Putrescine, Spermidine, Spermine, and Related Polyamine Alkaloids

Bienz, Stefan; Detterbeck, Richard; Ensch, Corinne; Guggisberg, Armin; Häusermann, Ursula A.; Meisterhans, Christian; Wendt, Barbara; Werner, Christa; Hesse, Manfred

doi:10.1002/chin.200330284

Cited by 3 publications

(10 citation statements)

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“…In species belonging to Arum genus, presence of alkaloids is mentioned but there are no detailed studies on this subject. Bienz et al [38] mentioned about the presence of N 1 ,N 6 -dicoumaroyl-putrescine, N 1 ,N 5 -dicoumaroyl-spermidine and N 1 ,N 10 -dicoumaroyl-spermidine in A. maculatum. Putrescine, spermidine and spermine derivatives that are taken as both endogenously and dietary play a role in wound healing and tumor growth.…”

Section: Lc/ms-ms Resultsmentioning

confidence: 99%

Activity Guided Fractionation of Arum italicum Miller Tubers and the LC/MS-MS Profiles

Ağalar¹,

Çiftçi²,

Göğer³

et al. 2017

Rec. Nat. Prod.

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Abstract:In this study, the polar extract of Arum italicum Miller tubers was fractionated by 'biological activity guided fractionation' method. MCF-7 (human breast adenocarcinoma) and A549 (non-small lung cancer) cancer cell lines were used to screen cytotoxic activity. Possible antiproliferative and apoptotic effects of each subfraction were evaluated by in vitro. As a result, E2 were cytotoxic against A549 cell lines while E3 and E6 showed good cytotoxic activities against both cancer cell lines. These three subfractions showed apoptotic and antiproliferative effects comparable with positive control. The chemical composition of each subfraction was determined by LC/MS-MS. Hydroxycinnamic acid derivatives, lignans and glycosides, hydroxycinnamic acidspermidine conjugates and oxylipins identified in subfractions were major secondary metabolites.

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Section: Lc/ms-ms Resultsmentioning

confidence: 99%

Activity Guided Fractionation of Arum italicum Miller Tubers and the LC/MS-MS Profiles

Ağalar¹,

Çiftçi²,

Göğer³

et al. 2017

Rec. Nat. Prod.

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“…The cleavage was performed following the peptide cleavage procedure reported in [45]. To the dry N 1 -FBz-spermidine-loaded resin (0.15 mmol, 3 4 of the total amount) was added a cleavage solution of TFA/TES/H 2 O (95/2.5/2.5, 5 mL) and shaken for 2 h. Subsequently, the resin was washed with TFA (2 × 5 mL) and the combined filtrates were evaporated in a nitrogen stream nitrogen until only an oily residue was remaining. The crude product was purified by HPLC (see Section 3.1).…”

Section: Cleavage Of Polyamines/oxopolyamines From the Resinmentioning

confidence: 99%

“…Yields were calculated based on the loading levels determined as described in Section 3.2.3. 3 J C,F = 8.2 Hz, C-2,6 FBn), 115.56 (q, 2 J C,F = 21.4 Hz, C-3,5 FBn), 49.34, 46.13, 43.96, 43.88, 43.74, 43.70, 36.19, 23.80, 22.65, 22.49, 22.20.…”

Section: Yields and Analytical Data For Compounds 1-18mentioning

confidence: 99%

“…In mammals, the most common polyamines are putrescine, spermidine and spermine [1], while plants and bacteria additionally contain the diamine cadaverine [2] (Figure 1). In addition to the simple polyamines, secondary metabolite-type natural products originate mostly from N-acylation of simple polyamines and subsequent further structural diversification, which leads to the polyamine alkaloids of plants, bacteria and fungi [3,4], and polyamine toxins, which are present in various species of insects and spiders [5].…”

Section: Introductionmentioning

confidence: 99%

“…NMR (DMSO-d 6 ): δ(ppm) = 165.09 (C-9), 163.79 (d,1 J C,F = 248.1 Hz, C-4 FBz), 157.96 (d, 2 J = 30,.5 Hz, CO TFA), 131.16 (d,4 J C,F = 2.9 Hz, C-1 FBz), 129.75 (d,3 J C,F = 9.0 Hz, C-2,6 FBz), 115 18. (d, 2 J C,F = 21.7 Hz, C-3,5 FBz), 39.25, 29.10, 28.59, 28.50, 27.01, 26.40, 25.78, Signal for 1 × CH 2 is not visible.…”

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confidence: 99%

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Solid-Phase Synthesis of Selectively Mono-Fluorobenz(o)ylated Polyamines as a Basis for the Development of 18F-Labeled Radiotracers

2021

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Polyamines are highly attractive vectors for tumor targeting, particularly with regards to the development of radiolabeled probes for imaging by positron emission (PET) and single-photon emission computed tomography (SPECT). However, the synthesis of selectively functionalized derivatives remains challenging due to the presence of multiple amino groups of similar reactivity. In this work, we established a synthetic methodology for the selective mono-fluorobenz(o)ylation of various biogenic diamines and polyamines as lead compounds for the perspective development of substrate-based radiotracers for targeting polyamine-specific membrane transporters and enzymes such as transglutaminases. For this purpose, the polyamine scaffold was constructed by solid-phase synthesis of the corresponding oxopolyamines and subsequent reduction with BH3/THF. Primary and secondary amino groups were selectively protected using Dde and Boc as protecting groups, respectively, in orientation to previously reported procedures, which enabled the selective introduction of the reporter groups. For example, N1-FBz-spermidine, N4-FBz-spermidine, N8-FBz-spermidine, and N1-FBz-spermine and N4-FBz-spermine (FBz = 4-fluorobenzoyl) were obtained in good yields by this approach. The advantages and disadvantages of this synthetic approach are discussed in detail and its suitability for radiolabeling was demonstrated for the solid-phase synthesis of N1-[18F]FBz-cadaverine.

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Profiling Glucosinolates, Flavonoids, Alkaloids, and Other Secondary Metabolites in Tissues of Azima tetracantha L. (Salvadoraceae)

Bennett

Mellon

Rosa

et al. 2004

J. Agric. Food Chem.

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Azima tetracantha L. (needle bush; bee sting bush; Salvadoraceae) is used as a food and for various herbal medicines in Africa, India, and Madagascar, but there is very little information on the secondary metabolites in this species. High concentrations of N-methoxy-3-indolylmethyl-glucosinolate, a common glucosinolate of Brassica crops such as Brussels sprouts and broccoli, were found in the roots and seeds of A. tetracantha. Lower concentrations were detected in the stems and young leaves. The roots also contained another indole glucosinolate that was provisionally identified, from MS data and comparison with indole glucosinolate standards, as N-hydroxy-3-indolymethyl-glucosinolate. The roots, stems, and leaves contained neoascorbigen (the condensation product of N-methoxy-indole-3-carbinol and ascorbic acid). The seeds of A. tetracantha contained a complex mixture of 26 flavonoids predominantly as glycosides and acyl-glycosides, with traces of aglycones. The core aglycones of these flavonoids were identified as quercetin, isorhamnetin (3'-O-methylquercetin), rhamnetin (7-O-methylquercetin), and rhamnazin (7, 3'-di-O-methylquercetin). No flavonoids or anthocyanins were detected in other tissues, and procyanidins were undetectable. The dimeric piperidine alkaloids azimine, azcarpine, and carpaine were found in all tissues of A. tetracantha.

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Putrescine, Spermidine, Spermine, and Related Polyamine Alkaloids

Cited by 3 publications

References 1 publication

Activity Guided Fractionation of Arum italicum Miller Tubers and the LC/MS-MS Profiles

Activity Guided Fractionation of Arum italicum Miller Tubers and the LC/MS-MS Profiles

Solid-Phase Synthesis of Selectively Mono-Fluorobenz(o)ylated Polyamines as a Basis for the Development of 18F-Labeled Radiotracers

Profiling Glucosinolates, Flavonoids, Alkaloids, and Other Secondary Metabolites in Tissues of Azima tetracantha L. (Salvadoraceae)

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