Tabernaelegantinals: Unprecedented cytotoxic bisindole alkaloids from Muntafara sessilifolia

Marion Girardot; Alice Gadea; Christiane Deregnaucourt; Alexandre Deville; Lionel Dubost; Bastien Nay; Alexandre MacIuk; Philippe Rasoanaivo; Lengo Mambu

doi:10.1002/ejoc.201101738

Tabernaelegantinals: Unprecedented cytotoxic bisindole alkaloids from Muntafara sessilifolia

Marion Girardot, Alice Gadea, Christiane Deregnaucourt, Alexandre Deville, Lionel Dubost, Bastien Nay, Alexandre MacIuk, Philippe Rasoanaivo, Lengo Mambu

Research output: Contribution to journal › Article › peer-review

Abstract

Bioassay-guided fractionation of the stem bark of Muntafara sessilifolia has led to the isolation of six new vobasinyl-iboga bisindole alkaloids, tabernaelegantinals A, B and E, and (3'R)-hydroxytabernaelegantines A, C and D, together with six known monomeric indole and two bisindole alkaloids. The structures of these alkaloids were established by NMR and MS analysis. The bisindole alkaloids demonstrated cytotoxicity against the human lung MRC-5 and rat skeletal muscle L-6 cell lines whereas only one monomeric indole alkaloid was found to be cytotoxic. Tabernaemontanine acetate was found to be selectively antiplasmodial against the chloroquine-resistant strain FcB1 of Plasmodium falciparum (5.3 μM IC ₅₀) over mammalian cell lines (selectivity index > 45). The tabernaelegantinals share an unprecedented α-amino aldehyde moiety, the biosynthetic origin of which is discussed.

Original language	English
Pages (from-to)	2816-2823
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	14
DOIs	https://doi.org/10.1002/ejoc.201101738
Publication status	Published - 1 May 2012
Externally published	Yes

Keywords

Alkaloids
Biological activity
Natural products
Structure elucidation

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10.1002/ejoc.201101738

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title = "Tabernaelegantinals: Unprecedented cytotoxic bisindole alkaloids from Muntafara sessilifolia",

abstract = "Bioassay-guided fractionation of the stem bark of Muntafara sessilifolia has led to the isolation of six new vobasinyl-iboga bisindole alkaloids, tabernaelegantinals A, B and E, and (3'R)-hydroxytabernaelegantines A, C and D, together with six known monomeric indole and two bisindole alkaloids. The structures of these alkaloids were established by NMR and MS analysis. The bisindole alkaloids demonstrated cytotoxicity against the human lung MRC-5 and rat skeletal muscle L-6 cell lines whereas only one monomeric indole alkaloid was found to be cytotoxic. Tabernaemontanine acetate was found to be selectively antiplasmodial against the chloroquine-resistant strain FcB1 of Plasmodium falciparum (5.3 μM IC 50) over mammalian cell lines (selectivity index > 45). The tabernaelegantinals share an unprecedented α-amino aldehyde moiety, the biosynthetic origin of which is discussed.",

keywords = "Alkaloids, Biological activity, Natural products, Structure elucidation",

author = "Marion Girardot and Alice Gadea and Christiane Deregnaucourt and Alexandre Deville and Lionel Dubost and Bastien Nay and Alexandre MacIuk and Philippe Rasoanaivo and Lengo Mambu",

year = "2012",

month = may,

day = "1",

doi = "10.1002/ejoc.201101738",

language = "English",

pages = "2816--2823",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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TY - JOUR

T1 - Tabernaelegantinals

T2 - Unprecedented cytotoxic bisindole alkaloids from Muntafara sessilifolia

AU - Girardot, Marion

AU - Gadea, Alice

AU - Deregnaucourt, Christiane

AU - Deville, Alexandre

AU - Dubost, Lionel

AU - Nay, Bastien

AU - MacIuk, Alexandre

AU - Rasoanaivo, Philippe

AU - Mambu, Lengo

PY - 2012/5/1

Y1 - 2012/5/1

N2 - Bioassay-guided fractionation of the stem bark of Muntafara sessilifolia has led to the isolation of six new vobasinyl-iboga bisindole alkaloids, tabernaelegantinals A, B and E, and (3'R)-hydroxytabernaelegantines A, C and D, together with six known monomeric indole and two bisindole alkaloids. The structures of these alkaloids were established by NMR and MS analysis. The bisindole alkaloids demonstrated cytotoxicity against the human lung MRC-5 and rat skeletal muscle L-6 cell lines whereas only one monomeric indole alkaloid was found to be cytotoxic. Tabernaemontanine acetate was found to be selectively antiplasmodial against the chloroquine-resistant strain FcB1 of Plasmodium falciparum (5.3 μM IC 50) over mammalian cell lines (selectivity index > 45). The tabernaelegantinals share an unprecedented α-amino aldehyde moiety, the biosynthetic origin of which is discussed.

AB - Bioassay-guided fractionation of the stem bark of Muntafara sessilifolia has led to the isolation of six new vobasinyl-iboga bisindole alkaloids, tabernaelegantinals A, B and E, and (3'R)-hydroxytabernaelegantines A, C and D, together with six known monomeric indole and two bisindole alkaloids. The structures of these alkaloids were established by NMR and MS analysis. The bisindole alkaloids demonstrated cytotoxicity against the human lung MRC-5 and rat skeletal muscle L-6 cell lines whereas only one monomeric indole alkaloid was found to be cytotoxic. Tabernaemontanine acetate was found to be selectively antiplasmodial against the chloroquine-resistant strain FcB1 of Plasmodium falciparum (5.3 μM IC 50) over mammalian cell lines (selectivity index > 45). The tabernaelegantinals share an unprecedented α-amino aldehyde moiety, the biosynthetic origin of which is discussed.

KW - Alkaloids

KW - Biological activity

KW - Natural products

KW - Structure elucidation

U2 - 10.1002/ejoc.201101738

DO - 10.1002/ejoc.201101738

M3 - Article

AN - SCOPUS:84860636298

SN - 1434-193X

SP - 2816

EP - 2823

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 14

ER -

Tabernaelegantinals: Unprecedented cytotoxic bisindole alkaloids from Muntafara sessilifolia

Abstract

Keywords

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