The biosynthesis of lunarine in seeds of Lunaria annua

Sagner, Silvia; Shen, Zhengwu; Deus-Neumann, Brigitte; Zenk, Meinhart H.

doi:10.1016/s0031-9422(97)00590-6

Cited by 20 publications

(17 citation statements)

References 23 publications

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“…The weak signal for a fragment at m/z 72 (<2%) also confirmed the substitution of N 1 and N 8 by sinapoyl groups (Parr et al, 2005) since acyl migration may account for low levels of this fragment (Youhnovski et al, 1998). Within the Brassicaceae, N 1 ,N 8 -disubstituted spermidine derivatives have been identified in the seeds of Lunaria annua (Sagner et al, 1998) and Brassica napus (Baumert et al, 2005), respectively.…”

Section: Spermidine Conjugates In Arabidopsis Seedsmentioning

confidence: 64%

“…We have identified two sinapoyl spermidine derivatives in Arabidopsis seed: S1, N 1 -((49-O-glycosyl)-sinapoyl),N 8 -sinapoylspermidine, and S2, N 1 ,N 8 -disinapoylspermidine (Figure 1). In the seeds of other species within Brassicaceae, cyclic spermidine alkaloids derived from N 1 ,N 8 -dicoumaroylspermidine and N-isoferuloyl-N99-2-hydroxyisoferuloyl spermidine have been found in L. annua (Sagner et al, 1998) and in B. napus (Baumert et al, 2005), respectively.…”

Section: Discussionmentioning

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: Spermidine Conjugates In Arabidopsis Seedsmentioning

confidence: 64%

Section: Discussionmentioning

confidence: 99%

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

et al. 2009

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“…aphelandrine (277)) are a rare class of naturally occurring polyamide conjugates present in the Brassicaceae, Acantahaceae, Scrophulariaceae and Ephedraceae family (Facchini et al, 2002;Nezbedová et al, 2001;Sagner et al, 1998).…”

Section: Q10mentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

137

109

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a b s t r a c tEthnopharmacological relevance: N-Alkylamides (NAAs) are a promising group of bioactive compounds, which are anticipated to act as important lead compounds for plant protection and biocidal products, functional food, cosmeceuticals and drugs in the next decennia. These molecules, currently found in more than 25 plant families and with a wide structural diversity, exert a variety of biologicalpharmacological effects and are of high ethnopharmacological importance. However, information is scattered in literature, with different, often unstandardized, pharmacological methodologies being used. Therefore, a comprehensive NAA database (acronym: Alkamid) was constructed to collect the available structural and functional NAA data, linked to their occurrence in plants (family, tribe, species, genus). Materials and methods: For loading information in the database, literature data was gathered over the period 1950-2010, by using several search engines. In order to represent the collected information about NAAs, the plants in which they occur and the functionalities for which they have been examined, a relational database is constructed and implemented on a MySQL back-end. Results: The database is supported by describing the NAA plant-, functional-and chemical-space. The chemical space includes a NAA classification, according to their fatty acid and amine structures. Conclusions: The Alkamid database (publicly available on the website http://alkamid.ugent.be/) is not only a central information point, but can also function as a useful tool to prioritize the NAA Q8 choice in the evaluation of their functionality, to perform data mining leading to quantitative structure-property relationships (QSPRs), functionality comparisons, clustering, plant biochemistry and taxonomic evaluations.

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“…12 In the case of lunarine, a macrocyclic spermidine alkaloid from Lunaria annua, the incorporation of the 14 C-labelled coumaroyl spermidine indicates that hydroxycinnamoyl amides are precursors of this type of alkaloids. 13 But knowledges about the enzymes involved in the further steps of cyclization or acylation were completely lacking until recently. The biosynthesis of aphelandrine (9) and orantine (10) proceeds presumably by one of the pathways shown in Scheme 1.…”

Section: The Aphelandrine Biosynthesismentioning

confidence: 99%

“…This assumption is based on the established large distribution of mono-, di-and polycinnamoyl substituted polyamines as natural secondary metabolites in the plant kingdom and by the fact that N(1), N(10)-bis (p-coumaroyl)-spermidine is involved in the biosynthesis of the macrocyclic spermidine alkaloid lunarine. 13 Moreover, a large group of similar compounds, including coumaroylspermidines has been isolated from the anthers of different Aphelandra species. 23 According to the second possibility (Scheme 1, right), the key intermediate in the biosynthesis of aphelandrine (9) has been proposed to be (S)-4′-hydroxyprotoverbine (7) which is formed from 1-cinnamoylspermine (5a) or 1-coumaroylspermine (5b) derivative via macrocyclization by Michael type addition.…”

Section: Biosynthetic Precursors Of Dihydroxyverbacinementioning

confidence: 99%