Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides

Tobari, Akihiko; Teshima, Mutsumi; Koyanagi, Junich; Kawase, Masami; Miyamae, Hiroshi; Yoza, Kenji; Takasaki, Akihiko; Nagamura, Yoich; Saito, Setsuo

doi:10.1016/s0223-5234(00)00151-3

Cited by 51 publications

(31 citation statements)

References 23 publications

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“…In this case, the methyl group at C-20 is epimerized (20R to 20S) and, at the same time, the configuration at C-22 changes from S to R. In contrast to the "iso" reaction, this isomerisation is observed on very mild acid treatment (dilute acetic acid). Ziegler et al [104] evaluated the evidence for this result and provided a rationale that has found support in more recent work [105]. In essence, the isomerization occurs via the seco-compound that forms the kinetically favored, but thermodynamically unfavored, product (20R) in the presence of a weak acid (Figure 14).…”

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confidence: 91%

Steroidal Glycoalkaloids: Isolation, Structure, Analysis, and Biosynthesis

Ghisalberti

2006

Natural Product Communications

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In recent years, the steroidal glycoalkaloids have emerged as an important class of bioactive compounds. Their occurrence in a number of foods and their diverse biological activities has encouraged the development of more efficient procedures for their isolation, purification and analysis, and more sensitive methods of detection and structure determination. This review is mainly concerned with new approaches for the characterization of these metabolites. The formation of artifacts of isolation and purification is discussed. The limited information on their biosynthesis is summarized.

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confidence: 91%

Steroidal Glycoalkaloids: Isolation, Structure, Analysis, and Biosynthesis

Ghisalberti

2006

Natural Product Communications

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“…Rhizoma Anemarrhenae (RA), known as 'zhimu' in China, which is listed in the Chinese Pharmacopoeia, is used to remove heat, quench fire, promote the production of body fluid (China Pharmacopoeia Committee, 2000; Deng et al, 2005), and it has also been found to have antimicrobial activity, decrease the blood glucose level, inhibit platelet aggregation and carcinoma development, decrease radiation injury, and act as an anti-dementia agent (Lee et al, 2010;Nakashima et al, 1993;Tobari et al, 2000;Kang et al, 2011). However, it has been reported that the pharmacological effects of RA are closely associated with processing methods, and different processing methods result in different pharmacological effects.…”

Section: Introductionmentioning

confidence: 99%

Determination of the chemical constituents of the different processed products of Anemarrhena asphodeloides Rhizomes by high‐performance liquid chromatography quadrupole time‐of‐flight mass spectrometry

Peng

Zhao

Lin

et al. 2015

Biomedical Chromatography

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In this work, high-performance liquid chromatography (HPLC) coupled with a hybrid quadrupole time of-flight mass spectrometry (Q-TOF-MS/MS) was used to study chemical compositions of different processed products of Rhizoma Anemarrhenae (RA). A Grace Alltima(TM) C18 column (250 × 4.6 mm, 5 µm) was used for separation. Mobile phase consisted of 0.1% formic acid and acetonitrile, using gradient elution. ESI-MS data was acquired in both positive and negative mode. The experiment was established on the basis of a series of reference substances (two xanthone and seven saponins) to qualitatively identify the chemical compounds of different processed products of RA by MS analysis. There was no difference in the type of chemical constituents between different processed products of RA. A total of 25 compounds were identified, including four xanthones, 21 steroidal saponins and eight pairs of isomers.

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“…Additionally, the chemical shifts and coupling constants of H-26a (δ 3.64, d, J = 10.8 Hz) and H-26b (δ 3.69, d, J = 10.8 Hz) on the F ring of 1 were different from those (δ 3.36, d, J = 10.8 Hz for H-26a; δ 4.06, d, J = 10.8 Hz for H-26b) on the F ring of 7. The signals of both protons at the 26 position of 1 closely appeared at δ 3.64-3.69, different from those of 7, which indicates that compound 1 has a different F-ring structure [20]. The phase-sensitive NOESY spectrum provided certain information for the stereostructure assignments.…”

Section: Resultsmentioning

confidence: 97%