Alkaloids of from Thailand

A comprehensive review on phytochemistry and pharmacology of genus Kopsia: monoterpene alkaloids – major secondary metabolites

“…Aspidofractinines 1-204 have been generally associated with the esterication at nitrogen N-1 and carbon C-16, carbonylation at carbon C-5, expoxydation at carbons C-11 and C-12, and hydroxylation, or methoxylation at carbons C-11, C-12, C-16, C-17, and C-18. It was found that 5,22dioxokopsane (17), kopsamine (39), kopsamine N-oxide (40), kopsanone (41), kopsine (73), kopsilongine (91), kopsininic acid (117), kopsinilam (124), kopsinine (126), kopsinine-N(4)oxide (127), pleiocarpine (189), and (À)-venalstonine (201) might be seen as characteristic metabolites in the group of Kopsia aspidofractinines. For instance, compound 126 was recorded to appear in K. arborea twig and stem bark, K. dasyrachis stem, K. fruticosa stem bark, K. jasminiora stem bark, K. grandifolia stem bark, K. griffithii leaf and stem bark, K. hainanensis leaf, stem, stem bark and twig, K. larutensis stem, stem bark and leaf, K. officinalis root, stem, twig, leaf and fruit, K. singapurensis stem bark and leaf, K. pauciora stem, stem bark and leaf, and K. teoi stem bark, whereas its N(4)-oxide (127) presented in K. dasyrachis stem, K. griffithii stem bark, K. hainanensis stem and leaf, K. officinalis fruit and leaf, K. pauciora stem, and K. singapurensis bark.…”

“…22,30 Similarly, 16-epi-kopsinine (20), 16-epi-kopsinilam (21), 16-epi-17a-hydroxy-D 14,15 -kopsinine (22), 14,15-b-epoxykopsingine (23), N(1)-formylkopsininic acid (24), N(1)-formylkopsininic acid-N(4)-oxide (25), fruticosamine (26), fruticosiamine A (27), and fruticosine (28) were new aspidofractinines, and found in genus Kopsia for the rst time. 11,20,24,[31][32][33][34][35][36][37][39][40][41][42] The known metabolite 11-hydroxykopsilongine (29) has been detected in both the fruit and leaf of K. officinalis, 13,25 while 11-hydroxykopsingine (30), 5b-hydroxykopsinine (31), and 15-hydroxykopsamine (32) were rst isolated from polar extracts of K. teoi leaf, K. jasminiora stem bark, and K. singapurensis root, respectively. 24,34,35 Two known compounds 33 and 34 were products of 15a and 17a-hydroxylation of kopsinine, respectively (Fig.…”

“…In the meantime, the structure of the new metabolite 35 is closely related to kopsinine by 17a-OH and olenic double bond at carbons C-14 and C-15. 44 For a long time, Ruangrungsi et al (1987) successfully isolated two new aspidofractinines, named jasminiorine (36) and kopsijasmine (89), from the MeOH extract of K. jasminiora leaves, whereas (43)(44)(45)(46)(47) from the 80% EtOH extract of K. fruticosa aerial part. 52 Eleven new analogs, kopsiahainanins A-F (48-53) and kopsiahainins A-E (54-58) were among the new compounds found in the 80% EtOH extract of K. hainanensis twigs and leaves.…”

Recent progress in the chemistry of indole alkaloids and mould metabolites

“…Another new alkaloid, jasminiflorine, contains the fruticosine ring system, and is formulated as 12-methoxyfruticosine (240) ; it was isolated, together with the two known relatives, fruticosine (241) and fruticosamine (242). 134 The remaining alkaloid is also new, and is only the second member of the rare kopsidasinine (243) series to be encountered. On the basis of a detailed examination of its proton and 13C n.m.r.…”

Palladium-Catalyzed Asymmetric Allylic Alkylation/α-Iminol Rearrangement: A Facile Access to 2-Spirocyclic-Indoline Derivatives

“…Chiral polycyclic indoline ring represents a privileged core structure in a plethora of alkaloids and bioactive natural products. [1][2][3][4] Among them, 2-/3-spirocyclic-indolines with marvelous molecular complexity and diversity display a broad range of medicinal-relevant properties [5][6][7][8][9][10][11] (Figure 1). For example, vindolinine, isolated from the medicinal plant Catharanthus roseus (periwinkle), exhibits a strongly active against diabetes.…”