30343-72-7Relevant articles and documents
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LaLonde,R.T. et al.
, p. 4477 - 4480 (1970)
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LaLonde et al.
, p. 6342,6345, 6346, 6348 (1973)
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Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids
Korotkov, Alexander,Li, Hui,Chapman, Charles W.,Xue, Haoran,Macmillan, John B.,Eastman, Alan,Wu, Jimmy
, p. 10604 - 10607 (2015/09/02)
Herein, we describe the first total syntheses of five members of the dimeric nuphar alkaloids: (+)-6,6′-dihydroxythiobinupharidine (+)-1a, (+)-6-hydroxythiobinupharidine (+)-1-b, (-)-6,6′-dihydroxythionuphlutine (-)-2-a, (-)-6,6′-dihydroxyneothiobinupharidine (-)-3a, and (+)-6,6′-dihydroxyneothionuphlutine (+)-4-a. The latter two have not been found in nature. We have also made each of their enantiomers (-)-1a-b, (+)-2a, (+)-3a, and (-)-4a. The key step in these syntheses was the dimerization of an α-aminonitrile (a hydrolytically stable surrogate for its corresponding hemiaminal) with chiral Lewis acid complexes. We have also reassigned the literature structures of (+)-1-a-1b - for those instances in which the NMR spectra were obtained in CD3OD - to their corresponding CD3O-adducts. Our efforts provide for the first time apoptosis data for (-)-3a, (+)-4a, and all five non-natural enantiomers prepared. The data indicate high apoptotic activity regardless of the enantiomer or relative stereochemical configuration at C7 and C7′. Nuphars are speedy killers: For the first time several of the hydroxylated dimeric nuphar alkaloids and their unnatural enantiomers have been synthesized. First-ever apoptosis data for many of these compounds is provided.
Crude drugs from aquatic plants. VI. On the alkaloid constituents of Chinese Nupharis Rhizoma, the dried rhizoma of Nuphar pumilum (TIMM.) DC. (Nymphaceae) : Structures and rearrangement reaction of thiohemiaminal type nuphar alkaloids
Yoshikawa, Masayuki,Murakami, Toshiyuki,Wakao, Shuji,Ishikado, Atsushi,Murakami, Nobutoshi,Yamahara, Johji,Matsuda, Hisashi
, p. 1815 - 1824 (2007/10/03)
From Chinese Nupharis Rhizoma, the dried rhizoma of Nuphar pumilum (TIMM.) DC. (Nymphaceae), four thiohemiaminal type nuphar alkaloids with potent immuno-suppressive activity, 6-hydroxythiobinupharidine, 6,6′-dihydroxythiobinupharidine, 6-hydroxythionuphlutine B, 6′-hydroxythionuphlutine B, have been isolated together with nine inactive nuphar alkaloids. The configurations of the 6- and 6′-hydroxyl groups in those thiohemiaminal type nuphar alkaloids were confirmed on the basis of their 2D-NMR analysis. During the course of chemical elucidation of those thiaspirane type dimeric sesquiterpene alkaloids, new rearrangement reaction of the thiaspirane ring in thiohemiaminal type alkaloids with 6-hydroxyl group was found and the reaction pathway was discussed. By using this rearrangement reaction, 6-hydroxythionuphlutine B was chemically related with 6-hydroxythiobinupharidine, so that the absolute stereostructures of thionuphlutine B and its related compounds such as 6-hydroxythionuphlutine B, 6′-hydroxythionuphlutine B, and thionuphlutine B β-sulfoxide, were characterized.
