直距翠雀花中的降二萜生物碱

从直距翟雀花（Ｄｅｌｈｉｎｉｕｍ ｏｒｔｈｏｃｅｎｔｒｕｎ Ｆｒａｎｃｈ．）全草的甲醇提取物中分离得到了３个降二萜生物碱,通过ＮＭＲ,ＭＳ等波谱分析将其结构鉴定为７,１０－二羟基８,１、４,１６三甲氧基１９,２０－二去氢乌头烷（７β,８β,１４α,１６β）（１）,２０－乙基－２,３－二去氢－６,１０二羟基－７,８－二氧亚甲菜－１,１４,１６－三甲氧基乌头烷（１α,６β,１４α,１６β）（２）和翼北     

Norditerpenoid alkaloids of Delphinium denudatum as cholinesterase inhibitors

Three new norditerpenoids alkaloids, 1β-hydroxy,14β-acetyl condelphine (1), jadwarine-A (2), jadwarine-B (3) along with two known alkaloids isotalatizidine hydrate (4) and dihydropentagynine (5) were isolated from medicinal plant Delphinium denudatum. The structures of natural products 1–5 were established on the basis of HR-EIMS, ¹H and ¹³C NMR (1D & 2D) spectroscopic data as well as by comparison from literature data. The structures of compound 1 and 4 were also confirmed by single crystal X-ray diffraction studies. In-vitro AChE and BChE enzyme inhibitory activities of compounds 1–5 and molecular docking studies were performed to investigate the possible molecular inhibitory mechanism of the isolated natural products. Compound 2, 4 and 5 showed competitive inhibitory effects by inhibiting AChE and BChE, respectively, while 1 and 3 showed non-competitive inhibition. This work is the first report that provides a supporting evidence about the use of constituents of Delphinium denudatum in cerebral dementia and Alzheimer diseases.     

Norditerpene alkaloids from Delphinium linearilobum and antioxidant activity

From the roots of Delphinium linearilobum (Trautv.) N. Busch two new norditerpene alkaloids linearilobin and linearilin, and the known alkaloids lycoctonine, 14-acetyltalatizamine, browniine, cammaconine, talatizamine, and cochlearenine were isolated. Spectroscopic techniques were used for structure determination. Antioxidant activity was performed by DPPH and metal chelating activity assays.     

Alkaloids from Delphinium pentagynum

Aerial parts of a collection of Delphinium pentagynum Lam. from Niebla, Southern Spain, furnished one diterpene alkaloid, 2-dehydrodeacetylheterophylloidine, two norditerpene alkaloids, 14-demethyl-14-isobutyrylanhweidelphinine and 14-demethyl-14-acetylanhweidelphinine, the known alkaloids 14-deacetylnudicauline, methyllycaconitine, 14-deacetyl-14-isobutyrylnudicauline, 14-acetylbrowniine, browniine, delcosine, lycoctonine, 18-methoxygadesine, neoline, karakoline and the aporphine alkaloid magnoflorine. Structures of the alkaloids were established by MS, 1D and 2-D NMR techniques.     

Dianthramide glucosides from tissue cell cultures of Delphinium staphisagria L

Tissue cell cultures of Delphinium staphisagria L. produced three dianthramide glucosides N-(2'-beta-glucopyranosylsalicyl)-5-hydroxyanthranilic acid methyl ester, N-(2'-beta-glucopyranosyl-5'-methoxysalicyl)-5-hydroxyanthranilic acid methyl ester and N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxy-6-methoxyanthranilic acid methyl ester, together with known methyl esters of N-salicylanthranilic acid and N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid. Structures of the glucosides were established by MS, 1-D and 2-D NMR techniques.     

Diterpenoid alkaloids and flavonoids from Delphinium albocoeruleum Maxim

Ten compounds (1–10) including two C₂₀-diterpenoid alkaloids, five C₁₉-diterpenoid alkaloids, one triterpenoid and two flavonoids were isolated from the whole plant material of Delphinium albocoeruleum Maxim for the first time. The chemotaxonomic significance of these compounds was summarized.     

Norditerpene and diterpene alkaloids from Aconitum variegatum

Aerial parts of Aconitum variegatum L. from the Pyrenees furnished four norditerpene alkaloids, 16 beta-hydroxycardiopetaline, 8-ethoxysachaconitine, 14-acetylgenicunine B, N-deethyl-N-19-didehydrosachaconitine, five diterpene alkaloids 15-veratroyldictizine, 15-veratroyl-17-acetyldictizine, 15-veratroyl-17-acetyl-19-oxodictizine, N-ethyl-1 alpha-hydroxy-17-veratroyldictizine, variegatine and the known alkaloids sachaconitine, 14-O-acetylsachaconitine, karakoline, talatizamine, 10-hydroxytalatizamine, 14-acetyltalatizamine, 14-acetyl-10-hydroxytalatizamine, N-methylarmepavine, pengshenin B, delsoline, dihydrodelsoline, delcosine and genicunin B. Structures of the alkaloids were established by MS, 1D- and 2D-NMR techniques.     

Cytotoxic Alangium alkaloids from Alangium longiflorum

Seven alkaloids (1-7) were isolated from the stem bark of Alangium longiflorum. Compound 1, (-)-10-O-demethylisocephaeline, was isolated for the first time as a naturally occurring product from a plant source. All structures were elucidated by detailed spectroscopic analysis. Biological evaluation showed that 2, 10-O-demethylcephaeline, exhibited potent cytotoxic activity against human lung carcinoma (A549) and breast adenocarcinoma (MCF-7) with ED(50) values of 0.013 and 0.062 microM, respectively. The stereoisomer 1 was less potent than 2, and related compounds with different hydroxy/methoxy substitution patterns were also less potent or inactive. Thus, compound 2 merits attention as a cytotoxic lead for further study.     

Six naphthylisoquinoline alkaloids and a related benzopyranone from a Congolese Ancistrocladus species related to Ancistrocladus congolensis

From the roots of a recently discovered Ancistrocladus taxon, with close affinities to Ancistrocladus congolensis regarding molecular ITS sequence data, six naphthylisoquinoline alkaloids, 5'-O-demethylhamatine (2), 5'-O-demethylhamatinine (3), 6-O-demethylancistroealaine A (4), 6,5'-O,O-didemethylancistroealaine A (5), 5-epi-6-O-methylancistrobertsonine A (6), and 5-epi-4'-O-demethylancistrobertsonine C (7), have been isolated, along with a likewise benzopyranone carboxylic acid, 8. The structural elucidation succeeded by chemical, spectroscopic, and chiroptical methods. Their bioactivities were tested against protozoan parasites causing severe tropical diseases. Furthermore, eight known related alkaloids were identified.     

四川翠雀属三新种

描述了在中国四川发现的毛茛科翠雀属三新种:拟直距翠雀花Delphinium orthocentroides W.T.Wang,宽爪翠雀花D.platyony chinum W.T.Wang和大藏翠雀花D.dazangense W.T.Wang。     

Flavonoid glycosides and isoquinolinone alkaloids from Corydalis bungeana

Two flavonol O-glycosides identified as the 3-O-alpha-arabinopyranosyl(1'-->6')-beta-glucopyranoside 7-O-beta-glucopyranosides of kaempferol and quercetin were isolated from the whole plant of Corydalis bungeana Turcz. together with eight known flavonol O-glycosides. Two isoquinolinone alkaloids were also obtained from the same source, including the new derivative, 6,7-methylenedioxy-2-(6-acetyl-2,3-methylenedioxybenzyl)-1(2H)-isoquinolinone. The structures were determined by spectroscopic methods (NMR and high-resolution MS).     

Insecticidal pyrido[1,2-a]azepine alkaloids and related derivatives from Stemona species

Eight new alkaloids, the pyrido[1,2-a]azepines stemokerrin, methoxystemokerrin-N-oxide, oxystemokerrin, oxystemokerrin-N-oxide, and pyridostemin, along with the pyrrolo[1,2-a]azepines dehydroprotostemonine, oxyprotostemonine, and stemocochinin were isolated from four Stemona species together with the known compounds protostemonine, stemofoline, 2'-hydroxystemofoline, and parvistemonine. Their structures were elucidated by 1H and 13C NMR including 2D methods and two key compounds additionally by X-ray diffraction. Besides the formation of a six membered piperidine ring, additional oxygen bridges and N-oxides contributed to structural diversity. The co-occurrence of pyrrolo- and pyridoazepines suggested biosynthetic connections starting from more widespread protostemonine type precursors. Bioassays with lipophilic crude extracts against Spodoptera littoralis displayed very strong insecticidal activity for the roots of S. curtisii and S. cochinchinensis, moderate activity for S. kerrii, but only weak effects for the unidentified species HG 915. The insect toxicity was mainly caused by the accumulation of stemofoline, oxystemokerrin, and dehydroprotostemonine displaying two different modes of action. Based on the various insecticidal activities of 13 derivatives structure-activity relationships became apparent.     

新疆翠雀属(毛茛科)一新种——文采新翠雀花

报道了产于中国新疆天山的翠雀属(毛茛科)一新种——文采新翠雀花Delphinium neowentsaii C. Y. Yang。该种的叶为肾形,叶柄基部不扩展,花较小,组成稀疏总状花序,花梗被贴伏短柔毛,上萼片的距圆锥状钻形,长13-15 mm,基部宽约3 mm,外面疏被短柔毛,萼片蓝色,与西伯利亚的疏花翠雀花D. laxiflorum DC.很相似,但其花瓣和退化雄蕊均为淡黄色而易于区别。     

Uraline,a New Norditerpenoid Alkaloid from Aerial Parts of <Emphasis Type="Italic">Delphinium uralense</Emphasis> Nevski

Uraline, a new norditerpenoid alkaloid, was isolated from aerial parts of Delphinium uralense. The structure of 1α,7,8-trihydroxy-6β,14α,16β-trimethoxy-18-N-(2-methyl)succinylanthranoyloxyaconane was ascribed to the new compound on the basis of ¹H and ¹³C NMR, IR, and mass spectra. The known alkaloids methyllycaconitine and delcorine were also isolated from the plant.__________Translated from Bioorganicheskaya Khimiya, Vol. 31, No. 4, 2005, pp. 425–429.Original Russian Text Copyright © 2005 by Gabbasov, Tsyrlina, Spirikhin, Danilov, Yunusov.     

Insecticidal sesquiterpene pyridine alkaloids from Euonymus species

Three insecticidal sesquiterpene pyridine alkaloids with a beta-dihydroagarofuran sesquiterpene skeleton, euoverrine A (1), B (2), and euophelline (3), and a known compound, euojaponine C (4), were isolated from the root bark of Euonymus verrucosides, E. fortunei and E. phellomana by bioassay-guided fractionation. Their chemical structures were elucidated mainly by analyses NMR and MS spectral data.     

Secondary and tertiary isoquinoline alkaloids from Xylopia parviflora

From the secondary and tertiary alkaloidal fractions of the root and the bark of Xylopia parviflora (Annonaceae), the isoquinoline alkaloids, 10,11-dihydroxy-1,2-dimethoxynoraporphine and parvinine were isolated, along with 39 known alkaloids. Their structures were determined on the basis of analysis of spectroscopic data.     

Pregnane alkaloids from Pachysandra axillaris

Nine new pregnane alkaloids, pachysamines J-R (1-9), together with seven known ones, were isolated from Pachysandra axillaris. The chemical structures of the new alkaloids were elucidated by spectroscopic methods. All the compounds were evaluated for their inhibitory activities against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 cell lines. Compound 15 possessed moderate activities against A-549, SK-BR-3, and PANC-1 cells, with the IC₅₀ values of 11.17, 4.17, and 10.76 μM, respectively. Besides, compound 11 showed cytotoxicities against A-549 cell, with the IC₅₀ values as 24.94 μM.     

Characterisation of alkaloids from some Australian Stephania (Menispermaceae) species

Chemical investigations of some Stephania species native to Australia and reportedly employed by Aboriginal people as therapeutic agents, are described. The alkaloids from the forest vines Stephania bancroftii F.M. Bailey and S. aculeata F.M. Bailey (Menispermaceae) have been isolated and characterised. The major alkaloids in the tuber of the former species are (-)-tetrahydropalmatine and (-)-stephanine, whereas these are minor components in the leaves, from which a C-7 hydroxylated aporphine has been identified. The major tuber alkaloids in S. aculeata are (+)-laudanidine, and the morphinoid, (-)-amurine, whose absolute stereochemistry has been established by X-ray structural analysis of the methiodide derivative. No significant levels of alkaloids were detected in S. japonica. Complete and unambiguous 1H and 13C NMR data are presented for these alkaloids.     

Absolute configuration of tropane alkaloids from Schizanthus species by vibrational circular dichroism

The absolute configuration (AC) of 6β-hydroxy-3α-senecioyloxytropane (1), 3α-hydroxy-6β-tigloyloxytropane (2), 3α-hydroxy-6β-senecioyloxytropane (3), and 3α-hydroxy-6β-angeloyloxytropane (4) was assigned as (1R,3R,5S,6R) using density functional theory (DFT) calculations at the B3LYP/DGDZVP level of theory in combination with experimental vibrational circular dichroism (VCD) measurements and comparison with the spectra of similar tropanes. The AC of 1 followed from a sample isolated from Schizanthus grahamii, while those of the mixture of 2 and 3, isolated from the same source, were determined by comparing the VCD measurement to a weighted calculation of the individual VCD spectra according to a 69:31 ratio of 2:3 determined by ¹H NMR signal integration. In turn, Schizanthus pinnatus provided a 7:3 mixture of 1:4 whose AC was determined using the experimental VCD absorptions in the 1150-950 cm⁻¹ spectral region which were compared with those observed for 1-3 and with those described for other 3α,6β-tropanediol derivatives.