Celacinnine, a novel macrocyclic spermidine alkaloid prototype

Abstract

The isolation and structural elucidation of the novel alkaloids celacinnine (1) , celallocinnine (4) , celabenzine (5), and celafurine (6) , characterized by the presence of a 13-membered ring reflecting spermidine and cinnamoyl precursorial units, are reported.

Scocycamides, a Pair of Macrocyclic Dicaffeoylspermidines with Butyrylcholinesterase Inhibition and Antioxidation Activity from the Roots of Scopolia tangutica

“…With continuous efforts to seek structurally unique bioactive compounds from S. tangutica , a pair of (+)-( S )-scocycamide and (−)-( R )-scocycamide, featuring a unique 6/18 fused bicyclic framework with spermidine and catechol units, were separated and identified. Their skeleton is notably different from those of the reported cyclization products and spermidine-derived alkaloids including dovyalicins A–D, motoporamines, celacinnine, dihydroperiphylline, inandenine, oncinotine, lunarine, lunaridine, codonocarpine, and isocodonocarpine . Scocycamide was a new subtype of macrocyclic dicaffeoylspermidine derivatives.…”

“…This Michael addition cyclization reaction with C–C bond formation was unique among the study of macrocyclic spermidine derivertives. More commonly, the cyclization occurred by the formation of C–O or C–N bond, such as in celacinnine, dihydroperiphylline, and codonocarpine …”

“…This Michael addition cyclization reaction with C−C bond formation was unique among the study of macrocyclic spermidine derivertives. More commonly, the cyclization occurred by the formation of C−O or C−N bond, such as in celacinnine, 17 dihydroperiphylline, 18 and codonocarpine. 22 Inspired by the fact that spermidine alkaloids possess therapeutic potential for AD 7 and that inhibition of butyrylcholinesterase (BChE) has been proven to be beneficial to AD therapies, 27,28 we evaluated the inhibitory activity of (+)-(S)-scocycamide and (−)-(R)-scocycamide on BChE in vitro.…”

A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf

“…A broad biological activity has been revealed by members of the polyamine family, and the toxic or cytotoxic effects exhibited by several of these compounds [4][5][6][7][8][9]. The occurrence and biosynthesis of these macrocyclic structures has a restricted distribution in Nature [10], occurring in limited plant families, such as the Celastraceae [11][12][13]. This family is included among the families of higher plants with highinterest activity and compounds for the treatment of cancer.…”

Conjugate addition of 6-membered hydrazine to chiral tert-butyl (E)-2-(p-tolylsulfinyl)cinnamates. Synthesis of (S)-celacinnine

“…ex A. Rich) R. Wilczek, 10 the roots of Tripterygium wilfordii Hook, 10 Maytenus serrata (Hochst. ex A.…”