New phlegmarane-type, cernuane-type, and quinolizidine alkaloids from two species of Lycopodium

Two new phlegmarane-type alkaloids, cermizines A (1) and B (2), three new quinolizidine alkaloids, cermizine C (3) and senepodines G (4) and H (5), and a new C₁₆N₂ type alkaloid consisting of a quinolizidine and a piperidine ring, cermizine D (6), as well as two new cernuane-type alkaloids, cernuine N-oxide (7) and lycocernuine N-oxide (8), have been isolated together with cernuine (9) and lycocernuine (10) from the club moss Lycopodium cernuum and L. chinense. The relative stereochemistry of 1-4 and 6, and the absolute stereochemistry of 5, 7, and 8 were elucidated by combination of NOESY correlations, modified Mosher's method, chemical transformations, and computational methods. Cermizine D (6) might be a biosynthetic intermediate of cernuane-type alkaloids such as 7-10.     

Biphenyl ether and biphenyl quinolizidine lactone alkaloids from Heimia salicifolia

Three new biphenyl ether quinolizidine lactone alkaloids (1–3) and 13 new biphenyl quinolizidine lactone alkaloids (4–16) were isolated from Heimia salicifolia (Lythraceae) together with seven known alkaloids. Their structures were determined by spectroscopic analyses and chemical conversions.     

New quinolizidine and diaza-adamantane alkaloids from Acosmium dasycarpum (Vog.) Yakovlev—Fabaceae

The phytochemical investigation of the methanol crude extract obtained from Acosmium dasycarpum (Vog.) Yakovlev root bark led to the isolation of the quinolizidine alkaloids lupanine, acosmine, acosminine and lupanacosmine, as well as the diaza-adamantane alkaloids panacosmine and dasycarpumine. Lupanacosmine (4) and dasycarpumine (6) have been described for the first time herein.     

Indolizidine and quinolizidine alkaloids

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including arthropods and amphibians; alkaloids from the genera Polygonatum, Prosopis and Poranthera; phenanthroindolizidine and phenanthroquinolizidine alkaloids; Nuphar alkaloids; lupine alkaloids; and alkaloids from marine sources. 130 references are cited.     

Indolizidine and quinolizidine alkaloids

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including ants, amphibians and beetles; indolizidine alkaloids from the genera Polygonatum, Prosopis and Elaeocarpus; indolizidine and phenanthroindolizidine alkaloids; alkylquinolizidine alkaloids, including myrtine, epimyrtine, plumerinine and Lycopodium metabolites; Lythraceae and Nuphar alkaloids; lupine alkaloids; and alkaloids from marine sources. 150 references are cited.     

Indolizidine and quinolizidine alkaloids

This review covers the isolation, structure determination, synthesis and biological activity of indolizidine and quinolizidine alkaloids from microbial, plant and animal sources. Included in the review are slaframine; hydroxylated indolizidines and their analogues; alkaloids from ants and amphibians; metabolites of the genera Prosopis, Streptomyces and Nuphar and the Lythraceae; phenanthroindolizidines and related alkaloids; lupin alkaloids; and alkaloids from sponges. tunicates and coccinellid beetles. The literature from July 2000 to June 2001 is reviewed, and 172 references are cited.     

Indolizidine and quinolizidine alkaloids

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids from microbial, plant and animal sources. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including ants, amphibians and beetles; ipalbidine, phenanthroindolizidines and related alkaloids; Lycopodium alkaloids; lupine alkaloids; and alkaloids from bacterial and marine sources. The literature from July 2002 to June 2003 is reviewed, and 174 references are cited.     

Determination of quinolizidine alkaloids in Sophora medicinal plants by capillary electrophoresis

A new capillary electrophoresis (CE) method for the determination of quinolizidine alkaloids in Sophora medicinal plants was developed. A total of seven alkaloid components (cytisine, sophocarpine, matrine, lehmannine, sophoranol, oxymatrine and oxysophocarpine) were separated within 15 min. The running buffer was a 50 mM phosphate buffer containing 1%HP-β-CD and 3.3% isopropanol. The linear calibration ranges were 5.50-88.0 μg ml⁻¹ for cytisine and lehmannine, 5.00-88.0 μg ml⁻¹ for sophocarpine and sophoranol, 5.60-89.6 μg ml⁻¹ for matrine and oxysophocarpine, and 24.0-384 μg ml⁻¹ for oxymatrine. The recoveries of the seven alkaloids were 96.0-102.9% with relative standard deviations from 1.50 to 3.00% (n = 5). The method was successfully applied to different Sophora medicinal plants including Sophora flavescens, Sophora tonkinensis and Sophora alopecuroides.     

Mamanine and pohakuline,two unprecedented quinolizidine alkaloids from sophorachrysophylla

From the bark of the endemic Hawaiian tree Sophora chrysophylla Seem. we have isolated two unprecedented quainolizidine alkaloids, mamanine (4) and pohakuline (5). Both bases are 1-hydroxymethylenequinolizidines which are linked at C-3 to α-pyridone or α-piperidone moieties. The alkaloids may be intermediates in a heretofore unknown biogenetic pathway of Sophora alkaloids.     

Indolizidine and quinolizidine alkaloids

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids from microbial, plant and animal sources. Included in the review are slaframine; the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from amphibians and marine sources; plumerinine; ipalbidine, phenanthroindolizidines and related alkaloids; lasubine-II: and lupin alkaloids. The literature from July 2001 to June 2002 is reviewed, and 142 references are cited.     

Daphtenidines A-D, new Daphniphyllum alkaloids from Daphniphyllum teijsmannii

Daphtenidines A-D (1-4), four new alkaloids were isolated from the leaves of Daphniphyllum teijsmannii, and the structures including relative stereochemistry were elucidated on the basis of spectroscopic data. Daphtenidines A (1) and B (2) were possessing daphnilactone A-type skeleton. This is the second isolation of daphnilactone A-type alkaloids from natural sources. Daphtenidine C (3) was 4-acetoxy form of daphmanidin A, while daphtenidine D (4) was 14-dehydro form of yuzurimine.     

Calyciphyllines H-M, new Daphniphyllum alkaloids from Daphniphyllum calycinum

Six new Daphniphyllum alkaloids, calyciphyllines H-M (1-6), were isolated from the leaves and stems of Daphniphyllum calycinum (Daphniphyllaceae). The structures and relative stereochemistry of 1-6 were elucidated on the basis of spectroscopic data, and the absolute stereochemistry of 3 was assigned by PGME method.