Mutagenic principles in Sinomeni Caulis et Rhizoma. I. The structure of a mutagenic alkaloid, N-demethyl-N-formyldehydronuciferine, in the neutral fraction of the methanol extract.

Abstract

A mutagenic principle in the neutral fraction of the methanol extract from Sinomeni Caulis et Rhizoma (Menispermaceae) was isolated by conventional techniques, and identified as a new dehydroaporphine alkaloid, N-demethyl-N-formyldehydronuciferine, on the basis of mass, ultraviolet, proton and carbon-13 nuclear magnetic resonance spectra, and X-ray analysis. N-Demethyl-N-formyldehydronuciferine was mutagenic to Salmonella typhimurium TA98 and TA 100.

New Alkaloids and Cytotoxic Principles from Sinomenium acutum

“…Sinomenine exerted a significant apoptotic effect on NCI-H460 cells through the mitochondrial pathway [33]. Compounds 16,18, and 19 showed differential P-gp MDR inhibition activity in the MES-SA/DX5 and HCT15 cells [34]. The cytotoxicity against different cancer cell lines of alkaloid compounds used in this study is not surprising.…”

“…Repeated chromatography of a CHCl 3 fraction of S. acutum over silica gel and Sephadex LH-20 afforded 1-36 (l " Fig. 1), of which 4-36 were identified as the following alkaloids by comparing their spectral data with those reported in the literature: sinomenine (4) [5], sinoracutine (5) [11], cephatonine (6) [16], bianfugecine (18) [17], menisporphine (19) [16], 6-O-demethyldauriporphine (20) [18], N-demethyl-N-formyl-dehydronuciferine (21) [18], disinomenine (22) [4], glaziovin (23) [19], N-feruloyltyramine (24) [20], N-feruloylmethoxytyramine (25) [21], N-pcoumaroyltyramine (26) [22], and nrothalifoline (27) [23]; lignans: 5,5′-dimethoxy-7-oxolariciresinol (28) [23], syringaresinol (29) [35], and secoisolariciresinol (30) [24]; norisoprenoids: blumenol A (31) [25], blumenol B (32) [26], dl-dehydrovomifolidol (33) [24], and 3-hydroxy-β-damascenone (34) [27]; and other compounds: glaberidel (35) [23] and lup-20(29)-en-3β,30-diol (36) [28]. Compound 1 showed a positive reaction to Dragendoff ʼs reagent.…”

“…Cytotoxicity of the isolated compounds was examined for the MCF-7, H460, HT-29, and CEM human cancer cell lines. Dauriporphine (16), 6-O-demethylmenisporphine (17), bianfugecine (18), menisporphine (19), and 6-O-demethyldauriporphine (20) showed differential effects in their cytotoxic activity on the target cancer cell lines. Significant angiogenesis inhibitions of 16 and 19 were also observed.…”

β-Phenylethylamines and the isoquinoline alkaloids

“…An X-ray-crystallographic study of luteidine has shown this alkaloid to have the structure (208), enantiomeric with that reported Regecoline (209) has been prepared by the oxidation of the corresponding phenolic tetrahydroisoquinoline kesselringine photochemically and with iodine.544 Homoglaucine (210; R' = Me, R2 = H) has been synthesized by the oxidation of homolaudanosine with ruthenium(1v) trifluoroacetate,222 0-methylkreysigine (210; R' = Me, R2 = OMe) has been obtained by oxidizing 5'-methoxyhomolaudanosine with thallium(II1) t r i f l u o r ~a c e t a t e , ~~~ and 0-acetylhomothalicmidine (210; R1 = Ac, R2 = H) has been prepared by the acid-catalysed cyclization of the quinone ketal (2 1 1)546 and its 4-acetoxy-3-methoxy-isomer has been prepared in the same way from the isomeric ketal (212).547 The homoaporphine system has also been synthesized by photochemical cyclization of the bromo-amide (213) both ortho and para to the hydroxyl group, followed by Bischler-Napieralsky ring-closure and reduction. 546…”

Alkaloidal Constituents of Tinospora Crispa

“…Known compounds 2-10 were identified as tinoscorside A [11], N-formylanonaine [12], N-formyldehydroanonaine [13], N-formylnornuciferine [12], N-demethyl-N-formyldehydronornuciferine [14], magnoflorine [15], paprazine [16,17], N-trans-feruloyltyramine [15,16], and cytidine [18], respectively. The structures of these compounds were identified by comparing their spectroscopic data with reported data.…”