Berberis alkaloids. XXXIV. Turcomanine — a new alkaloid fromBerberis turcomanica

Abstract

UDC 547.044/046Berberine, isocorydine, glaucine, thalicmidine, aromoline, oxyacanthine, and the new 1-benzylisoquinoline alkaloid turcomanine have been isolated from Berberis turcomanica Kar. The structure of the new alkaloid has been established on the basis of chemical transformations and spectral characteristics. This is the first time that isocorydine, thalicmidine, arornoline, and oxyacanthine have been isolated from this plant.Continuing an investigation of Berberis turcomanica Kar. [1-3], we have studied the alkaloid composition of the leaves of this plant gathered in the incipient fruit-bearing stage in the region of Kara-Kala.Chloroform extraction yielded 0.17% of bases, by the separation of which on a silica gel column seven alkaloids, including one new one (1), were isolated. Berberine and glaucine have been isolated previously but this is the f'trst time that oxyacanthine, aromoline, isocorydine, and thalicmidine have been isolated from this plant. All the known bases were identified by their spectral characteristics and by direct comparison with authentic specimens.Compound (1) was an optically inactive phenolic base forming a hydrobromide sparingly soluble in the majority of organic solvents.The UV spectrttm of (1) was close to that of papaverine [4]. Its IR spectrum contained absorption bands of active hydrogen in the 3380-2750 cm -1 region, corresponding to the stretching vibrations of free and associated OH groups. In the mass spectrum the strongest peaks were those of the M + and [-M -1] + ions which showed the aromatic nature of the alkaloid.When (1) was acetylated with acetic anhydride in pyridine the triacetyl derivative (2) was obtained. The mass spectrum of (2) contained the peak of the molecular ion with m/z 423 and the peaks of ions with m/z 381, 339, 297, corresponding to the successive elimination of three acetyl groups. In the IR spectrum of (2) the band of active hydrogen had disappeared and the absorption band of an ester group had appeared at 1773 cm -1.

Phytopharmacology and Clinical Updates of Berberis Species Against Diabetes and Other Metabolic Diseases

“…Turconidine (Karimov et al, 1993f) -Turcberine (Karimov et al, 1993c) Young shoot Berberine, isocorydine, glaucine, thalicmidine, aromoline, oxyacanthine, turcomanine, berberine, papaverine, cyclotriveratrilene (Khamidov et al, 1996d;Khamidov et al, 1996a)…”

β-Phenylethylamines and the isoquinoline alkaloids

“…Benzylisoquinoline alkaloids have been isolated from the following plant species, the six marked with asterisks being new alkaloids: Berber turcomanica 31,32 papaverine and turcomanine* 30 Papaver setigerum 33 laudanosine, papaverine, setigerine* 31a and setigeridine* 31b…”

“…Bisbenzylisoquinoline alkaloids have been isolated from the following plant species, the six marked with asterisks being new alkaloids: Berberis crataegina 50 aromoline, berbamine, isotetrandrine and oxyacanthine Berberis turcomanica 32 aromaline and oxyacanthine Dehaasia triandra 51 homoaromoline and thalrugosinone Hernandia nymphaeifolia 14 vatteamine 2 -N-oxide* 45 Isopyrum thalictroides 52 fangchinoline, isopyruthaline* 46 and isopythaline* 47 Mahonia aquifolium 53 aquifoline, aromoline, baluchistanamine, berbamine, obamegine and oxyacanthine Pachygone dasycarpa 54 angchibangkine* 48, atherospermoline, cosculine, 2 -norcosculine, daphnoline, fangchinoline, isoboldine, 7-O-demethyl-N-methylpeinamine, penduline, tetrandrine, tricordatine and 12-O-methyltricordatine* 49 Stephania cepharantha 1 berbamine, 2-norberbamine, cepharanthine, 2-norcepharanthine, cepharanoline, 2-norcepharanoline, cycleanine, 3,4-dehydrocycleanine* 50, homoaromoline, isotetrandrine, 2-norisotetrandrine, obaberine, obamegine, secocepharanthine, stephababerine, 3,4-dehydrostephasuberine and thalugosinone. Angchibangkine 48 represents a new type of bisbenzylisoquinoline alkaloid, having a skeleton isomeric with that of all of the alkaloids of the trilobine group, which have the arrangement of three diphenyl ether linkages shown in 49.…”

“…Berberis crataegina 50 berberine, columbamine, jatrorrhizine and palmatine Berberis ilicifolia 87 ilicifoline* 70 Berberis turcomanica 31,32 berberine Corydalis racemosa 88 tetrahydropalmatine Eschscholtzia californica 89 berberine Fumaria densiflora 90 coptisine, scoulerine, sinactine, stylopine and N-methylstylopine chloride Fumaria indica 91 8-hydroxystylopine glucoside* 71 Hernandia nymphaeifolia 92 N-methylcoralydine chloride Meconopsis cambrica 81 mecambridine and N-methylmecambridine chloride Meconopsis robusta 81 coptisine and corysamine Papaver setigerum 33 coptisine, scoulerine and stylopine Polyalthia cerasoides 93 cerasodine* 72a and cerasonine* 72b Stephania cepharantha 1 scoulerine Zanthoxylum nitidum 37 cis-N-methylcanadine chloride. Ilicifoline is the first dimeric berberine of its type to be discovered.…”

“…Aporphine alkaloids have been isolated from the following plant species, the eleven marked with asterisks being new alkaloids: Berberis crataegina 50 magnoflorine Berberis turcomanica 32 glaucine, isocorydine and thalicmidine Cissampelos glaberrima 137 cissaglaberrimine* 112 Dehaasia triandra 51,138 dehydroisocorydione* 113, isocorydione* 114a, norisocorydione* 114b, isoboldine, norisocorydine, Nmethyllaurotetanine, N-methyllindcarpine and nantenine Fumaria densiflora 90 corytuberine Hernandia nymphaeifolia 14,92 hernandaline, 7-formyldehydrohernangine* 115 and N-methylovigerine Magnolia sieboldii 139 magnoporphine* 116 Meconopsis cambrica 81 corytuberine, magnoflorine, mecambroline, roemerine and roemeroline Meconopsis robusta 81 corytuberine and magnoflorine Ocotea benesii 140 3-hydroxynuciferine* 118, 3-hydroxydehydronuciferine* 119 and isocorydine Ocotea holdrigeana 141 corytuberine, isocorydine and norisocorydine Papaver caucasicum 80 nuciferine, nornuciferine and roemerine…”