Dehydropleiocarpine alkaloids from Kopsia profunda

Leuconoxine, Kopsinitarine, Kopsijasmine, and Kopsinone Derivatives from Kopsia

“…Notable features include an unsubstituted indole ring, absence of a carbamate substituent on the indolic nitrogen from the observed NH resonance at δ 4.32, a vinylic singlet at δ 7.03, the downfield shift being characteristic of a β-hydrogen of an α,β-unsaturated carbonyl moiety, and a trisubstituted double bond (δ C 134.9, 146.0). The latter two features are reminiscent of dehydropleiocarpine-type alkaloids − and correspond to the presence of unsaturation across the 16,17-bridge in aspidofractinine compounds. Comparison with the Kopsia alkaloid kopsijasmine 33 from K. jasminiflora showed similar NMR data except for the absence of the carbamate function.…”

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

“…As shown in Table 1, more than two hundred aspidofractinines have been isolated to date, and they derive from various parts of K. arborea , K. dasyrachis , K. fruticosa , K. grandifolia , K. griffithii , K. hainanensis , K. hainanensis , K. jasminiflora , K. larutensis , K. macrophylla , K. officinalis , K. pauciflora , K. profunda , K. singapurensis , and K. teoi . 4,7–59,61–79,81 From Fig. 1, Kopsia aspidofractinines 1–204 occurred in both monomer and dimer forms, but they did not bind to sugar units.…”

“…11,25,75 Aspidofractinines were further observed in other Kopsia plants. For instance, apart from known compounds, five new derivatives N (1)-methoxycarbonyl-11,12-methylenedioxy-Δ 16,17 -kopsinine ( 154 ), N (1)-methoxycarbonyl-12-methoxy-Δ 16,17 -kopsinine ( 155 ), N (1)-methoxycarbonyl-11,12-methylenedioxy-Δ 16,17 -kopsinine N (4) oxide ( 157 ), N (1)-methoxycarbonyl-12-hydroxy-Δ 16,17 -kopsinine ( 158 ), and N (1)-methoxycarbonyl-12-methoxy-Δ 16,17 -kopsinine N (4) oxide ( 159 ) were characteristics of K. profunda , 4,77 or lahadinines A–B ( 145–146 ), 12-methoxy-10-demethoxykopsidasinine ( 167 ), paucidactines D–E ( 180–181 ), paucidactinine ( 182 ), paucidisine ( 183 ), paucidirinine ( 184 ), paucidirisine ( 185 ), pauciduridine ( 186 ), paucifinine ( 187 ), and paucifinine- N -oxide ( 188 ) were new metabolites isolated from the parts of K. pauciflora. 19,51,76…”

Anti-Inflammatory Indole Alkaloids from the Stems of Kopsia officinalis

“…13 [18] 非常相似, 不同之处在于化合物 3 多 三个碳信号[δ C 31.0 (q), 207.5 (s)和 52. [30] . 通过比较化合物 6 与白坚木碱型已 知生物碱 kopsinic acid (20) [25] [31] .…”