1986
DOI: 10.1016/0039-128x(86)90003-6
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Effects of α- and β-tigogenin cellobiosides on cholesterol absorption

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Cited by 14 publications
(3 citation statements)
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“…Through their earlier work with alfalfa saponins, they recognized the importance of isolating pure saponin components in order to better assess their pharmacological and toxicological properties (20). They prepared the synthetic spirostane saponins, diosgenin glucoside and tigogenin cellobioside, and demonstrated their effects on cholesterol absorption (21) and sterol balance in monkeys (22). Tigogenin cellobioside (tiqueside, CP-88,818) was later shown to decrease TPC concentrations in a variety of animals (23) and in humans (24).…”
mentioning
confidence: 99%
“…Through their earlier work with alfalfa saponins, they recognized the importance of isolating pure saponin components in order to better assess their pharmacological and toxicological properties (20). They prepared the synthetic spirostane saponins, diosgenin glucoside and tigogenin cellobioside, and demonstrated their effects on cholesterol absorption (21) and sterol balance in monkeys (22). Tigogenin cellobioside (tiqueside, CP-88,818) was later shown to decrease TPC concentrations in a variety of animals (23) and in humans (24).…”
mentioning
confidence: 99%
“…Enzymatic hydrolysis of 2 with naringinase gave 1a and d -glucose. The 1 H- and 13 C-NMR signals of the diglycoside moiety, which were assigned based on 1 H- 1 H correlation spectroscopy (COSY) and 1 H-detected heteronuclear multiple coherence (HMQC) spectra, indicated the presence of a terminal β- d -glucopyranosyl unit [δ H 5.20 (d, J = 7.9 Hz, H-1′′ of Glc (II)); δ C 104.9 (CH), 74.8 (CH), 78.2 (CH), 71.5 (CH), 78.4 (CH), 62.3 (CH 2 )] and a C-4 glycosylated β- d -glucopyranosyl unit [δ H 4.87 (d, J = 7.8 Hz, H-1′ of Glc (I)); δ C 106.4 (CH), 75.2 (CH), 76.9 (CH), 81.6 (CH), 76.2 (CH), 62.3 (CH 2 )] in the molecule of 2 [20] . In the HMBC spectrum of 2 , long-range correlations were observed between H-1′′ of Glc (II) and C-3′ of Glc (I), and between H-1′ of Glc (I) and C-3 of the aglycone moiety at δ C 88.7.…”
Section: Resultsmentioning
confidence: 99%
“…Recently, the inhibition of cholesterol absorption by steroid disaccharides has been studied at Pfizer Central Research for the treatment of atherosclerosis. Tiqueside, tigogenyl β- O -cellobioside 1 , which was first described by Rene Malinow et al, reached phase 2 clinical studies. While tiqueside was efficacious and well-tolerated, its relatively weak potency discouraged further development. Structural modification of the steroid nucleus led to the discovery of the more potent pamaqueside, 11-ketotigogenyl β- O -cellobioside 2 .…”
mentioning
confidence: 99%