13C nuclear magnetic resonance spectra of the spirobenzylisoquinoline alkaloids and related model compounds

1977 ◽  
Vol 55 (18) ◽  
pp. 3304-3311 ◽  
Author(s):  
Donald W. Hughes ◽  
Bala C. Nalliah ◽  
Herbert L. Holland ◽  
David B. MacLean
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Isoquinoline Alkaloids ◽  
Model Compounds ◽  
Related Model ◽  
Nuclear Magnetic Resonance Spectra ◽  
13C Nuclear Magnetic Resonance ◽  
C Nmr ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The natural abundance 13C nuclear magnetic resonance spectra of a number of spirobenzylisoquinoline alkaloids and related model compounds have been recorded. The carbon resonances of the alkaloids were assigned by comparison with the spectra of other isoquinoline alkaloids and with those of the model compounds. It has been shown that 13C nmr spectroscopy may be used to differentiate between diastereomers in this series.

scholarly journals 13C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds

1976 ◽  
Vol 54 (14) ◽  
pp. 2252-2260 ◽  
Author(s):  
Donald W. Hughes ◽  
Herbert L. Holland ◽  
David B. MacLean
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Isoquinoline Alkaloids ◽  
Model Compounds ◽  
Related Model ◽  
Nuclear Magnetic Resonance Spectra ◽  
Almost All ◽  
Unambiguous Assignment ◽  
C Nmr ◽  
Magnetic Resonance Spectra

The natural abundance 13C nuclear magnetic resonance spectra of a number of isoquinoline alkaloids and related model compounds have been recorded. In almost all cases comparison of the spectra of the alkaloids with those of the model compounds has permitted unambiguous assignment of the alkaloid carbon resonances. The ability of 13C nmr spectroscopy to distinguish between diastereomeric pairs of both protoberberine and phthalideisoquinoline alkaloids has been demonstrated.

13C nuclear magnetic resonance spectra of some C19-diterpenoid alkaloids and their derivatives

1979 ◽  
Vol 57 (13) ◽  
pp. 1652-1655 ◽  
Author(s):  
S. William Pelletier ◽  
Naresh V. Mody ◽  
Rajinder S. Sawhney
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Conformational Changes ◽  
Nmr Spectra ◽  
Diterpenoid Alkaloids ◽  
Nuclear Magnetic Resonance Spectra ◽  
13C Nuclear Magnetic Resonance ◽  
C Nmr ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The natural abundance carbon-13 nuclear magnetic resonance spectra of some C19-diterpenoid alkaloids and their alkamines (lappaconitine, lappaconine, lapaconidine, ranaconine, 14-dehydrobrowniine, aconine, pseudoaconine, deoxyaconine, and hypaconine) have been determined at 15.03 MHz. With the aid of proton decoupling techniques, additivity relationships, and comparison with spectra of related alkaloids, self-consistent and unambiguous assignments of nearly all carbon resonances for these alkaloids have been made. Some important chemical shift trends have been observed, which are useful for identifying the basic C19-diterpenoid alkaloid skeleton and the hydroxy and methoxy group substitution patterns in these alkaloids. On the basis of 13C nmr spectra of lappaconitine and lappaconine, the anthranoyl ester moiety is assigned to the C-4 position in lappaconitine. The 13C nmr spectra of lapaconidine, aconine, and pseudoaconine taken in pyridine and chloroform have been compared to determine the conformational changes of the ring A hydroxy groups in these alkaloids.

Nuclear magnetic resonance spectra and structures of some C-glycosyl flavonoids

1965 ◽  
Vol 18 (4) ◽  
pp. 531 ◽  
Author(s):  
WE Hillis ◽  
DHS Horn
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Model Compounds ◽  
Related Model ◽  
Nuclear Magnetic Resonance Spectra ◽  
Optical Rotations ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

From an examination of the nuclear magnetic resonance spectra, optical rotations, and other properties of a number of flavonoid C-glycosides, their acetates, and related model compounds, it is concluded that vitexin, bayin, puerarin, and isohemiphloin are C-β-D-glucosides with the sugar substituent in the 8-position of the flavonoid nucleus. Hemiphloin and saponaretin are two of the corresponding 6-substituted compounds. In hemiphloin and isohemiphloin the phenyl B ring has the equatorial configuration.

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