Chuanbeinone, a novel D/E -(22R,25S)-5α-cevanine alkaloid from chinese herbal drug, chuan-bei-mu
Chuanbeinone: D/E -(22R, 25S)-20-deoxy-5α-cevanine-3β-ol-6-on: was isolated from chinese herbal drug, c̈huan-bei-mü (from some subspecies of Franch.
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Cirrhosinones A-H, 24-hydroxy cevanine-type alkaloids from Fritillaria cirrhosa
2022, PhytochemistryCitation Excerpt :This was also supported by the chemical shifts of H-17 in the known compounds (9–14). In addition, the correlations between the relative configurations of 3-OH, 7-OH, 22-C, 24-OH, and 25-Me and the 1H NMR and 13C NMR data were also summarized (Table 3) during detailed assignments of the NMR data of compounds 1–14 and a literature survey (Lin et al., 1995; Lee et al., 1988; Wang et al., 2021; Hu et al., 2018; Kaneko et al., 1985, 1986). Microglia are important immune cells in the brain, and their activation has been implicated in a number of neurodegenerative diseases and different types of brain injury (Yang et al., 2018).
The Veratrum and Solanum Alkaloids
2015, Alkaloids: Chemistry and BiologyCitation Excerpt :Later, two more representatives with this stereochemistry (i.e., with a cis-D/E-ring connection), hupehemonoside (44, see Figure 5)61 and hupeheninate (45, see Figure 5),62 were described. Also, chuanbeinone (46, see Figure 5),63 delafrine (47, see Figure 5), and delafrinone (48, see Figure 5)64 were isolated from F. delavayi. Fritillaria ussuriensis was thoroughly investigated and a total of eight new cevanine-type alkaloids were discovered between 1982 and 1990: pingbeimine A (49, see Figure 5),65 pingbeimine B (50, see Figure 5),66 and pingbeimine C (51, see Figure 5)67 as well as 3-β-d-petilinineglucoside (52, see Figure 5)68 were isolated in the group of Xu.
Antitussive, expectorant and anti-inflammatory activities of four alkaloids isolated from Bulbus of Fritillaria wabuensis
2012, Journal of EthnopharmacologyCitation Excerpt :13C NMR (50 MHz, CDCl3), δ: 37.4(C-1), 30.4(C-2), 70.8(C-3), 30.4(C-4), 56.4(C-5), 210.8(C-6, CO), 46.8(C-7), 42.0(C-8), 54.7(C-9), 38.1(C-10), 29.8(C-11), 46.5(C-12), 34.1(C-13), 40.1(C-14), 26.7(C-15), 18.7(C-16), 39.0(C-17), 59.7(C-18), 12.6(C-19), 72.0(C-20), 22.3(C-21), 63.4(C-22), 19.5(C-23), 29.4(C-24), 27.7(C-25), 61.3(C-26), 17.2(C-27). The melting point, 1H NMR, 13C NMR data were consistent with those reported in the literature (Itô et al., 1976; Kaneko et al., 1986; Zhang et al., 1998; Chen et al., 2004). Imperialine-β-N-oxide, m.p., 231–234 °C, 1H NMR (200 MHz, CDCl3), δ: 0.81(3H, s, 19-CH3), 1.12(3H, s, 21-CH3), 3.53(3-αH), 1.46(d, 27-CH3).
Antitussive, expectorant and anti-inflammatory alkaloids from Bulbus Fritillariae Cirrhosae
2011, FitoterapiaCitation Excerpt :Alkaloids isolated from the BFC were identified based on spectral data (1H-, 13C-NMR, DEPT, and mass spectra, etc.). Their structures were determined by comparing the sample's spectral data with those reported in the literature [7–10]. After column chromatography, we obtained imperialine (I), chuanbeinone (II), verticinone (III), and verticine (IV) Fig. 1.
Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry
2010, Journal of Chromatography ACitation Excerpt :Many species of Fritillaria were traditionally used as herbal remedies in Japanese, Turkish, Pakistani and south-east Asian folk medicines [1–3], while bulbs of many Fritillaria species growing in China have been used as antitussive and expectorant herbs using the Chinese name “Beimu” in traditional Chinese medicine (TCM) for thousands of years [4]. Based on various chemical and pharmacological studies, steroidal alkaloids from Fritillaria species (Fritillaria alkaloids, FAs), which including verticine, verticinone, peimisine, ebeiedine, ebeiedinone, hupehenine, imperialine, puqietinone etc., have been demonstrated as the major bioactive ingredients in “Beimu” [5–11]. And they commonly possess various biological activities, such as antihypertensive [5,6], anticholinergic [7–9], antitumour [10], antiasthmatic and antitussive activities [10,11].