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Spiralosides A-C, Three New C27-Steroidal Glycoalkaloids from the Fruits of Solanum spirale.

Li D, Zhao YL, Qin XJ, Liu L, Yang XW, Chen YY, Wang B, Wei X, Liu YP, Luo XD - Nat Prod Bioprospect (2016)

Bottom Line: Three new C27-steroidal glycoalkaloids, spiralosides A-C (1-3), were obtained from the total alkaloids of Solanum spirale by chromatographic methods.On the basis of spectroscopic evidence, spiralosides A-C were elucidated as (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl (1), (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (2), (22R,25S)-22,26-epiminocholest-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (3), respectively.The total alkaloids of S. spirale have been screened for their antitussive and expectorant effects in intact animal model.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China.

ABSTRACT
Three new C27-steroidal glycoalkaloids, spiralosides A-C (1-3), were obtained from the total alkaloids of Solanum spirale by chromatographic methods. On the basis of spectroscopic evidence, spiralosides A-C were elucidated as (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl (1), (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (2), (22R,25S)-22,26-epiminocholest-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (3), respectively. The total alkaloids of S. spirale have been screened for their antitussive and expectorant effects in intact animal model.

No MeSH data available.


Related in: MedlinePlus

Key ROESY () correlations of 1
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Fig3: Key ROESY () correlations of 1

Mentions: The ROESY correlations of Me-19/H-4b/H-2b/H-11b/H-8, H-3/H-2a, and H-11a/H-9/H-14 indicated the α-orientation of H-3, H-9 and H-14, β-orientation of H-8 (Fig. 3). ROESY corrections of Me-18 with H-20, of H-20 with H-16 positioned α-orientation for both Me-21 and OH-16, β-orientation for H-20. ROESY corrections of Me-18 with H-20 also indicated a 17β-side chain, as well as on the biogenetical derivation of C-27 steroidal alkaloids [21]. And a missing effect between H-17 and H-20 displayed, at least approximately, antiperiplanar positions of H-17 and H-20. The coupling constant 3J17,20 = 12.4 Hz was in agree with this assumption [7]. Furthermore, the coupling constant 3J20,22 = 6.0 Hz suggested that they should be on the same side and the C-22 of configuration is R [22]. Besides, ROESY corrections of H-22 with H-23b, of Me-27 with H-23a indicated H-22 and H-25 both are axial bonds and the C-25 of configuration is S. So compound 1 was determined as (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl, named spiraloside A. All of the signals of 1H- and 13C-NMR were assigned by HSQC, HMBC, 1H-1H COSY and ROESY spectra (Table 1).Fig. 3


Spiralosides A-C, Three New C27-Steroidal Glycoalkaloids from the Fruits of Solanum spirale.

Li D, Zhao YL, Qin XJ, Liu L, Yang XW, Chen YY, Wang B, Wei X, Liu YP, Luo XD - Nat Prod Bioprospect (2016)

Key ROESY () correlations of 1
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4940254&req=5

Fig3: Key ROESY () correlations of 1
Mentions: The ROESY correlations of Me-19/H-4b/H-2b/H-11b/H-8, H-3/H-2a, and H-11a/H-9/H-14 indicated the α-orientation of H-3, H-9 and H-14, β-orientation of H-8 (Fig. 3). ROESY corrections of Me-18 with H-20, of H-20 with H-16 positioned α-orientation for both Me-21 and OH-16, β-orientation for H-20. ROESY corrections of Me-18 with H-20 also indicated a 17β-side chain, as well as on the biogenetical derivation of C-27 steroidal alkaloids [21]. And a missing effect between H-17 and H-20 displayed, at least approximately, antiperiplanar positions of H-17 and H-20. The coupling constant 3J17,20 = 12.4 Hz was in agree with this assumption [7]. Furthermore, the coupling constant 3J20,22 = 6.0 Hz suggested that they should be on the same side and the C-22 of configuration is R [22]. Besides, ROESY corrections of H-22 with H-23b, of Me-27 with H-23a indicated H-22 and H-25 both are axial bonds and the C-25 of configuration is S. So compound 1 was determined as (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl, named spiraloside A. All of the signals of 1H- and 13C-NMR were assigned by HSQC, HMBC, 1H-1H COSY and ROESY spectra (Table 1).Fig. 3

Bottom Line: Three new C27-steroidal glycoalkaloids, spiralosides A-C (1-3), were obtained from the total alkaloids of Solanum spirale by chromatographic methods.On the basis of spectroscopic evidence, spiralosides A-C were elucidated as (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl (1), (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (2), (22R,25S)-22,26-epiminocholest-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (3), respectively.The total alkaloids of S. spirale have been screened for their antitussive and expectorant effects in intact animal model.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China.

ABSTRACT
Three new C27-steroidal glycoalkaloids, spiralosides A-C (1-3), were obtained from the total alkaloids of Solanum spirale by chromatographic methods. On the basis of spectroscopic evidence, spiralosides A-C were elucidated as (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl (1), (22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (2), (22R,25S)-22,26-epiminocholest-3β,16α-diol-N-acetyl-3-O-β-D-glucopyranosyl (3), respectively. The total alkaloids of S. spirale have been screened for their antitussive and expectorant effects in intact animal model.

No MeSH data available.


Related in: MedlinePlus