Alkaloids from Daphniphyllum longeracemosum

A new alkaloid, daphnilongeridine ( 1 ), together with six known alkaloids, daphmacropodine ( 2 ), daphmacrine ( 3 ), codaphniphylline ( 4 ), daphniyunnine A ( 5 ), daphniyunnine C ( 6 ), and daphniyunnine E ( 7 ), were isolated from the leaves and stems of Daphniphyllum longeracemosum. The so far elusive configuration at C(25) of daphmacropodine ( 2 ) was assigned on the basis of ROESY correlations.     

New Alkaloids from Daphniphyllum longeracemosum Rosenth.

Two new pentacyclic alkaloids, daphnilongertone ( 1 ) and 11‐hydroxydaphnigracine ( 2 ), together with the known congener dehydrodaphnigracine ( 3 ), were isolated from the fruits of Daphniphyllum longeracemosum. Their structures were elucidated spectroscopically. Compound 3 was isolated for the first time as a natural product.     

Further Daphniphyllum Alkaloids from the Leaves of Daphniphyllum macropodum Miq.

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.     

Three New Alkaloids,Paxiphyllines C – E,from Daphniphyllum paxianum

Nine Daphniphyllum alkaloids, including three new ones, paxiphyllines C–E ( 1 – 3 , resp.), were isolated from the twigs and the leaves of Daphniphyllum paxianum. Paxiphylline C ( 1 ) represents the first example of Daphniphyllum alkaloids with a carbonyldioxy group. Their structures were elucidated on the basis of spectroscopic data.     

Alkaloids from the Twigs and Leaves of Daphniphyllum macropodum

Three new alkaloids, macrodumines A–C ( 1 – 3 , resp.), along with ten known analogs, were isolated from the twigs and leaves of Daphniphyllum macropodum. Their structures were elucidated on the basis of spectroscopic methods. The 11‐OH configuration of the known alkaloid hydroxydaphgraciline ( 4 ) was assigned as α for the first time by comparing the NMR data with those of macrodumine C ( 3 ).     

Alkaloids from the Fruits of Daphniphyllum macropodum

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.     

Alkaloids from Fruits of Daphniphyllum oldhamii

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.     

交让木树皮中的新虎皮楠生物碱的结构研究

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。     

Two New Daphniphyllum Alkaloids from Daphniphyllum calycinum

Two new daphniphyllum alkaloids named 2‐hydroxyyunnandaphnine D ( 1 ) and methyl 7‐hydroxyhomodaphniphyllate ( 2 ), together with eight known alkaloids, daphnioldhanin D, calyciphylline F, calyciphylline B, deoxycalyciphylline B, daphnicyclidin H, macropodumine C, 9,10‐epoxycalycine A, and yunnandaphnine A, were isolated from the stems and leaves of Daphniphyllum calycinum. Their structures and relative configurations were established on the basis of spectral evidence (including 2D‐NMR) and subsequently confirmed by a single‐crystal X‐ray crystallographic diffraction analysis.     

Further Alkaloids from the Leaves of Trigonostemon lii

Four new indole alkaloids, trigonoliimines D–G ( 1 – 4 , resp.), were isolated from Trigonostemon lii. Their structures were elucidated by spectroscopic methods, including extensive 1D‐ and 2D‐NMR experiments.     

Evollionines A–C,Three New Alkaloids Isolated from the Fruits of Evodia rutaecarpa

A phytochemical study of the CHCl₃ extract of the dried unripe fruits of Evodia rutaecarpa (Juss. ) Benth. (Rutaceae) resulted in the isolation of three new alkaloids, evollionines A–C ( 1 – 3 , resp.), together with two known compounds, evodianinine and wuzhuyumide I. The structures of the new compounds were elucidated on the basis of detailed spectroscopic evidence and confirmed in the case of compound 1 by single‐crystal X‐ray analysis.     

Two New Alkaloids from Daphniphyllum angustifolium Hutch.

Daphangustifolines A and B ( 1 and 2 ), two new Daphniphyllum alkaloids were isolated from the whole plant of Daphniphyllum angustifolium Hutch . Their structures were established on the basis of spectroscopic data. Their cytotoxicity against HL‐60, MCF‐7, and A549 cell lines was also evaluated.     

Alkaloids from the Leaves and Stems of Daphniphyllum calycinum

One new alkaloid, named caldaphnidine H ( 1 ), together with eight known ones, daphnioldhanin G ( 2a ), methyl homosecodaphniphyllate ( 3 ), daphnezomine M ( 4 ), daphniyunine A ( 5 ), calyciphylline A ( 6 ), deoxycalyciphylline B ( 7 ), deoxyisocalyciphylline B ( 8 ), and calyciphylline B ( 9 ) was isolated from the leaves and stems of Daphniphyllum calycinum. The structure of 1 was established by spectral methods, especially 2D‐NMR techniques. The structure of daphnioldhanin G ( 2b ) reported previously was revised to 2a mainly by single‐crystal X‐ray diffraction and spectral analysis.     

Yunnandaphninines F and G,New C30 Alkaloids from Daphniphyllum yunnanense

Eight C₃₀ Daphniphyllum alkaloids, including two new ones, yunnandaphninines F and G ( 1 and 2 , resp.), were isolated from the leaves and stems of Daphniphyllum yunnanense. Their structures were elucidated on the basis of the spectroscopic data.     

Five New C19‐Diterpenoid Alkaloids from Aconitum hemsleyanum

Five new C₁₉‐diterpenoid alkaloids, named hemsleyaconitines A–E ( 1 – 5 , resp.), were isolated from Aconitum hemsleyanum Pritz. By UV, IR, MS, 1D‐ and 2D‐NMR analyses, their structures were elucidated as 18‐dehydroxygeniculatine D ( 1 ), 6‐hydroxy‐14‐O‐veratroylneoline ( 2 ), 14‐O‐acetyl‐8‐ethoxysachaconitine ( 3 ), 18‐veratroylkaracoline ( 4 ) and 8‐O‐ethylaustroconitine B ( 5 ).     

Diterpenoid Alkaloids from Delphinium tatsienense

Three new C₂₀‐diterpenoid alkaloids, along with twenty‐two known alkaloids, were isolated from the whole herbs of Delphinium tatsienense. The new alkaloids include a vakognavine‐type C₂₀‐diterpenoid alkaloid, designated as tatsienenseine A ( 1 ), and two hetisine‐type C₂₀‐diterpenoid alkaloids, designated as tatsienenseines B ( 2 ) and C ( 3 ). Their structures were elucidated by IR, HR‐ESI‐MS, 1D‐ and 2D‐NMR analyses.     

Daphnoldines A and B,Two New Yuzurine Alkaloids with a Four‐Ring System,from the Fruits of Daphniphyllum oldhami

Two new yuzurine alkaloids, daphnoldines A ( 1 ) and B ( 2 ), possessing a rare four‐ring system, were isolated from the fruits of Daphniphyllum oldhami. Their structures were established on the basis of extensive spectroscopic analyses. Daphnoldine A ( 1 ) is the first example of Daphniphyllum alkaloids bearing a hydroxymethyl group at C(14).     

New Diterpene Alkaloids from Aconitum sungpanense var. leucanthum

Five new C₁₉ diterpene alkaloids, leucanthumsines A ( 1 ), B ( 2 ), C ( 3 ), D ( 4 ), and E ( 5 ), were isolated from the Chinese medicinal herb Aconitum sungpanense var. leucanthum, together with the known C₁₉ diterpene alkaloids pseudaconine, neoline, 1‐O‐methyldelphisine, crassicaudine, chasmanine, talatisamine, indaconitine, ezochansmanine, and leueantine D. The structures of these new alkaloids were elucidated by HR‐MS and advanced NMR methods, including ¹H‐ and ¹³C‐NMR (DEPT), ¹H,¹H‐COSY, HMQC, and HMBC experiments.     

Three New Sesquiterpene Pyridine Alkaloids from Euonymus fortunei

Three new macrocyclic β‐dihydroagarofuran‐type sesquiterpene pyridine alkaloids, fortuneines A ( 1 ), B ( 2 ), and C ( 3 ), together with the four known alkaloids wilfornine E ( 4 ), aquifoliunine E‐I ( 5 ), euoverrine B ( 6 ), and euojaponine I ( 7 ), were isolated from the aerial parts of Euonymus fortunei. Their structures were elucidated by spectroscopic methods, including HR‐ESI‐MS, ¹H‐ and ¹³C‐NMR, DEPT, ¹H,¹H‐COSY, HSQC, HMBC, and ROESY. This is the first isolation of the above sesquiterpene pyridine alkaloids from this plant, except for compound 6 .