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      Steroidal and Phenolic Glycosides from the Bulbs of Lilium pumilum DC and Their Potential Na +/K + ATPase Inhibitory Activity

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          Abstract

          A new steroidal saponin, named pumilum A ( 1), and a new phenolic glycoside, threo-1-(4′-hydroxy-2′-methoxyphenyl)-2-(2′′,4′′-dihydroxyphenyl)-1,3-propanediol-4′- O- β-D-glucopyranoside ( 7) were isolated from the methanolic extract of the bulbs of Lilium pumilum DC, along with five known steroidal saponins. Their chemical structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR techniques and chemical methods. In addition, the inhibitory activity of all the isolates on Na +/K + ATPase was evaluated.

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          Isolation and Structural Determination of Steroidal Glycosides from the Bulbs of Easter Lily (Lilium longiflorum Thunb.)

          John P Munafo, Ahalya Ramanathan, Leslie Jimenez … (2010)
          The bulbs of the Easter lily ( Lilium longiflorum Thunb.) are used as a food and medicine in several Asian cultures, and they are cultivated as an ornamental plant throughout the world. A new steroidal glycoalkaloid and two new furostanol saponins, along with two known steroidal glycosides, were isolated from the bulbs of L. longiflorum. The new steroidal glycoalkaloid was identified as (22R,25R)-spirosol-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->2)-[6-O-acetyl-beta-d-glucopyranosyl-(1-->4)]-beta-d-glucopyranoside. The new furostanol saponins were identified as (25R)-26-O-(beta-d-glucopyranosyl)-furost-5-en-3beta,22alpha,26-triol 3-O-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl-(1-->3)-beta-d-glucopyranoside and (25R)-26-O-(beta-d-glucopyranosyl)-furost-5-en-3beta,22alpha,26-triol 3-O-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-xylopyranosyl-(1-->3)-beta-d-glucopyranoside. The previously known steroidal glycosides, (22R,25R)-spirosol-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-glucopyranosyl-(1-->4)-beta-d-glucopyranoside and (25R)-26-O-(beta-d-glucopyranosyl)-furost-5-en-3beta,22alpha,26-triol 3-O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-glucopyranosyl-(1-->4)-beta-d-glucopyranoside were identified in L. longiflorum for the first time. These new compounds from L. longiflorum and the isolation methodologies employed can be used for studies on the biological role of steroidal glycosides in plant development and plant-pathogen interactions, as well as for studies in food and human health, for which little is known.
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            Constituents in Easter lily flowers with medicinal activity.

            W Rumbeiha, G. Nair, Jill Francis (2004)
            Easter lily (Lilium longiflorum) flowers have been used in traditional medicine for alleviating many ailments. However, the chemical basis of its bioactivity has not been investigated. We have determined bioactive components in Easter lily flowers using lipid peroxidation and cyclooxygenase enzyme inhibitory assays and found to be kaempferol (1), kaempferol glycosides (2, 3, 4, 8, 9 and 10), quercetin glycosides (5, 6 and 7), a regaloside (11), a chalcone (12) and a fatty acid fraction (13). The structures of compounds were determined by NMR, IR, UV/VIS and mass spectroscopic studies. Compound 1 showed the highest COX-1 inhibition (94.1%) followed by 3, 8 and 12 with 38.7, 30.8 and 32.4%, respectively. Only compound 1 inhibited COX-2 enzyme by 36.9% at 80 ppm. In lipid peroxidation inhibitory assay, kaempferol showed 37 and 100 % inhibitions at 1 and 10 ppm, respectively. At 10 ppm, more than 20% inhibition was observed for compounds 4, 7, 10, 11 and 12 and 53% for compound 3. The compounds reported in here are isolated for the first time from Easter lily flowers including novel compounds 10, 11 and 12. Our results suggest that kaempferol and quercetin flavonoids contributed to the anecdotal medicinal properties of Easter lily flowers.
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              Atropurosides A-G, new steroidal saponins from Smilacina atropurpurea.

              Sherry R. Jacob, Cong Li, Chong Yang … (2006)
              Atropurosides A-G (1-7), seven new steroidal saponins, which possess new polyhydroxylated aglycones, were isolated from the rhizomes of Smilacina atropurpurea (Convallariaceae), together with a known saponin, dioscin (8). Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR techniques and chemical methods. Antifungal testing of the eight compounds indicated that atropurosides B (2) and F (6) were fungicidal against Candida albicans, Candida glabrata, Cryptococcus neoformans, and Aspergillus fumigatus with minimum fungicidal concentrations (MFCs) < or = 20 microg/ml, while dioscin (8) was selectively active against C. albicans and C. glabrata (MFC < or = 5.0 microg/ml). Furthermore, the antifungal saponins 2, 6, and 8 were evaluated for their in vitro cytotoxicities in a panel of human cancer cell lines (SK-MEL, KB, BT-549, SK-OV-3, and HepG2) and non-cancerous Vero cells. All showed moderate cytotoxicities. It appears that the antifungal activity of these steroidal saponins correlates with their cytotoxicity against mammalian cells.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 03 September 2012
                Publication date Collection: September 2012
                Volume: 17
                Issue: 9
                Pages: 10494-10502
                Affiliations
                [1 ]Chemistry Science and Technology School, Zhanjiang Normal University, 29 Cunjin Road, Zhanjiang 524048, China; Email: zhanghualing303@ 123456163.com (H.L.Z.); xiajingming88@ 123456163.com (J.-M.X.)
                [2 ]Development Center for New Materials Engineering Technology in Universities of Guangdong, Zhanjiang Normal University, 29 Cunjin Road, Zhanjiang 524048, China; Email: fengzongcai921@ 123456163.com
                [3 ]Department of Pharmacy, Shaoyang Medical College Level Speciaity School, 18 Baoqing Road, Shaoyang 422000, China; Email: chunyanfull@ 123456yahoo.com.cn
                Author notes
                [* ] Author to whom correspondence should be addressed; Email: zlzhou@ 123456hotmail.com ; Tel.: +86-137-2690-5138; Tel./Fax: +86-075-9318-3176.
                Article
                Publisher ID: molecules-17-10494
                DOI: 10.3390/molecules170910494
                PMC ID: 6268628
                PubMed ID: 22945028
                SO-VID: 5b2f1862-e133-4112-aa3c-988cf998c870
                Copyright © © 2012 by the authors; licensee MDPI, Basel, Switzerland.
                License:

                This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                Date received : 02 July 2012
                Date revision received : 25 August 2012
                Date accepted : 29 August 2012
                Categories
                Subject: Article

                Keywords: lilium pumilum dc,pumilum a,na+/k+ atpase
                Data availability:
                Keywords: lilium pumilum dc, pumilum a, na+/k+ atpase

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