Strychnochrysine, a New Bisindole Alkaloid from the Roots of<i>Strychnos nux-vomica</i>

Biala, Rose Gadi; Tits, Monique; Penelle, Jacques; Frédérich, Michel; Brandt, Viviane; Prosperi, Christelle; Llabrès, Gabriel; Angenot, Luc

doi:10.1021/np9703454

Cited by 14 publications

(13 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All 1 H and 13 (d = 5.57, t, J = 6.7 Hz). These chemical shifts and coupling constants supported the hypothesis of a hydroxyethylidene unit and were in agreement with the values observed in isostrychnine, 18-hydroxyisoretuline (22) and strychnochrysine (23).…”

Section: Resultssupporting

confidence: 88%

New Antimalarial and Cytotoxic Sungucine Derivatives from Strychnos icaja Roots

Frédérich¹,

Pauw²,

Llabrès³

et al. 2000

Planta Med

Self Cite

View full text Add to dashboard Cite

Reinvestigation of Strychnos icaja Baillon resulted in the isolation of vomicine, isostrychnine and of three new sungucine derivatives, named isosungucine (8), 18-hydroxy-sungucine (9) and 18-hydroxy-isosungucine (10). They were identified by detailed spectroscopic methods. The complete 1H- and 13C-NMR study of sungucine was also realized. Some of these compounds were highly active against Plasmodium falciparum in vitro and more particularly against the chloroquine-resistant strain. Compound 10 showed a selective antiplasmodial activity, with > 100-fold greater toxicity towards Plasmodium falciparum, relative to cultured human cancer cells (KB and HeLa lines) or fibroblasts (WI38).

show abstract

Section: Resultssupporting

confidence: 88%

New Antimalarial and Cytotoxic Sungucine Derivatives from Strychnos icaja Roots

Frédérich¹,

Pauw²,

Llabrès³

et al. 2000

Planta Med

Self Cite

View full text Add to dashboard Cite

show abstract

“…This signal was correlated in the HMBC spectrum to C-5, C-20, C-19, C-3, C-2, C-15 and C-14, in the ROESY spectrum to H-5 and H-18, in the COSY spectrum to H-5 and H-19 and then attributed to H-21 ( Table 1). The deshielded 1 H and 13 C shifts of CH-21 were consistent with those of strychnochrysine or afrocurarine, possessing a pyridinium ring D in their corynane moiety [9], [10]. The aromatization of ring D of strychnopentamine could explain the major other modifications compared to the spectra of 1 and 2.…”

supporting

confidence: 53%

Chrysopentamine, an Antiplasmodial Anhydronium Base fromStrychnos usambarensisLeaves

Frédérich

Cristino²,

Choi³

et al. 2004

Planta med

View full text Add to dashboard Cite

A new derivative of strychnopentamine was isolated from the leaves of Strychnos usambarensis. This compound, named chrysopentamine, was identified by detailed spectroscopic methods (UV, IR, HR-ESI-MS, 1D and 2D NMR). Chrysopentamine presented an original hydroxy substitution on C-14 and an aromatization of the ring D of strychnopentamine leading to anhydronium base properties and exhibited strong antiplasmodial properties (IC (50) less than 1 microM).

show abstract

“…Strychni Se men from S. nux-vomica was a fa mous crude drug that acted as a CNS stim u lant and was also used as a pes ti cide. The lit er a ture has re ported many com po nents, such as indole al ka loids, monoterpene al ka loids, iridoids, flavonoids and ste roids from Strychnos spe cies, [3][4][5] but phytochemical ex am i na tion of S. cathayensis has not yet been con ducted. In ves ti ga tion of the stem of S. cathayensis has led to the iso la tion of one new com pound, a secoiridoid, secostrychnosin ( 1), seven com pounds, 4-tert-butyl-2oxazolidinone (2), 3-acetoxyindole (3), indole-2-carboxylic acid (4), benzocaine (5), 3-acetylindole (6), butylparaben (7) and 2-hydroxy-3-methoxybenzaldehyde (8), which were isolated for the first time from na ture and 50 known com pounds from the stem of S. cathayensis .…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents from Strychnos Cathayensis

Cheng

Tsai

Chen

2001

J Chinese Chemical Soc

View full text Add to dashboard Cite

Grad u ate In sti tute of Nat u ral Prod ucts, Kaohsiung Med i cal Uni ver sity, Kaohsiung 807, Tai wan, R.O.C.Secostrychnosin (1), a new secoiridoid, as well as seven com pounds never be fore iso lated from na ture: 4-tert-butyl-2-oxazolidinone (2), 3-acetoxyindole (3), indole-2-carboxylic acid (4), benzocaine (5), 3acetylindole (6), butylparaben (7) and 2-hydroxy-3-methoxybenzaldehyde (8), to gether with fifty other known com pounds, have been iso lated from the stem of Strychnos cathayensis. These com pounds in clude twenty-three al ka loids, twelve benzenoids, four ste roids, three flavonoids, three iridoids, two triterpenoids, two secoiridoids, two fatty ac ids, one lignan, one acetophenone, one coumarin, one chromane, one tetraterpenoid, one tan nin, and one or ganic acid. The struc tures of these com pounds were de ter mined by means of spec tral anal y ses.

show abstract

Strychnochrysine, a New Bisindole Alkaloid from the Roots ofStrychnos nux-vomica

Abstract: The reinvestigation of Strychnos nux-vomica resulted in the isolation of a colored monoquaternary bisindole alkaloid from the roots. The structure of this new orange substance, strychnochrysine (1), was defined by detailed spectroscopic methods.

Cited by 14 publications

References 13 publications

New Antimalarial and Cytotoxic Sungucine Derivatives from Strychnos icaja Roots

New Antimalarial and Cytotoxic Sungucine Derivatives from Strychnos icaja Roots

Chrysopentamine, an Antiplasmodial Anhydronium Base fromStrychnos usambarensisLeaves

Chemical Constituents from Strychnos Cathayensis

Contact Info

Product

Resources

About