<i>N</i>-Glucosides of Fairy Chemicals, 2-Azahypoxanthine and 2-Aza-8-oxohypoxanthine, in Rice

Choi, Jae-Hoon; Wu, Jing; Sawada, Azusa; Takeda, Syougo; Takemura, Hirohide; Yogosawa, Kaoru; Hirai, Hirofumi; Kondo, Mitsuru; Sugimoto, Kunihisa; Asakawa, Tomohiro; Inai, Makoto; Kan, Toshiyuki; Kawagishi, Hirokazu

doi:10.1021/acs.orglett.7b03736

Cited by 21 publications

(21 citation statements)

References 15 publications

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“…Compounds 6 – 9 were isolated from 1 -treated rice, suggesting that plants have a pathway to biosynthesize 6–9 endogenously 18 . Although labeled 6 – 9 have not been chemically synthesized, 1 and 6 – 9 were eluted in the same fraction in the new method (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, N -glucosides, AOH-1-β-D-glucoside ( 6 ), AOH-7-β-D-glucoside ( 7 ), AOH-9-β-D-glucoside ( 8 ), and AHX-1-β-D-glucoside ( 9 ) were isolated as the metabolites of 1 and 3 from 1 -treated rice and further metabolisms of 1 and 3 were revealed (Fig. 1) 18 . Contrary to them, molecular mechanism, endogeny, and biosynthetic pathway of 2 in plants had remained unclear.…”

Section: Introductionmentioning

confidence: 98%

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A Fairy Chemical, Imidazole-4-carboxamide, is Produced on a Novel Purine Metabolic Pathway in Rice

Takemura

Choi

Matsuzaki

et al. 2019

Sci Rep

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Rings or arcs of fungus-regulated plant growth occurring on the floor of woodlands and grasslands are commonly called “fairy rings”. Fairy chemicals, 2-azahypoxanthine (AHX), imidazole-4-carboxamide (ICA), and 2-aza-8-oxohypoxanthine (AOH), are plant growth regulators involved in the phenomenon. The endogeny and biosynthetic pathways of AHX and AOH in plants have already been proven, however, those of ICA have remained unclear. We developed a high-sensitivity detection method for FCs including ICA and the endogenous ICA was detected in some plants for the first time. The quantitative analysis of the endogenous level of ICA in rice and Arabidopsis were performed using 13 C-double labeled ICA. In addition, the incorporation experiment and enzyme assay using the labeled compound into rice and partially purified fraction of rice indicated that ICA is biosynthesized from 5-aminoimidazole-4-carboxamide (AICA), a metabolite on the purine metabolic pathway. The relationship between ICA and AHX was also discussed based on quantitative analysis and gene expression analysis.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

A Fairy Chemical, Imidazole-4-carboxamide, is Produced on a Novel Purine Metabolic Pathway in Rice

Takemura

Choi

Matsuzaki

et al. 2019

Sci Rep

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“…In the experiment using 3 , 20 and 21 were obtained. 25) LC-MS/MS showed that all the glucosides are also endogenous in rice. One of the plant hormone families, cytokinins, has a purine carbon-skeleton like 1 and 3 and is also converted into N -glucosides and O -glucosides in plants.…”

Section: The Proof Of Endogenous Existence Of Fairy Chemicals and Thementioning

confidence: 99%

Are fairy chemicals a new family of plant hormones?

Kawagishi

2019

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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2-Azahypoxanthine (AHX, 1 ) and imidazole-4-carboxamide (ICA, 2 ) were isolated from a fairy-ring-forming fungus Lepista sordida . AHX was converted into a metabolite 2-aza-8-oxo-hypoxanthine (AOH, 3 ) in plants. It was found out that these three compounds, named as fairy chemicals (FCs), endogenously exist in plants and are biosynthesized via a new purine metabolic pathway. FCs provided tolerance to the plants against various stresses and regulated the growth of all the plants. In addition, FCs increased the yield of rice, wheat, and other crops in the greenhouse and/or field experiments.

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“…The isolation of three new chlorinated sesquiterpenes from a culture broth of L. sordida, named lepistatins A-C (see structures 60-62 in Figure 11), was reported by a Korean research group along with their antibacterial and antiproliferative activities [143]. In conclusion, polysaccharides from L. sordida were determined to possess immunoregulatory [145], antiproliferative [146], anticancer [146,147], and antiradical activities [148], while different secondary metabolites showed antimicrobial [149], cytotoxic [149], and plant growth regulatory activities [151][152][153][154]. Figure 12) were active against the plant parasitic nematode Meloidogyne incognita, and showed weak antimicrobial effects against Nadsonia fulvescens and Penicillium notatum.…”

Section: Lepista Sordida (Schumach) Singermentioning

confidence: 83%

“…Compounds 50-52 (see structures in Figure 11), named lepistamides A-C, were also isolated, in conjunction with diatretol, from samples of L. sordida collected in China [150]. A group of Japanese researchers isolated plant-growth regulating compounds, 2-azahypoxanthine (53), 2-aza-8-oxohypoxanthine (54), and imidazole-4-carboxamide (55) [151][152][153][154], whereas compounds 56-59 (see structures in Figure 11), showing inhibitory activity of the bentgrass root growth, were isolated from a culture broth [155]. The isolation of three new chlorinated sesquiterpenes from a culture broth of L. sordida, named lepistatins A-C (see structures 60-62 in Figure 11), was reported by a Korean research group along with their antibacterial and antiproliferative activities [143].…”

Section: Lepista Sordida (Schumach) Singermentioning

confidence: 99%

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

et al. 2020

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Mushrooms have a long history of uses for their medicinal and nutritional properties. They have been consumed by people for thousands of years. Edible mushrooms are collected in the wild or cultivated worldwide. Recently, mushroom extracts and their secondary metabolites have acquired considerable attention due to their biological effects, which include antioxidant, antimicrobial, anti-cancer, anti-inflammatory, anti-obesity, and immunomodulatory activities. Thus, in addition to phytochemists, nutritionists and consumers are now deeply interested in the phytochemical constituents of mushrooms, which provide beneficial effects to humans in terms of health promotion and reduction of disease-related risks. In recent years, scientific reports on the nutritional, phytochemical and pharmacological properties of mushroom have been overwhelming. However, the bioactive compounds and biological properties of wild edible mushrooms growing in Southeast Asian countries have been rarely described. In this review, the bioactive compounds isolated from 25 selected wild edible mushrooms growing in Southeast Asia have been reviewed, together with their biological activities. Phytoconstituents with antioxidant and antimicrobial activities have been highlighted. Several evidences indicate that mushrooms are good sources for natural antioxidants and antimicrobial agents

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N-Glucosides of Fairy Chemicals, 2-Azahypoxanthine and 2-Aza-8-oxohypoxanthine, in Rice

Cited by 21 publications

References 15 publications

A Fairy Chemical, Imidazole-4-carboxamide, is Produced on a Novel Purine Metabolic Pathway in Rice

A Fairy Chemical, Imidazole-4-carboxamide, is Produced on a Novel Purine Metabolic Pathway in Rice

Are fairy chemicals a new family of plant hormones?

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

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