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See detailTriterpenoid saponins from the stem bark of pentaclethra eetveldeana
Pertuit, D.; Kapundu, M.; Mitaine-Offer, A.-C. et al

in Natural Product Communications (2019), 14(7),

Two previously undescribed triterpenoid saponins together with 4 known ones were isolated from the stem bark of Pentaclethra eetveldeana De Wild. & Th. Dur. Their structures were elucidated by ... [more ▼]

Two previously undescribed triterpenoid saponins together with 4 known ones were isolated from the stem bark of Pentaclethra eetveldeana De Wild. & Th. Dur. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments in combination with mass spectrometry as 3- O-β- d -glucopyranosyl- (1→2)- [β- d -glucopyranosyl- (1→3)]-β- d -glucopyranosyl- (1→4)- β- d -glucopyranosyl- (1→3)-α- l -rhamnopyranosyl- (1→2)-[β- d-glucopyranosyl- (1→4)]-α- l -arabinopyranosyloleanolic acid and 3- O -β- d -glucopyranosyl- (1→2)-[β- d -glucopyranosyl- (1→3)]-β- d -glucopyranosyl- (1→4)-β- d -glucopyranosyl- (1→3)- α -l -rhamnopyranosyl- (1→2)-[β- d -glucopyranosyl- (1→4)]-α- l -arabinopyranosylhederagenin. © The Author(s) 2019. [less ▲]

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See detailTriterpenoid saponins from the root bark of haplocoelum congolanum
Pertuit, D.; Mitaine-Offer, A.-C.; Miyamoto, T. et al

in Natural Product Communications (2019), 14(5),

Two undescribed triterpenoid saponins together with 5 known ones were isolated from the root bark of Haplocoelum congolanum Hauman. Their structures were elucidated by spectroscopic methods including one ... [more ▼]

Two undescribed triterpenoid saponins together with 5 known ones were isolated from the root bark of Haplocoelum congolanum Hauman. Their structures were elucidated by spectroscopic methods including one-dimensional and two-dimensional nuclear magnetic resonance experiments in combination with mass spectrometry as 3-O-(4-O-[3-hydroxy-3-methylglutaryl])-α-l-arabinopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-α-l-arabinopyranosyloleanolic acid and 3-O-α-l-arabinofuranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-α-l-arabinopyranosyloleanolic acid. © The Author(s) 2019 [less ▲]

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See detailMoandaensine, a dimeric indole alkaloid from Strychnos moandaensis (Loganiaceae)
Verpoorte, Robert; Frederich, Michel ULiege; Delaude, Clément ULiege et al

in Phytochemistry Letters (2010), 3

Moandaensine contains a rare anhydronium base subunit. It presents a moderate antiplasmodial activity with IC values of 11.2 microM and 9.2 microM against , respectively, the chloroquino sensitive FCA 20 ... [more ▼]

Moandaensine contains a rare anhydronium base subunit. It presents a moderate antiplasmodial activity with IC values of 11.2 microM and 9.2 microM against , respectively, the chloroquino sensitive FCA 20 GHA and chloroquino resistant W2 strains of Plasmodium falciparum [less ▲]

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See detailTriterpene saponins from four species of the polygalaceae family
Mitaine-Offer, A. C.; Miyamoto, T.; Jolly, C. et al

in Helvetica Chimica Acta (2005), 88(11), 2986-2995

Twelve triterpene saponins were isolated by successive M PLC over silica gel from four species of Polygalaceae: From Polygala ruwenzoriensis, five new saponins 1-5 of which 1-4 as two pairs of (E)/(Z ... [more ▼]

Twelve triterpene saponins were isolated by successive M PLC over silica gel from four species of Polygalaceae: From Polygala ruwenzoriensis, five new saponins 1-5 of which 1-4 as two pairs of (E)/(Z)-isomers, together with the four known compounds tenuifoline, (E)- and (Z)-senegasaponin b, (E)- and (Z)-senegin II, and polygalasaponin XXVIII, from the genus Carpolobia. one new saponin 6 from C alba and the known arillo-side (11) from C. lutea, and another new triterpene glycoside 7 from Polygala arenaria. Their structures were established mainly by 600-MHz 2D-NMR techniques (H-1,H-1-COSY, TOCSY, NOESY, HSQC, HMBC) as 3-O-(beta-D-glucopyranosyl)presenegenin 28-[O-alpha-L-arabinopyranosyl-(1 -> 4)-O-beta-D-xylopyranosyl-(1 -> 4)-O-alpha-L-rhamnopyranosyl-(1 -> 2)-4-O-[(E)-4-methoxycinnamoyl]-beta-D-fucopyranosyl] ester (1) and its (Z)-isomer 2, 3-O-(beta-D-glucopyranosyl)presenegenin 28-[O-alpha-L-arabinopyranosyl-(1 -> 4)-O-beta-D-xylopyranosyl-(1 -> 4)-O-alpha-L-rhamnopyranosyl-(1 -> 2)-4-O-[(E)-3,4-dimethoxycinnamoyl]-beta-D-fucopyranosyl] ester (3) and its (Z)-isomer 4, 3-O-(beta-D-glucopyranosyl)presenegenin 28-[O-beta-D-galactopyranosyl-(1 -> 4)-O-beta-D-xylopyranosyl-(1 -> 4)-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-fucopyranosyl] ester (5), 3-O-(beta-D-glucopyranosyl)presenegenin 28-[O-alpha-L-arabinopyranosyl-(1 -> 3)-O-[beta-D-galactopyranosyl-(1 -> 4)]-O-beta-D-xylopyranosyl-(1 -> 4)-O-alpha-L-rhamnopyranosyl-(1 -> 2)-O-[beta-D-apiofuranosyl-(1 -> 3)]-4-O-acetyl-beta-D-fucopyranosyl] ester (6), and 3-O-(beta-D-glucopyranosyl)presenegenin 28-[O-beta-D-galactopyranosyl-(1 -> 4)-O-[beta-D-glucopyranosyl-(1 -> 3)]-O-beta-D-xylo-pyranosyl-(1 -> 4)-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-fucopyranosyl] ester (7) (presenegenin = (2 beta, 3 beta, 4 alpha)-2,3,27-trihydroxyolean-12-ene-23,28-dioic acid). acid). [less ▲]

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See detailAcylated preatroxigenin glycosides from Atroxima congolana
Elbandy, M.; Miyamoto, T.; Delaude, Clément ULiege et al

in Journal of Natural Products (2003), 66(9), 1154-1158

Six new acylated bisdesmosidic preatroxigenin saponins named atroximasaponins E-1, E-2 (1, 2), F-1, F-2 (3, 4), and G(1), G(2) (5, 6) were isolated as three inseparable mixtures of the trans- and cis-p ... [more ▼]

Six new acylated bisdesmosidic preatroxigenin saponins named atroximasaponins E-1, E-2 (1, 2), F-1, F-2 (3, 4), and G(1), G(2) (5, 6) were isolated as three inseparable mixtures of the trans- and cis-p-methoxycinnamoyl derivatives, from the roots of Atroxima congolana. Their structures were established through extensive NMR spectroscopic analysis as 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin E-1, 1), and its cis-isomer, atroximasaponin E-2 (2), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin F-1, 3), and its cis-isomer, atroximasaponin F-2 (4), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-apiofuranosyl-(1-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin G(1), 5), and its cis-isomer, atroximasaponin G(2) (6), respectively. [less ▲]

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See detailAntiplasmodial activity of alkaloids from various Strychnos species
Frederich, Michel ULiege; Jacquier, M. J.; Thepenier, P. et al

in Journal of Natural Products (2002), 65(10), 1381-1386

The in vitro antiplasmodial activities of 69 alkaloids from various Strychnos species were evaluated against chloroquine-resistant and chloroquine-sensitive lines of Plasmodium falciparum. The compounds ... [more ▼]

The in vitro antiplasmodial activities of 69 alkaloids from various Strychnos species were evaluated against chloroquine-resistant and chloroquine-sensitive lines of Plasmodium falciparum. The compounds, comprising mainly indolomonoterpenoid alkaloids, exhibited a wide range of biological potencies in the antiplasmodial assays. The most active alkaloids were also tested for cytotoxicity against HCT-116 colon cancer cells to determine their antiplasmodial selectivity. As a result of these studies, structure-activity relationships for these alkaloids have begun to emerge. Alkaloids presenting four types of bisindole skeleton exhibited potent and selective activities against Plasmodium. They were sungucine-type (IC(50) values ranging from 80 nM to 10 microM), longicaudatine-type (IC(50) values ranging from 0.5 to 10 microM), matopensine-type (IC(50) values ranging from 150 nM to 10 microM), and usambarine-type alkaloids. Within the last structural type, isostrychnopentamine (49) and ochrolifuanine A (46) were found to be active against chloroquine-sensitive and -resistant strains (IC(50) values of 100-150 and 100-500 nM, respectively), and dihydrousambarensine (51) exhibited a 30-fold higher activity against the chloroquine-resistant strain (IC(50) = 32 nM) than against the chloroquine-sensitive one. [less ▲]

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See detailThree new triterpene saponins from two species of Carpolobia
Mitaine-Offer, A. C.; Miyamoto, T.; Khan, I. A. et al

in Journal of Natural Products (2002), 65(4), 553-557

Three new acetylated triterpene saponins 1-->3 were isolated from the roots of Carpolobia alba and C. lutea. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D ... [more ▼]

Three new acetylated triterpene saponins 1-->3 were isolated from the roots of Carpolobia alba and C. lutea. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)- beta-D-xylopyranosyl-(1-->3)1-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fueopyranosyl ester, 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)- [alpha-L-arabinopyranosyl-(1-->3)1-beta-D-xylopyranosyl-(1-->4)-a-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)- beta-D-fucopyranosyl ester, and 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-xylopyranosyl-(1-->4)- [beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-Dfucopyranosyl ester, respectively. [less ▲]

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See detailNovel acylated triterpene glycosides from Muraltia heisteria
Elbandy, M.; Miyamoto, T.; Chauffert, B. et al

in Journal of Natural Products (2002), 65(2), 193-197

Four new acylated triterpene glycosides (1-4) have been isolated as two inseparable mixtures of the trans- and cis-3,4,5-trimethoxycinnamoyl derivatives (1,2 and 3,4) from the roots of Muraltia heisteria ... [more ▼]

Four new acylated triterpene glycosides (1-4) have been isolated as two inseparable mixtures of the trans- and cis-3,4,5-trimethoxycinnamoyl derivatives (1,2 and 3,4) from the roots of Muraltia heisteria. The structures of these compounds were elucidated by various 1D and 2D NMR techniques, including H-1 and C-13, COSY, NOESY, HSQC, TOCSY, and HMBC experiments and FABMS. Compounds 3 and 4 were shown to be cytotoxic in a human colon cancer cell line but did not show any ability to potentiate in vitro cisplatin cytotoxicity. [less ▲]

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See detailFive new medicagenic acid saponins from Muraltia ononidifolia
Elbandy, M.; Miyamoto, T.; Delaude, Clément ULiege et al

in Helvetica Chimica Acta (2002), 85(9), 2721-2728

Five new triterpene saponins 1-5 were isolated from the roots of Muraltia ononidifolia E. MEY along with the two known saponins 3-O-[O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]medicagenic ... [more ▼]

Five new triterpene saponins 1-5 were isolated from the roots of Muraltia ononidifolia E. MEY along with the two known saponins 3-O-[O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]medicagenic acid 28-[O-beta-D-xylopyranosyl-(l --> 4)-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl] ester and 3-O-(beta-D-glucopyranosyl)medicagenic acid 28-[O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl] ester (medicagenic acid = (4alpha,2beta,3beta)-2,3-dihydroxyolean-12-ene-23,28-dioic acid). Their structures were elucidated mainly by spectroscopic experiments, including 2D-NMR techniques, as 3-O-(beta-D-glucopyranosyl)medicagenic acid 28-[O-beta-D-apiofuranosyl-(l --> 3)-O-beta-D-xylopyranosyl-(1 --> 4)-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl] ester (1), 3-O-(beta-D-glucopyranosyl)medicagenic acid 28-{[O-beta-D-xylopyranosyl-(1 --> 4)-O-[beta-D-apiofuranosyl-(1 --> 3)]-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl} ester (2), 3-O-[O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]medicagenic acid 28-[O-beta-D-xylopyranosyl-(1 --> 4)-O-[beta-D-apiofuranosyl-(1 --> 3)]-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl] ester (3), 3-O-[O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]medicagenic acid 28-[O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl] ester (4), and 3-O-[O-beta-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]medicagenic acid (5). [less ▲]

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See detailNew strictosidine beta-glucosidase from Strychnos mellodora
Brandt, Viviane; Geerlings, Arjan; Tits, Monique ULiege et al

in Plant Physiology and Biochemistry (2000), 38(3), 187-192

A stable strictosidine glucosidase was isolated from dried powdered material of Strychnos mellodora. The kinetic parameters Km and Vmax of the purified glucosidases from catharanthus roseus and S ... [more ▼]

A stable strictosidine glucosidase was isolated from dried powdered material of Strychnos mellodora. The kinetic parameters Km and Vmax of the purified glucosidases from catharanthus roseus and S. mellodora towards strictosidine, dolichantoside and palicoside were determined and compared. [less ▲]

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See detailBeta-Carboline Glucoalkaloids from Strychnos mellodora
Brandt, Viviane; Tits, Monique ULiege; Geerlings, A. et al

Conference (1999, May)

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See detailQuatre alcaloïdes à noyau bèta-carboline isolés des écorces de tronc du Strychnos mellodora
Brandt, Viviane; Tits, Monique ULiege; Geerlings, A et al

Poster (1999, May)

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See detailbeta-carboline glucoalkaloids from Strychnos mellodora
Brandt, Viviane; Tits, Monique ULiege; Geerlings, A. et al

in Phytochemistry (1999), 51(8), 1171-1176

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See detailLes strychnos africains et leurs alcaloïdes
Delaude, Clément ULiege; Delaude, Lionel ULiege

in Bulletin de la Société Royale des Sciences de Liège (1997), 66(4), 183-286

In the Greek Antiquity, the term strychnos was first coined to describe various toxic Solanacae. Nowadays, the genus Strychnos created by Linnaeus in 1753 is the numerically most important genus from the ... [more ▼]

In the Greek Antiquity, the term strychnos was first coined to describe various toxic Solanacae. Nowadays, the genus Strychnos created by Linnaeus in 1753 is the numerically most important genus from the Loganiaceae family and comprises 196 species growing in the warm regions of Asia (58 species), America (64) and Africa (75). Species on the three continents are almost totally segregated. Only Strychnos potatorum is common to Asia and Africa. The toxicity of Strychnos was empirically well-known from time immemorial. Inhabitants of South-Eastern Asia and India had an ancestral knowledge of Strychnos nux vomica, whose deadly poisonous seeds were later imported and marketed in Europe to kill rodents and small predators. Concentrated extracts from Amazonian Strychnos, known as curares, are also remarkable hunting poisons, used by South American Indians. Accordingly, modern scientific investigations of Strychnos and their alkaloids started with Asian or American species used as traditionnal poisons. Strychnine was the first alkaloid found in Strychnos. It was isolated from Asian S. nux vomica in 1818, but its structure was fully elucidated only in the 1950s. Meanwhile, various curarizing alkaloids from American Strychnos were identified. Based on these early results, Strychnos alkaloids were initially classified according to their geographical origin. Asian Strychnos were assumed to contain strychnine and related compounds, whereas curarizing ammonium salts were associated with American Strychnos. African species were assimilated to their Asian counterparts and deemed of less interest. During the last three decades, however, systematic screening of African Strychnos has revealed the presence of numerous, varied alkaloids in these plants and demonstrated that the correlation between geographical distribution and alkaloid content was erroneous. Presently, 47 African species have been investigated and their alkaloids analyzed, significantly more than Asian and American materials (about 10 and 20 species, respectively). In this review, we present the alkaloids isolated so far from African Strychnos. 309 structures are listed and sorted according to their molecular weight, the most useful index key in modern research based on mass spectrometry. [less ▲]

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See detailGlucoindole Alkaloids from Stem Bark of Strychnos Mellodora
Tits, Monique ULiege; Brandt, V.; Wauters, Jean-Noël ULiege et al

in Planta Medica (1996), 62(1), 73-4

Three glucoindole alkaloids, dolichantoside (1), strictosidine (2), and palicoside (3), have been identified in the stem bark of Strychnos mellodora (Loganiaceae), collected in Zimbabwe. The chiroptical ... [more ▼]

Three glucoindole alkaloids, dolichantoside (1), strictosidine (2), and palicoside (3), have been identified in the stem bark of Strychnos mellodora (Loganiaceae), collected in Zimbabwe. The chiroptical (CD) data are compared. [less ▲]

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See detail2,7-dihydroapogeissoschizine from root bark of strychnos Gossweileri
Quetin-Leclercq, Joëlle; Dive, Georges ULiege; Delaude, Clément ULiege et al

in Phytochemistry (1994), 35(2), 533-536

In this paper, we describe the isolation and structural determination of 2,7-dihydroxyapogeissoschizine, a new alkaloid from the root bark of Strychnos gossweileri. Elucidation of its structure is based ... [more ▼]

In this paper, we describe the isolation and structural determination of 2,7-dihydroxyapogeissoschizine, a new alkaloid from the root bark of Strychnos gossweileri. Elucidation of its structure is based mainly on 1D and 2D NMR studies; its conformation was optimized by energy minimization. This type of skeleton is related to geissoschizine but with the notable diffrence that the 1 and 17 positions are joined giving an additional fused ring. Such a seven-membered ring has ,to our knowledge, only been observed in apogeissoschizine, obtained after chemical tratment of two alkaloids ( geissospermine and geissoschizine). 2,7-dihydroxyapogeissoschizine is therefore, the first natural product possessing this skeleton. According to a preliminary test, this new alkaloid shows low toxicity to B16 melanoma cells, but not for non-cancer 3T3 fibroblasts cultured in vitro.THese results have to be confirmed by further tests. [less ▲]

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See detailRevision of the structure of strychnofluorine, an alkaloid of Strychnos gossweileri
Quetin-Leclercq, Joëlle; Coune, Claude; Delaude, Clément ULiege et al

in Phytochemistry (1992), 31(12), 4347-4349

The structure of strychnofluorine, an indole alkaloid isolated in 1980 from the root bark of Strychnos gossweileri, has been revised. Strychnofluorine proved to be identical with 18 ... [more ▼]

The structure of strychnofluorine, an indole alkaloid isolated in 1980 from the root bark of Strychnos gossweileri, has been revised. Strychnofluorine proved to be identical with 18-hydroxynorfluorocurarine that has been isolated as a minor (contaminated) alkaloid from Strychnos ngouniensis in 1983. [less ▲]

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See detailRevision of the structure of strychnofluorine
Quetin-Leclercq, Joëlle; Warin, Roger; Delaude, Clément ULiege et al

in Journal de Pharmacie de Belgique (1992), 47(3), 242

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See detailRevision of the Structure of Strychnochromine
Quetin-Leclercq, Joëlle; Angenot, Luc ULiege; Dupont, Léon et al

in Tetrahedron Letters (1991), 32(34), 4295-4298

The structure of strychnochromine, an unusual alkaloid isolated from a new batch of the root bark of Strychnos gossweileri has been revised . To confirm the indoline structure ( proposed in 1988) and to ... [more ▼]

The structure of strychnochromine, an unusual alkaloid isolated from a new batch of the root bark of Strychnos gossweileri has been revised . To confirm the indoline structure ( proposed in 1988) and to establish the stereochemistry of the compound extensive 2D-NMR experiments were carried out. The COSY experiments mostly confirmed the previous observations but the COLOC maps did not fit the first proposed structure!The problem was solved by single-crystal X-ray analysis of the p-bromobenzoyl ester of strychnochromine. The new structure, with its tetrahydroquinoline ring, is very unusual in Strychnos species but the formation of quinolines from indole alkaloids has already mentioned in some other plants ( Cinchona, Alstonia, Hunteria..). [less ▲]

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See detailMatadine, a cytotoxic alkaloid from Strychnos gossweileri
Quetin-Leclercq, Joëlle; Coucke, P.; Delaude, Clément ULiege et al

in Phytochemistry (1991), 30(5), 1697-1700

Matadine, a new alkaloid, has been isolated from the root bark of Strychnos gossweileri. Elucidation of its structure is mainly based on 1H and 1D NMR studies. Its cytotoxic activity has been tested on ... [more ▼]

Matadine, a new alkaloid, has been isolated from the root bark of Strychnos gossweileri. Elucidation of its structure is mainly based on 1H and 1D NMR studies. Its cytotoxic activity has been tested on cancer cells and normal cells. Matadine is an anhydronium base as serpentine, that exerts also a selective inhibiting activity on B16 melanoma cells while it is less toxic in human 2002 non-cancer cells. This selective activity might be well due , as it seems to be the case for serpentine and alstonine, to a higher affinity of matadine for destabilized single-stranded DNA as mainly present in cancer cells. [less ▲]

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