Natural Products in the Chemical Industry

Schaefer, Bernd

doi:10.1007/978-3-642-54461-3

Cited by 44 publications

(29 citation statements)

References 56 publications

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“…Moreover, we examined more anchorene and anchor root formation under nitrogen deficient conditions compared to those of normal growing seedlings, indicating that ANRs may improve nutrient uptake and pointing to potential for applications in agriculture or horticulture. It is worth mentioning that the carotenoid cleavage product anchorene is a commercially available compound used as building block for the manufacturing of different carotenoids on an industrial scale (48).…”

Section: Discussionmentioning

confidence: 99%

Anchorene is an endogenous diapocarotenoid required for anchor root formation in Arabidopsis

Jia

et al. 2018

Preprint

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Arabidopsis root development is predicted to be regulated by yet unidentified carotenoidderived metabolite(s). In this work, we screened known and putative carotenoid cleavage products and identified anchorene, a predicted carotenoid-derived dialdehyde (diapocarotenoid) that triggers anchor root development. Anchor roots are the least characterized type of root in Arabidopsis. They form at the root-shoot junction, particularly upon damage to the root apical meristem. Using Arabidopsis reporter lines, mutants and chemical inhibitors, we show that anchor roots originate from pericycle cells and that the development of this root type is auxindependent and requires carotenoid biosynthesis. Transcriptome analysis and treatment of auxinreporter lines indicate that anchorene triggers anchor root development by modulating auxin homeostasis. Exogenous application of anchorene restored anchor root development in carotenoid-deficient plants, indicating that this compound is the carotenoid-derived signal required for anchor root development. Chemical modifications of anchorene led to a loss of anchor root promoting activity, suggesting that this compound is highly specific. Furthermore, we demonstrate by LC-MS analysis that anchorene is a natural, endogenous Arabidopsis metabolite. Taken together, our work reveals a new member of the family of carotenoid-derived regulatory metabolites and hormones. SignificanceUnknown carotenoid-derived compounds are predicted to regulate different aspects of plant development. Here, we characterize the development of anchor roots, the least characterized root type in Arabidopsis, and show that this process depends on auxin and requires a carotenoid-derived metabolite. We identified a presumed carotenoid-derivative, anchorene, as the likely, specific signal involved in anchor root formation. We further show that anchorene is a natural metabolite that occurs in Arabidopsis. Based on the analysis of auxin reporter lines and transcriptome data, we provide evidence that anchorene triggers the growth of anchor roots by modulating auxin homeostasis. Taken together, our work identifies a novel carotenoid-derived growth regulator with a specific developmental function.

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Section: Discussionmentioning

confidence: 99%

Anchorene is an endogenous diapocarotenoid required for anchor root formation in Arabidopsis

Jia

et al. 2018

Preprint

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“…Ebenso erwiesen die Reagentien 1-3 vielseitigen Nutzen in der Synthese von anellierten 6-gliedrigen Heterocyclen wie Chinolinen, einem Benzo [b]thieno [2,3-b]pyridin und Naphthyridinen, [19] welche relevante Bausteine für pharmazeutische Anwendungen darstellen. [20] Somit ergaben Pd-katalysierte Negishi-Kreuzkupplungen [21] der Alkenylzink-Reagentien (3a-b)m it 1-Halogen-2-nitroarenen (15 a-g)d ie entsprechenden alkenylierten Nitroarene von Ty p 16,w elche nach Indium-oder Zink-vermittelter Reduktion [22] und saurer Acetalspaltung die anellierten Pyridine 17 a-i in 41-70 %A usbeute lieferten (Schema 6).…”

Section: Des Weiteren Konnte Unsere Methode Zur Synthese Vonunclassified

Polyfunktionelle Lithium‐, Magnesium‐ und Zinkalkenyl‐Reagentien als Grundbausteine für die Synthese komplexer Heterocyclen

et al. 2016

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Neue konjunktive b-silylierte organometallische Li-, Mg-und Zn-Reagentien wurden hergestellt und für den Aufbau einer Vielzahl von polyfunktionalisierten 5-, 6-und 7gliedrigen Heterocyclen wie Furane,P yrrole,C hinoline, Benzo[b]thieno[2,3-b]pyridin, Naphthyridine,k ondensierte Pyrazole und 2,3-Dihydrobenzo[c]azepine verwendet. Die endständige Silylgruppe konnte in den meisten Heterocyclenklassen in neue Kohlenstoff-Kohlenstoff-Bindungen umgewandelt werden. Schema 1. Die konjunktiven Reagentien 1-3 (Met = Li, MgCl und ZnCl). Schema 2. Synthese der Acetal-haltigenm etallorganischen Reagentien 1-3 ausgehend von den Trialkylsilyl-substituierten propargylischen Alkoholen 6a-b.

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“…The results indicated that of the double mutants, only BmeTC Y167A/D373C produced Figure 1. Photooxygenation of 1 to produce volatile compounds (2)(3)(4)(5). Tricyclic triterpene, (+)-ambrein (1), is the primary source of ambergris-derived odor components [2][3][4][9][10][11] .…”

Section: Construction Of the System For Artificial Biosynthesis Ofmentioning

confidence: 99%

“…Photooxygenation of 1 to produce volatile compounds (2)(3)(4)(5). Tricyclic triterpene, (+)-ambrein (1), is the primary source of ambergris-derived odor components [2][3][4][9][10][11] . Photooxidative degradation of 1 by 1 O 2 around its central double bond produces volatile compounds with smaller molecular weights 2-4,9-11 .…”

Section: Construction Of the System For Artificial Biosynthesis Ofmentioning

confidence: 99%

“…After wetting samples with filter papers and evaporating the solvent, we compared the scents and found that the scents associated with UV and RB treatments of 1 were similar to those obtained from the ethanol tinctures of two ambergris, whereas the scents associated with TPP and MB treatments were different. Notably, the yield of valuable fragrance compound 3, which is used as a substitute for ambergris samples [1][2][3][4] , was 6-21 times higher in MB treated 1 than that obtained from the ethanol tinctures of two ambergris (Fig. 7b).…”

Section: Conversion Of Synthetic 1 Into Volatile Componentsmentioning

confidence: 99%

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Construction of an artificial system for ambrein biosynthesis and investigation of some biological activities of ambrein

Yamabe¹,

Kawagoe²,

Okuno³

et al. 2020

Sci Rep

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Ambergris, a sperm whale metabolite, has long been used as a fragrance and traditional medication, but it is now rarely available. The odor components of ambergris result from the photooxidative degradation of the major component, ambrein. The pharmacological activities of ambergris have also been attributed to ambrein. However, efficient production of ambrein and odor compounds has not been achieved. Here, we constructed a system for the synthesis of ambrein and odor components. First, we created a new triterpene synthase, “ambrein synthase,” for mass production of ambrein by redesigning a bacterial enzyme. The ambrein yields were approximately 20 times greater than those reported previously. Next, an efficient photooxidative conversion system from ambrein to a range of volatiles of ambergris was established. The yield of volatiles was 8–15%. Finally, two biological activities, promotion of osteoclast differentiation and prevention of amyloid β-induced apoptosis, were discovered using the synthesized ambrein.

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Natural Products in the Chemical Industry

Cited by 44 publications

References 56 publications

Anchorene is an endogenous diapocarotenoid required for anchor root formation in Arabidopsis

Anchorene is an endogenous diapocarotenoid required for anchor root formation in Arabidopsis

Polyfunktionelle Lithium‐, Magnesium‐ und Zinkalkenyl‐Reagentien als Grundbausteine für die Synthese komplexer Heterocyclen

Construction of an artificial system for ambrein biosynthesis and investigation of some biological activities of ambrein

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