First diamino Daphniphyllum alkaloid, daphnipaxinin, with an unprecedented heterohexacyclic skeleton from Daphniphyllum paxianum

[structure: see text] The first diamino Daphniphyllum alkaloid, daphnipaxinin (1), with an unprecedented hexacyclic fused skeleton, along with a known alkaloid, daphnicyclidin A (2), was isolated from the stem of Daphniphyllum paxianum Rosenth. The structure and absolute stereochemistry of 1 were established by spectral methods, especially two-dimensional NMR techniques and CD analysis.     

Calyciphylline D, a novel alkaloid with an unprecedented fused-pentacyclic skeleton from Daphniphyllum calycinum

[structure: see text]. Calyciphylline D (1), a novel Daphniphyllum alkaloid with an unprecedented fused-pentacyclic skeleton containing a 8-azatricyclo[4.2.1.0.4,8]nonane ring system, has been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.     

Calyciphyllines A and B,two novel hexacyclic alkaloids from Daphniphyllum calycinum

[structure: see text] Two types of Daphniphyllum alkaloids with unprecedented fused-hexacyclic ring systems, calyciphyllines A (1) and B (2), have been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structures and relative stereochemistry were elucidated on the basis of spectroscopic data.     

Daphniglaucins A and B,novel polycyclic quaternary alkaloids from Daphniphyllum glaucescens

[structure: see text] Two cytotoxic quaternary Daphniphyllum alkaloids with an unprecedented fused-polycyclic skeleton containing a 1-azoniatetracyclo[5.2.2.0.(1,6)0.(4,9)]undecane ring system, daphniglaucins A (1) and B (2), have been isolated from the leaves of Daphniphyllum glaucescens. Their structures and relative stereochemistry were elucidated on the basis of spectroscopic data.     

Daphnicyclidins A-H, novel hexa- or pentacyclic alkaloids from two species of Daphniphyllum.

Eight highly modified Daphniphyllum alkaloids with unprecedented fused hexa- or pentacyclic skeletons, daphnicyclidins A-H (1-8), have been isolated from the stems of Daphniphyllum humile and D.teijsmanni, and their structures were elucidated on the basis of spectroscopic data and chemical means. The stereochemistry was elucidated by combination of NOESY correlations, X-ray crystallographic data, and CD analyses.     

Daphmanidin A,a novel hexacyclic alkaloid from Daphniphyllum teijsmanii

A novel alkaloid with an unprecedented fused-hexacyclic skeleton, daphmanidin A (1), and a new pentacyclic alkaloid, daphmanidin B (2), have been isolated from the leaves of Daphniphyllum teijsmanii, and the structures were elucidated on the basis of spectroscopic data. The relative and absolute stereochemistry of 1 was determined by combination of NOESY correlations and a modified Mosher method.     

Calyciphylline G, a novel alkaloid with an unprecedented fused-hexacyclic skeleton from Daphniphyllum calycinum

Calyciphylline G (1), a novel Daphniphyllum alkaloid with an unprecedented fused-hexacyclic skeleton containing a 5-azatricyclo[6.2.1.0^1,5]undecane ring, has been isolated from the stem of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.     

Macropodumines D and E, two new alkaloids with unusual skeletons from Daphniphyllum macropodum Miq

[structure: see text] Two new complex polycyclic alkaloids, macropodumines D (1) and E (2), both possessing unprecedented skeletons, along with four known related alkaloids, were isolated from the leaves and barks of Daphniphyllum macropodum Miq. The structures including the relative stereochemistry of new compounds 1 and 2 were elucidated on the basis of detailed spectroscopic data analysis.     

Calyciphylline C, a novel Daphniphyllum alkaloid from Daphniphyllum calycinum

Calyciphylline C (1), a novel Daphniphyllum alkaloid with unprecedented fused-hexacyclic ring system, has been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.     

Daphmanidins C and D, novel pentacyclic alkaloids from Daphniphyllum teijsmanii

[structure: see text] Two novel alkaloids with an unprecedented fused-pentacyclic skeleton, daphmanidins C (1) and D (2), have been isolated from the leaves of Daphniphyllum teijsmanii, and the structures were elucidated on the basis of spectroscopic data. The relative stereochemistry of 1 and 2 was assigned by combination of NOESY correlations and a simulation analysis. Daphmanidin C (1) elevated activity of NGF biosynthesis.     

Calycilactone A, a novel hexacyclic alkaloid from Daphniphyllum calycillum

A novel Daphniphyllum alkaloid with a rearranged fused-hexacyclic ring system, calycilactone A, was isolated from the leaves of Daphniphyllum calycillum (Daphniphyllaceae), and the structure and relative stereochemistry of the new compound were elucidated on the basis of spectroscopic data.     

Calyciphyllines E and F, novel hepta- and pentacyclic alkaloids from Daphniphyllum calycinum

Two new Daphniphyllum alkaloids, calyciphyllines E (1) and F (2), have been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structures and relative stereochemistry were elucidated on the basis of spectroscopic data.     

Daphniglaucin C, a novel tetracyclic alkaloid from Daphniphyllum glaucescens

A novel Daphniphyllum alkaloid with an unprecedented tetracyclic ring system consisting of an octahydroindole and a hexahydroazulene rings, daphniglaucin C (1), has been isolated from the leaves of Daphniphyllum glaucescens and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data. Daphniglaucin C (1) inhibited the polymerization of tubulin.     

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.     

Daphnilongerine, an unprecedented fused pentacyclic ring system alkaloid from Daphniphyllum longeracemosum Rosenth.

An unusual yuzurine-type alkaloid daphnilongerine (1), with an unprecedented fused pentacyclic skeleton in addition to seven known ones, daphnigracine (2), daphnezomine R, daphnigraciline, yuzurine, longistylumphyllines A, daphnilongeranin C, and calycinine A, was isolated from the fruits of Daphniphyllum longeracemosum. The structure and relative stereochemistry of 1 were determined by spectroscopic analysis.     

Daphnezomines P, Q, R and S, new alkaloids from Daphniphyllum humile

Four new alkaloids, daphnezomines P-S (1-4), have been isolated from the fruits of Daphniphyllum humile, and the structures and the stereochemistry were elucidated on the basis of spectroscopic data including 2D NMR and MS/MS spectra, and chemical correlations. Daphnezomines P (1) and Q (2) were the first Daphniphyllum alkaloids with an iridoid glycoside moiety.     

Daphniglaucins D-H, J, and K, new alkaloids from Daphniphyllum glaucescens

Five new fused-hexacyclic alkaloids, daphniglaucins D (1), E (2), F (3), G (4), and H (5), and two new yuzurimine-type alkaloids, daphniglaucins J (6) and K (7), have been isolated from the leaves of Daphniphyllum glaucescens, and the structures and relative stereochemistry were elucidated on the basis of spectroscopic data and chemical means.     

Daphcalycine,a novel heptacycle fused ring system alkaloid from Daphniphyllum calycinum

A novel Daphniphyllum alkaloid, daphcalycine (1), was isolated together with known daphnicyclidin D (2) from the stem bark of Daphniphyllum calycinum. The highly condensed polycyclic structure, established by spectral analysis, possessed an unusual framework: a central quinuclidine like tricycle produced by fusion of a piperidine, a tetrahydropyran, and an oxazine ring in turn condensed to surrounding three penta-, one hexa-, and one hepta-membered rings. The relative configuration of 11 carbon stereocenters of 1 was elucidated on the basis of NOESY.     

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.     

Angustimine and angustifolimine: two new alkaloids from Daphniphyllum angustifolium

Two new alkaloids, angustimine (1) featuring an unprecedented skeleton, and angustifolimine (2) being a rare diamino Daphniphyllum alkaloid, were isolated from Daphniphyllum angustifolium. Their structures were elucidated by extensive spectroscopic analysis. The biosynthetic origin of 1 was postulated. Cytotoxic activities of 1 and 2 were tested, and all of them were inactive.