Macrocyclic Spermine Alkaloids fromVerbascum: Isolation, Structure Elucidation, and Syntheses of the (E/Z)-Isomeric Pairs (S)-Verbasikrine/(S)-Isoverbasikrine and (S)-Verbamekrine/(S)-Isoverbamekrine

Youhnovski, Nikolay; Drandarov, Konstantin; Guggisberg, Armin; Hesse, Manfred

doi:10.1002/(sici)1522-2675(19990804)82:8<1185::aid-hlca1185>3.0.co;2-p

Cited by 14 publications

(4 citation statements)

References 6 publications

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“…Verbascum L. species contain a wide range of compounds, such as glycosides (Klimek, 1996;Skaltsounis et al, 1996;Kalpoutzakis et al, 1999;Elgindi & Mabry, 2000), alkaloids (Youhnovski et al, 1999), and saponins (Hartleb & Seifert, 1994). Members of the family Scrophulariaceae have been reported to contain a group of unusual macrocyclic spermine alkaloids (Seifert et al, 1982;Koblikova et al, 1983).…”

Section: Resultsmentioning

confidence: 97%

Evaluation of Antimicrobial Activity of Some EndemicScrophulariaceae. Members from Turkey

Dülger

Uğurlu

2005

Pharmaceutical Biology

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The methanol extracts obtained from endemic Scrophulariaceae members Verbascum protractum Fenel ex Tchihat., Verbascum bellum Hub.-Mor., Verbascum dalamanicum Hub.-Mor., Scrophularia mersinensis Lall, Scrophularia cryptophila Boiss. & Heldr., Pedicularis olympica Boiss., and Veronica lycica E. Lehm. have been investigated for their antimicrobial activity. Antimicrobial activity was determined with Escherichia coli ATCC 11230, Staphylococcus aureus ATCC 6538P, Klebsiella pneumoniae UC57, Pseudomonas aeruginosa ATCC 27853, Proteus vulgaris ATCC 8427, Bacillus cereus ATCC 7064, Mycobacterium smegmatis CCM 2067, Listeria monocytogenes ATCC 15313, Micrococcus luteus CCM 169, Candida albicans ATCC 10231, Rhodotorula rubra DSM 70403, and Kluyveromyces fragilisATCC 8608 by the disk diffusion method. The extracts of all Scrophulariaceae members used in this study had strong antimicrobial activity against the Gram-positive bacteria and yeast cultures.

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Section: Resultsmentioning

confidence: 97%

Evaluation of Antimicrobial Activity of Some EndemicScrophulariaceae. Members from Turkey

Dülger

Uğurlu

2005

Pharmaceutical Biology

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“…HCHO at room temperature, protoverbine (1) forms quantitatively the corresponding aminal, which was also detected and isolated from the alkaloid mixture by prep. TLC in 0.03% yield and given the name protomethine (2).…”

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confidence: 99%

“…A possible biosynthetic pathway is shown in Scheme 1. By transannular condensation with endogenous HCHO, (S)-protoverbine (1) gives (S)-protomethine (2). An additional acyl group ((E)-cinnamoyl, (E)-4-methoxycinnamoyl, or (E)-3,4-dimethoxycinnamoyl) could be introduced at N(9)), to the N(1),N(13)-protected (S)-protomethine (2), yielding the alkaloids of the verbamethine group ((S)-3a ± f).…”

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confidence: 99%

Protoverbine, the Parent Member of a Class of Macrocyclic Spermine Alkaloids

Guggisberg

Drandarov

Hesse

2000

HCA

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The 17‐membered macrocyclic spermine alkaloids protoverbine ((8S)‐8‐phenyl‐1,5,9,13‐tetraazacycloheptadecan‐6‐one, 1) and its N(9),N(13)‐methylene‐bridged derivative protomethine ((2S)‐2‐phenyl‐1,5,9,14‐tetraazabicyclo[12.3.1]octadecan‐4‐one, 2) were isolated from Verbascum pseudonobile Stoj. et Stef. (Scrophulariaceae) and characterized. The synthesis of their racemates is described. The possible role of (S)‐protoverbine (1) and (S)‐protomethine (2) as precursors in the biogenesis of the whole class of N(1),N(9)‐ and/or N(13)‐substituted alkaloids, the groups of verbamethine ((S)‐3a – f), verbacine ((S)‐4a – f), incasine B′/verdoline ((S)‐5a – f), verbamedine ((S)‐6a – f), and verbascenine ((S)‐7a – f), is discussed.

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“…This information confirmed that the ethanol is a more effective solvent for extraction of antimicrobial substances in V. thapsus. Verbascum L. species contain a wide range of compounds, such as glycosides, alkaloids, and saponins (10)(11)(12)(13)(14). Members of the family Scrophulariaceae have been reported to contain a group of unusual macrocyclic spermine alkaloids (15)(16).…”

Section: Methodsmentioning

confidence: 69%

Methicillin-dirençli Staphylococcus aureus Bakterilerine Karşı Verbascum thapsus Bitkisinin Anti-Staphylococcal Aktivitesi

Dulger¹,

Tütenocakli²,

Dülger³

2017

Konuralp Tıp Dergisi

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Macrocyclic Spermine Alkaloids fromVerbascum: Isolation, Structure Elucidation, and Syntheses of the (E/Z)-Isomeric Pairs (S)-Verbasikrine/(S)-Isoverbasikrine and (S)-Verbamekrine/(S)-Isoverbamekrine

Cited by 14 publications

References 6 publications

Evaluation of Antimicrobial Activity of Some EndemicScrophulariaceae. Members from Turkey

Evaluation of Antimicrobial Activity of Some EndemicScrophulariaceae. Members from Turkey

Protoverbine, the Parent Member of a Class of Macrocyclic Spermine Alkaloids

Methicillin-dirençli Staphylococcus aureus Bakterilerine Karşı Verbascum thapsus Bitkisinin Anti-Staphylococcal Aktivitesi

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