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Journal articles on the topic 'Spirostan saponin'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Dąbrowska-Balcerzak, Karolina, Jadwiga Nartowska, Iwona Wawer, Paweł Siudem, and Katarzyna Paradowska. "Spirostanol Sapogenins and Saponins from Convallaria majalis L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling." Molecules 26, no. 10 (2021): 2999. http://dx.doi.org/10.3390/molecules26102999.

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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; 5

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2

Pérez-Labrada, Karell, Ignacio Brouard, Cercis Morera, Francisco Estévez, Jaime Bermejo, and Daniel G. Rivera. "‘Click’ synthesis of triazole-based spirostan saponin analogs." Tetrahedron 67, no. 40 (2011): 7713–27. http://dx.doi.org/10.1016/j.tet.2011.08.003.

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3

Higano, Taro, Minpei Kuroda, Maki Jitsuno, and Yoshihiro Mimaki. "Polyhydroxylated Steroidal Saponins from the Rhizomes of Convallaria majalis." Natural Product Communications 2, no. 5 (2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200504.

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Six new polyhydroxylated spirostanol saponins (1–6) were isolated from the methanolic extract of the rhizomes of Convallaria majalis. On the basis of extensive spectroscopic analysis, including 2D NMR data, and a few chemical transformations, the structures of 1–6 were determined to be 1β,2β,3β-trihydroxy-5β-spirost-25(27)-en-5-yl β-D-galactopyranoside (1), (25 S)-1β,2β,3β-trihydroxy-5β-spirostan-5-yl β-D-galactopyranoside (2), 1β,2β,3β,4β-tetrahydroxy-5β-spirost-25(27)-en-5-yl β-D-galactopyranoside (3), (25 S)-1β,2β,3β,4β-tetrahydroxy-5β-spirostan-5-yl β-D-galactopyranoside (4), 1β,2β,3β,4β-t

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4

Alvarez, Laura, Maria del Carmen Pérez, José Luis González, Victor Navarro, Maria Luisa Villarreal, and John Otto Olson. "SC-1, An Antimycotic Spirostan Saponin from Solanum chrysotrichum." Planta Medica 67, no. 4 (2001): 372–74. http://dx.doi.org/10.1055/s-2001-14332.

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5

D., N. Singh, and Verma N. "Furostan saponin and GC-MS study toward ascertaining the point of linkage between sugars moieties of spirostan saponin from the rhizomes of Agapanthus africanus (Linn.)." Journal Of Indian Chemical Society Vol. 87, Aug 2010 (2010): 999–1003. https://doi.org/10.5281/zenodo.5801240.

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Department of Chemistry, K. S. Saket PG College, Dr. Ram Manohar Lohia Avadh University, Faizabad-224 001, Uttar Pradesh, India E-mail : dnsinghsaket@yahoo.com Manuscript received 26 October 2008, revised 9 February 2010, accepted 25 February 2010 The linkage between the sugars moieties of antifungal spirostan saponin, (25<em>R</em>)-5α-spirost-7-en-2α,3β,5α-trioi-3-<em>O</em>-{-<em>O</em>-α-L-rhamnopyranosyl-(1→2)-<em>O</em>-[β-D-galactopyranosyi-(1→3))·P·D-glucopyranoside} of Agapa11thus africanus (Linn.) have been determined by the a

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6

Silva, Graziela M., Aloa M. De Souza, Luciene S. Lara, et al. "A New Steroidal Saponin from Agave brittoniana and Its Biphasic Effect on the Na+-ATPase Activity." Zeitschrift für Naturforschung C 60, no. 1-2 (2005): 121–27. http://dx.doi.org/10.1515/znc-2005-1-222.

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A new steroidal saponin, 3-{(O-6-deoxy-α-ʟ-mannopyranosyl-(1→4)-O-β-ᴅ-glucopyranosyl-( 1→3)-O-[O-β-ᴅ-glucopyranosyl-(1→3)-β-ᴅ-glucopyranosyl-(1→2)]-O-β-ᴅ-glucopyranosyl-( 1→4)-β-ᴅ-galactopyranosyl)oxy}-6-hydroxy-(3β,5α,6α,25R)-spirostan-12-one, was isolated from Agave brittoniana Trel. The structure was determined by extensive NMR spectroscopy studies and chemical conversions. Its effects on the Na+-ATPase and (Na++K+)-ATPase activities of the proximal tubule from pig kidney were evaluated. It was observed that this steroidal saponin exerts a biphasic effect on the Na+-ATPase activity. It is c

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7

Candra, Ellyawati, Kimihiro Matsunaga, Hironori Fujiwara, et al. "Two steroidal saponins from Camassia cusickii induce L1210 cell death through the apoptotic mechanism." Canadian Journal of Physiology and Pharmacology 79, no. 11 (2001): 953–58. http://dx.doi.org/10.1139/y01-068.

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Two steroidal saponins, tigogenin hexasaccharide-1 (TGHS-1, (25R)-5α-spirostan-3β-yl 4-O-[2-O-[3-O- (α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-3-O-[4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-β-D-glucopyranosyl]- β-D-galactopyranoside) and tigogenin hexasaccharide-2 (TGHS-2, (25R)-5α-spirostan-3β-yl 4-O-[2-O-[3-O- (β-D-glucopyranosyl)-β-D-glucopyranosyl]-3-O-[4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-β-D-glucopyranosyl]- β-D-galactopyranoside), were isolated from the fresh bulbs of Camassia cusickii. In murine leukemic L1210 cells, both compounds showed cytotoxicity with an EC50 value of

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8

Li, Ming, and Biao Yu. "Facile Conversion of Spirostan Saponin into Furostan Saponin: Synthesis of Methyl Protodioscin and Its 26-Thio-analogue." Organic Letters 8, no. 13 (2006): 2679–82. http://dx.doi.org/10.1021/ol060594w.

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9

Okubo, Shinya, Tomoe Ohta, Yukihiro Shoyama, and Takuhiro Uto. "Steroidal Saponins Isolated from the Rhizome of Dioscorea tokoro Inhibit Cell Growth and Autophagy in Hepatocellular Carcinoma Cells." Life 11, no. 8 (2021): 749. http://dx.doi.org/10.3390/life11080749.

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Our preliminary screening identified an extract from the rhizome of Dioscorea tokoro, which strongly suppressed the proliferation of HepG2 hepatocellular carcinoma cells and inhibited autophagy. This study aimed to isolate active compounds from the rhizome of D. tokoro that exert antiproliferative effects and inhibit autophagy. The bioassay-guided fractionation of the active fraction led to the isolation of two spirostan-type steroidal saponins, dioscin (1) and yamogenin 3-O-α-l-rhamnopyranosyl (1→4)-O-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranoside (2), and the frostane-type steroidal saponin pr

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10

Ren, Rui, Ming-yan Zhang, Tengyun Shu, Ya-ting Kong, Li-hua Su, and Hai-zhou Li. "Steroidal Saponins from Water Eggplant (Fruits of Solanum torvum) Exhibit Anti-Epileptic Activity against Pentylenetetrazole-Induced Seizure Model in Zebrafish." Molecules 29, no. 6 (2024): 1316. http://dx.doi.org/10.3390/molecules29061316.

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The fruits of Solanum torvum Swartz, a wild relative of eggplant, are consumed as a wild vegetable in tropical regions of Africa, Asia, and South America. In traditional Chinese medicine, it is believed to have anti-inflammatory and sedative effects. In the Philippines, water decoction is used to treat hyperactivity disorder. Twenty-two steroidal saponins were isolated and purified from the fruits grown in Yunnan, China, including six new compounds: torvosides U–Z (1–6). During drying and cooking, the saponins may undergo transformation, resulting in small amounts of sapogenins. These transfor

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11

Lunga, Irina, Carla Bassarello, Pavel Kintia, Stepan Shvets, Sonia Piacente, and Cosimo Pizza. "Steroidal Glycosides from the Seeds of Hyoscyamus niger L." Natural Product Communications 3, no. 5 (2008): 1934578X0800300. http://dx.doi.org/10.1177/1934578x0800300512.

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The investigation of the steroidal glycosides of the seeds of Hyoscyamus niger L. led to the isolation of two new spirostane saponins (2, 6) together with seven known glycosides with either furostane or spirostane aglycones. On the basis of chemical and spectroscopic evidence, the structures of 2 and 6 were elucidated as (25 R)-5α-spirostan-3β-ol 3- O-β-D-glucopyranosyl-(1→3)-β-D-galactopyranoside (2) and (25 R)-5α-spirostan-3β-ol 3- O-β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside (6). The given compounds have been found for the first time in the genus Hyoscyamus.

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12

Mohamed, Mona A. "Spirostanol Saponins from Asparagus sprengeri and Their Molluscicidal Activity." Natural Product Communications 2, no. 7 (2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200705.

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Two new spirostane saponins namely (25 R)-6α-[(β-D-glucopyranosyl)oxy]-5α-spirostan-3β-yl β-D-galactopyranoside (1) and (25 R)-6α-[(β-D-glucopyranosyl)oxy]-27-hydroxy-5α-spirostan-3β-yl β-D-glucopyranoside (2), together with three known metabolites (25 S)-5β-spirostan-3-β-yl O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (3), (25 R)-5α-spirostan-3-β-yl O-β-D-galactopyranosyl-(1→2)- O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (4) and (25 R)-5α-spirostan-3-β-yl O-β-D-glucopyranosyl-(1→3)- O-[β-D-xylopyranosyl-(1→2)]- O-β-D-glucopyranosyl-(1→4)-β-D-glactopyranoside (5) were identified from t

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13

Tapondjou, Leon A., Kristina Jenett-Siems, Karsten Siems, Alexander Weng, and Matthias F. Melzig. "Flavonol Glycosides and Cytotoxic Steroidal Saponins from Furcraea Tuberosa (Agavaceae)." Natural Product Communications 12, no. 3 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200309.

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Phytochemical analysis of the mature fruits of Furcraea tuberosa (Agavaceae) resulted in the isolation of a new bisdesmosidic spirostanol saponin (1), along with eight known steroidal glycosides (2–9), one known phenolic carboxylic acid ester (10) and three known flavonol glycosides (11–13). The structures of these compounds were assigned using a combination of 1D and 2D NMR techniques including 1H, 13C, COSY, TOCSY, HSQC and HMBC NMR, and confirmed by mass spectrometry. Thus the new saponin was elucidated as (25 R)–6α-(β-D-glucopyranosyloxy)-5α-spirostane-3β- O-[(6- O-hexadecanoyl)-β-D-glucop

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14

Phan, Vy Thiện, Vy Vũ Thụy Nguyễn та Giàu Bích Ngọc Lư. "Khảo sát hoạt tính sinh học của ba saponin phân lập từ quả cà dại hoa trắng Solanum torvum Sw". Journal of Science and Technology 5, № 1 (2022): 6. http://dx.doi.org/10.55401/jst.v5i1.709.

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Từ nghiên cứu trước đó, tác giả đã phân lập được ba saponin, neochlorogenin 6-O-α- L-rhamnopyranosyl-(1→3)-β-D-quinovopyranosid (S-1), (25S)-6α-hydroxy-5α- spirostan-3-on-6-O-α-L-rhamnopyranosyl-(1→3)-β-D-quinovopyranosid (S-2) và solanolactosid A (S-3) từ phân đoạn cao ethyl acetat (EtOAc) của quả cà dại hoa trắng Solanum torvum Sw. Dựa trên một số nghiên cứu về tiềm năng của các glycosid steroid trong quả Solanum torvum Sw. có 3 saponin được thử hoạt tính độc tế bào. Kết quả cho thấy S-1 và S-2 có hoạt tính độc tế bào đáng được quan tâm. S-1 có khả năng ức chế mạnh 3 dòng tế bào ung thư HepG

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15

Elier, Galarraga M., Anne-Claire Mitaine-Offer, Juan Manuel Amaro-Luis, et al. "Steroidal Saponins from the Fruits of Cestrum ruizteranianum." Natural Product Communications 6, no. 12 (2011): 1934578X1100601. http://dx.doi.org/10.1177/1934578x1100601209.

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Seven spirostane and furostane-type glycosides were isolated from the aqueous methanolic extract of the fruits of Cestrum ruizteranianum and characterized mainly by 2D NMR spectroscopy and mass spectrometry. These known saponins belong to the Δ5-spirostene and Δ5-furostene series and are reported in this species for the first time.

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16

Bai, Cai Hong, Hai Bo He, Fan Cheng та ін. "A Steroidal Saponin RCE-4 Inhibits Lipopolysaccharide-Stimulated Inflammatory Responses via Blocking PI3K/Akt-Mediated Nf-κB Activation in RAW264.7 Cells". Applied Mechanics and Materials 568-570 (червень 2014): 1901–6. http://dx.doi.org/10.4028/www.scientific.net/amm.568-570.1901.

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Steroidal saponin: (1β,3β,5β,25S)-spirostan-1,3-diol1-[α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside] (RCE-4) is the most abundant and bioactive members in Reineckia carnea, has been reported to possess antiinflammatory activity, but the underlying mechanisms remain largely unknown. The present aim was to study expression of inflammatory cytokines, on the basis of this investigation, the possible mechanism of RCE-4 was elucidated. In the present study, we found that the concentrations of TNF-α, IL-1β and IL-6 released from LPS-stimulated RAW264.7cells significantly increased compared to control

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17

Ruan, Jingya, Lu Qu, Wei Zhao, et al. "Identification and Structural Analysis of Spirostanol Saponin from Yucca schidigera by Integrating Silica Gel Column Chromatography and Liquid Chromatography/Mass Spectrometry Analysis." Molecules 25, no. 17 (2020): 3848. http://dx.doi.org/10.3390/molecules25173848.

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Yucca schidigera Roezl (Mojave), a kind of ornamental plant belonging to the Yucca genus (Agavaceae), whose extract exhibits important roles in food, beverage, cosmetic and feed additives owing to its rich spirostanol saponins. To provide a comprehensive chemical profiling of the spirostanol saponins in it, this study was performed by using a multi-phase liquid chromatography method combining a reversed phase chromatography T3 column with a normal phase chromatography silica column for the separation and an ESI-Q-Exactive-Orbitrap MS in positive ion mode as the detector. By comparing the reten

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18

Abbas, Fawkeya. "STEROIDAL SAPONINS FROM SOLANUM UNGUICULATUM (A.) RICH." Scientia Pharmaceutica 69, no. 2 (2001): 219–34. http://dx.doi.org/10.3797/scipharm.aut-01-23.

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Seven steroidal saponins were isolated for the first time from the green berries of Solanum unguiculatum. Their structures were determined by spectroscopic analysis as well as hydrolysis of the glycosides into the corresponding sapogenins, diosgenin, chlorogenin, diosgenin-3-O-β-D-galactopyranoside, diosgenin-3-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside, 3β-hydroxyl-(25R) 5 α-spirostan-6-one (laxogenin) 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranoside, isonarthogenin-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranoside and 25(S) spirost-5-en-3 β, 17 α,

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19

Mimaki, Yoshihiro, Tsukasa Aoki, Maki Jitsuno, Akihito Yokosuka, Ceyda Sibel Kiliç, and Maksut Coşkun. "Steroidal Saponins from the Rhizomes of Ruscus Hypophyllum." Natural Product Communications 3, no. 10 (2008): 1934578X0800301. http://dx.doi.org/10.1177/1934578x0800301018.

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Phytochemical screening of the rhizomes of Ruscus hypophyllum (Liliaceae) has resulted in the isolation of five spirostanol saponins (1-5) including a new saponin (4) and nine furostanol saponins (6–14) including three new saponins (9–11), together with a known cholestane glycoside (15) and a new cholestane glycoside (16). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence. The spirostanol saponins 1, 2, and 5 showed moderate cytotoxic activity against HL-60 human promyelocytic leukemia cells.

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20

Ahmad, Viqar Uddin, Fehmida T. Baqai, and Roshan Ahmad. "A Diosgenin Tetrasaccharide from Cestrum nocturnum." Zeitschrift für Naturforschung B 50, no. 7 (1995): 1104–10. http://dx.doi.org/10.1515/znb-1995-0722.

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A new monodesmosidic spirostanol glycoside extracted from the fresh leaves of Cestrum nocturnum was identified as spirost-5-ene-3-ol, [3β,25R]-3-O-[{α-L-rhamnopyranosyl-(1→4)- α-L-rhamnopyranosyl-(1→2)}-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside. The name proposed for this saponin is nocturnoside B. The structure elucidation was done on the basis of 1 D and 2 D spectroscopic studies [DEPT. HeteroCOSY, HMBC, COSY-45°, HOHAHA ] and chemical analysis.

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21

Teponno, Rémy B., Beaudelaire K. Ponou, Dennis Fiorini, Luciano Barboni, and Léon A. Tapondjou. "Chemical Constituents from the Roots of Furcraea bedinghausii Koch." International Letters of Chemistry, Physics and Astronomy 16 (September 2013): 9–19. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.16.9.

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Phytochemical investigation of the roots of Furcraea bedinghausii Koch. Led to the isolation of a mixture of two new homoisoflavones, 5,7-dihydroxy-3-(3,4-methylenedioxybenzyl)-chromone (4a) and 5,7-dihydroxy-3-(4-methoxybenzyl)-chromone (4b), together with the known β-sitosterol (1), 7,4'-dihydroxyhomoisoflavane (2), dihydrobonducellin (3), kaempferol (5), 5,7-dihydroxy-3-(4-hydroxybenzyl)-chromone (6), 1-linoleylglycerol (7), 6’-linoleyl-3-O-β-D-glucopyranosyl-β-sitosterol (8), trans-3,3’,5,5’-tetrahydroxy-4’-methoxystilbene (9), yuccaol C (10), yuccaol D (11), 3-O-b-D-glucopyranosyl-b-sitos

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22

Teponno, Rémy B., Beaudelaire K. Ponou, Dennis Fiorini, Luciano Barboni, and Léon A. Tapondjou. "Chemical Constituents from the Roots of <i>Furcraea bedinghausii</i> Koch." International Letters of Chemistry, Physics and Astronomy 16 (August 5, 2013): 9–19. http://dx.doi.org/10.56431/p-i1m5h3.

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Phytochemical investigation of the roots of Furcraea bedinghausii Koch. Led to the isolation of a mixture of two new homoisoflavones, 5,7-dihydroxy-3-(3,4-methylenedioxybenzyl)-chromone (4a) and 5,7-dihydroxy-3-(4-methoxybenzyl)-chromone (4b), together with the known β-sitosterol (1), 7,4'-dihydroxyhomoisoflavane (2), dihydrobonducellin (3), kaempferol (5), 5,7-dihydroxy-3-(4-hydroxybenzyl)-chromone (6), 1-linoleylglycerol (7), 6’-linoleyl-3-O-β-D-glucopyranosyl-β-sitosterol (8), trans-3,3’,5,5’-tetrahydroxy-4’-methoxystilbene (9), yuccaol C (10), yuccaol D (11), 3-O-b-D-glucopyranosyl-b-sitos

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23

Hùng, Nguyễn Đức, Từ Quang Tân, and Chu Hoàng Mậu. "STUDY ON ISOLATION AND STRUCTURAL DETERMINATION OF STEROIDAL SAPONIN FROM THE LEAVES OF Dracaena fragrans." TNU Journal of Science and Technology 229, no. 05 (2024): 339–45. http://dx.doi.org/10.34238/tnu-jst.9402.

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Saponin là một hợp chất hóa học có thể tìm thấy ở hầu hết các bộ phận của cây. Một số saponin như protodioscin và protodioscin đã được lựa chọn cho chương trình sàng lọc thuốc chống ung thư của Viện Ung thư Quốc gia. Hiện nay, các công ty dược phẩm trên thế giới đang tập trung tìm kiếm các loại thuốc mới có nguồn gốc từ thực vật, đồng thời tìm cách phân lập các hợp chất đơn lẻ nhằm loại bỏ các hợp chất độc hại ra khỏi nguyên liệu ban đầu và thu thập các hợp chất có hoạt tính sinh học trong đó có saponin. Trong nghiên cứu này, saponin steroid với aglycone spirostanol đã được phân lập từ lá Drac

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24

Le, Hien Bich Thi, Van Anh Thi Tran, Hien Minh Nguyen, Linh Thuy Khanh Nguyen, Duc Viet Ho, and Hoai Thi Nguyen. "Aspidiata E, a New Spirostanol Saponin From Aspidistra triradiata and its Cytotoxic Activity." Natural Product Communications 18, no. 6 (2023): 1934578X2311794. http://dx.doi.org/10.1177/1934578x231179412.

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Aspidiata E (1), a new spirostanol saponin {(22 S*,25 R*)-1 β,3 β,4 β,5 β,6 β-pentahydroxyspirostan-2 β-yl β-D-xylopyranoside), together with 2 known compounds, (22 S*,25 R*)-spirost-5-ene-3 β-yl O- α-L-rhamnopyranosyl-(1→2)- O-[ O- α-L-rhamnopyranosyl-(1→5)- α-L-arabinofuranosyl-(1→4)]- β-D-glucopyranoside (2), and (22 S*)-16-[( β-D -glucopyranosyl)oxy]-1 β,3 β,22-trihydroxycholest-5-en-1 β-yl α-L-rhamnopyranoside (3), were isolated from Aspidistra triradiata. Their structures were determined by NMR spectroscopic and high resolution electrospray ionisation mass spectrometry analysis and by co

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25

Mochizuki, Emiko, Takao Yamamoto, Yoshihiro Mimaki, and Yutaka Sashida. "Ultraviolet Derivatization of Steroidal Saponin in Garlic and Commercial Garlic Products as p-Nitrobenzoate for Liquid Chromatographic Determination." Journal of AOAC INTERNATIONAL 87, no. 5 (2004): 1063–69. http://dx.doi.org/10.1093/jaoac/87.5.1063.

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Abstract A method is described for determination of the steroidal saponin, eruboside B, originating in garlic and garlic products as the p-nitrobenzoyl chloride (PNBC) derivative by reversed-phase liquid chromatography (with ultraviolet detection at 260 nm. Proto-eruboside B was extracted from garlic (Allium sativum L.); subjected to solid-phase extraction (SPE) with a C18 cartridge, Florisil column chromatography, and silica gel column chromatography; and then enzymatically converted to eruboside B, which was applied as an external standard. Steroidal saponins in garlic and commercial garlic

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26

MAMTA, TANDON, and N. SHUKLA Y. "Arundinoside A- a New Spirostane Saponin from Chlorophytum arundinaceum." Journal of Indian Chemical Society Vol. 74, Jan 1997 (1997): 56–58. https://doi.org/10.5281/zenodo.5877777.

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Central Institute of Medicinal and Aromatic Plants. Lucknow-226 015 <em>Manuscript received 28 October 1994. revised 16 March 1995, accepted 8 June 1995</em> Arundinoside A- a New Spirostane Saponin from Chlorophytum arundinaceum  

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Qu, Lu, Jingya Ruan, Song Wu, et al. "Separation and Bioactive Assay of 25R/S-Spirostanol Saponin Diastereomers from Yucca schidigera Roezl (Mojave) Stems." Molecules 23, no. 10 (2018): 2562. http://dx.doi.org/10.3390/molecules23102562.

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In order to find a simple, generic, efficient separation method for 25R/S-spirostanol saponin diastereomers, the liquid chromatographic retention behaviors of C12 carbonylation and C12 unsubstituted 25R/S-spirostanol saponin diastereomers on different stationary phases (C8, C18, C30 columns) and different mobile phases (MeOH-1% CH3COOH and CH3CN-1% CH3COOH) were investigated. A C30 column was firstly found to offer the highest efficiency for the separation of this kind of diastereomers than C8 and C18 columns. Meanwhile, the analysis results indicated that both CH3CN-1% CH3COOH and MeOH-1% CH3

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28

Chileh-Chelh, Tarik, Rosalía López-Ruiz, Ana M. García-Cervantes, et al. "Cytotoxicity and Chemotaxonomic Significance of Saponins from Wild and Cultured Asparagus Shoots." Molecules 29, no. 14 (2024): 3367. http://dx.doi.org/10.3390/molecules29143367.

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The shoots of Asparagus L. are consumed worldwide, although most species belonging to this genus have a restricted range, and several taxa remain unstudied. In this work, a total of four taxa from different locations were scrutinized and compared with cultivated A. officinalis. All shoots were screened for saponins via LC-MS, and in vitro antiproliferative activities against the HT-29 colorectal cancer cell line were assessed via the MTT assay. The total saponins (TS) contained in the crude extracts ranged from 710.0 (A. officinalis) to 1258.6 mg/100 g dw (A. acutifolius). The richness of the

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29

K. Agrawal, Pawan, Pawan K. Agrawal, Umar Mahmood, and Raghunath S. Thakur. "Torvonin-B, a Spirostane Saponin from Solanum torvum." HETEROCYCLES 29, no. 10 (1989): 1895. http://dx.doi.org/10.3987/com-89-5032.

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30

Ferreira, Fernando, Alvaro Vazquez, Patrick Moyna, and Lennart Kenne. "Foliumin, a spirosten lactone saponin from Solanum amygdalifolium." Phytochemistry 36, no. 6 (1994): 1473–78. http://dx.doi.org/10.1016/s0031-9422(00)89745-9.

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31

Pang, Xu, Hong Zhi Huang, Yang Zhao, Cheng-Qi Xiong, Li Yan Yu, and Bai-Ping Ma. "Conversion of furostanol saponins into spirostanol saponins improves the yield of diosgenin from Dioscorea zingiberensis by acid hydrolysis." RSC Advances 5, no. 7 (2015): 4831–37. http://dx.doi.org/10.1039/c4ra12709a.

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32

Sang, Shengmin, Aina Lao, Hongcheng Wang, and Zhongliang Chen. "Two New Spirostanol Saponins fromAlliumtuberosum." Journal of Natural Products 62, no. 7 (1999): 1028–29. http://dx.doi.org/10.1021/np980486l.

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33

Qu, Lu, Jianli Wang, Jingya Ruan, et al. "Spirostane-Type Saponins Obtained from Yucca schidigera." Molecules 23, no. 1 (2018): 167. http://dx.doi.org/10.3390/molecules23010167.

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34

Mahmood, Umar, Pawan K. Agrawal, and Raghunath S. Thakur. "Torvonin-A, a spirostane saponin from Solanum torvum leaves." Phytochemistry 24, no. 10 (1985): 2456–57. http://dx.doi.org/10.1016/s0031-9422(00)83069-1.

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35

Rezgui, Abdelmalek, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, and Marie-Aleth Lacaille-Dubois. "Spirostane-type Saponins from Dracaena fragrans « Yellow Coast »." Natural Product Communications 10, no. 1 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000111.

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Three steroidal glycosides were isolated from the bark of Dracaena fragrans (L.) Ker Gawl. « Yellow Coast », and a fourth from the roots and the leaves. Their structures were characterized on the basis of extensive 1D and 2D NMR experiments and mass spectrometry, and by comparison with NMR data of the literature. These saponins have the spirostane-type skeleton and are reported in this species for the first time.

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36

El-Sayed, Mortada. "MOLLUSCICIDAL SPIROSTANOL SAPONINS FROM AGAVE HETERACANTHA." Bulletin of Pharmaceutical Sciences. Assiut 20, no. 2 (1997): 147–53. http://dx.doi.org/10.21608/bfsa.1997.68754.

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CAROTENUTO, A., E. FATTORUSSO, V. LANZOTTI, and S. MAGNO. "Spirostanol saponins of Allium porrum L.fn1." Phytochemistry 51, no. 8 (1999): 1077–82. http://dx.doi.org/10.1016/s0031-9422(98)00712-2.

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38

Bahuguna, S., and O. P. Sati. "Spirostanol saponins from Yucca aloifolia rhizomes." Phytochemistry 29, no. 1 (1990): 342–43. http://dx.doi.org/10.1016/0031-9422(90)89070-p.

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39

Zhang, Zhong-Quan, Jian-Chao Chen, Xian-Ming Zhang, Zhong-Rong Li, and Ming-Hua Qiu. "Two New Spirostanol Saponins fromReineckia carnea." Helvetica Chimica Acta 91, no. 8 (2008): 1494–99. http://dx.doi.org/10.1002/hlca.200890162.

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40

Liu, Bo, Bingxin Li, Gang Chen, Yingni Pan, Di Zhou, and Ning Li. "Spirostane saponins with a rearranged A/B ring system isolated from the rhizomes of Ophiopogon japonicus." Phytochemistry 193 (January 31, 2022): 1–9. https://doi.org/10.1016/j.phytochem.2021.112975.

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Liu, Bo, Li, Bingxin, Chen, Gang, Pan, Yingni, Zhou, Di, Li, Ning (2022): Spirostane saponins with a rearranged A/B ring system isolated from the rhizomes of Ophiopogon japonicus. Phytochemistry (112975) 193: 1-9, DOI: 10.1016/j.phytochem.2021.112975, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112975

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41

Lunga, Irina, Pavel Kintia, Stepan Shvets, Carla Bassarello, Sonia Piacente, and Cosimo Pizza. "Steroidal Saponins from the Seeds of Hyoscyamus Niger L." Chemistry Journal of Moldova 3, no. 1 (2008): 89–93. http://dx.doi.org/10.19261/cjm.2008.03(1).10.

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Ten steroidal saponins have been isolated form the seeds of Hyoscyamus niger L. for the first time and their structures have been elucidated. Seven saponins belong to spirostane series, two are furostane-type and one is pregnane glycoside. Hyoscyamosides B, C and C2 are new steroidal saponins, which have never been reported before in literature. Complete assignments of the 1H and 13C NMR chemical shifts for all these glycosides were achieved by means of one- and two-dimensional NMR techniques, including 1H–1H COSY, HSQC, HMBC and ROESY spectra.

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42

de Souza, Aloa Machado, Lucienne da Silva Lara, Jose Osvaldo Previato, et al. "Modulation of Sodium Pumps by Steroidal Saponins." Zeitschrift für Naturforschung C 59, no. 5-6 (2004): 432–36. http://dx.doi.org/10.1515/znc-2004-5-626.

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Costus spicatus, used in Brazilian traditional medicine to expel kidney stones, contains steroidal saponins with different chemical characteristics. In spite of its popular utilization as potent diuretic, no scientific reports correlate this activity with the chemical constituents of the extract. Therefore, two steroidal saponins (3β,22a,25R)-26-(β-ᴅ-glucopyranosyloxy)-2-methoxyfurost-5-en-3-yl O-ᴅ-apio-β-ᴅ-furanosyl-(1→2)-O-[6-deoxy-α-ʟ-mannopyranosyl- (1→4)]-β-ᴅ-glucopyranoside (1) and (3β,22α,25R)-spirostan-3-yl O-ᴅ-apio-β-ᴅ-furanosyl- (1→2)-O-[6-deoxy-α-ʟ-mannopyranosyl-(1→4)]-β-ᴅ-glucopyr

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43

Ilyas, M., U. U. Pateh, A. M. Musa, and M. Mohammed. "Steroidal and triterpenoidal saponins from the stem bark extract of Stachytarpheta angustifolia Mill (Vahl) Verbenaceae." Journal of Scientific and Innovative Research 3, no. 2 (2014): 207–16. http://dx.doi.org/10.31254/jsir.2014.3215.

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Two saponins were isolated from the stem bark extract of Stachytarpheta angustifolia. Their structures were established by spectroscopic and chemical analysis as (23S, 25S) - 5α - spirostan – 24 – one - 3β, 23 – diol – 3 – O – {α – L – rhamnopyranosyl – (1→2) – [O – β - D - glucopyranosyl – (1→4)] – β - D – galactopyranoside} (1) and 3β – O –( β- D - Xylopyranosyl – (1-3) – α – L – arabinopyranosyl) - 20β, 23-dihydroxy urs – 12 – en – 28 – O – [- α – L – rhamnopyranosyl – (1-3) – α – L – rhamnopyranosyl – (1-6) – β - D - glucopyranosyl -] ester.

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44

Agrawal, Pawan K., Torsten Burkholz, and Claus Jacob. "Revisit to 25R/25S Stereochemical Analysis of Spirostane-type Steroidal Sapogenins and Steroidal Saponins via 1H NMR Chemical Shift Data." Natural Product Communications 7, no. 6 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700605.

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An approach based on the difference (Δab = δa – δb) between 1H NMR chemical shifts (δa, δb) of the geminal protons of oxymethylene (H2-26) (Δab = <0.2 for 25 R; Δab = >0.5 for 25 S) is proposed for ascertaining 25 R/25 S orientation of the 27-methyl group for (22 R)-spirostane-type steroidal sapogenins and steroidal saponins. These studies suggested the 25 R-orientation of the 27-Me group for the steroidal saponins isolated by Temraz et al. from Tribulus alatus.

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45

Wang, Zhen-Fang, Bing-Bing Wang, Yang Zhao, et al. "Furostanol and Spirostanol Saponins from Tribulus terrestris." Molecules 21, no. 4 (2016): 429. http://dx.doi.org/10.3390/molecules21040429.

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46

Osorio, Jaime Niño, Oscar M. Mosquera Martinez, Yaned M. Correa Navarro, Kazuki Watanabe, Hiroshi Sakagami, and Yoshihiro Mimaki. "Polyhydroxylated Spirostanol Saponins from the Tubers ofDioscoreapolygonoides." Journal of Natural Products 68, no. 7 (2005): 1116–20. http://dx.doi.org/10.1021/np0580356.

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47

Acharya, Debabrata, Anne-Claire Mitaine-Offer, Nutan Kaushik, et al. "Cytotoxic Spirostane-Type Saponins from the Roots ofChlorophytum borivilianum." Journal of Natural Products 72, no. 1 (2009): 177–81. http://dx.doi.org/10.1021/np800559z.

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48

Kostadinova, Emanuela P., Kalina I. Alipieva, Tetsuo Kokubun, Rilka M. Taskova, and Nedjalka V. Handjieva. "Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana." Phytochemistry 68, no. 9 (2007): 1321–26. http://dx.doi.org/10.1016/j.phytochem.2007.02.014.

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49

TANDON, M., and Y. N. SHUKLA. "ChemInform Abstract: Arundinoside A - A New Spirostane Saponin from Chlorophytum arundinaceum." ChemInform 29, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199825228.

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50

Haladová, Mária, Eva Eisenreichová, Pavel Mučaji, Miloš Buděšínský, and Karel Ubik. "Steroidal Saponins from Lilium candidum L." Collection of Czechoslovak Chemical Communications 63, no. 2 (1998): 205–10. http://dx.doi.org/10.1135/cccc19980205.

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(25S)-3β-{β-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyloxy}spirost-5-en-27-ol and (25R,26R)-3β-{β-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyloxy}-26-methoxyspirost-5-ene were isolated from the ethanolic extract of fresh bulbs and petals of Lilium candidum L. Their structures were derived mainly from NMR and mass spectra.

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