Naucleactonin D, an Indole Alkaloid and other Chemical Constituents from Roots and Fruits of Mitragyna inermis

Abstract

Phytochemical investigation of the roots and fruits of Mitragyna inermis (Rubiaceae) resulted in the isolation of a new indole alkaloid, named naucleactonin D (1), together with fourteen known compounds: nauclefiline (2), naucleficine (3), nauclefidine (4), angustoline (5), angustine (6), barbinervic acid (7), quinovic acid 3-O-α-L-rhamnopyranoside (8), betulinic acid (9), a mixture of ursolic (10) and oleanolic acid (11), a mixture of stigmasterol and β -sitosterol, β -sitosterol 3-O-β -D-glucopyranoside, and strictosamide (12) as the major compound. The structures of the isolated compounds were elucidated by detailed spectroscopic analysis and by comparison with published data. No 13 C NMR data for 2 and 3 exist in the literature and compounds 2, 3, 5, 7, and 12 are reported for the first time from the genus Mitragyna. The crude extract and isolated compounds were tested in vitro for their preliminary cytotoxicity against brine shrimps (Artemia salina).

Psychopharmacological Indole Alkaloids from Terrestrial Plants

“…Minor compounds such as the monoterpenes 3-oxo-α-ionyl-O-β-D- (Figure 6.15) Sitosterol, stigmasterol, and daucosterol are some of the common phytosterols that are reported in many species of Mitragyna, such as M. speciosa (Phongprueksapattana et al 2008), M. rotundifolia (Kang et al 2006b), M. inermis (Donfack et al 2012), and M. stipulosa (Fatima et al 2002 …”

Medicinal Plants Used in Mali for the Treatment of Malaria and Liver Diseases

“…The macerated fruits and seeds are used in animal breeding to activate the estrous cycle [122]. The crude extract and the isolated compounds were tested in vitro for their preliminary cytotoxicity against Artemia salina [123]. Alkaloid rich extract derived from M. inermis induced a strong inhibition of protein synthesis in mammalian cells, but did not exhibit mutagenic or genotoxic activity [108].…”

“…Bioactive compounds of the plant are mainly indole alkaloids [100]. In 2012, a new indole alkaloid, named naucleactonin D, together with fourteen known compounds, identified as nauclefiline, naucleficine, nauclefidine, angustoline, angustine, barbinervic acid, quinovic acid, 3-O-α-L-rhamnopyranoside, betulinic acid, a mixture of ursolic and oleanolic acid, a mixture of stigmasterol and βsitosterol, β-sitosterol, 3-O-β-D-glucopyranoside, and strictosamide were isolated from the roots and fruits of M. inermis [123].…”

Secondary Metabolites from Rubiaceae Species

“…Indole alkaloids: naucleactonin D; nauclefilline; angustoline; angustine; naucleficine; nauclefidine Triterpenes: barbinervic acid; quinovic acid; 3-O-α-L-rhamnopyranoside acid; betulinic acid; oleanolic acid; ursolic acid; strictosamide [120] Oxindole alkaloids: mitraphylline; isomitraphylline; speciophylline; pteropodine [121] Mitragyna parvifolia Oxindole alkaloids: 16,17-dihydro-17β-hydroxyisomitraphylline; 16,17-dihydro-17β-hydroxymitraphylline; 2-isomitraphylline; mitraphylline [122] Mitragyna rotundifolia Mitragyna speciosa Indole alkaloids: mitragynine; speciogynine; speciociliatine; 7-hydroxy-mitragynine; paynantheine [124] Nauclea cadamba Gluco-indole alkaloids: 3β-dihydroisocadambine; cadambine; 3α-dihydrocadambine; 16-carbomethoxynaufoline; nauclechine; 5,11,12,5α…”