] and sarpagine (22) [24] (Figure 1). Among the known compounds, compounds 11, 12 and 15 were first identified from genus Rauvolfia and 5, 7, 11, 12, 15, 18 and 22 were isolated from R. serpentina for the first time.…”

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confidence: 99%

“…The structures of the known compounds were determined through analysis of their spectroscopic data in comparison with reported values, and they were identified as a mixture of -sitosterol (2) and NPC Natural Product Communications stigmasterol (3) [9], reserpinine (4) [10], tetrahydroalstonine (5) [11,12], reserpine (6) [12,13], venoterpine (7) [14,15], yohimbine (8) [16] [19], rescidine (15) [12], 7-deoxyloganic acid (16) [20], ajmaline (17) [7], suaveoline (18) [21], (+)-tetraphyllicine (19) [22], loganic acid (20) [23], 3-hydroxysarpagine (21) [6] and sarpagine (22) [24] (Figure 1). Among the known compounds, compounds 11, 12 and 15 were first identified from genus Rauvolfia and 5, 7, 11, 12, 15, 18 and 22 were isolated from R. serpentina for the first time.…”

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A New Ajmaline-type Alkaloid from the Roots of Rauvolfia serpentina

Rukachaisirikul

Chokchaisiri

Suebsakwong

et al. 2017

Natural Product Communications

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A new ajmaline-type alkaloid, 21-O-methylisoajmaline (1), together with twenty-one known compounds, a mixture of -sitosterol (2) and stigmasterol (3), reserpinine (4), tetrahydroalstonine (5), reserpine (6), venoterpine (7), yohimbine (8), 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (9), isoajmaline (10), 3-epi--yohimbine (11), methyl 3,4,5-trimethoxy-trans-cinnamate (12), a mixture of -sitosterol 3-O--D-glucopyranoside (13) and stigmasterol 3-O--Dglucopyranoside (14), rescidine (15), 7-deoxyloganic acid (16), ajmaline (17), suaveoline (18), (+)-tetraphyllicine (19), loganic acid (20), 3-hydroxysarpagine (21), and sarpagine (22), were isolated from the roots of Rauvolfia serpentina. Their structures were elucidated by spectroscopic data analysis and comparison with literature data. Compounds 11, 12 and 15 were for the first time identified from the genus Rauvolfia and 5, 7, 11, 12, 15, 18 and 22 were found from R. serpentina for the first time. Compound 11 showed moderate anticholinesterase activity with IC 50 value of 15.58 M, whereas 6 exhibited strong vasorelaxant activity with the EC 50 value of 0.05 M.

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Plantes de Nouvelle‐Calédonie. 94e Communication. Alcaloïdes monoterpéniques de Scaevola racemigera DÄNIKER

Skaltsounis

Michel

Tillequin

et al. 1985

Helvetica Chimica Acta

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Monoterpene Alkaloids of Scaevoiu racemigera DANIKERNine alkaloids have been isolated from the aerial parts of Scaevola racemigera. Two of them are the known compounds cantleyine (1) and tetrahydrocantleyine (2). The seven others are novel alkaloids, strychnovoline (3), 6-0-nicotinoylstrychnovoline (4), 6-0-nicotinoyltetrahydrocantleyine (S), 6-0-(5-vinylnicotinoyl)tetrahydrocantleyine (6), racemigerine (7), 6,7-epoxyracemigerine (8), and scaevoline (9). The structures of the new compounds have been elucidated by their spectral data and confirmed by chemical correlations. Moreover, the absolute configuration of 2, which had not been previously determined, has been elucidated.Le genre Scaevola L. (Goodeniactes) est constitut d'une centaine d'espices de plantes largement rtpandues dans les rtgions cijti6res des iles de 1'OcCan Indien et de l'Octan Pacifique [2]. I1 comporte, selon les auteurs, dix a douze esp6ces en Nouvelle-Caledonie [3-51 parmi lesquelles Scaevola racemigera DANKER [6] se distingue par son inflorescence en grappe spiciforme [4]. Des essais preliminaires rkalists par deux d'entre nous (J.P. et C.C.) ont montrk la presence d'alcaloides dans les parties aeriennes de cette espke. Compte tenu des donntes chimiques limittes disponibles sur la famille des GoodtniacCes et de l'absence de description d'alcaloides dans le genre Scaevola L., nous avons abordC l'ttude de Scaevola racemigera DANIKER. Ses parties aeriennes ont permis l'obtention de 0,25 YO d'alcaloides apr& extraction selon un protocole classique. Apr6s chromatographies successives sur colonnes de silice, neuf alcaloides ont ete isolCs. Leurs spectres UV les rattachent tous au groupe des alcaloides monoterpkniques.Deux de ces alcaloi'des ont Ct C identifies a des produits connus: cantleyine (1) [7-91 et tetrahydrocantleyine (2) [ 101. Cependant, la configuration absolue de la tttrahydrocantleyine n'avait pas Ct C anttrieurement determinte. Les sept autres alcaloi'des sont des produits nouveaux. I1 s'agit de la strychnovoline (3), de son ester nicotinique 4, des esters nicotinique et vinyl-Snicotinique de la tetrahydrocantleyine (5 et 6), de la racemigkrine ') 93e communication: [I].

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The configuration of venoterpine

Cited by 14 publications

References 4 publications

Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans

Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans

A New Ajmaline-type Alkaloid from the Roots of Rauvolfia serpentina

Plantes de Nouvelle‐Calédonie. 94e Communication. Alcaloïdes monoterpéniques de Scaevola racemigera DÄNIKER

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