Distinction of Absolute Configuration at C-22 of C-23-Hydroxyspirostane and C-23-Hydroxyspirosolane Glycosides

Matsushita, Sayaka; Yanai, Yoshihiro; Fusyuku, Asami; Ikeda, Tsuyoshi; Ono, M.; Nohara, Toshihiro

doi:10.1248/cpb.55.1079

Cited by 11 publications

(6 citation statements)

References 7 publications

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“…Moreover, the NOESY cross peak δ H 1.74 (Agly H-25)/δ H 3.80 (Agly H-23), and the HSQC correlation between this latter proton and the deshielded C-23 at δ C 66.9, indicated a OH group at C-23 in its equatorial position (S configuration at C-23). From these results and by comparison with spectral data reported in the literature, the aglycone of 1 was identified as (23S, 25R)-spirost-5-ene-3β, 23-diol (isoplexigenin B) [16,17]. The 1 H NMR spectrum of 1 displayed signals for four anomeric protons at δ H 4.85 (d, J = 5.96 Hz), 5.05 (d, J = 7.6 Hz), 5.81 (s) and 6.19 (s) ( Table 1), which gave correlations in the HSQC spectrum with four anomeric carbon signals at δ C 99.8, 106.9, 101.1 and 101.7, respectively, indicating the presence of four sugar units.…”

Section: Resultsmentioning

confidence: 62%

Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: Confirmation of their synonymy

et al. 2012

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Section: Resultsmentioning

confidence: 62%

Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: Confirmation of their synonymy

et al. 2012

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“…In addition, soladulcidine (22 R , 25 R ) has a stereoisomer, tomatidine (22 S , 25 S ), the aglycone of α-tomatine found in the stems and leaves of tomato plants. The 13 C-NMR peak at 33.73 ppm (C23) and 45.87 ppm (C26) further confirmed that the aglycone of 5,6-dihydrosolasonine is soladulcidine [21].…”

Section: Resultsmentioning

confidence: 89%

Comparative Study of the Chemical Constituents and Bioactivities of the Extracts from Fruits, Leaves and Root Barks of Lycium barbarum

et al. 2019

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The fruits, leaves and root barks of L. barbarum plant are widely used as functional foods and as ingredients in traditional Chinese prescriptions and patent medicines. They are considered to have different pharmacological activities and health benefits because of their diverse constituents. Here, the chemical constituents of the extracts from fruits, leaves and root barks of L. barbarum were compared by ultra-high performance liquid chromatography coupled with high resolution mass spectrometry (UPLC-HR-MS). A total of 131 compounds were identified and seven of them were quantified. Among them, 98, 28 and 35 constituents were detected in fruits, leaves and root barks respectively. Dicaffeoylspermidine/spermine derivatives were the most detected compounds (74/131); among them, dicaffeoylspermine isomers and propionyl-dicaffeoylspermidine were found in root barks in very large amounts (e.g., kukoamine B = 10.90 mg/g dry powder); dicaffeoyl-spermidine isomers were detected in fruits/leaves in a high amount, and many of their glycosylated derivatives were mainly detected in fruits. In addition, six saponins from L. barbarum fruits were reported for the first time, and 5,6-dihydrosolasonine was reported for the first time in plants. The activity assays showed that the root bark extract possessed the strongest antioxidative activity and cytotoxicity, which was presumed due to the large amount of dicaffeoylspermine/spermidines in root barks. Fourteen potential bioactive components from fruits were identified by a target cell-based screening method. These results will help to understand the different biological activities of these three parts of L. barbarum plant and will benefit the discovery of new functional components.

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“…22,23 In the case of 22-β-O-spirostanol, the H 3 -21 absorbs frequency at δ H 1.52−1.54, H-16 at δ H 5.18−5.20, and C-20 at δ C 43.0−44.1. 23,24 Compound 1 exhibited a chemical shift of H 3 -21 at δ H 1.11, H-16 at δ H 4.46 and C-20 at δ C 39.6, thus suggesting the 22-α-O-configuration for the sapogenol. By virtue of that, the aglycone of compound 1 aglycone was characterized as (22S,23R,25S)-3β,6α,23-trihydroxy-5α-spirostane.…”

Section: ■ Results and Discussionmentioning

confidence: 98%

New Polyhydroxylated Steroidal Saponins from Solanum paniculatum L. Leaf Alcohol Tincture with Antibacterial Activity against Oral Pathogens

Valerino-Díaz

Turro

Vilegas

et al. 2018

J. Agric. Food Chem.

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Solanum paniculatum L. is widely used in Brazilian folk medicine for the treatment of liver and gastrointestinal disorders as well as for culinary purposes and beverage production. Fractionation of hydroalcoholic [ethanol (EtOH) 70%] tincture from S. paniculatum leaves led to the isolation of six new spirostanic saponins which included 6- O-α-l-rhamnopyranosyl-(1''→3')-β-d-quinovopyranosyl-(22 S,23 R,25 S)-3β,6α,23-trihydroxy-5α-spirostane (1), 6- O-β-d-xylopyranosyl-(1''→3')-β-d-quinovopyranosyl-(22 S,23 R,25 R)-3β,6α,23-trihydroxy-5α-spirostane (4), 3- O-α-l-rhamnopyranosyl-(1''→3')-β-d-quinovopyranosyl-(22 S,23 S,25 R)-3β,6α,23-trihydroxy-5α-spirostane (5), 3- O-β-d-xylopyranosyl-(1''→3')-β-d-quinovopyranosyl-(22 S,23 S,25 R)-3β,6α,23-trihydroxy-5α-spirostane (6), 6- O-α-l-rhamnopyranosyl-(1''→3')-β-d-quinovopyranosyl-(22 S,25 S)-1β,3β,6α-trihydroxy-5α-spirostane (7), and 6- O-β-d-xylopyranosyl-(1''→3')-β-d-quinovopyranosyl-(22 S,25 S)-3β,4β,6α-trihydroxy-5α-spirostane (8) together with two known spirostanic saponins (2, 3). The structures of these compounds were determined by one-dimensional (1D) and two-dimensional (2D) NMR experiments in addition to high-resolution electrospray ionization mass spectrometry (HRESIMS) analyses. The 70% alcohol tincture, used as phytomedicine, exhibited promising activities against oral pathogens, including, Steptococcus sanguinis, St. oralis, St. mutans, St. mitis, and Lactobacillus casei with minimal inhibitory concentration (MIC) values ranging from 6.25 to 50 μg/mL. The saponin fraction, nonetheless, showed lower activity against all the strains tested (from 100 to >400 μg/mL).

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Distinction of Absolute Configuration at C-22 of C-23-Hydroxyspirostane and C-23-Hydroxyspirosolane Glycosides

Abstract: It has been revealed that the absolute configurations at C-22 of 23-hydroxyspirostane and 23-hydroxyspirosolane could be unambiguouly judged by the 1 H-and 13 C-NMR spectroscopies.

Cited by 11 publications

References 7 publications

Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: Confirmation of their synonymy

Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: Confirmation of their synonymy

Comparative Study of the Chemical Constituents and Bioactivities of the Extracts from Fruits, Leaves and Root Barks of Lycium barbarum

New Polyhydroxylated Steroidal Saponins from Solanum paniculatum L. Leaf Alcohol Tincture with Antibacterial Activity against Oral Pathogens

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