[Isolation and identification of steroidal saponins in total saponin from Dioscorea nipponica Makino].
ABSTRACT To investigate the water-soluble steroidal saponins in total saponin from Dioscorea nipponica Makino and look for new active compounds.
The compounds were isolated with silica gel, PTLC and HPLC, and their structures were elucidated by acid hydrolysis, physical and chemical data and spectral analysis (IR, NMR, MS, HMQC, HMBC) as well as chemical correlations.
The two steroidal saponins (water-insoluble saponin and water-soluble saponin) were isolated from the total saponin of Dioscorea nipponica Makino. The structures were elucidated as diosgenin 3-O-[alpha-L-rhamnopy ranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]]-beta-D-glucopyranoside (I), diosgenin 3-O-[alpha-L-rhamnopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside (II).
Compound II is a new steroidal saponin and firstly isolated from Dioscorea nipponica Makino. It was named as dioscin Dc.
- SourceAvailable from: Zulfiqar Ali
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- "D. nipponica Makino is also associated with antiobesity, antiinflammation, and anticancer properties . Previous studies of D. nipponica have reported the presence of steroidal glycosides    , phenanthrene derivatives  , water soluble non-saponin components [benzyl 1- O-β-D-glucopyranoside, leonuriside A, icariside D2, pyrocatechol 1-O-β-D-glucopyranoside, (+) syringaresinol-4-O-β-D-glucopyrano- side, cyclo-(leu-tyr), and adenosine , and a phenolic acid (piscidic acid) . In the present study, a phytochemical investigation of D. nipponica rhizomes was undertaken to discover new chemical constituents. "
ABSTRACT: Nine glycosides of spirostan (1-7) and furostan (8 and 9) type steroids including a new compound, 7-oxodioscin (1), were isolated from the rhizomes of Dioscorea nipponica. The structure of 1 was established as (25R)-3beta-O-[(alpha-L-rhamnopyranosyl-(1 --> 4)-O-[alpha-L-rhamnopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl)oxy]spirost-5-en-7-one by extensive spectroscopic techniques including HRESI-TOFMS, 1D and 2D NMR, and chemical methods. Known compounds were elucidated as dioseptemloside G (2), (25R)-dracaenoside G (3), orbiculatoside B (4), dioscin (5), progenin III (6), gracillin (7), (3beta3,22alpha,25R)-26-(beta-D-glucopyranosyloxy)-22-methoxyfurost-5-en-3-yl O-[alpha-L-rhamnopyranosyl-(1 --4)]-beta-D-glucopyranoside (8), and methylprotodioscin (9).Natural product communications 03/2013; 8(3):319-21. · 0.92 Impact Factor
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ABSTRACT: The acetone, chloroform, ethyl acetate, hexane and methanol leaf extracts of Acalypha indica, Achyranthes aspera, Leucas aspera, Morinda tinctoria and Ocimum sanctum were studied against the early fourth-instar larvae of Aedes aegypti L and Culex quinquefasciatus Say. The larval mortality was observed after 24 h exposure. All extracts showed moderate larvicidal effects; however, the highest larval mortality was found in the ethyl acetate extract of A. aspera. In the present study, bioassay-guided fractionation of A. aspera led to the separation and identification ofa saponin as a potential mosquito larvicidal compound, with LC50 value of 18.20 and 27.24 ppm against A. aegypti and C. quinquefasciatus, respectively. 1H NMR, 13C NMR and mass spectral data confirmed the identification of the active compound. This is the first report on the mosquito larvicidal activity of the saponin from the ethyl acetate extract of A. aspera. This study investigates the potential of crude extracts from commonly used medical herbs in India as an environmentally safe measure to control the vector of dengue and lymphatic filariasis.Parasitology Research 05/2008; 103(1):223-9. DOI:10.1007/s00436-008-0962-z · 2.33 Impact Factor
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ABSTRACT: A green and efficient method for the large-scale preparation of dioscin from Dioscorea nipponica Makino, a well known traditional Chinese medicinal herb, was developed. The preparation procedure consisted of two separation steps. In the first step, several types of macroporous resins including NKA-II, DA201, DM-301, AB-8, D1400, D4020, X-5, HPD-100 and D101 were investigated in order to choose the best resin. D101 resin was selected according to its adsorption and desorption properties. Other parameters during static and dynamic procedures were also investigated. In order to obtain a pure target, a second step was established, which involved the screening of various types of macroporous resins (D900, D318, D315, D280 and D301). The results demonstrated that D900 resin was the most suitable resin for use in this study. Under these conditions, the large-scale preparation of dioscin was carried out. The purity of dioscin after the first step was increased 9.16-fold from 9.35% to 85.64% with a recovery of 81.47%. The purity of dioscin then increased to 96.55% with a recovery of 89.64% after the second purification. A total of 1.486 kg of pure dioscin was produced from 100.0 kg raw material by the developed two-step macroporous resin column chromatography method using only aqueous ethanol as the solvent. Our study provides a green and efficient protocol for industrial-scale preparation of dioscin for pharmaceutical use.Chemical Engineering Journal 11/2010; 165(1-165):281-289. DOI:10.1016/j.cej.2010.09.045 · 4.32 Impact Factor