Studies on the constituents of Aspidistra elatior Blume. II. On the steroidal glycosides of the leaves.

Konishi, Tenji; Kiyosawa, Shu; Shoji, Jun

doi:10.1248/cpb.32.1451

Cited by 19 publications

(9 citation statements)

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“…[5][6][7][8][9] During the year 1955-1994, Japanese scholars reported some steroidal sapogenins and steroidal saponins from this plant. [10][11][12][13] The steroidal constituents from the underground parts of R. carnea exhibited inhibitory activity on cAMP phosphodiesterase and a potent inhibitor, showing almost equal IC 50 values compared to papaverine, was isolated.…”

Section: Regular Articlementioning

confidence: 99%

Three Steroids with Unique Structural Feature of 5.BETA.-Spirostan-1.BETA.,3.BETA.,17.ALPHA.-trihydroxyl from Reineckia carnea

Zhang

Chen

Jian

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleReineckia carnea (ANDR.) KUNTH belongs to the family Liliaceae, it is the only species of the genus Reineckia and indigenous to China and Japan.1) As a perennial ever-green herb, it can grow well on soils polluted by heavy metals and can produce a repairing effect on the soil that was polluted by copper.2) The Chinese name "ji xiang cao" means it can bring luck and fortune to people, especially when it was cultivated as ornamental plant and flowers. The whole plant has been used as an antitussive, an antarthritic, a hemostatic, and an antitode in traditional Chinese medicine.3) It is one of the most important ingredients of many medical prescriptions of Miao Minority in China and has been successfully developed into a medicine to treat cough and sore throats.4) The genus Reineckia is taxonomically close to Rohdea, Tupistra, Convallaria, Aspidistra, Liriope and Ophiopogon, and their chemical constituents are characterised by steroidal saponins with polyhydroxylated skeletons. [5][6][7][8][9] During the year 1955-1994, Japanese scholars reported some steroidal sapogenins and steroidal saponins from this plant. [10][11][12][13] The steroidal constituents from the underground parts of R. carnea exhibited inhibitory activity on cAMP phosphodiesterase and a potent inhibitor, showing almost equal IC 50 values compared to papaverine, was isolated.13) Formerly, we reported three spirostanol steroids from R. carnea:14) now, the 17a-OH derivatives of the three spirostanol steroids, corresponding to 25(S)-5b-spirostan-1b,3b,17a-triol (1), 25(S)-5b-spirostan-1b,3b,17a-were isolated from this plant. Compounds 1, 2, and 3 are the first naturally occurring steroids possessing unique structural feature of 5b-spirostan-1b,3b,17a-trihydroxyl. This paper describes the isolation and structural elucidation of these new compounds based on spectroscopic data and chemical transformation.Compound 1 C-NMR and distortionless enhancement by polarization transfer (DEPT) spectrum of 1 showed a quaternary carbon signal at d 110.6, which is the characteristic C-22 of a spirostanol skeleton. 17) On comparison between the 13 C-NMR spectrum of 1 with that of rhodeasapogenin [25(S)-5b-spirostan-1b,3b-diol], 14,18) the signal due to the C-17 carbon, which was observed at d 63.1 (CH) in rhodeasapogenin, appeared at d 89.6 as a quaternary carbon signal, accompanied by downfield shifts of the signals due to C-13 (ϩ5.5 ppm), C-16 (ϩ9.6 ppm), and C-20 (ϩ2.7 ppm) and upfield shifts of signals due to C-12 (Ϫ10.4 ppm), C-14 (Ϫ3.5 ppm), and C-21 (Ϫ5.9 ppm); in addition, the molecu-

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Section: Regular Articlementioning

confidence: 99%

Three Steroids with Unique Structural Feature of 5.BETA.-Spirostan-1.BETA.,3.BETA.,17.ALPHA.-trihydroxyl from Reineckia carnea

Zhang

Chen

Jian

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The glycoside, neopentologenin 5- O -β-glucopyranoside had been isolated from Rhodea japonica (THUNB.) ROTH and Apidistra elatior BLUME [ 15 ]. This is the first report on the isolation and structural characterization of 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 7 (neopentologenin) and their glycosides, 5- O -β-galactoside 9 and 5- O -β-arabinonoside 11 , from Convallaria majalis .…”

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%

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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“…Aspidistra elatior is notable as the first member of the Liliaceae to yield a steroidal magnesium sulphate monohydroxideas its pentahydroxyfurostanol glycoside, with the sulphate group not on a sugar but on the nucleus (8). The magnesium compound (17) was isolated via ion exchange resin and so the metal of the natural compound was not identified.…”

Section: -Glucmentioning

confidence: 99%

Recent Developments in our Knowledge of Steroids¹

Hardman¹

1987

Planta Med

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Annually, the American Chemical Abstracts has some 3000 references to plant steroids or related compounds. This is a review of 34 selected papers mainly from the literature of [1984][1985]. Plant steroids as raw material for the pharmaceutical industry; tissue culture for steroids; horticultural trials of species for sapogenins; the in Vitro use of enzymes to increase the yield of sapogenins from plant material. New furostanol precursors of diosgenin; the cytotoxic activity of these and related compounds; their possible role in plant mineral metabolism. Microorganisms in the biotransformation of steroids; the exploitation of waste material as a source of sterols; the use of fungal spores on diatomaceous particles; the use of fungal protoplasts; hydrophobic resin as a product reservoir in such transformations. Brassinosteroids, their distribution as plant growth hormones; their microquantitative bioassay; physiological studies towards their use for enhancement of crop production; patented analogues obtained by partial synthesis. Ecdysones, their wide distribution in plants; their possible functions: effect on photosynthetic and respiratory rates; root protection against soil nematodes; dietary value in animal nutrition; their use in insect control. 29-Fluorophytosterols as pro-insecticides; fungal pregnanes as insecticides. Cardiac glycosides; ecological significance in plant-insect-bird relationships; new cardenolides, naturally occurring and those obtained by partial synthesis; the use of mesophyll cells in tissue culture; crossbreeding of Digitalis species. Steroidal alkaloids: reference to their annual review and to a steroidal antibiotic; the types of alkaloids now defineable in the Buxaceae and their chemotaxonomic significance for the new ones from the single genus family, Didymelaceae.

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Studies on the constituents of Aspidistra elatior Blume. II. On the steroidal glycosides of the leaves.

Cited by 19 publications

References 0 publications

Three Steroids with Unique Structural Feature of 5.BETA.-Spirostan-1.BETA.,3.BETA.,17.ALPHA.-trihydroxyl from Reineckia carnea

Three Steroids with Unique Structural Feature of 5.BETA.-Spirostan-1.BETA.,3.BETA.,17.ALPHA.-trihydroxyl from Reineckia carnea

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

Recent Developments in our Knowledge of Steroids¹

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Studies on the constituents of Aspidistra elatior Blume. II. On the steroidal glycosides of the leaves.

Cited by 19 publications

References 0 publications

Three Steroids with Unique Structural Feature of 5.BETA.-Spirostan-1.BETA.,3.BETA.,17.ALPHA.-trihydroxyl from Reineckia carnea

Three Steroids with Unique Structural Feature of 5.BETA.-Spirostan-1.BETA.,3.BETA.,17.ALPHA.-trihydroxyl from Reineckia carnea

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

Recent Developments in our Knowledge of Steroids1

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Recent Developments in our Knowledge of Steroids¹