Alkaloids of Caryomene olivascens (Menispermaceae). Bisbenzylisoquinoline with new structure.

Lavault, M.; Fournet, Alain; Guinaudeau, Hélène; Bruneton, J.

doi:10.1248/cpb.34.1148

Cited by 28 publications

(22 citation statements)

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“…A downfield shift of N 0.8 ppm has been observed for H-1 (or H-1') when syn to the N-oxide oxygen. The downfield shift is less pronounced when an anti-relationship obtains (1,2). In the present instance, H-1' appears at 6 4.46 whereas the corresponding absorption in berbamine is at 6 3.85.…”

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confidence: 41%

Berbamine 2'-β-N-oxide, a New Bisbenzylisoquinoline from Berberis brandisiana

Hussain¹,

Siddiqui²,

Khan³

et al. 1986

J. Nat. Prod.

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Berberís brandisiana Ahrendt (Berberidaceae) is a shrub that grows in northern Pakistan. A study of the alkaloidal contents of its aerial parts has resulted in the isolation of the new bisbenzylisoquinoline (+)-berbamine 2'ß--oxide (1), C37N40N2O7.sembles in it's general features the spectrum for berbamine (1). Notable divergences, however, were the chemical shifts of the 2'-N-methyl group and the aliphatic H-', H-V, and H-3'. It is known that the 2-N-methyl (or 2'-Nmethyl) signal of a bisbenzylisoquino-The mass spectrum of the alkaloid shows molecular ion mlz 624 of medium intensity (38%). This is accompanied by two strong peaks, mlz 608 (100%) and mlz 198 (97%). The mlz 608 peak is due to loss of an oxygen atom from the molecular ion. The mlz 198 peak corresponds to the doubly charged upper half of the mlz 608 species.Inasmuch as the net loss of one oxygen in the mass spectrum is diagnostic of an N-oxide, our alkaloid was reduced with zinc in HC1 to afford the known (+)-berbamine.The 360 MHz (CDC13) nmr spectrum of berbamine 2'^-N-oxide has been summarized around expression 1.

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confidence: 41%

Berbamine 2'-β-N-oxide, a New Bisbenzylisoquinoline from Berberis brandisiana

Hussain¹,

Siddiqui²,

Khan³

et al. 1986

J. Nat. Prod.

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“…The access to the 5,7-fused system has only been reported for compounds without the a-methylene-g-lactone moiety [20,21]. We therefore thought that semisynthesis of xanthatin derivatives would be more fruitful, starting from xanthatin 1 and xanthinin 4 isolated from Xanthium macrocarpum as already described [14].…”

Section: Introductionmentioning

confidence: 95%

“…Compounds 1 and 4 were extracted and isolated from the leaves of Xanthium macrocarpum [14]. All reagents and solvents were general purpose grade.…”

Section: Chemistrymentioning

confidence: 99%

“…These activities had legitimised our efforts towards the study of their total synthesis, that culminated with the discovery of a new pathway to ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives [11,12]. More recently, we have also reported on the antifungal activities of xanthatin 1 [13], a xanthanolide previously isolated from Xanthium macrocarpum [14]. This type of sesquiterpenic lactones is already known for their antimicrobial [15], antimalarial [16], cytotoxic [17] and farnesyl transferase inhibitory activities [18].…”

Section: Introductionmentioning

confidence: 96%

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Synthesis of reduced xanthatin derivatives andin vitroevaluation of their antifungal activity

Pinel¹,

Landreau²,

Séraphin³

et al. 2005

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Huit sont connues : un dCrivC monopontk 1 1-12', la (+)-lindoldhamine 1 ; trois dCrivCs dipontCs 7-8', 11-12' de configuration lR,lrS, la (+)-daphnoline 2, la (+)-daphnandrine 3 et la (+)-bisnoraromoline 4; quatre dCrivCs a enchainement dibenzo-dioxine (6-7', 7-8', 11-12') de configuration l S , l l S : (+)-cocsuline 10, (+)-cocsoline 11 et (+)-0-mCthyl cocsoline 12, ou de configuration lR,llS : c'est le cas de la (+)-apateline 13. Tous ces alcaloi'des ont dCja Ct C isolCs a plusieurs reprises, en particulier a partir de diverses MCnispermacCes ( 6 4 , et (12). Cette conklation prouve la structure proposte pour la (+)-pangkoramine 7 (ou (+)-bisnor-2,2' candicusine) (tableau 2).…”

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