N1,N5,N10-Tris(4-hydroxycinnamoyl)spermidines fromMicrodesmis keayana Roots

Zamblé, Alexis; Şahpaz, Sevser; Hennebelle, Thierry; Carato, Pascal; Bailleul, François

doi:10.1002/cbdv.200690107

Cited by 32 publications

(29 citation statements)

References 16 publications

(19 reference statements)

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“…We could identify doublets at 6.45 and 7.70 ppm with 3 J HH 16 Hz in 1:1 ratio, which correlate in the COSY spectrum, and which we assign as trans-ethylenic peaks by comparision with literature reports (Zamble et al, 2006(Zamble et al, , 2007 for tris (4-hydroxycinnamoyl)spermidines. We predict, based on literature and symmetry considerations, that the presence of only two 16-Hz doublets favors the assignment as N 1 -((49-O-glycosyl)-sinapoyl),N 8 -sinapoylspermidine and 1 H NMR predictions (see Supplemental Figure 1 online) using both HNMR (ACD Labs) and ChemNMR (ChemDraw Ultra) to strengthen this prediction.…”

Section: Nmr Spectroscopysupporting

confidence: 74%

“…In addition to their occurrence in floral organs, HCAAs accumulate in seeds and sometimes also in roots. Diferuloylputrescine, diferuloylspermidine, and feruloyltyramine have been shown to accumulate in substantial quantities in rice (Oryza sativa) seeds (Bonneau et al, 1994), tyramine-derived HCAAs are present in tobacco (Nicotiana tabacum) roots (Hagel and Facchini, 2005) and also at high levels in the bark of Lycium chinense roots (Lee et al, 2004), and three tris-(4-hydroxycinnamoyl) spermidines are present in Microdesmis keayana roots (Zamble et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

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A Novel Polyamine Acyltransferase Responsible for the Accumulation of Spermidine Conjugates in Arabidopsis Seed

et al. 2009

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Hydroxycinnamic acid amides are a class of secondary metabolites distributed widely in plants. We have identified two sinapoyl spermidine derivatives, N-((4′-O-glycosyl)-sinapoyl),N′-sinapoylspermidine and N,N′-disinapoylspermidine, which comprise the two major polyamine conjugates that accumulate in Arabidopsis thaliana seed. Using metabolic profiling of knockout mutants to elucidate the functions of members of the BAHD acyltransferase family in Arabidopsis, we have also identified two genes encoding spermidine disinapoyl transferase (SDT) and spermidine dicoumaroyl transferase (SCT) activities. At2g23510, which is expressed mainly in seeds, encodes a spermidine sinapoyl CoA acyltransferase (SDT) that is required for the production of disinapoyl spermidine and its glucoside in Arabidopsis seed. The structurally related BAHD enzyme encoded by At2g25150 is expressed specifically in roots and has spermidine coumaroyl CoA acyltransferase (SCT) activity both in vitro and in vivo.

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Section: Nmr Spectroscopysupporting

confidence: 74%

Section: Introductionmentioning

confidence: 99%

A Novel Polyamine Acyltransferase Responsible for the Accumulation of Spermidine Conjugates in Arabidopsis Seed

et al. 2009

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“…Small quantities of diferuloylputrescine, diferuloylspermidine, and feruloyltyramine were found in rice (Oryza sativa) seeds (Bonneau et al 1994). Three tris-(4-hydroxycinnamoyl) spermidines were detected in Microdesmiskeayana roots and present at high levels in Lyciumchinense roots (Lee et al 2004;Zamble et al 2006).…”

Section: Introductionmentioning

confidence: 97%

Biosynthesis, physiology, and functions of hydroxycinnamic acid amides in plants

Macoy

Kim

Lee

et al. 2015

Plant Biotechnol Rep

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The study of hydroxycinnamic acid amides (HCAAs) which are a group of secondary metabolites has been an interesting one and has become one of the important researches at present. Accumulation of several plant amides was detected in various plants, which play important role in plant growth and development. This paper aims to review the biosynthesis, physiology, and functions of HCAA accumulation in plants during plant growth and development as well as in response to senescence and drought stress. HCAAs are secondary metabolites derived from phenylalanine and tyrosine pathway. Phenylalanine ammonia lyase (PAL) and 4-coumarate CoA ligase (4CL) hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl) transferase (THT) and tyrosine decarboxylase (TyDC) are essential enzymes for HCAA biosynthesis. HCAAs contribute to many developmental processes as well as plant responses against biotic and abiotic stress responses. However, there is a need to specifically investigate the role of many HCAAs in view of plant molecular biology since it is still not fully conceptualized and explained at present.

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“…5) In a previous paper three new tris(4-hydroxycinnamoyl)spermidines have been reported. 6) Continuing investigations on the roots of M. keayana have now led to the isolation and structural elucidation of two other new compounds, one quinoline derivative xanthoquininamide 1 and one tris(4-hydroxycinnamoyl)spermine keayanine 2.…”

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confidence: 99%

Two New Quinoline and Tris(4-hydroxycinnamoyl)spermine Derivatives from Microdesmis keayana Roots

Zamblé

Hennebelle

Şahpaz

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Microdesmis keayana LÉONARD (Pandaceae) is a tropical shrub, the leaves of which are used in the Ivory Coast against malaria and some other parasites. Its antiplasmodial, 1,2) antitrypanosomal 3) and anthelmintic 4) activities have already been tested. Its roots are also used by traditional healers as a remedy for sexual dysfunction. An aqueous extract of these roots, recently tested, exhibited vasorelaxing properties, explained by an increase in nitric oxide (NO) in the vascular bed, via antioxidant properties and stimulation of endothelial nitric oxide synthase (eNOS) mRNA expression.5) In a previous paper three new tris(4-hydroxycinnamoyl)spermidines have been reported. 6) Continuing investigations on the roots of M. keayana have now led to the isolation and structural elucidation of two other new compounds, one quinoline derivative xanthoquininamide 1 and one tris(4-hydroxycinnamoyl)spermine keayanine 2. Results and DiscussionXanthoquininamide (1) was obtained as a pale yellow powder soluble in methanol. It showed an [MϩH] ϩ peak at m/z 189 in the ESI-MS data. The 1 H-NMR spectrum in MeOD was very simple and all chemical shifts and couplings which were observed between d H 7.3 and d H 8.8, including a not-so-common Jϭ4.5 Hz between H-2 and H-3, 7) were consistent for a quinoline derivative which was substituted on C-6 or C-7 (because of the ABX system) and on C-4. Mono-( 1 H and 13 C) and bidimensional (COSY, HMQC, HMBC) NMR experiments, as well as comparison with data of previously described quinine-like alkaloids, 8) made it possible to establish the structure of 1 as 6-hydroxyquinoline-4-carboxamide.1 H-and 13 C-NMR chemical shifts are given in Table 1. To our knowledge, this is the first report of both the natural occurrence of 1 and of its complete spectroscopic data, although it has already been synthesised from xanthoquininic acid by amidification. 9)Compound 2 was characterized both by ESI-MS and NMR data. In the electrospray mass spectrum, a [MϩH] ϩ peak was observed at m/z 701. Typical fragments were observed on ESI-MS spectrum at m/z 147 and m/z 177, corresponding to one coumaroyl and two feruloyl residues respectively, according to the relative heights of both signals. The subtraction of these three elements from the molecular mass of the compound (m/z 700) gave a mass of 199, compatible with a tri-substituted spermine. The positions of all three acyl moieties were determined by ESI-MS (see Fig. 2 Purification of a Microdesmis keayana hydromethanolic root extract led to the isolation of two new natural compounds, xanthoquininamide (6-hydroxyquinoline-4-carboxamide) and tris(4-hydroxycinnamoyl)spermine (N 5 -(p-coumaroyl)-N 1 ,N 14 -diferuloylspermine) which was named keayanine. Their structures were determined using spectroscopic analyses (ESI-MS, 1D-and 2D-NMR).

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N1,N5,N10-Tris(4-hydroxycinnamoyl)spermidines fromMicrodesmis keayana Roots

Cited by 32 publications

References 16 publications

A Novel Polyamine Acyltransferase Responsible for the Accumulation of Spermidine Conjugates in Arabidopsis Seed

A Novel Polyamine Acyltransferase Responsible for the Accumulation of Spermidine Conjugates in Arabidopsis Seed

Biosynthesis, physiology, and functions of hydroxycinnamic acid amides in plants

Two New Quinoline and Tris(4-hydroxycinnamoyl)spermine Derivatives from Microdesmis keayana Roots

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