A new natural auaternary indole slkaloid isolated from Tabernaemontana laeta Mart. (Apocynaceae)

Abstract

Um novo alcalóide quaternário natural, N b -metilvoachalotina (1), três alcalóides indólicos diméricos, conodurina (2), voacamina (3) e tabernamina (4), e os três alcalóides monoméricos 19S-heyneanina (5), coronaridina (6) e voacangina (7) foram isolados da casca das raízes de Tabernaemontana laeta. Os triterpenos conhecidos 3-O-acetil-a-amirina, 3-O-acetil-b-amirina, 3-O-acetil-lupeol e 3-O-acetiltaraxasterol e os fitoesteróides b-sitosterol e seu derivado 3-O-b-Dglicopiranosídeo foram também identificados. As estruturas dos compostos foram elucidadas com base na análise de dados espectroscópicos.A new natural quaternary alkaloid, N b -methylvoachalotine (1), was obtained from the root bark of Tabernaemontana laeta together with three dimeric indole alkaloids, conodurine (2), voacamine (3) and tabernamine (4), and the monomeric indole alkaloids 19S-heyneanine (5), coronaridine (6) and voacangine (7). The known triterpenes a-amyrin acetate, b-amyrin acetate, lupeol acetate and taraxasterol acetate and the phytosterol b-sitosterol and its 3-O-b-D-glucoside were also identified. The structures of the compounds were elucidated based on spectroscopic studies.

Chemical constituents from Tabernaemontana catharinensis root bark: a brief NMR review of indole alkaloids and in vitro cytotoxicity

“…This is the first report on the presence of the alkaloids 7, 8, 9 and 12 in T. catharinensis while 10 has never been described. Besides, EH extract yielded ten known triterpenes: 20(30)-taraxasten-3β-yl (13), iso-lupeyl (14), bauerenyl (15), β-amyrin (16), pseudotaraxastenyl (17), α-amyrin (18), iso-ursenyl (19), lupeyl (20) and 20(30)-ursen-3β-yl (21) acetates; and two steroids: stigmasterol (22) and sitosterol (23). Three known pentacyclic triterpenes were isolated from neutral fraction EAc2: betulinic acid (25), oleanolic acid (26) and ursolic acid (27).…”

“…Of the 12 alkaloids isolated 10 are of the ibogan class and the other 2 of the corynanthean class. They were identified by comparison with published data (UV, IR, 1 H NMR, 13 C NMR and MS) 3,5,[9][10][11][12][13][14] .…”

Isolamento, identificação e avaliação da atividade antileucêmica de alcaloides indólicos monoterpênicos de Tabernaemontana salzmannii (A. DC.), Apocynaceae

“…Em publicações anteriores relatamos o isolamento e identificação de alcaloides indólicos monoterpênicos das espécies T. laeta (Medeiros et al, 1999(Medeiros et al, , 2001(Medeiros et al, , 2003 e T. hystrix (Monnerat et al, 2005a), bem como a atividade anticolinesterásica de dezessete alcaloides indólicos (Vieira et al, 2008).…”

Occurrence of triterpenyl acetates in soil and their potential as chemotaxonomical markers of Asteraceae

“…species are reputed to contain lupeyl acetates (Jakupovic et al, 2011;Madrigal et al, 1975), but this component is also present in various other families such as Amaranthaceae, Cucurbitaceae, Euphorbiaceae, Moraceae and Apocynaceae (e.g. Jewers and Manchada, 1970;Dutta and Ray, 1972;Woldu et al, 1988;Yoshizumi et al, 1998;Medeiros et al, 2001;Gasparetto et al, 2010). Taraxasteryl and -taraxasteryl acetates were overwhelmingly detected in Asteraceae, with 153 and 29 occurrences, respectively (Dutta and Ray, 1972;Madrigal et al, 1975;Jordon-Thaden and Louda, 2003;Jakupovic et al, 2011), and also in a few Apocynaceae (6 and 2 occurrences, respectively; Jewers and Manchada, 1970;Thakur et al, 1984;Abbott et al, 1990;Sen et al, 1992;Medeiros et al, 2001;Zhang et al, 2006;Yin et al, 2007;Pereira et al, 2008).…”

“…Jewers and Manchada, 1970;Dutta and Ray, 1972;Woldu et al, 1988;Yoshizumi et al, 1998;Medeiros et al, 2001;Gasparetto et al, 2010). Taraxasteryl and -taraxasteryl acetates were overwhelmingly detected in Asteraceae, with 153 and 29 occurrences, respectively (Dutta and Ray, 1972;Madrigal et al, 1975;Jordon-Thaden and Louda, 2003;Jakupovic et al, 2011), and also in a few Apocynaceae (6 and 2 occurrences, respectively; Jewers and Manchada, 1970;Thakur et al, 1984;Abbott et al, 1990;Sen et al, 1992;Medeiros et al, 2001;Zhang et al, 2006;Yin et al, 2007;Pereira et al, 2008). Bauerenyl acetate was found in three Asteraceae spp., four Apocynaceae and Euphorbia chrysocoma (Cava et al, 1967;Cicció-Alberti and Hoet, 1981;Lao et al, 1983;Shi et al, 2005;Pereira et al, 2008;Jakupovic et al, 2011).…”