Chromatographic Study of the Alkaloids of Aquilegia formosa

Constantine, G.H.; Vitek, M.; Sheth, Kirti; Catalfomo, P.; Sciuchetti, Leo A.

doi:10.1002/jps.2600550926

Cited by 10 publications

(5 citation statements)

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“…In the tribe Thalictreae itself aporphine and protoberberine alkaloids have been established only in a few species of Aquilegia and Isopyrum. This is in contrast to the Thalictrum species where a great variety of isoquinoline alkaloids are biosynthesized (132)(133)(134)(135)(136)(137). ADDENDUM Six additional species have been studied and the following alkaloids were described:…”

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confidence: 88%

“…IX. Two ether bridges-8-7'; 12-13': (127) thalrugosaminine, (128) thal isopine, (129) thalisopidine, (130) O-methylthalisopine, (131) thaligosinine, (132) thaligosine. Aporphine-benzylisoquinolines (133) thalicarpine, (134) thalmelatine, (135) thalictropine, (136) (+)-thalictrogamine, (137) (-f)-pennsylvanine, (138) thalipine, (139) pennsylvanamine, (140) dehydrothalicarpine, (141) thalidoxine**, (142) northalicarpine, (143) revolutopine, (144) thalirevoline, (145) thalilutidine, (146) thalilutine, (147) thalirevolutine, (148) foetidine (fetidine), ( 149) adiantifoline (150) 0desmethyldiantifoline, (151) dehydrothalmelatine, (152) thaliadanine, (153) thalmelatidine, (154) thalmineline.…”

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Chemosystematics of Thalictrum minus Complex

Dutschewska¹,

Kuzmanov²

1982

J. Nat. Prod.

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Twenty-eight native Bulgarian populations of Thalictrum minus complex (Ranunculaceae) show a clear correlation between the cytotype and the type of dimer isoquinoline alkaloids (2n=42 with BBI and 2n=70 with ABI alkaloids). A similar correlation is evident also in the genus Thalictrum L. There are probably different evolutionary lines: in one the biogenesis reaches to the BBI types and in the other to the ABI types.

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confidence: 88%

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Chemosystematics of Thalictrum minus Complex

Dutschewska¹,

Kuzmanov²

1982

J. Nat. Prod.

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“…Ultraviolet absorption spectra of the alkaloid fraction of the control group of A. caerulea showed broad absorbance maxima at 275 and 325 nm in a 1:1.1 ratio. Many alkaloids with an aporphine nucleus such as magnofiorine, glaucine, and boldine display characteristic spectra with roughly equivalent maxima near 270-280 and 300-310 nm whereas some quaternary salts (berberine, for example) absorb near 265 and 345 nm (Pelletier, 1970;Constantine et al, 1966). The identity of the species giving rise to the observed absorptions is currently uncertain.…”

Section: Chemical Antioxidants Fmentioning

confidence: 99%

“…Basic alkaloids have not been unambiguously reported to occur in Aquilegia species; only quarternary salts (berberine, magnofiorine) having an isoquinoline skeleton have been identified (Constantine et al, 1966;Winek, Beal & Cava, 1964). In view of the potent singlet oxygen-quenching activity observed with alkaloids of this class (Larson & Marley, 1984), it seems reasonable to postulate a photochemical (defensive role for the basic alkaloid fraction of Aquilegia species.…”

Section: Chemical Antioxidants Fmentioning

confidence: 99%

Differential responses of alpine and non‐alpine Aquilegia species to increased ultraviolet‐B radiation

Larson

Garrison

Carlson

1990

Plant Cell & Environment

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Two species of columbines, Aquilegia caerulea (which lives in alpine environments) and A. canadensis (a lower-elevation species) responded to artificially increased levels of solar UV-B radiation by becoming significantly shorter and developing a significantly greater number of leaves. The degree of shortening was greater in A. canadensis, the nonalpine species, while the number of leaves increased faster in A. caerulea. Significant differences in gashandling and water-use physiological responses were noted, with UV-B treatment leading to decreased water-use efficiency in both species. Concentrations of flavonoids increased significantly in both species following light exposure, whereas alkaloids in A. caerulea appeared to be destroyed by UV-B. No significant changes occurred in ^-carotene concentrations in either species.

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“…1-Benzyltetrahydroisoquinoline base, reticuline, is the key biological precursor of a large number of alkaloids (27). The quaternary aporphine alkaloid, magnoflorine, showed marked hypotensive activity (28).…”

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The Alkaloids of Thalictrum foliolosum

Bhakuni¹,

Singh²

1982

J. Nat. Prod.

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Trimethylsparsiflorine (1), a new apoiphine alkaloid; known tertiary alkaloids thalicarpine (3), thalidasine (4), thalrugosidine (5) and reticuline (6); and the quaternary alkaloids magnoflorine, berberine and palmatine were isolated from the rhizome of Thalictrum foliolosum DC.Thalictrum foliolosum DC. (Ranunculaceae), a tall perennial herb, is one of the seven species of genus Thalictrum found in India (1). Extracts of the roots of the plant have been used by the natives in many ailments (1,2). The quaternary alkaloids, magnoflorine (3,4), jatrorrhizine (5), berberine (5), and palmatine (5) were isolated earlier from the plant. Thalictrum species have been known to produce a variety of alkaloids of chemical and biological interest (6-11). The alcoholic extract of the leaves, stems, and roots of T. foliolosum exhibited spasmolytic activity in a broad biological screen (12). This activity was concentrated, in the follow up studies, in the alkaloidal fraction of the extract. This prompted us to reinvestigate the alkaloidal constituents of T. foliolosum. The investigation resulted in the isolation of a new aporphine alkaloid, N,0,0-trimethylsparsiflorine (1), two known bisbenzylisoquinoline alkaloids, thalidasine (4) and thalrugosidine (5), one 1-benzylisoquinoline aporphine alkaloid, thalicarpine (3), one 1-benzyltetrahydroisoquinoline alkaloid, reticuline (6), two protoberberine alkaloids, berberine and palmatine and a quaternary aporphine alkaloid, magnoflorine. The tertiary alkaloids (3), ( 4), ( 5) and ( 6) were isolated for the first time from this species, whereas the quaternary alkaloids had been previously isolated from the rhizome of the plant., , -Trimethylsparsiflorine (1) was assigned the molecular formula C20H23O3N on the basis of high resolution mass spectrometry. The ir spectrum of the base (v max. 1600, 1560, 1490, 1360 and 1210 cm-1)in conjunction with its uv spectrum (X max. 216, 274 and 298 nm, no change in alkali) suggested the presence of an aporphine system in the molecule.The nmr spectrum of the base integrated for 23 protons. A signal at 2.30 (s, 3H) was assigned to one N-methyl group. The signals for three aromatic methoxyl groups were at 3.49 (s, 3H), 3.64 (s, 3H) and 4.00 (s, 3H), respectively. In the aromatic region there were four protons. A singlet at 6.32 was assigned to C-3 proton. A double doublet for an ortho and meta coupled proton centered at 6.54 (dd, = 8.0 and /2 = 2.0 Hz) was due to the proton at C-9. A doublet for one proton at 6.86 (d, 7 = 8.0 Hz) was assigned to an ortho coupled proton at C-8. The characteristic low field signal for the C-l 1 proton appeared as a doublet at 7.74 (d, 7 = 2.0 Hz). In the mass spectrum of the base, the molecular ion peak appeared at m/e 325 (M+). Other significant peaks in the mass spectrum were at m/e 324 (M+-1), 310 (M+-15), 294 (M+-31) and 282 (M+-43). The mass fragmentation pattern of the base was that of aporphine alkaloid type (13).The base remained unchanged on treatment with Ac20/pyridine or diazomethane. When refluxed with CH3I, it f...

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Chromatographic Study of the Alkaloids of Aquilegia formosa

Cited by 10 publications

References 4 publications

Chemosystematics of Thalictrum minus Complex

Chemosystematics of Thalictrum minus Complex

Differential responses of alpine and non‐alpine Aquilegia species to increased ultraviolet‐B radiation

The Alkaloids of Thalictrum foliolosum

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