New Steroidal Alkaloids from Rhizomes of Veratrum album

Atta-ur-Rahman, _; Ali, Rahmat; Choudhary, M. Iqbal; Şener, Bilge; Turkoz, Songul

doi:10.1021/np50083a002

Cited by 24 publications

(10 citation statements)

References 7 publications

(11 reference statements)

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“…23 Later on, two minor steroidal alkaloids, verussurine 6 and verabenzoamine 7, were isolated from the same source. The former structure was assigned to be 7-O-acetyl-15-O-(2methylbutyroyl)-3-O-veratroylgermine, while the latter structure, previously determined as 7-O-acetyl-15-O-(2-methylbutyroyl)-3-O-veratroylgermine, 24 was revised to 15-O-(2-methylbutyroyl)-3-O-veratroylgermine by analysis of extensive spectral data. 25 Extraction of the rhizomes of V. album, collected in Turkey, afforded the new compound neojerminalanine 8, whose structure was established on the basis of spectroscopic investigation; stereochemical assignments at the various asymmetric centers were based on chemical shift comparisons with those of the known Veratrum alkaloid neojermerine.…”

Section: Cevanine Typementioning

confidence: 99%

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Chemistry, bioactivity and geographical diversity of steroidal alkaloids from the Liliaceae family

Jiang

2006

Nat. Prod. Rep.

182

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Plants belonging to the Liliaceae family have been the topic of research in many phytochemical and pharmacological laboratories because they contain structurally complex and biologically fascinating steroidal alkaloids. This review, citing 153 references, summarises the chemistry, bioactivity and geographical diversity of steroidal alkaloids isolated from Veratrum and Fritillaria species, so as to illustrate the chemo-diversity and biological significance of these alkaloids, along with their geographical distribution where this is discernible.

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Section: Cevanine Typementioning

confidence: 99%

“…80 Further chemical investigation on the same species led to the isolation of two new steroidal alkaloids, viz. jervinone 74 24 and 1-hydroxy-5,6-dihydrojervine 75. 81 The species V. patulum, indigenous to Liaoning Province, China, furnished a new steroidal compound, verapatuline 76.…”

Section: Jervine Typementioning

confidence: 99%

Chemistry, bioactivity and geographical diversity of steroidal alkaloids from the Liliaceae family

Jiang

2006

Nat. Prod. Rep.

182

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“…The chloroform partition (30 g) was subjected to chromatography on a silica gel column eluting with gradient mixtures of CHCl 3 and MeOH (0 to 100% MeOH) as eluent. Seventeen cevanine‐type steroidal alkaloids were eventually purified and identified as protoveratrine A, deacetyl protoveratrine A, dideacetyl protoveratrine A, xinganveratrine, germinalinine, gerbudin, germindine, germerin, stenophylline A, germanidin, macckinine, germanitrine, verussurine, verabenzoamine, angeloylzygadenin, veratroylzygadenin and zygadenin based on chemical reactions, spectral analysis ( 1 HNMR, 13 C‐NMR, 2D NMR, MS, UV and IR) and by comparison of their spectral data with those reported previously in the literature 13–25. The purified compounds were kept at 4°C.…”

Section: Methodsmentioning

confidence: 99%

Characterization and identification of steroidal alkaloids in the Chinese herb Veratrum nigrum L. by high‐performance liquid chromatography/electrospray ionization with multi‐stage mass spectrometry

Tang

Liu

et al. 2007

Rapid Comm Mass Spectrometry

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Electrospray ionization multi-stage mass spectrometry (ESI-MS(n)) was performed to study the fragmentation behaviour of seventeen steroidal alkaloids (4 protoverine-type alkaloids, 10 germine-type alkaloids and 3 zygadenin-type alkaloids) from the Chinese herb Veratrum nigrum L. The MS(n) spectra of the [M+H](+) ions for steroidal alkaloids provided a wealth of structural information on the substituted groups. In positive ion mode, the three types of alkaloids showed very different characteristic ions: m/z 436 or 418 for protoverine-type alkaloids; m/z 438, 420 or 402 for germine-type alkaloids; m/z 440 or 422 for zygadenin-type alkaloids. These fragments were used to deduce their mass spectral fragmentation mechanisms. Furthermore, the primary compounds in methanolic extracts of the herb of Veratrum nigrum L. were investigated by using liquid chromatography (LC)/ESI-MS(n). As a result, 21 steroidal alkaloids (5 protoverine-type alkaloids, 14 germine-type alkaloids and 2 zygadenin-type alkaloids) were selectively identified from 27 determined peaks. Eleven compounds were unambiguously identified by comparing with standard compounds and ten compounds were tentatively identified or deduced according to their MS(n) data. Two of these compounds (xingangermine and deacetyl xinganveratrine) were found to be novel steroidal alkaloids. In addition, the chemical structures of two pairs of steroidal alkaloid isomers were deduced by comparing their fragment ions. Given the important structural information of known and unknown steroidal alkaloids in crude herbal extracts, this study is useful for identifying these types of steroidal alkaloids in crude materials rapidly and selectively.

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“…Our research for bioactive substances from V. taliense now led to the isolation of three new alkaloids (Fig. 1), 3-Oacetylveralkamine (1), veralkamine 3-(b-d-glucopyranoside) (2), and 6,7-epoxyverdine (3), together with five known alkaloids, veramitaline [6], veralkamine (4), angeloylzygadenine [7], veratroylzygadenine [8], and veramiline 3-(b-d-glucopyranoside) [9]. Moreover, the NMR data of compound 4 are given here for the first time.…”

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confidence: 99%

Three New Pregnane Alkaloids from Veratrum taliense

Sun

Chen

Zhou

et al. 2012

Helvetica Chimica Acta

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Three new alkaloids, 3‐O‐acetylveralkamine (1), veralkamine 3‐(β‐D‐glucopyranoside) (2), and 6,7‐epoxyverdine (3), together with five known alkaloids, veramitaline, veralkamine (4), angeloylzygadenine, veratroylzygadenine, and veramiline 3‐(β‐D‐glucopyranoside), were isolated from the whole plants of Veratrum taliense. Their structures were elucidated on the basis of spectroscopic analysis, and the NMR data of veralkamine (4) are given for the first time. In addition, the cytotoxic activities of all isolated compounds, except for veramitaline, were tested.

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New Steroidal Alkaloids from Rhizomes of Veratrum album

Cited by 24 publications

References 7 publications

Chemistry, bioactivity and geographical diversity of steroidal alkaloids from the Liliaceae family

Chemistry, bioactivity and geographical diversity of steroidal alkaloids from the Liliaceae family

Characterization and identification of steroidal alkaloids in the Chinese herb Veratrum nigrum L. by high‐performance liquid chromatography/electrospray ionization with multi‐stage mass spectrometry

Three New Pregnane Alkaloids from Veratrum taliense

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