A Bisdesmosidic Cholestane Glycoside from the Rhizomes of ...

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Fig. 4. 1 H-NMR spectrum (A) and δ 4.75 selective TOCSY spectrum (B) of compound 1 (600 MHz, in C 5 D 5 N). compound 1 displayed a quasimolecular Meanwhile, peak at m/z 765 [M + Na] + and m/z 781 [M + K] + . ion The MS/MS spectrum of the [M + Na] + of a hydroxy group (18 Da) in aglycone moiety, a loss unit (146 Da) and a glucose unit (162 Da), rhamnose In addition, it exhibited the peaks at m/z 403 respectively. + Na − Glc − Rhm − 3H 2 O] + due to the successive [M of two saccharide moieties and three hydroxy groups. loss peaks at m/z 695 [M + Na − C 5 H 10 ] + resulted from The cleavage of side chain of the aglycone (Fig. 5). the the basis of the obtained data, the structure of On 1 was assigned as (22S)-cholest-5-ene- compound 1-O-α-L-rhamnopyranosyl 16-O-β- 1β,3β,16β,22-tetrol (Mimaki et al., 1999). This compound D-glucopyranoside to rare cholestane bisdesmosides possessing belongs residues linked to a polyhydroxycholesterol disaccharide Bisdesmosidic cholestane glycosides have been aglycone. from several Liliaceae plants. Since compound 1 isolated firstly isolated from a plant source, Allium jesdianum, was has been reported to be isolated from tubers or bulbs or it of Liliaceae plants (Dai et al., 2000; Fattorusso et al., seed Sang et al., 2000; Higano et al., 2007). Partial 2000; or overlapped signals in CD 3 OD has been assignment reported (Fattorusso et al., 2000). However, previously is the first report of a bisdesmodic cholestane this from the genus Polygonatum. In this study, the glycoside assignment of 1 H-NMR spectrum by HSQC, TOCSY full NOESY experiments was also provided. and compound 1 was reported not to have shown Although activity against HL-60 cells, this compound cytotoxic weak cytotoxic activity with the IC 50 value, 63.6 exhibited in human MCF-7 breast cancer line (Mimaki et al., µM Meanwhile, TGR5 is an emerging bile acid G- 1999). receptor target for the potential treatment protein-coupled metabolic disorders or inflammation (Atul and Pranab, of 186 Natural Product Sciences ion showed the at m/z 747 [M + Na − H 2 O] + , 601 [M + Na − Rhm − peaks 2 O] + and 585 [M + Na − Glc − H 2 O] + resulting from H 2009; Thijs et al., 2011). For example, TGR5 activation
Fig. 5. ESI MS spectrum of the sodium cationized compound 1 (A) and MS/MS spectrum of the molecular ion at m/z 765 (B-D). a significant reduction of the body weight of mice induces a high fat diet (Watanabe, 2006). Since compound 1 fed the same cholestane structure with bile acids, ligands has this receptor, TGR5 assay was accomplished with this for using Chinese hamster ovary (CHO) cells and a isolate acid, lithocholic acid as a positive control. However, bile compound failed to show agonistic activity on TGR5 this It was suggested that it could have resulted from receptor. of negatively charged functional groups or presence lack a double bond to increase molecular rigidity or bulky of moieties of this bisdesmosidic cholestane saccharide (Atul and Pranab, 2009). glycoside work was supported by 2010 Jinju National This Industry Academic Cooperation Foundation University Dictionary of Chinese Medicinal Materials, Shanghai Anonymous, and Technological Press, Shanghai, Vol. 2, pp. 2041-2044, Scientific 1978. P.K., Jain, D.C., Gupta, R.K., and Thakur, R.S., Carbon-13 Agrawal, spectroscopy of steroidal sapogenins and steroidal saponins. NMR 24, 2479-2496 (1985). Phytochemistry P.K., NMR Spectroscopy in the structural elucidation of Agrawal, and glycosides. Phytochemistry 31, 3307-3330 oligosaccharides (1992). M.-J., Kim, C.Y., Yoon, K.D., Ryu, M.Y., Cheong, J.H., Chin, Y.W., Ahn, Kim, J., Steroidal Saponins from the Rhizomes of Polygonatum and J. Nat. Prod. 69, 360-364 (2006). sibiricum. Tiwari. and Pranab, Maiti., TGR5: an emerging bile acid G-proteincoupled Atul, receptor target for the potential treatment of metabolic Drug Discov. Today 14, 523-530 (2009). disorders. H., Zhou, J., Deng, S., and Tan, N., Glycosides from Ophiopogon Dai, Tianran Chanwu Yanjiu Yu Kaifa 12, 5-7 (2000). japonicas. E., Lanzotti, V., Taglialatela-Scafati, O., Rosa, M.D., and Fattorusso, A., Cytotoxic saponins from bulbs of Allium porrum L. J. Ianaro, Food Chem. 48, 3455-3462 (2000). Agric. Vol. 17, No. 3, 2011 187 References Acknowledgment Grant. Hara, S., Okabe, H., and Mihashi, K., Gas-Liquid Chromatographic
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