Studies on the Alkaloids of Formosan Lauraceous Plants. XVII. Alkaloids of Phoebe Formosana Hay. 1

Nine alkaloids have been isolated from the woods and the barks of Phoebe formosana Hayata and four of these have been identified with laurolitsine) (IV), roemerine (V), ushinsunine (VI) and oxoushinsunine (liriodenine) (VII).     

Isoquinoline Alkaloids from Neolitsea Konishii

By combination of centrifugal partition chromatography (CPC) and common separation methods, twelve known bases were isolated and characterized from the first chemical investigation of Neolitsea konishii (H.) K. & S. They belong to isoquinoline alkaloids of four types: eight aporphines, nornuciferine (1), N-methyllaurotetanine (2), laurolitsine (3), boldine (4), laurotetanine (5), isoboldine (6), actinodaphine (7) and corytuberine (8); two proaporphines, stepharine (9) and glaziovine (10); one benzylisoquinoline, reticuline (11); and one morphinan, pallidine (12). Among these, compounds 3, 6 and 11 are abundant and will be modified for pharmacological tests. The content of various alkaloids in the plant is useful as a basis for chemotaxonomy.     

Studies on the Alkaloids of Formosan Lauraceous Plants. XVI.) Alkaloids of Neolitsea Variabillima (Hay.) Kanehira Et Sasaki

Three alkaloids have been isolated from the barks of Neolitsea variabilima (Hay.) Kanehira et Sasaki, and these have been identified with L-hernovine (XIII), L-nandigerine (XIV), and L-N-methylhernovine (XV) respectively.     

Five New β‐Carboline‐Type Alkaloids from Stellaria dichotoma var. lanceolata

Five new β‐carboline‐type alkaloids, dichotomines F–J ( 1 – 5 , resp.), along with nine known compounds, dichotomides I, III, V, and VII ( 6 – 9 , resp.), stellarines A and C ( 10 – 11 , resp.), dichotomine B ( 12 ), glucodichotomine B ( 13 ), and 1‐acetyl‐3‐carboxy‐β‐carboline ( 14 ), were isolated from the roots of Chinese medicinal plant Stellaria dichotoma L. var. lanceolata. Their structures were determined by chemical and spectroscopic means. Compounds 12 and 13 exhibited moderate cytotoxicity.     

Alkaloids from Bulbocodium vernum L. Content material of Liliaceae-Wurmbaeoidaea

From whole plants of Bulbocodium vernum L. the flavone luteoline (I) and the alkaloids colchicine (II), N-formyl-N-deacetylcolchicine (III), 3-demethylcolchicine (V), (+)-bulbocodine (IX) and (?)-kreysigine (XI) were isolated in crystals. The presence of 2-demethylcolchicine (IV), ß- (VII) and γ-lumicolchicine (VIII), demecolcine (VI) and five not identified alkaloids was demonstrated by thin-layer chromatography. On the basis of ultraviolet, infrared and mass spectra, PMR.-analysis (Overhauser effect), and circular dichroism, the (6a-R, 8a-S)homo-proaporphine structure IX, with one methoxy group at C-2, has been assigned to (+)-bulbocodine. The (6a-R)-structure (XI) was deduced for (?)-kreysigine by comparing its optical rotation and circular dichroism which the values of (?)-multifloramine (X), the structure of which is known.     

Two New Aporphine Alkaloids from Litsea glutinosa

Chemical examination of the BuOH extract of the leaves and twigs of Litsea glutinosa collected from Xishuangbanna resulted in the isolation of two new aporphine alkaloids, namely litseglutine A ( 1 ) and B ( 2 ), along with two known aporphine alkaloids, boldine ( 3 ) and laurolitsine ( 4 ). The structures of the new alkaloids have been elucidated on the basis of spectra analysis as 6‐demethyl‐9‐methoxy‐1,2‐(methylenedioxy)aporphin‐10‐ol (=6,7,7a,8‐tetrahydro‐10‐methoxy‐5H‐benzo[g]‐1,3‐benzodioxolo[6,5,4‐de]quinolin‐11‐ol; 1 ) and 1,10,11‐trimethoxyaporphin‐2‐ol (=5,6,6a,7‐tetrahydro‐1,10,11‐trimethoxy‐6‐methyl‐4H‐dibenzo[de,g]quinolin‐2‐ol; 2 ).     

Alkaloids of Aconitum rubricundum

The known alkaloids isolappaconitine (I), 9-deoxylappaconotine (II), lycaconitine (III), puberaconitine (IV), lycoctonine (V), ranaconitine (VI), ajacine (VII), and septentriodine (VII), and an unidentified alkaloid with mp 203–205°C have been isolated from the epigeal part of the Far-Eastern plantAconitum rubricundum. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 403–407, May–June, 1991.     

Über Alkaloide aus Laurelia novae-zelandiae A. CUNN. 5. Mitteilung über natürliche und synthetische Isochinolinderivate

From an extract of Laurelia novae-zelandiae A. CUNN . the aporphine alkaloids (?)-pukateine (I), (?)-pukateine methyl ether (II), (?)-roemerine (IV), (?)-mecambroline (V), (+)-boldine (VII), (+)-isoboldine (VIII), (+)-laurolitsine (IX), and the proaporphine alkaloid (+)-stepharine (X) were isolated. Compounds II and V were up to now not described as natural alkaloids. These and the alkaloids IV, VII, VIII, IX and X are new for L. novae-zelandiae.     

Chemical Constituents from the Roots of Neolitsea hiiranensis

One triterpenoid, taraxerone ( 1 ); four germacrane-type sesquiterpene lactones, linderane ( 2 ), linderalactone ( 6 ), pseudoneolinderane ( 7 ), (+)-linderadine ( 8 ); one sesquiterpene dilactone, pseudoneoliacine ( 10 ); three elemane-type sesquiterpenes, isolinderalactone ( 3 ), compound 4 and sericealactone ( 9 ); one eudesmane type sesquiterpene, cryptomeridol ( 11 ); one glucoside, β-sitosterol-β-D-glucoside ( 12 ) along with β-sitosterol (5) were isolated from the roots of Neolitsea hiiranensis. The structures of these compounds were identified on the basis of spectral properties.     

Additional Isoquinoline Alkaloids from Lltsea Cubeba

By combination of centrifugal partition chromatography (CPC) and common separation methods, seven additional known bases were isolated and characterized from the reinvestigation of L. cubeba besides three previously isolated bases- isocorydine (10), N-methyllaurotetanine (9), and boldine (2). They are laurolitsine (1), laurotetanine (3), isoboldine (4), norisocorydine (5), N-methyllindcarpine (7), isodomesticine (8), and glaziovine (6). Among these, compound 9 is the most abundant (7.5 × 10^?4) and will be modified for pharmacological tests. This work will be of value for chemotaxonomy.     

Studies on the Alkaloids of Formosan Corydalis Species: Part III. Alkaloids of Corydalis Tashiroi Makino

Six alkaloids have been isolated from Corydalis tashirol Makino and four of these were identified as palmatine(I), dl-tetrahydropalmatine(III), I-tetrahydropalmatine(III) and protopine(V).     

New Stephaoxocane Alkaloids from Stephania longa

Three new stephaoxocane‐type alkaloids, stephalonganines A–C ( 1 – 3 ), together with the known eletefine ( 4 ), were isolated from the whole plant of Stephania longa. Their structures were fully characterized spectroscopically, and the absolute configurations of the new alkaloids were assigned by comparison of their circular‐dichroism (CD) data with those of 1,2‐dihydrostephaoxocanine ( 5 ), in combination with 2D‐NMR experiments.     

New Diterpenoid Alkaloids from Aconitum liangshanicum

One new C₁₉‐diterpenoid alkaloid, named liangshantine ( 1 ), and three new C₂₀‐diterpenoid alkaloids, liangshansines A–C ( 2 – 4 , resp.), as well as eight known compounds, were isolated from the roots of Aconitum liangshanicum. The structures of these new alkaloids were elucidated by spectroscopic methods.     

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.     

Studies on the Alkaloids of Lotus Receptacle

From lotus receptacle (seed pod of Nelumbo nucifera Gaertn., four alkaloids, nuciferine (I), N-nornuciferine (VIII), oxoushinsunine (IX) and N-norarmepavine (X) were isolated. Identification of these bases were carried out by their spectral data and direct comparison with authentic samples. It is interesting that oxoushinsunine (IX), a cytotoxic alkaloid shows tumor inhibitory activity against nasopharynx carcinoma reported recently by D. Warthen et al¹³⁾. The biscoclaurine (IV and V) and quaternary water soluble base (VI) only occures in the embryo. Comparison their alkaloids distribution in each part of Formosan lotus was listed in the Table 1.     

Further Alkaloids from the Fruits of Daphniphyllum longeracemosum

Three new Daphniphyllum alkaloids, daphlongeranines C–E ( 1 – 3 ), along with 13 known ones, were isolated from the fruits of Daphniphyllum longeracemosum. Their structures were elucidated on the basis of extensive spectroscopic analyses, especially 2D‐NMR experiments.     

Alkaloids from Fritillaria Hupehensis

Phytochemical investigation of the bulbs of Fritillaria hupehensis resulted in the isolation and structural elucidation of a new highly conjugated alkaloid of veratramine type identified as 3β,23β-dihydroxy-7,12（14）-dien-5α- veratramin-6-one （1）, together with two known alkaloids, ebeinine （2） and zhebeinine （3）, which were isolated for the first time from F. hupehensis. The structures of alkaloids 1-3 were established by extensive 1D and 2D NMR spectral analyses.     

Three New Pregnane Alkaloids from Veratrum taliense

Three new alkaloids, 3‐O‐acetylveralkamine ( 1 ), veralkamine 3‐(β‐D ‐glucopyranoside) ( 2 ), and 6,7‐epoxyverdine ( 3 ), together with five known alkaloids, veramitaline, veralkamine ( 4 ), angeloylzygadenine, veratroylzygadenine, and veramiline 3‐(β‐D ‐glucopyranoside), were isolated from the whole plants of Veratrum taliense. Their structures were elucidated on the basis of spectroscopic analysis, and the NMR data of veralkamine ( 4 ) are given for the first time. In addition, the cytotoxic activities of all isolated compounds, except for veramitaline, were tested.     

Longistylumphyllines A–C,Three New Alkaloids from Daphniphyllum longistylum

Three new alkaloids, longistylumphyllines A–C (1–3), together with the six known alkaloids deoxycalyciphylline B, deoxyisocalyciphylline B, methyl homosecodaphniphyllate, daphnicyclidin A, daphnicyclidin B, and daphnicyclidin F, were isolated from the stems and leaves of Daphniphyllum longistylum. Their structures and relative configuration were elucidated on the basis of spectroscopic data, especially 1D and 2D NMR techniques.     

Monoterpenoid Indole Alkaloids Bearing an N4‐Iridoid from Gelsemium elegans

Five new alkaloids, gelseganines A–D ( 1 – 4 ) and humantenine N₄‐oxide ( 5 ), were isolated from the stems and leaves of Gelsemium elegans. Compounds 1 – 4 represent a rare class of monoterpenoid indole alkaloids that bear an N₄‐iridoid unit. The structures of 1 – 5 were determined by spectroscopic analysis, single‐crystal X‐ray diffraction, and chemical correlation, and their absolute configurations were elucidated by CD analysis. A plausible biogenetic pathway for alkaloids 1 – 5 was also postulated.