The alkaloids and other constituents from the root and stem of Aristolochia elegans

Two new aristolactams, aristolactam E (1) and aristolactam-AIIIa-6-O-beta-D-glucoside (2), three novel benzoyl benzyltetrahydroisoquinoline ether N-oxide alkaloids, aristoquinoline A (3), aristoquinoline B (4), and aristoquinoline C (5), and a new biphenyl ether, aristogin F (6), together with 62 known compounds have been isolated from the root and stem of Aristolochia elegans Mast. The structures of the new natural products were established on the basis of spectral evidence. Some of the isolated compounds were examined for their antioxidative and antityrosinase activities. Occurrence of the isoquinolones, biphenyl ethers, and benzoyl benzyltetrahydroisoquinoline ether alkaloids in the same plant indicated the definite possibility of these metabolites as biotransformation intermediates of bisbenzyltetrahydroisoquinoline alkaloids. This can be useful to solve the catabolic process of bisbenzyltetrahydroisoquinoline alkaloids.     

Indole alkaloids from the leaves of Philippine Alstonia scholaris

The first seco-uleine alkaloids, manilamine (1) (18-hydroxy-19,20-dehydro-7,21-seco-uleine) and N4-methyl angustilobine B (2), were isolated from the (pH 5) alkaloid extract of Philippine Alstonia scholaris leaves together with the known indole alkaloids 19,20-(E)-vallesamine (3), angustilobine B N4-oxide (4), 20(S)-tubotaiwine (5), and 6,7-seco-angustilobine B (6). The structure of the alkaloids was established from MS and NMR experiments.     

Structures of Sarcorucinine D and Pachyaximine A,B

In this paper, three new alkaloids, sarcorucinine D (1), and paehyaximine A, B (2, 3) were isolated from Sarcococca ruscifolia Stapf and Pachysandra axillaris Franch, respectively. The structures of sarcorucinine D (1) and pachyaximine A, B (2, 3) were elucidated to be 3β-hydroxyl-20α-dimethylamino-5α-pregnane (1); and 3β-methoxyl-20α-dimethylamino-pregne-5-ne (2); and 3β-methoxyl-16-hydroxyl-20α-dimethylaminopregne-5-ne (16-hydroxyl-pachyaxi- mine A) (3), respectively.     

Secophnane-type alkaloids from Daphniphyllum oldhami

Four new alkaloids, daphnioldhanins D-G (1-4, resp.), together with five known alkaloids, daphmacropodine (5), secodaphniphylline (6), deoxycalyciphylline B (7), deoxyisocalyciphylline B (8), and daphmanidin A (9), were isolated from the roots of Daphniphyllum oldhami. Their structures were elucidated on the basis of spectroscopic data and chemical methods. Compound 1 at 2.0 microM showed potent antioxidant activity against H(2)O(2)-induced impairment in PC12 cells.     

A Study on the Alkaloidal Components from Delphinium gyalanura Marq. et Shaw

From the roots of Delphinium gyalanum Marq. et Shaw native to China, a pair of new regioisomeric diterpenoid alkaloids as a mixture, named gyalanine A and B, was isolated whose structures were shown to be 4 and 5, respectively, on the basis of spectral data. The known diterpenoid alkaloids, delsemine A(1) and B(2), methyllycaconitine (3) and lycoctonine, were also obtained.     

5',6'-dehydroguiachrysine and 5',6'-dehydroguiaflavine, two curarizing quaternary indole alkaloids from the stem bark of Strychnos guianensis

Two new quaternary indole alkaloids 5',6'-dehydroguiachrysine (1) and 5',6'-dehydroguiaflavine (2) were isolated from Strychnos guianensis stem bark. Their structures were determined by analysis of spectral data. Their inhibitory effects on neuromuscular transmission are also reported and compared to that of other quaternary alkaloids.     

Melohenryines A and B,two new indole alkaloids from Melodinus henryi

Two new monoterpenoid indole alkaloids, melohenryines A and B (1 and 2), along with six known indole alkaloids, were isolated from the twigs and leaves of Melodinus henryi. Structures of the new alkaloids were established by extensive spectroscopic techniques including NMR spectroscopy and mass spectrometry. Melohenryine A (1) represents the first example of monoterpenoid indole alkaloids characterized an ester carbonyl group at C-19 position. All of the new compounds were evaluated for in vitro cytotoxicity against several human cancer cell lines.     

Lyconadins D and E, and complanadine E, new Lycopodium alkaloids from Lycopodium complanatum

Three new Lycopodium alkaloids, lyconadins D (1) and E (2), and complanadine E (3), were isolated from the club moss Lycopodium complanatum. Lyconadin D (1) was the first example of fastigiatine-type alkaloid isolated from Lycopodium complanatum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Complanadine E (3) enhanced mRNA expression for NGF.     

Two New Diterpenoid Alkaloids from Spiraea japonica L.f.var. Fortunei (Planchon) Rehd.

Two new hetisine-type C20-diterpenoid alkaloids named spiraqine (1) and 6-hydroxylspiraqine (2), and four known alkaloids, namely spiredine (3), spiradine A (4), spiradine B (5), and spirasine Ⅴ/Ⅵ (6),were isolated from Spiraea japonica L. f. var. fortunei (Planchon) Rehd. The structures of the alkaloids were elucidated using nuclear magnetic resonance analysis (1H-NMR, 13C-NMR, DEPT, HMQC, and HMBC) and mass spectrometry data.     

Nematicidal alkaloids and related compounds produced by the fungus Penicillium cf. simplicissimum

A new nematicidal alkaloid, peniprequinolone (1), together with the known alkaloids penigequinolones A and B (2a, 2b), 3-methoxy-4-hydroxy-4-(4'-methoxyphenyl)quinolinone (3), and 3-methoxy-4,6-dihydroxy-4-(4'-methoxyphenyl)quinolinone (4), were isolated from Penicillium cf. simplicissimum (Oudemans) Thom. Cyclopenin (5) and a compound (6a/6b) structurally related to cyclopenin also were isolated from the fungus, and their structures were established by spectroscopic analysis. The biological activities of 1, 2, 3, 4, and 5 were examined by a bioassay with root-lesion nematodes.     

Alpneumines A–H,new anti-melanogenic indole alkaloids from Alstonia pneumatophora

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.     

Carinatumins A-C, new alkaloids from Lycopodium carinatum inhibiting acetylcholinesterase

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.     

Alkaloids from Portulaca oleracea L

Five alkaloids (oleraceins A, B, C, D and E) were isolated from Portulaca oleracea L., and their structures determined by spectroscopic methods as 5-hydroxy-1-p-coumaric acyl-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside, 5-hydroxy-1-ferulic acyl-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside, 5-hydroxy-1-(p-coumaric acyl-7'-O-beta-D-glucopyranose)-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside, 5-hydroxy-1-(ferulic acyl-7'-O-beta-D-glucopyranose)-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside and 8,9-dihydroxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one, respectively.     

Two new imidazolone-containing alkaloids and further metabolites from the ascomycete fungus Tricladium sp

Tricladins A and B (1 and 2, resp.), new imidazolone-containing alkaloids, together with five known metabolites, bacillamides A, B (3 and 4, resp.), 20-hydroxyaflavinine (5), N-(2-phenylethyl)acetamide (6), and N(b)-acetyltryptamine (7), have been isolated from the crude extract of the ascomycete fungus Tricladium sp. The structures of 1 and 2 were elucidated primarily by NMR and MS methods. Compound 2 showed marginal cytotoxicity against MDA-MB-231 human breast cancer cells, whereas the known metabolite 4 displayed an inhibitory effect on HIV-1 replication in C8166 cells.     

Lycoparins A-C, new alkaloids from Lycopodium casuarinoides inhibiting acetylcholinesterase

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.     

Five new diterpenoid alkaloids from Aconitum sczukinii Turcz.

Ten diterpenoid alkaloids, including five new ones, sczukiniline A–E (1-5), were isolated from the root of Aconitum sczukinii. Their structures were elucidated based on the interpretation of spectroscopic data (HRESI-MS, IR, 1D- and 2D-NMR). Among the five new diterpenoid alkaloids, 1-3 are hetidine-type C₂₀-diterpenoid alkaloids, while compounds 4 and 5 are lycoctonine-type C₁₉-diterpenoid alkaloids. Noteworthily, sczukiniline A (1) features a novel ester group between C-12 and C-14, forming a D ring containing a lactone structure, resulting in a new skeleton of hetidine-type C₂₀-diterpenoid alkaloid.     

长序虎皮楠果实中的一个新的生物碱（英文）

从长序虎皮楠（Daphniphyllum longeracemosum）果实的甲醇提取物中分离得到一个新的虎皮楠生物碱和三个已知的环烯醚萜苷型虎皮楠生物碱。通过现代波谱解析技术鉴定为daphlongeranine F（1）,caldaphnidine F（2）,daphcalycinosidine B（3）and daphcalycinosidine C（4）。其中,三个环烯醚萜苷虎皮楠生物碱系首次从该种分离得到。     

Alstilobanines A-E, new indole alkaloids from Alstonia angustiloba

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.     

Two New Diterpenoid Alkaloids from Spiraea japonica L. f. var.fortunei （Planchon） Rehd.

Two new hetisine-type C20-diterpenoid alkaloids named spiraqine (1) and 6-hydroxylspiraqine (2), and four known alkaloids, namely spiredine (3), spiradine A (4), spiradine B (5), and spirasine V/VI (6),were isolated from Spiraea japonica L. f. var.fortunei (Planchon) Rehd. The structures of the alkaloids were elucidated using nuclear magnetic resonance analysis (1H-NMR, ^13C-NMR, DEPT, HMQC, and HMBC) and mass spectrometry data.     

Tropane alkaloids from Erythroxylum zeylanicum O.E. Schulz (Erythroxylaceae)

Six tropane alkaloids were isolated from the Sri Lankan endemic plant Erythroxylum zeylanicum O.E. Schulz (Erythroxylaceae) and structurally elucidated by NMR and MS measurements. Three of them, erythrozeylanines A [1R,3R,5S,6R-6-acetoxy-3-(3',4',5'-trimethoxybenzoyloxy)tropane], B [cis-3 beta-(cinnamoyloxy)tropane], and C [cis-6 beta-acetoxy-3 alpha-(cinnamoyloxy)tropane] are new, whereas the others have already been found in other Erythroxylum species. For the first time, the absolute configuration of a tropane alkaloid (erythrozeylanine A) has been determined by quantum chemical CD calculations.