Search

A new dimeric indole alkaloid, vincazalidine A consisting of an aspidosperma type and a modified iboga type with 1-azatricyclo ring system consisting of one azepane and two piperidine rings coupled with an oxazolidine ring was isolated from Catharanthus roseus, and the structure including absolute stereochemistry was elucidated on the basis of spectroscopic data as well as DP4 statistical analysis. Vincazalidine A induced G2 arrest and subsequent apoptosis in human lung carcinoma cell line, A549 cells., (© 2024. The Author(s) under exclusive licence to The Japanese Society of Pharmacognosy.)

A new C 27 N 3 -type Lycopodium alkaloid consisting of two decahydroquinolines and a piperidine, cryptadine C (1) was isolated from Lycopodium cryptomerinum. The structure and relative configuration of 1, which is related to those of cryptadines A and B, lycoperine A, and hupercumine A, was elucidated on the basis of spectroscopic data. Cryptadine C showed moderate inhibitory activity against acetylcholinesterase., (© 2023. The Author(s) under exclusive licence to The Japanese Society of Pharmacognosy.)

Two new bisindole alkaloids, bisnaecarpamines A (1) and B (2), possessing a vobasine-sarpagine type skeleton were isolated from the bark of Tabernaemontana macrocarpa Jack. Their structures were elucidated by extensive spectroscopic methods and chemical correlation. The absolute configurations of compounds 1 and 2 were established using TDDFT-ECD calculation of the selected isomers. Bisnaecarpamine A exhibited potent antimalarial activity against Plasmodium falciparum 3D7 strain with IC 50 value of 28.8 µM.

A novel class of C 38 N 4 Lycopodium alkaloid, hupercumine A (1), consisting of two octahydroquinolines, a decahydroquinoline, and a piperidine, and a new C 27 N 3 -type alkaloid, hupercumine B (2), were isolated from Huperzia cunninghamioides (Hayata) Holub. The structures and absolute configurations of 1 and 2 were elucidated on the basis of spectroscopic data, chemical means, and biogenetic point of view. Hupercumines A (1) and B (2) showed moderate inhibitory activity against acetylcholinesterase.

Justidrusamides A-D (1-4), four new alkaloids containing 2-aminobenzyl alcohol, succinic acid, and 2,3-dihydroxy-2-(1-hydroxyethyl) butanoic acid skeletons have been isolated from leaves of Justicia gendarussa, and their structures were elucidated using 2D NMR data and chemical means. This is the first report of a 2,3-dihydroxy-2-(1-hydroxyethyl) butanoic acid derivative in nature.

Four new chromone alkaloids, chrotacumines G-J (1-4), have been isolated from the barks of Dysoxylum acutangulum. Their structures and absolute configurations were elucidated on the basis of NMR and CD data. Chrotacumines G and J (1 and 4) showed osteoclast differentiation inhibitory activity in a dose dependent manner., (Copyright © 2014 Elsevier Ltd. All rights reserved.)

Eight new guaipyridine sesquiterpene alkaloids, rupestines F-M (1-8) were isolated from the leaves of Artemisia rupestris and their structures were elucidated on the basis of 2D-NMR data. The absolute configurations of 1-8 have been assigned by comparison of their experimental and calculated circular dichroism (CD) spectra.

Four new alkaloids, cassiarins G, H, J, and K (1-4) which showed moderate antiplasmodial activity against Plasmodium falciparum 3D7, were isolated from the leaves of Cassia siamea (Leguminosae) and the structures of 1-4 were elucidated by 1D- and 2D-NMR analysis and X-ray crystallographic analysis.

A novel alkaloid, cassiarin F (1), which showed potent antiplasmodial activity against Plasmodium falciparum in vitro, was isolated from the flowers of Cassia siamea, and its structure was elucidated on the basis of 2D NMR analyses. A total synthesis of 1 was also achieved by employing the Suzuki coupling constructing biaryl unit, nucleophilic aromatic substitution, and Houben-Hoesch type ring construction as key steps., (© 2011 American Chemical Society)

Eucophylline (1), a new tetracyclic vinylquinoline alkaloid, was isolated from the bark of Leuconotis eugenifolius together with leucophyllidine (2). The structure and absolute configuration of 1 were elucidated on the basis of 2D NMR correlations and simulated CD analysis. Leucophyllidine (2) showed iNOS inhibitory activity and decreased the iNOS protein expression dose-dependently.

Two new bisindole alkaloids, bisnicalaterines B and C (1 and 2) consisting of an eburnane and a corynanthe type of skeletons, were isolated from the bark of Hunteria zeylanica. Their absolute structures were determined by combination of NMR, CD, and computational methods, and each of them was shown to be in an atropisomeric relationship. Bisnicalaterines B and C (1 and 2) showed potent vasorelaxant activity on isolated rat aorta.

Three new alkaloids, cassiarins C-E (1-3), and a new chromone, 10,11-dihydroanhydrobarakol (4), which showed moderate antiplasmodial activity against Plasmodium falciparum 3D7, were isolated from flowers of Cassia siamea, and the structures of 1-4 were elucidated by 2D NMR analysis and chemical transformation. Cassiarin D (2) was a dimeric compound consisting of 5-acetonyl-7-hydroxy-2-methylchromone and cassiarin C (1), and cassiarin E (3) was a dimer of cassiarins A and C (1).

Four new chromone alkaloids, chrotacumines A-D (1-4), consisting of a 5,7-dihydroxy-2-methylchromone, an N-Me piperidine ring, and an ester side chain were isolated from Dysoxylum acutangulum, and their structures including absolute configurations were elucidated on the basis of spectroscopic data interpretation including 2D NMR, CD spectra, and X-ray analysis. The known compound rohitukine (5) showed moderate cytotoxicity against human HL-60 promyelocytic leukemia and HCT-116 colon cancer cells.

A novel C(19)N-type Lycopodium alkaloid, malycorin A (1) consisting of a serratinane skeleton with 2-propanol unit has been isolated from the club moss Lycopodium phlegmaria, together with two new C(16)N-type alkaloids, malycorins B (2) and C (3), and the structures and relative stereochemistry were elucidated on the basis of spectroscopic data.

Bioassay-guided purification from the seeds of Peganum harmala led to the isolation of harmine (1), harmaline (2), vasicinone (3), and deoxyvasicinone (4). Harmine (1) and harmaline (2) showed a moderate in vitro antiplasmodial activity against Plasmodium falciparum. Quinazoline alkaloid, vasicinone (3), showed a vasorelaxant activity against phenylephrine-induced contraction of isolated rat aorta.

Three new Lycopodium alkaloids, lycoparins A-C (1-3), have been isolated from the club moss Lycopodium casuarinoides. Structures and stereochemistry of 1-3 were elucidated on the basis of 2D NMR correlations. Lycoparins C (3) exhibited an inhibitory activity against acetylcholinesterase, while lycoparins A (1) and B (2) did not show activity.

Two novel C(27)N(3)-type Lycopodium alkaloids, cryptadines A (1) and B (2) consisting of two octahydroquinoline rings (C(11)N) and a piperidine ring (C(5)N), have been isolated from the club moss Lycopodium cryptomerinum, and their structures and relative stereochemistry were elucidated on the basis of spectroscopic data, chemical transformations, and computational methods. Cryptadines A (1) and B (2) exhibited an inhibitory activity against acetylcholinesterase.

The new Daphniphyllum alkaloids, pordamacrines A (1) and B (2), have been isolated from the leaves of Daphniphyllum macropodum, and their structures were elucidated on the basis of interpretation of spectroscopic data and by the single-crystal X-ray diffraction analysis of 2. Pordamacrines A (1) and B (2) exhibited moderate vasorelaxant effects on the rat aorta.

[structure: see text] A novel C(27)N(3)-type pentacyclic Lycopodium alkaloid, lycoperine A (1) consisting of two octahydroquinoline rings and a piperidine ring, was isolated from the club moss Lycopodium hamiltonii. The structure and relative stereochemistry were elucidated on the basis of 2D NMR data and chemical transformation. Lycoperine A (1) exhibited an inhibitory activity against acetylcholinesterase.

Three new alkaloids, lycopodatines A (1), B (2), and C (3), have been isolated from the club moss Lycopodium inundatum, and the structures and absolute configuration were elucidated on the basis of 2D NMR data and chemical transformation.

[sstructure: see text] A novel, fused-tetracyclic Lycopodium alkaloid, nankakurine A (1), consisting of a cyclohexane ring and a 3-aza-bicyclo[3.3.1]nonane ring connected to a piperidine ring through a spiro carbon, was isolated from the club moss Lycopodium hamiltonii. The structure and relative stereochemistry were elucidated on the basis of spectroscopic data.

A novel C(27)N(3)-type Lycopodium alkaloid consisting of a fastigiatine-type skeleton (C(16)N(2)) and a quinolizidine moiety (C(11)N), himeradine A (1), has been isolated from the club moss Lycopodium chinense, and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.

Research has been conducted on C (sub)27 N (sub)3 -type alkaloid from Lycopodium chinense which consists of fastigiatine-type skeleton and quinolizidine moiety himeradine A. The authors describe the isolation of this compound and the study of its structure and stereochemistry.

Abstract: Eight new indole alkaloids, alpneumines A–H (1–8) were isolated from the Malaysian Alstonia pneumatophora (Apocynaceae) and their structures were determined by MS and 2D NMR spectroscopic methods. Alpneumines E and G (5 and 7), vincamine, and apovincamine showed anti-melanogenesis in B16 mouse melanoma cells. [Copyright &y& Elsevier]

Abstract: Three new picraline-type alkaloids, alstiphyllanines E–G (1–3) and a new ajmaline-type alkaloid, alstiphyllanine H (4) were isolated from the leaves of Alstonia macrophylla together with 16 related alkaloids (5–20). Structures and stereochemistry of 1–4 were fully elucidated and characterized by 2D NMR analysis. Alstiphyllanines E and F (1 and 2) showed moderate Na+-glucose cotransporter (SGLT1 and SGLT2) inhibitory activity. A series of a hydroxy substituted derivatives 21–28 at C-17 of the picraline-type alkaloids have been derived as having potent SGLT inhibitory activity. 10-Methoxy-N(1)-methylburnamine-17-O-veratrate (6) exhibited potent inhibitory activity, suggesting that the presence of an ester side chain at C-17 may be important to show SGLT inhibitory activity. Structure activity relationship of alstiphyllanines on inhibitory activity of SGLT was discussed. [Copyright &y& Elsevier]

Abstract: Three novel C27N3-type Lycopodium alkaloids, lycochinines A–C (1–3) consisting of an octahydroquinoline or a decahydroquinoline, a quinolizidine, and a piperidine, were isolated from the club moss Lycopodium chinense. The relative stereochemistry of 1–3 was determined by a combination of NOESY correlations and chemical transformations. [Copyright &y& Elsevier]

Abstract: Five new alkaloids, alstilobanines A (1)–E (5) were isolated from Alstonia angustiloba (Apocynaceae) and their structures were determined by MS and 2D NMR spectral analysis. Alstilobanines A–E showed a moderate vasorelaxant activity against phenylephrine-induced contraction of isolated rat aorta. [Copyright &y& Elsevier]

Abstract: Two novel C27N3-type Lycopodium alkaloids, cryptadines A (1) and B (2) consisting of two octahydroquinoline rings (C11N) and a piperidine ring (C5N), have been isolated from the club moss Lycopodium cryptomerinum, and their structures and relative stereochemistry were elucidated on the basis of spectroscopic data, chemical transformations, and computational methods. Cryptadines A (1) and B (2) exhibited an inhibitory activity against acetylcholinesterase. [Copyright &y& Elsevier]

Abstract: Three new Lycopodium alkaloids, carinatumins A–C (1–3), have been isolated from the club moss Lycopodium carinatum. Structures and stereochemistry of 1–3 were elucidated on the basis of 2D NMR correlations. Carinatumins A (1) and B (2) exhibited a potent inhibitory activity against acetylcholinesterase. [Copyright &y& Elsevier]

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

Four new C22N2 Lycopodium alkaloids, senepodines B–E (2–5), consisting of an octahydroquinoline ring and a quinolizidine ring have been isolated together with senepodine A (1) from the club moss Lycopodium chinense. The relative and absolute stereochemistry of 2-5 were determined by combination of NOESY correlations and chemical transformation, while the absolute configuration of 1 was assigned by exciton chirality method. [Copyright &y& Elsevier]

Three new alkaloids, lyconesidines A (1), B (2), and C (3), have been isolated from the club moss Lycopodium chinense, and the structures and absolute stereochemistry were elucidated on the basis of 2D NMR data, X-ray analysis, and modified Mosher''s method. [Copyright &y& Elsevier]

[Display omitted] A new trimeric monoterpenoid indole alkaloid, divaricamine A (1) consisting of a vobasine-vobasine-iboga type skeleton, was isolated from the root of Tabernaemontana divaricata. The structure including absolute stereochemistry was elucidated on the basis of 2D NMR data and CD spectrum. Divaricamine A (1) showed potent anti-malarial activity. [ABSTRACT FROM AUTHOR]

Abstract: A novel C16N2-type Lycopodium alkaloid consisting of a quinolizidine with a 6-dimethylaminohexyl side chain, hupermine A (1), was isolated from the club moss of Huperzia phlegmaria, and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data. [Copyright &y& Elsevier]

Abstract: Novel C16N2-type Lycopodium alkaloids consisting of a decahydroquinoline with an aminohexyl side chain, lycobelines A–C (1–3), were isolated from the club moss of Huperzia goebelii, and their structures and relative stereochemistry were elucidated on the basis of spectroscopic data and chemical correlations. [Copyright &y& Elsevier]

Abstract: A novel C20N-type Lycopodium alkaloid with an unprecedented fused-hexacyclic ring system consisting of a γ-lactone, an aza-cycloheptene, an aza-cyclohexane, a cyclohexane, a cyclopentane, and tetrahydrofuran rings, lycotetrastine A (1) was isolated from the club moss of Huperzia tetrasticha. The structure and absolute stereochemistry were elucidated on the basis of 2D NMR correlations and X-ray analysis. [Copyright &y& Elsevier]

Compound (I) exhibits moderate cell growth inhibitory activity. [ABSTRACT FROM AUTHOR]

Structures of three new aspidofractinines (I), (II), and (III), a new aspidospermatan (IV) and a new akuamiline (V) isolated from the roots of Kopsia singapurensis are elucidated. [ABSTRACT FROM AUTHOR]

Abstract: Seven new Lycopodium alkaloids, lannotinidines A–G (1–7), have been isolated from the club moss Lycopodium annotinum and L. annotinum var. acrifolium. Stereochemistry of 1–7 was elucidated by combination of NOESY correlations and chemical transformation. Lannotinidines B–E (2–5) elevated NGF mRNA expression. [Copyright &y& Elsevier]

Four new alkaloids, cassiarin G (I), H (II), J (III) and K (IV), are isolated. [ABSTRACT FROM AUTHOR]

Abstract: Seven new ajmaline type alkaloids, alstiphyllanines I–O (1–7) were isolated from the leaves of Alstonia macrophylla together with six related alkaloids (8–13). Structures and stereochemistry of 1–7 were fully elucidated and characterized by 2D NMR analysis. A series of alstiphyllanines I–O (1–7) as well as the known ajmaline type alkaloids (8–13) showed that they relaxed phenylephrine (PE)-induced contractions against rat aortic ring. Among them, vincamedine (10) showed potent vasorelaxant activity, which may be mediated through inhibition of Ca2+ influx through voltage-dependent Ca2+ channels (VDCs) and/or receptor-operated Ca2+ channels (ROCs) as well as partially mediated the NO release from endothelial cells. The presence of substituents at both N-1 and C-17 may be important to show vasorelaxation activity. [Copyright &y& Elsevier]

isolation and structure elucidation of the new vobasine-iboga type bisindole alkaloid, voacalgine F (I) [ABSTRACT FROM AUTHOR]

The chromone alkaloids, chrotacumines G-J [(Ia)-(Id)] are obtained from the barks of Dysoxylum acutangulum. [ABSTRACT FROM AUTHOR]

Eight new guaipyridine sesquiterpene alkaloids, rupestines F-M, are isolated and their structures and absolute configurations are elucidated. [ABSTRACT FROM AUTHOR]