Alkaloids of Hunteria zeylanica

Lavaud, Catherine; Massiot, Georges; Vercauteren, Joseph; Men‐Olivier, L. Le

doi:10.1016/s0031-9422(00)95285-3

Cited by 37 publications

(21 citation statements)

References 9 publications

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“…632,3728). De plus, on note en sm les ions caracteristiques d'une partie kopsinine ayant perdu 14 unites de masse par rapport aux fragments observes avec la pleiomutine, comme cela avait et6 remarqut pour la (+) kopsoffine 1 (1) ou la (-) norplkiomutine 3 (2). Le dichroi'sme circulaire du dimkre 2 est identique a celle de la kopsoffine, ce qui fixe la configuration absolue de ce nouveau dimere que nous nommons (+)-kopsoffinol.…”

unclassified

“…En effet, les dimkres de type aspidospermane-eburnane etaient jusque-la connus seulement dans la tribu des Carissees, sous-famille des Plumerio'idees [Pleiocarpa (3) et Hunteria (2)]. L'insulopinine, dont la structure proposee est proche de De telles comparaisons peuvent conduire a reexaminer la parent6 possible entre des genres classes en tribus et sousfamilles en fonction de la nature du fruit (7,8 …”

unclassified

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Kopsia pauciflora, I. Structure et Configuration Absolue de Nouveaux Alcaloïdes Indoliques Dimeres de Type Aspidospermane-Eburnane de la Serie Pleiomutine-Kopsoffine

Kan-Fan¹,

Sévenet²,

Husson³

et al. 1985

J. Nat. Prod.

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unclassified

Kopsia pauciflora, I. Structure et Configuration Absolue de Nouveaux Alcaloïdes Indoliques Dimeres de Type Aspidospermane-Eburnane de la Serie Pleiomutine-Kopsoffine

Kan-Fan¹,

Sévenet²,

Husson³

et al. 1985

J. Nat. Prod.

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“…A ces deux types s'est ajoute le type landomigine. La lanceomigine (11) [2] [7] [8] isomere de la corymine (7) et de l'hydroxy-17-pseudoakuammigine (4) n'est plus une indoline mais une tktrahydroquinoliine.…”

Section: I)unclassified

Réarrangements en milieu acide trifluoroacétique de deux alcaloïdes indoliques: la desformocorymine et la dihydrocorymine

Massiot¹,

Lavaud²,

Vercauteren³

et al. 1983

Helvetica Chimica Acta

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SummaryThe rearrangement in trifluoroacetic acid of two indole alkaloids of the echitamine series, desformocorymine (14) and dihydrocorymine (9), has been investigated. Desformocorymine (14) was tranformed into a mixture of carbinolamines 17a, b, with the akuammiline skeleton, which were reduced (Et,SiH, CF,CO,H) into an isomer 12 of cathafoline (6). This sequence constitutes the first example of an interconversion of the corymine skeleton into the akuammiline skeleton (Scheme 2). In the case of dihydrocorymine (9), the rearrangement followed a different pathway owing to the formation of a hemiacetal between the primary alcohol CH2(17)-OH and a carbonyl formed at C(3). Treatment of this hemiacetal 26 with aqueous base led to its opening with concomitant formation of a lactam. I3C-NMR seems to indicate that this lactam exists under a hydrated form 27. This highly unstable intermediate was cleanly transformed (MeONa-MeOH) into a 2-acyl indole 30 (Scheme 4 ) , the structure of which was determined by X-ray crystallography. The formation of this acylindole involves the rupture of the C(7)-C(16) bond; it is the reverse of the reaction generally postulated as occurring in the biogenesis of the pentacyclic alkaloids. The structure of a by-product 34 was established as 17-hydroxymethylvincoridine by X-ray crystallography.The acid-catalyzed rearrangements involve the rupture of the Ph-N-C-N chromophore, with formation of a carbonyl at C(3). The reversibility of these steps is used in an easy correlation of dihydrocorymine and of 3-epidihydrocorymine via their trifluoroacetates.

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“…is the only species endemic in Hainan Province, China. This plant has been used by the natives as medicine to cure yaws and reduce boils and skin irritations [1].Previous chemical investigations on the Hunteria genus have led to the isolation of more than 45 indole alkaloids [2][3][4][5][6][7][8]. Nearly 30 of them were reported from H. zeylanica.…”

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confidence: 99%

“…For example, compounds 6, 7, 8, and 10 can also be found in Ceylon H. zeylanica [2]. Compounds 7, 8 and 9 were reported from this species growing in Kenya of Africa [3]. In addition, compound 6 exists also in Tailand H. zeylanica [4].…”

mentioning

confidence: 99%

Indole alkaloids from leaves and stems of Hunteria zeylanica

Tang

et al. 2009

Chem Nat Compd

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Investigation of the leaves and stems of Hunteria zeylanica resulted in the isolation of one new indole alkaloid, 11-hydroxyrhazimanine (1), and nine known analogs 2-10. Their structures were determined by 1D and 2D NMR analyses. Decarbomethoxydihydrogambirtannin (2), dihydroantirhine (3), and 3-oxomehranine (4) were isolated from Hunteria genus for the first time.The genus Hunteria (Apocynaceae), which includes eight species, is distributed mainly in the tropical areas of Asia and Africa. Hunteria zeylanica (Retz.) is the only species endemic in Hainan Province, China. This plant has been used by the natives as medicine to cure yaws and reduce boils and skin irritations [1].Previous chemical investigations on the Hunteria genus have led to the isolation of more than 45 indole alkaloids [2][3][4][5][6][7][8]. Nearly 30 of them were reported from H. zeylanica. In this paper, we describe the isolation and chemical characterization of 10 indole alkaloids from H. zeylanica, including one new compound, named 11-hydroxyrhazimanine (1), and nine known ones, i.e., decarbomethoxydihydrogambirtannin (2) [9], dihydroantirhine (3) [10], 3-oxomehranine (4) [11], eburnamonine (5) [12], eburnamenine (6) [12], eburnamine (7) [12], pleiocarpamine (8) [13], geissoschizol (9) [14], and tuboxenine (10) [15].

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Alkaloids of Hunteria zeylanica

Cited by 37 publications

References 9 publications

Kopsia pauciflora, I. Structure et Configuration Absolue de Nouveaux Alcaloïdes Indoliques Dimeres de Type Aspidospermane-Eburnane de la Serie Pleiomutine-Kopsoffine

Kopsia pauciflora, I. Structure et Configuration Absolue de Nouveaux Alcaloïdes Indoliques Dimeres de Type Aspidospermane-Eburnane de la Serie Pleiomutine-Kopsoffine

Réarrangements en milieu acide trifluoroacétique de deux alcaloïdes indoliques: la desformocorymine et la dihydrocorymine

Indole alkaloids from leaves and stems of Hunteria zeylanica

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