Di-coumaroylspermidines and tri-coumaroylspermidines in anthers of different species of the genus Aphelandra

Werner, Christa; Hu, W. W. L.; Lorenzi-Riatsch, Annalaura; Hesse, Manfred

doi:10.1016/0031-9422(95)00288-i

Cited by 54 publications

(42 citation statements)

References 7 publications

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“…In this regard, the case of anthers exhibiting a prevalent signature of high idMS/MS specialization, greater than all other reproductive organs, is particularly germane. In line with our observation of the manufacture of a specific set of metabolites in this tissue (Dataset S1), previous studies have shown that metabolites, notably certain phenolic derivatives, are abundant and highly specific for the tapetum (specialized layer of nutritive cells and source of precursors for the pollen coat within anthers) of anthers and pollen grains (39)(40)(41). The biosynthesis of these phenolic derivatives, with potential roles in pollen coat composition and establishment of fertilization barriers, has been linked to rapid metabolic gene evolution through retroposition and neofunctionalization (42).…”

Section: Cross-tissue Intensity Variationsupporting

confidence: 87%

Illuminating a plant’s tissue-specific metabolic diversity using computational metabolomics and information theory

Heiling

Baldwin

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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Secondary metabolite diversity is considered an important fitness determinant for plants' biotic and abiotic interactions in nature. This diversity can be examined in two dimensions. The first one considers metabolite diversity across plant species. A second way of looking at this diversity is by considering the tissue-specific localization of pathways underlying secondary metabolism within a plant. Although these cross-tissue metabolite variations are increasingly regarded as important readouts of tissue-level gene function and regulatory processes, they have rarely been comprehensively explored by nontargeted metabolomics. As such, important questions have remained superficially addressed. For instance, which tissues exhibit prevalent signatures of metabolic specialization? Reciprocally, which metabolites contribute most to this tissue specialization in contrast to those metabolites exhibiting housekeeping characteristics? Here, we explore tissue-level metabolic specialization in Nicotiana attenuata, an ecological model with rich secondary metabolism, by combining tissue-wide nontargeted mass spectral data acquisition, information theory analysis, and tandem MS (MS/MS) molecular networks. This analysis was conducted for two different methanolic extracts of 14 tissues and deconvoluted 895 nonredundant MS/MS spectra. Using information theory analysis, anthers were found to harbor the most specialized metabolome, and most unique metabolites of anthers and other tissues were annotated through MS/MS molecular networks. Tissuemetabolite association maps were used to predict tissue-specific gene functions. Predictions for the function of two UDP-glycosyltransferases in flavonoid metabolism were confirmed by virus-induced gene silencing. The present workflow allows biologists to amortize the vast amount of data produced by modern MS instrumentation in their quest to understand gene function.secondary metabolism | mass spectrometry | metabolomics | information theory | Nicotiana attenuata P lants are elegant synthetic chemists making use of their metabolic prowess to produce complex blends of structurally diverse chemicals. Commonly quoted estimates state that plants produce somewhere on the order of 200,000 chemical structures. Secondary metabolites, also referred to as specialized metabolites or natural products, contribute to the largest fraction of this structural diversity. Compared with their counterparts in central metabolism (primary metabolites), secondary metabolite groups have diversified to the extreme in plant lineages, likely as a result of the multiple ecological roles they fulfill (1). The high degree of plasticity of secondary metabolism pathways is consistent with the existence of large families of metabolism-related genes such as cytochrome P450s and UDP-glycosyltransferases in plant genomes that can create structural and chemical modifications almost without limits. The majority of metabolic gene functions remain unknown, however, either because the metabolites that they produce are unknown or signi...

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Section: Cross-tissue Intensity Variationsupporting

confidence: 87%

Illuminating a plant’s tissue-specific metabolic diversity using computational metabolomics and information theory

Heiling

Baldwin

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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“…The principal tri-p-coumaroylspermidine, i.e. ; afterwards, this EEE isomer was isolated successively from Rosaceae, 14) Quercus dentata pollen, 15) anthers of Aphelandra tetraffona and A. chamissoniana (a ZZZ isomer also was isolated concomitantly), 12) sunflower (Helianthus annuus L.) pollen, 16) and Brazilian bee pollen. 17) Pharmacologically, this principal compound has been reported to have anti-human immunodeficiency virus (HIV) infection, 11,18) anti-Helicobacter pylori, 19) anti-tumor, 20,21) anti-fungal, 22) and antioxidant activities.…”

Section: Resultsmentioning

confidence: 94%

“…The 9,11,12) among which the structural difference comes essentially from both the geometric isomerism of a CϭC bond and the arrangement of three p-coumaroyl groups at N1, N5, and N10. To fix two cis p-coumaroyl groups and one trans pcoumaroyl group in the molecule, a heteronuclear multiple bond correlation (HMBC) experiment was carried out.…”

Section: Resultsmentioning

confidence: 99%

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

Zhao

Qin

Gai

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Safflower (Carthamus tinctorius L.), a member of the family Compositae, geologically distributes in all regions in China, and is utilized for producing herbal medicines for the treatment of inflammatory diseases, hyperlipemia, arteriosclerosis, gynecological disorders, and osteoporosis. 1) To date, it has been known to contain flavonoids, 2) cartharmin, safflower yellow A, quinochalone, safflomin, cartorimine, alkaloids, 3) lignans, fatty acids, 4) triterpene alcohols, 5) and serotonin derivatives.6-8) Additionally, several coumaroylspermidine analogs also were found in safflower, i.e., a principal analog N 1 ,N 5 ,N 10 -(E)-tri-p-coumaroylspermidine (EEE) and its three cis-trans isomers [N 1 ,N 5 9) indicating that that some other geometric isomers of tri-p-coumaroylspermidine could exist in the natural plant. In our previous preliminary screening, we discovered that safflower extracts (especially ethyl acetate extract (HE) and n-butyl alcohol fraction) had regulatory actions on the monoamine transports in transporter-transgenic Chinese hamster ovary (CHO) cells, that is, activations of dopamine (DA)/norepinephrine (NE) uptake and an inhibition of serotonin (5HT) uptake, 10) implying that there may be some constituent(s) acting as serotonin transporter (SERT) blocker(s). In this study, we thereby chose to isolate and characterize the structurally unknown, SERT-targeting compound(s) from the HE fraction by using an activity-directed extraction method and a series of NMR techniques. Finally, one of the active isolates was identified and elucidated as N 1 ,N 5 -(Z)-N 10 -(E)-tri-p-coumaroylspermidine (CX), a new tri-p-coumaroylspermidine as postulated previously by us. Results and DiscussionThe ethyl acetate extract of safflower (Carthamus tinctorius L.) was separated by column chromatography on silica gel and Sephadex LH-20 in combination with a concomitant bioactivity-tracing technique (detailed paradigm described in Supplemental) to afford a bioactive compound CX (designated as carthamide X by us) (Fig. 1). HPLC showed that the purity of CX sample was 95.6% (while the content of CX in HE was only 0.028%). Due to the sensitivity, validity, and feasibility, 10) our screening platform previously established by using isotope-ligand-detection methods is suggested suitable for tracing some structurally unknown/unstable compounds with a sparse content in natural plants when combined with phytochemical techniques, which could, however, be hard to be isolated by traditional phytochemical method alone.The We previously reported that safflower (Carthamus tinctorius L.) ethyl acetate extract (HE) possessed an inhibitory action on serotonin (5HT) uptake in Chinese hamster ovary (CHO) cells expressing 5HT transporter (SERT) (S6 cells). Here, HE was adopted to go through an activity-guided isolation, and then an ingredient with potent SERT inhibitory action was obtained, which was elucidated as N

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“…The structure had been established by spectral analysis of its permethylated product. 7) Most recently, this compound was isolated from the species of the genera Aphelandra 8) and Helianthus annuus L. 9) However, the 1 H-NMR spectrum of this compound had not yet been assigned clearly. In the present experiment, this compound was isolated as a pure E-form and its 500 MHz 1 H-NMR spectrum could be interpreted by detailed analysis of its 2D NMR spectra.…”

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confidence: 99%

Inhibitory Effects on HIV-1 Protease of Tri-p-coumaroylspermidine from Artemisia caruifolia and Related Amides.

Nakamura

Hattori

2001

Chem. Pharm. Bull.

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Di-coumaroylspermidines and tri-coumaroylspermidines in anthers of different species of the genus Aphelandra

Cited by 54 publications

References 7 publications

Illuminating a plant’s tissue-specific metabolic diversity using computational metabolomics and information theory

Illuminating a plant’s tissue-specific metabolic diversity using computational metabolomics and information theory

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

Inhibitory Effects on HIV-1 Protease of Tri-p-coumaroylspermidine from Artemisia caruifolia and Related Amides.

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