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.     

Sorellin und Hobartin,zwei neue Indolalkaloide aus Aristotelia peduncularis (LABILL.) HOOK. F. 173. Mitteilung über organische Naturstoffe

Sorelline and Hobartine, Two New Indole Alkaloids from Aristotelia peduncularis (LABILL .) HOOK . F. From Aristotelia peduncularis (LABILL .) HOOK . F. two new indole alkaloids, sorelline ( 1 ) and hobartine ( 2 ), have been isolated. Their structures were elucidated on the basis of spectroscopic data (the formulae represent their relative configurations). The alkaloids 1 and 2 have closely related structures with a monosubstituted indole moiety and an unrearranged monoterpene unit in the aliphatic part.     

粪箕笃中两个新颖的含硝基莲花氏烷型生物碱

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.     

Two New Bis‐alkaloids from the Aerial Part of Piper flaviflorum

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.     

Two New Cytotoxic Alkaloids from Mappianthus iodoides Hand.‐Mazz.

Two new alkaloids, mappine A ( 1 ) and mapposidic acid ( 2 ), together with eleven known compounds, were isolated from the stems of Mappianthus iodoides Hand.‐Mazz. Their structures were elucidated by means of spectroscopic and mass‐spectrometric analyses, particularly 1D‐ and 2D‐NMR spectroscopy. The cytotoxic activities of the two new alkaloids were also evaluated.     

Die Isolierung weiterer Alkaloide aus Pleiocarba talbotii WERNHAM. 150. Mitteilung über Alkaloide

From the leaves of the Apocynaceae Pleiocarpa talbotii WERNHAM three new indole alkaloids were isolated and identified as 3,4,5,6-tetradehydrotalbotine ( 2 ), 5,6-dehydrotalbotine ( 3 ) and deformyl talbotinic acid methylester ( 4 ). From the stem bark of the same plant normacusine B (tombozine) was isolated.     

N(a)-Demethylseredamin,ein neues Alkaloid aus Rauwolfia sumatrana; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide

From Rauwolfia sumatrana Jack (Apocynaceae) the two new indole alkaloids serpentinine and N_(a)-demethylseredamine were isolated. By chemical and spectroscopic evidence and by correlation experiments the latter was shown to have structure 2 . the exact position of the aromatic methoxyl group was established by an investigation of the brominated derivative 12 . The aromatic ORD. Cotton effect of N_(a)-acetyl-N_(a)-demethyl-seredamine ( 5 ) and its O-acetyl derivative 4 as well as the ketone Cotton effect of purpeline ( 9 ) suggest that all the alkaloids of the seredamine group have the same absolute stereochemistry as ajmaline ( 1 ). This was confirmed by a direct chemical correlation of seredamine ( 7 ) with ajmaline.     

Alkaloide aus Evonymus europaea L.

From the seeds of Evonymus europaea L. (Celastraceae) the three previously described alkaloids A, B and C were isolated and their empirical formulae determined by mass spectrometry. Alkaloid B, now named evozine, C₃₂H₃₉NO₁₅ ( 14 ), alkaloid A, now named evorine, C₃₄H₄₁NO₁₆ ( 15 ), and alkaloid C, shown to be identical with Parter's & Libiseller's evonine, C₃₆H₄₃NO₁₇ ( 17 ), are respectively tri-, tetra-, and penta-O-acetyl derivatives of deacetylevonine ( 13 ), C₂₆H₃₃NO₁₂. Vigorous alkaline hydrolysis of the latter yields the previously known evonic acid ( 3 ). Deacetylevonine ( 13 ) is an ester of evonic acid ( 3 ) and a hypothetical polyhydroxy compound C₁₅H₂₄O₁₀ ( 2 ), which is unstable on alkaline hydrolysis. By partial saponification and partial acetylation, these three alkaloids can be converted into each other, at the same time giving rise to a fourth alkaloid D ( 16 ), C₃₄H₄₁NO₁₆, which we name iso-evorine. This had been obtained already by M. Osowiecki (unpublished).     

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.     

Lycopodium Alkaloids from Lycopodium obscurum L.

Two new Lycopodium alkaloids, named obscurumines F and G ( 1 and 2 , resp.), together with eleven known alkaloids, were isolated from the club moss Lycopodium obscurum L. Their structures were elucidated on the basis of spectroscopic analyses.     

Lokalisierung der Ketogruppe in Inandenin-onen. 160. Mitteilung über Alkaloide

Localization of the keto group in Inandenin-ones . By Schmidt degradation of the spermidine alkaloids inandenine-12-on ( 1 ) and inandenine-13-on ( 2 ) from Oncinotis inandensis followed by hydrolysis, acetylation and esterification four different types of products were obtained: the dicarboxylic diesters 9 and 10 , the ω-amino-carboxylic esters 11 and 12 , the acetylated polyamines 14 and 15 , and the acetylated triaminecarboxylic esters 16 and 17 . By GLC. and mass spectral analysis of these degradation products, and by comparison with synthetic compounds it was possible to confirm the structures 1 and 2 . The same alkaloid mixture ( 1+2 ) was obtained from the leaves of Oncinotis nitida BENTH .     

Nachweis von Desacetylakuammilin und 10-Methoxy-desacetylakuammilin in Vinca minor L. 147. Mitteilung über Alkaloide

The two indole alkaloids desacetylakuammiline ( 2 ) and 10-methoxy-desacetylakuammiline ( 4 ) were shown to occure in the upper parts of the small periwinkel Vinca minor L. The structure of the hitherto unknown 10-methoxy-desacetylakuammiline was established on the bases of chemical, spectroscopic and o.r.d. evidence.     

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。     

Alkaloids from the Roots of Stemona tuberosa

Four new alkaloids, didehydrotuberostemonine A ( 1 ), stemoninone ( 2 ), tuberostemospiroline ( 3 ), and tuberostemonine L ( 4 ), together with seven known alkaloids, were isolated from the roots of Stemona tuberosa. Their structures were elucidated on the basis of spectroscopic analysis. The known alkaloids were identified as 2‐oxostenine ( 5 ), tuberostemonine ( 6 ), sessilifoliamide H ( 7 ), tuberostemonone ( 8 ), didehydrotuberostemonine ( 9 ), bisdehydrostemoninine ( 10 ), and tuberostemoamide ( 11 ).     

New Diterpenoid Alkaloids from Aconitum recemulosum Franch.

Two new diterpenoid alkaloids, racemulosines A ( 1 ) and B ( 2 ), were isolated from the roots of Aconitum racemulosum Franch . The structures of the new alkaloids were elucidated by analysis of physical and spectroscopic data, and the structure of 1 was further confirmed by a single‐crystal X‐ray diffraction analysis. Furthermore, compound 1 , at 2.25?10^?4 mol/l, showed moderate activity against platelet aggregation induced by PAF (platelet‐activation factor).     

Über die Struktur der makrocyclischen Spermidin-Alkaloide Oncinotin,Neooncinotin und Isooncinotin. 151. Mitteilung über Alkaloide

Three spermidine alkaloids – oncinotine ( 1 ), neooncinotine ( 3 ), and isooncinotine ( 2 ) – have been isolated from the stem bark of Oncinotis nitida BENTH . (Scheme 1); 1 and 3 are so far an unseparable mixture. However, by treatment of this mixture with K-t-butoxide, neooncinotine is completely converted into isooncinotine, and oncinotine, the main alkaloid, is obtained in pure form. The structural assigment of these alkaloids is based on chemical and spectral evidence. Thus oncinotine ( 1 ) has been degraded via 24 (Scheme 4) and 32 to the putrescine derivative 35 and the piperidine derivative 34 (Scheme 5). Similarly neooncinotine ( 3 ) and isooncinotine ( 2 ), have given 34 along with the 1, 3-diaminopropane derivative 36 (Scheme 5). The major decomposition pathways of 24 , 35 and 36 in the mass spectra are described in Schemes 8, 6 and 7 respectively. The absolute configuration of 1 , 2 and 3 is derived by chiroptical correlations with (R)-(?)-N-methylconiine ( 38 ).     

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).     

Novel Alkaloids from Stemona sessilifolia

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.     

Steroidal Alkaloids from Veratrum dahuricum (Turcz.) Loes. f. with Genotoxicity on Brain Cell DNA in Mice

Two new steroidal alkaloids, 2β‐hydroxyverdine ( 1 ) and tomatillidine 3‐O‐β‐D ‐glucopyranoside ( 2 ), were isolated from the root and rhizome of Veratrum dahuricum (Turcz .) Loes . f., together with four known compounds, i.e., 16‐O‐(2‐methylbutyroyl)germine ( 3 ), veramitaline ( 4 ), jervine ( 5 ), and veratroylzygadenine ( 6 ). Their structures were established by extensive spectroscopic analysis, as well as by comparison with data in literature. Compounds 1 – 6 exhibited genotoxicity on brain cell DNA of the cerebellum and cerebral cortex in mice, evaluated by using single‐cell gel electrophoresis (comet assay).     

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.