Constituents of Convallaria. VIII. Structure of Convallagenin-B.

Kimura, Masao; Toma, M.; Yoshizawa, Itsuo

doi:10.1248/cpb.15.1713

Cited by 3 publications

(8 citation statements)

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“…26 ppm evidenced 25S-spirostanol configuration. Compound 6 was found to be 25S-spirostan-1β,3β,4β,5β-tetrol, identical with convallagenin-B (III) isolated from C. keisukei [ 5 ].…”

Section: Resultsmentioning

confidence: 92%

“…The convallasapogenin-A was elucidated as 25S-5β-spirostan-1β,3β,5β-triol [ 5 ], one of the few 25S trihydroxysapogenins, contrary to the 25R series, more frequently isolated from natural plant sources. The tetrols and their hydroxylation pattern are also interesting.…”

Section: Discussionmentioning

confidence: 99%

“…However, no corresponding 25S-5β-spirostan derivative was isolated. Convallagenin-B, isolated by Kimura et al [ 5 ] was the first tetrahydroxy steroidal sapogenin with 25S configuration, and can be regarded as a 25S isomer of kitigenin, 25R-spirostan-1β,3β,4β,5β-tetrol. The 25S-5β-spirostan-1β,3β,4β,5β-tetrol 6 is a new representative of tetrol of the 25S series.…”

Section: Discussionmentioning

confidence: 99%

“…The known compounds are: 5β-25(S)-spirostan-1β,3β,4β,5β-tetrol, (convallagenin B) 6 [ 5 ]; 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol (pentologenin) 7 [ 14 ] and 5β-25(S)-spirostan-1β,2β,3β,4β,5β-pentol (neopentologenin) 8 [ 15 ].…”

Section: Methodsmentioning

confidence: 99%

“…Convallasaponins were isolated from the flowers of C. keisukei [ 4 , 5 , 6 , 7 , 8 , 9 ] and from the roots of C. majalis [ 10 , 11 ]. Tschesche and co-workers isolated convallamaroside, a 22-hydroxyfurostanol saponin with three sugar chains (at C-27, C-3 and C-1); by its partial hydrolysis and cyclization of the side chain, the convallamaronin was formed, of which, the aglycone is convallamarogenin, identified in 1973 as Δ25-5β,20β,22α-spirosten-1β,3β-diol 1 .…”

Section: Introductionmentioning

confidence: 99%

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Spirostanol Sapogenins and Saponins from Convallaria majalis L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling

et al. 2021

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Two new spirostanol sapogenins (5β-spirost-25(27)-en-1β,2β,3β,5β-tetrol 3 and its 25,27-dihydro derivative, (25S)-spirostan-1β,2β,3β,5β-tetrol 4) and four new saponins were isolated from the roots and rhizomes of Convallaria majalis L. together with known sapogenins (isolated from Liliaceae): 5β-spirost-25(27)-en-1β,3β-diol 1, (25S)-spirostan-1β,3β-diol 2, 5β-spirost-25(27)-en-1β,3β,4β,5β-tetrol 5, (25S)-spirostan-1β,3β,4β,5β-tetrol 6, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 7 and (25S)-spirostan-1β,2β,3β,4β,5β-pentol 8. New steroidal saponins were found to be pentahydroxy 5-O-glycosides; 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-O-β-galactopyranoside 9, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-O-β-arabinonoside 11, 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-O-galactoside 10 and 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-O-arabinoside 12 were isolated for the first time. The structures of those compounds were determined by NMR spectroscopy, including 2D COSY, HMBC, HSQC, NOESY, ROESY experiments, theoretical calculations of shielding constants by GIAO DFT, and mass spectrometry (FAB/LSI HR MS). An attempt was made to test biological activity, particularly as potential chemotherapeutic agents, using in silico methods. A set of 12 compounds was docked to the PDB structures of HER2 receptor and tubulin. The results indicated that diols have a higher affinity to the analyzed targets than tetrols and pentols. Two compounds (25S)-spirosten-1β,3β-diol 1 and 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-O-galactoside 9 were selected for further evaluation of biological activity.

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“…26 ppm evidenced 25S-spirostanol configuration. Compound 6 was found to be 25S-spirostan-1β,3β,4β,5β-tetrol, identical with convallagenin-B (III) isolated from C. keisukei [ 5 ].…”

Section: Resultsmentioning

confidence: 92%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%