Pyrrolo- and pyridoazepine alkaloids as chemical markers in Stemona species

Schinnerl, Johann; Brem, Brigitte; But, Paul Pui‐Hay; Vajrodaya, Srunya; Hofer, Otmar; Greger, Harald

doi:10.1016/j.phytochem.2007.03.002

Cited by 44 publications

(100 citation statements)

References 25 publications

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“…[1,7] Stemona alkaloids constitute a unique chemical feature of the family Stemonaceae and cannot be detected in any other plant families thus far. [1,2] Classification of Stemona alkaloids based on biosynthetic considerations confirms three skeleton types i.e.…”

Section: Resultsmentioning

confidence: 99%

“…[1] Stichoneurine group contains stichoneurine-and croomine-type alkaloids while protostemonine group contains protostemonine-type alkaloids. [1,7] Potent insect toxicity of Stemona plants is attributed to the derivatives of protostemonine-type alkaloids, especially the stemofoline derivatives, [1,8,9] whereas stichoneurine-type alkaloids possess only a remarkable insect repellance. [8] In contrast, stichoneurine-and croomine-type alkaloids were reported to be associated with antitussive activity.…”

Section: Resultsmentioning

confidence: 99%

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Microscopic Characterization as a Tool for Separation of Stemona Groups

Kongkiatpaiboon¹,

Keeratinijakal²,

Gritsanapan³

2010

Pharmacognosy Journal

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Introduction: Stemona plants have been traditionally used as an insecticide, scabicide and pediculocide, and for the treatment of skin and respiratory diseases. Stemona can be separated into two groups according to their morphological characters and bioactive components i.e. stichoneurine and protostemonine groups. Protostemonine group contains alkaloids that possess potent insecticidal activity while stichoneurine group accumulates alkaloids with antitussive activity. In Thailand, a vernacular name "Non Tai Yak" refers to the roots of different species of Stemona, making it confusing to discern different species. The purposes of this study are to investigate the microscopic characteristics of the roots of seven species of Stemona growing in Thailand and to distinguish and identify these groups of Stemona. Methods: Cross-sectional histology of fresh root samples and powdered drug characteristics of 7 species of Stemona were studied under a microscope. Results: The roots of Stemona in the stichoneurine group (S. tuberosa and S. phyllantha) contained a non-lignified large pith while the roots of protostemonine group (S. burkillii, S. cochinchinensis, S. collinsiae, S. curtisii and S. kerrii) had a small lignified one. The powder of stichoneurine group contained numerous thin-walled parenchyma, but only few thick-walled parenchyma and lignified fibers and vessels were present. In contrast, thick-walled parenchyma and lignified fibers and vessels were frequently found in the powdered roots of protostemonine Stemona. These characteristics could be used to discern between Stemona in the stichoneurine and protostemonine groups. Conclusions: The microscopic characterizations can be used as a primary tool to categorize and separate 2 main Stemona groups.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Microscopic Characterization as a Tool for Separation of Stemona Groups

Kongkiatpaiboon¹,

Keeratinijakal²,

Gritsanapan³

2010

Pharmacognosy Journal

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“…The stereoisomers of tuberostemonine such as tuberostemonine A to N, which have differences in their relative configurations, have been identified as new constituents of S. tuberosa in its previous phytochemical studies. 3,7,9,11 In the present study, a new tuberostemonine, (2S*,7aR*,8R*,8aS*,11S*,11aS*,11bR*,11cS*) (Figure 1) was isolated from the roots of S. tuberosa. The structure elucidation of compound 1 is described herein.…”

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confidence: 64%

“…[2][3][4] There have been several reports that S. tuberosa containes stichoneurine-and croomine-types alkaloids such as tuberostemonine, neotuberostemonine, and stemoninine, while non-tuberosa group contains protostemonine type alkaloids.…”

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confidence: 99%

Tuberostemonine O from the Roots of Stemona tuberosa

Kil¹,

Han²,

Seo³

2014

Bulletin of the Korean Chemical Society

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“…One class of compounds, not only outstanding due to its pharmacological profile but also due to complex and unusual molecular structures, is that of the Stemona alkaloids [2,3,9,10]. More than 100 derivatives have been identified, all of them bearing a tricyclic pyrrolo-or pyrido[1,2-a]azepine backbone [2,3,10] unrealized in any other plant family.…”

Section: Introductionmentioning

confidence: 99%

Nonaqueous capillary electrophoresis‐electrospray ionization‐ion trap‐mass spectrometry analysis of pyrrolo‐ and pyrido[1,2‐a]azepine alkaloids in Stemona

et al. 2008

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Stemona alkaloids represent an outstanding class of natural compounds due to their pharmacological profile and their complex and unusual molecular structures. The aim of this study was the development of the first CE method for the separation, identification and quantification of these pyrrolo- and pyrido[1,2-a]azepine derivatives in three Stemona species. The best results were obtained with a NACE-ESI-IT-MS method, utilizing an electrolyte of 50 mM ammonium acetate, 1 M acetic acid and 10% methanol in ACN and a separation voltage of 30 kV. Samples were injected voltage-assisted with 20 kV for 1 s. Isopropanol:water (1:1) was used as ESI sheath liquid at a flow rate of 3 microL/min. The assay was applied for the qualitative profiling of Stemona alkaloids in S. curtisii, S. collinsae and S. tuberosa. For unambiguous peak assignment of more than forty unidentified alkaloids MS/MS experiments were performed and fragmentation patterns studied. Subsequently the method was validated for the quantitative determination of four selected derivatives (RSD inter- and intraday <6%, LODs <7.5 microg/mL, LOQs <25.0 microg/mL, for all analytes, recovery rates >98.9%) in several Stemona sp. extracts.

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Pyrrolo- and pyridoazepine alkaloids as chemical markers in Stemona species

Cited by 44 publications

References 25 publications

Microscopic Characterization as a Tool for Separation of Stemona Groups

Microscopic Characterization as a Tool for Separation of Stemona Groups

Tuberostemonine O from the Roots of Stemona tuberosa

Nonaqueous capillary electrophoresis‐electrospray ionization‐ion trap‐mass spectrometry analysis of pyrrolo‐ and pyrido[1,2‐a]azepine alkaloids in Stemona

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