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1.
Johann Schinnerl Elisabeth Kaltenegger Thomas Pacher Srunya Vajrodaya Otmar Hofer Harald Greger 《Monatshefte für Chemie / Chemical Monthly》2005,136(9):1671-1680
Summary. Three new pyrroloazepine type alkaloids, stichoneurines A and B and 6-hydroxycroomine were isolated from the lipophilic root extracts of Stichoneuron caudatum and Stemona tuberosa collected in Thailand together with the already known croomine, tuberostemonine, and tuberostemonine A. The structures were elucidated by spectroscopic methods including H/H-COSY, HMQC, and HMBC. Information on the relative stereochemistries and conformational behaviour was obtained by analysis of the NOESY spectra. The formation of pyrroloazepine alkaloids in the genus Stichoneuron is reported for the first time and supports its affiliation to the family Stemonaceae. The occurrence of two different types of alkaloids, of the tuberostemonine and croomine series, in different geographical provenances of Stemona tuberosa is of special chemosystematic interest and may contribute to a more natural species delimitation within that complex group. 相似文献
2.
Johann Schinnerl Elisabeth Kaltenegger Thomas Pacher Srunya Vajrodaya Otmar Hofer Harald Greger 《Monatshefte für Chemie / Chemical Monthly》2005,119(Z3):1671-1680
Three new pyrroloazepine type alkaloids, stichoneurines A and B and 6-hydroxycroomine were isolated from the lipophilic root extracts of Stichoneuron caudatum and Stemona tuberosa collected in Thailand together with the already known croomine, tuberostemonine, and tuberostemonine A. The structures were elucidated by spectroscopic methods including H/H-COSY, HMQC, and HMBC. Information on the relative stereochemistries and conformational behaviour was obtained by analysis of the NOESY spectra. The formation of pyrroloazepine alkaloids in the genus Stichoneuron is reported for the first time and supports its affiliation to the family Stemonaceae. The occurrence of two different types of alkaloids, of the tuberostemonine and croomine series, in different geographical provenances of Stemona tuberosa is of special chemosystematic interest and may contribute to a more natural species delimitation within that complex group. 相似文献
3.
Detailed experimental approaches toward the pentacyclic Stemona alkaloids tuberostemonine and didehydrotuberostemonine and the close analogue 13-epituberostemonine are described. The syntheses originate with a hydroindolinone derivative that can be obtained on a large scale in a single step from carbobenzoxy-protected l-tyrosine. Highlights of the conversion of this hydroindolinone to the target structures are the three-fold use of ruthenium catalysts, first in azepine ring-closing metathesis and then in alkene isomerization and cross-metathesis propenyl-vinyl exchange, as well as the stereoselective attachment of a gamma-butyrolactone ring to a tetracycle core structure by use of a lithiated asymmetric bicyclo[3.2.1]octane (ABO) ortho ester. Structural analysis by density functional theory (DFT) methods revealed that the ease of oxidation of the natural product is likely due to the conformational preferences of the pyrrolidine and the fused cyclohexane rings. 相似文献
4.
Rong-Rong Zhang Hai-Yan Tian Yi Wu Xiao-Hui Sun Jian-Long Zhang Zhi-Guo Ma Ren-Wang Jiang 《中国化学快报》2014,25(9):1252-1255
One new stenine-type alkaloid,tuberostemonine D(1),together with five known stenine-type alkaloids(2–6) and two known stemoninine-type alkaloids(7 and 8),were isolated from the roots of Stemona tuberosa.Their structures were elucidated by extensive spectroscopic methods(IR,UV,MS,1D and 2D NMR),and the structure of 1 was further confirmed by X-ray diffraction analysis.First simultaneous isolation of stenine- and stemoninine-type alkaloids not only added a new chemical type and increased the chemical diversity of Stemona tuberosa,but also provided chemotaxonomic clues for the close relationship between genera Stemona and Stichoneuron,and favored retaining them in the same family. 相似文献
5.
Li‐She Gan Xiao‐Ning Wang Cheng‐Qi Fan Yan Wu Jian‐Min Yue 《Helvetica chimica acta》2007,90(12):2395-2400
Seventeen Daphniphyllum alkaloids, including two new pentacyclic alkaloids, yuzuric acid ( 1 ) and daphnezomic acid ( 2 ), and 15 known ones, were isolated from the fruits of Daphniphyllum oldhamii. The structures and configuration of the two new alkaloids were determined on the basis of spectroscopic methods, especially 2D NMR techniques. 相似文献
6.
Two new bis‐alkaloids, flavifloramides A ( 1 ) and B ( 2 ), as well as two known alkaloids, N‐trans‐feruloyltyramine ( 3 ) and paprazine ( 4 ), were isolated from the aerial part of Piper flaviflorum. The structures of the new compounds were elucidated by spectroscopic analyses, including 2D‐NMR techniques. 相似文献
7.
Two unusual nitro-substituted hasubanan-type alkaloids, stephalonines J (1) and K (2), together with ten known alkaloids, protostephanine, dehydrostephanine, (-)-stephanine, (-)-isolaureline, R-roemeroline, (+)-pronuciferine, ( +)-stephafine, ( + )-N-acetylstephafine, ( + )-lirioferine, and ( + )-norlirioferine, were isolated from the whole plant of Stephania longa. Their structures were characterized mainly by spectroscopic methods including IR, MS, and NMR experiments, and the structures of 1 and 2 were further confirmed through chemical correlations with the known alkaloids stephalonines A (1a) and B (2a), respectively. 相似文献
8.
Amaryllidaceae Alkaloids from Lycoris radiata 总被引:1,自引:0,他引:1
Tao Feng Yuan‐Yuan Wang Jia Su Yan Li Xiang‐Hai Cai Xiao‐Dong Luo 《Helvetica chimica acta》2011,94(1):178-183
A phytochemical investigation on bulbs of Lycoris radiata resulted in the isolation of three new Amaryllidaceae alkaloids, named 5,6‐dehydrodihydrolycorine ( 1 ), 6β‐acetoxycrinamine ( 2 ), and (+)‐8‐O‐acetylhomolycorine α‐N‐oxide ( 3 ), together with eleven known alkaloids, 4 – 14 . The structures of the new alkaloids were established by means of spectroscopic methods, and the known compounds were identified by comparison of their data with those in the literature. Compound 2 showed cytotoxicity against HL‐60, A‐549, and MCF‐7 cells, with IC50 values of 8.1, 24.3, and 15.0 μM , respectively. 相似文献
9.
Xiao‐Ning Wang Li‐She Gan Cheng‐Qi Fan Sheng Yin Jian‐Min Yue 《Helvetica chimica acta》2007,90(11):2156-2162
Three new alkaloids, N‐hydroxypaxdaphnine B ( 1 ), 21‐O‐acetylpaxdaphnine B ( 2 ), and methyl 17‐hydroxyhomodaphniphyllate ( 3 ), were isolated from the fresh fruits of Daphniphyllum macropodum, together with six known alkaloids. Their structures were established on the basis of extensive spectroscopic and mass‐spectrometric analyses in combination with chemical transformations. 相似文献
10.
Atta‐ur‐Rahman Zaheer‐ul‐Haq Asaad Khalid Shazia Anjum M.Riaz Khan M.Iqbal Choudhary 《Helvetica chimica acta》2002,85(2):678-688
Phytochemical investigation of Sarcococca saligna by extensive bioassay‐guided fractionation resulted in the isolation of the pregnane‐type steroidal alkaloids 1 – 15 , i.e. of the five new compounds 1 – 5 and the ten known alkaloids 6 – 15 . The structures of the new alkaloids salignenamide C ( 1 ), salignenamide D ( 2 ), 2β‐hydroxyepipachysamine D ( 3 ), salignenamide E ( 4 ), and salignenamide F ( 5 ) were elucidated with the help of modern spectroscopic techniques, while the known alkaloids axillarine C ( 6 ), axillarine F ( 7 ), sarcorine ( 8 ), N3‐demethylsaracodine ( 9 ), saligcinnamide ( 10 ), salignenamide A ( 11 ), vaganine A ( 12 ), axillaridine A ( 13 ), sarsalignone ( 14 ), and sarsalignenone ( 15 ) were identified by comparing their spectral data with those reported earlier. Inhibition of electric‐eel acetylcholinesterase (EC 3.1.1.7) and horse‐serum butyrylcholinesterase (EC 3.1.1.8) by alkaloids 1 – 15 were investigated. These new cholinesterase inhibitors may act as potential leads in the discovery of clinically useful inhibitors for nervous‐system disorders, particularly by reducing memory deficiency in Alzheimer's disease patients by potentiating and effecting the cholinergic transmission process. These compounds were found to inhibit both enzymes in a concentration‐dependent fashion with the IC50 values ranging from 5.21–227.92 μM against acetylcholinesterase and 2.18–38.36 μM against butyrylcholinesterase. 相似文献
11.
Two new alkaloids, sessilifolines A ( 1 ) and B ( 2a ), were isolated from the stems of Stemona sessilifolia, together with three known alkaloids, tuberstemonine ( 3 ), sessilifoliamide A ( 4 ), and stemoninoamide ( 5 ). Their structures were established by mass‐spectrometric and spectroscopic methods, especially 2D‐NMR techniques. 相似文献
12.
Three new ervatamine‐type indole alkaloids, 6‐oxo‐16,20‐episilicine ( 1 ), 16,20‐episilicine ( 2 ), and 6,16‐didehydro‐20‐episilicine ( 6 ), along with seven known alkaloids, were isolated from the whole plants of Ervatamia officinalis. Their structures were elucidated by spectroscopic methods. 相似文献
13.
Zhen‐Yu Li Ping Chen Hong‐Gui Xu Shu‐Ying Peng Yi‐Ming Yang Zhong‐Zhen Zhao Yue‐Wei Guo 《Helvetica chimica acta》2007,90(7):1353-1359
Five new polycyclic Daphniphyllum alkaloids, macropodumines F ( 1 ) and G ( 2 ), 17‐oxoyuzurimine ( 3 ), and macropodumines H ( 4 ) and I ( 5 ), were isolated from the leaves of D. macropodum Miq ., collected in Sichuan Province, China. The structures and relative configurations of the new compounds – as well as of four known, related alkaloids – were elucidated on the basis of in‐depth spectroscopic and mass‐spectrometric analyses, by chemical derivatization, and by comparison of spectroscopic data with those of known compounds. 相似文献
14.
Five minor alkaloids were isolated from the seeds of Camptotheca acuminata Decne. Two of them are new indole alkaloids named camptacumotine (1) and camptacumanine (2) respectively. The others are known indole alkaloids naucleficine (3), angustoline (4) and dihydroisoquinamine (5), which was isolated for the first time from the plant. 相似文献
15.
From the root bark of the apocynacea Hedranthera barteri (Hook. f.) Pichon were isolated the known indole alkaloids vobtusine ( 1 ), voacamine ( 2 ), callichiline ( 3 ), voacangine ( 4 ) and conoflorine ( 5 ), as well as the unknown plant bases amataine, goziline and owerreine, and also beninine and 1, 2-dehydrobeninine. The structures of the two last mentioned alkaloids were shown in an earlier publication to be 6 and 7 , respectively. Amataine, goziline and owerreine are bis-indole alkaloids, which on the basis of their chemical and spectroscopic (especially mass spectroscopic) properties have been assigned the structures 8 , 9 and 10 , respectively. 相似文献
16.
Three new diterpenoid alkaloids, along with eleven known alkaloids, were isolated from the whole herbs of Delphinium yunnanense. The new alkaloids include a rearranged‐type C19‐diterpenoid alkaloid, named yunnanenseine A ( 1 ), and two hetisine‐type C20‐diterpenoid alkaloids, named yunnanenseine B and C ( 2 and 3 , resp.). Their structures were elucidated by detailed NMR‐spectroscopic studies. 相似文献
17.
A new simple carbazole alkaloid, 4‐(7‐hydroxy‐3‐methoxy‐6‐methyl‐9H‐carbazol‐4‐yl)but‐3‐en‐2‐one ( 1 ), and two new dimeric carbazole alkaloids, bisglybomine B ( 2 ) and biscarbalexine A ( 3 ), together with seven known alkaloids, were isolated from the stems of Glycosmis pentaphylla. Their structures were elucidated by spectroscopic methods, especially 2D‐NMR techniques. 相似文献
18.
Xing‐De Wu Lei Wang Juan He Xing‐Yao Li Liao‐Bin Dong Xun Gong Xiu Gao Liu‐Dong Song Yan Li Li‐Yan Peng Qin‐Shi Zhao 《Helvetica chimica acta》2013,96(12):2207-2213
Two new indole alkaloids, 5‐oxodolichantoside ( 1 ) and deglycocadambine ( 2 ), were isolated from the twigs and leaves of Emmenopterys henryi, together with four known indole alkaloids and five known iridoids. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and confirmed by single‐crystal X‐ray diffraction studies. This is the first report on the isolation of indole alkaloids from this species. The indole alkaloids were evaluated for their cytotoxic activities against five human cancer lines. 相似文献
19.
本文报道从虎皮楠科植物交让木的树皮中分到4个新的和7个已知的虎皮楠生物碱的结构研究。4个新生物碱分别命名为脱氧交让木碱(dehydroxymacropodumineA)(1), 4,21-脱乙酰-23-脱甲基-脱氧交让木胺(4,21-deacetyl-23-demethyl-deoxyyuzurimine) (2),7-氧杂--脱氧交让木胺(7-oxo-deoxyyuzurimine)(3),和4-乙酰氧-虎皮楠素B (4-acetoxydaphmanidinB)(4)。新化合物1-4的结构是通过仔细解析其波谱数据和与已知结构相关的化合物波谱数据比较而确定。脱氧交让木碱(dehydroxymacropodumineA)(1) 具有罕见的11元环的大环内酯结构,是从自然界中分到的第二个具有这一新颖结构特征的生物碱。 相似文献
20.
Li‐Gen Lin Pham‐Huu Dien Chun‐Ping Tang Chang‐Qiang Ke Xin‐Zhou Yang Yang Ye 《Helvetica chimica acta》2007,90(11):2167-2175
Phytochemical investigation of the roots of Stemona cochinchinensis led to the isolation and structure elucidation of a new pyrido[1,2‐a]azepine‐type alkaloid, stemocochinamine ( 1 ), and of four new pyrrolo[1,2‐a]azepine‐type alkaloids, bisdehydrostemocochinine ( 2 ), isobisdehydrostemocochinine ( 3 ), neostemocochinine ( 4 ), and isoneostemocochinine ( 5 ), together with six known alkaloids. Their structures were established on the basis of extensive 1D‐ and 2D‐NMR analyses in combination with HR‐MS experiments. 相似文献