Metabolism of indole-3-acetic acid in rice: Identification and characterization of N-β-d-glucopyranosyl indole-3-acetic acid and its conjugates

Kai, Kenji; Wakasa, K.; Miyagawa, Hisashi

doi:10.1016/j.phytochem.2007.05.040

Cited by 24 publications

(23 citation statements)

References 25 publications

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“…, 2010). Kai et al. (2007) found in 2‐week‐old rice seedlings that the free IAA level was around 35 ng/g and was higher in the aerial parts when compared with the roots.…”

Section: Discussionmentioning

confidence: 92%

Over‐expression of OsPIN2 leads to increased tiller numbers, angle and shorter plant height through suppression of OsLAZY1

Chen¹,

Fan²,

Song

et al. 2011

Plant Biotechnology Journal

202

163

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SummaryCrop architecture parameters such as tiller number, angle and plant height are important agronomic traits that have been considered for breeding programmes. Auxin distribution within the plant has long been recognized to alter architecture. The rice (Oryza sativa L.) genome contains 12 putative PIN genes encoding auxin efflux transporters, including four PIN1 and one PIN2 genes. Here, we report that over-expression of OsPIN2 through a transgenic approach in rice (Japonica cv. Nipponbare) led to a shorter plant height, more tillers and a larger tiller angle when compared with wild type (WT). The expression patterns of the auxin reporter DR5::GUS and quantification of auxin distribution showed that OsPIN2 over-expression increased auxin transport from the shoot to the root-shoot junction, resulting in a non-tissue-specific accumulation of more free auxin at the root-shoot junction relative to WT. Over-expression of OsPIN2 enhanced auxin transport from shoots to roots, but did not alter the polar auxin pattern in the roots. Transgenic plants were less sensitive to N-1-naphthylphthalamic acid, an auxin transport inhibitor, than WT in their root growth. OsPIN2-over-expressing plants had suppressed the expression of a gravitropism-related gene OsLazy1 in the shoots, but unaltered expression of OsPIN1b and OsTAC1, which were reported as tiller angle controllers in rice. The data suggest that OsPIN2 has a distinct auxin-dependent regulation pathway together with OsPIN1b and OsTAC1 controlling rice shoot architecture. Altering OsPIN2 expression by genetic transformation can be directly used for modifying rice architecture.

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“…, 2010). Kai et al. (2007) found in 2‐week‐old rice seedlings that the free IAA level was around 35 ng/g and was higher in the aerial parts when compared with the roots.…”

Section: Discussionmentioning

confidence: 92%

Over‐expression of OsPIN2 leads to increased tiller numbers, angle and shorter plant height through suppression of OsLAZY1

Chen¹,

Fan²,

Song

et al. 2011

Plant Biotechnology Journal

202

163

View full text Add to dashboard Cite

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“…Finally, treatment of N-glucoside of IAA-amide (9 and 10) with 2 M NaOH afforded compounds 11 and 12, which were the same as compounds 1 and 2 by comparison with their TLC behavior and NMR spectra. The previously reported synthetic route consisted of nine steps, including two acetylation reactions 18 . In our syntheis, the acetylation and deacetylation steps required in previously reported cases could be removed, greatly enhancing its step economy.…”

Section: No Ginkgoside a (1)mentioning

confidence: 99%

“…Therefore, in order to ascertain their absolute configurations, compounds 1 and 2 were synthesized as shown in Fig. 3 via modification of a literature procedure 18,19 .…”

mentioning

confidence: 99%

Isolation of two rare N-glycosides from Ginkgo biloba and their anti-inflammatory activities

Cheng

Guo

Cui

et al. 2020

Sci Rep

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two rare N-β-D-glucopyranosyl-1H-indole-3-acetic acid conjugates, N-[2-(1-β-D-glucopyranosyl)-1Hindol-3-yl)acetyl]-L-glutamic acid (1) and N-[2-(1-β-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-aspartic acid (2) were isolated from Ginkgo biloba. The structures were elucidated by analyses of HRMS and NMR spectroscopic data. In addition, a simplified and efficient synthetic route for compounds 1 and 2 is also disclosed to determine the absolute configurations of them. This concise syntheses of compounds 1 and 2 may facilitate studies of the biology of this type alkaloids. Compounds 1 and 2 were also tested for their cytotoxic and anti-inflammatory activities. The biological evaluation showed that compounds 1 and 2 led to the decrease of interleukin (IL)-6, nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 at mRNA level in lipopolysaccharide (LPS)-stimulated murine macrophage RAW264.7 cells. Ginkgo biloba L., one of the most well-known medicinal plants worldwide, is considered as a living fossil due to its survival over millions of years 1. Pharmacological studies have shown that extracts from its leaves and seeds exhibit antiparasitic, antifungal, antibacterial and antiviral activities. G. biloba extracts have also found broad applications in the treatment of cognitive diseases 2-5. Since the discovery of ginkgolides A-C, a lot of phytochemical and pharmaceutical studies have been conducted on the G. biloba leaves 6-8. It is well known that G. biloba leaf extracts, mainly composed of ginkgolides, flavonoids and phenolic compounds, are frequently used in the treatment of cardiovascular, cerebrovascular, and neurological diseases 9,10. The dried seeds of G. biloba (called "baiguo" in Chinese), have been reported in the Chinese Pharmacopoeia as effective treatments for cough, asthma, enuresis, alcohol misuse, pyogenic skin infections and worm infestations in the intestinal tract 11,12. In contrast to extensive studies on G. biloba leaves, the seeds of G. biloba have received much less attention. In order to find structurally interesting and bioactive components from Ginkgo seeds and provide a better understanding of their functions, we conducted a phytochemical investigation of Ginkgo seeds. As a result, two N-β-D-glucopyranosyl-1H-indole-3-acetic acid conjugates were isolated from the title plant and the concise syntheses of 1 and 2 were also enclosed to determine the absolute configurations of compounds 1 and 2 (Fig. 1). Notably, compounds 1 and 2 are naturally isolated N-glycosides, which are rarely found in natural products. To the best of our knowledge, only very few examples have been reported previouly 13-17. Although compounds 1 and 2 were detected in an alkaline hydrolysate of rice extract using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) 18 , there are no examples of their isolation, absolute configurations determination and bioactivities. Reported herein are the structural identification, concise syntheses and bioactivities of them. Results and discussion Ginkgos...

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“…IAA is known to play a vital role in higher plants as a plant growth promoter and in signal transduction. In addition, it plays an effective role in stress tolerance (Kai et al, 2007;Agami et al, 2013). In addition, GA3 is believed to be involved in improving crop productivity under normal or stressful regimes (Bose et al, 2013), because it is linked with several growth and development processes (Swain et al, 2005;Al-Khassawneh, 2006).…”

Section: Discussionmentioning

confidence: 99%

Exogenous application of indole acetic acid (IAA) and giberrelic acid (GA3) induces changes in carbon and nitrogen metabolisms that affect tobacco (Nicotiana tabacum L.) production

Qian¹,

Li²,

Wu³

et al. 2018

PAK.J.BOT.

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Experiments, both pot and field trial, were conducted to examine the effects of exogenously applied IAA and GA3 (at 0, 10, 20 and 30 days after topping) individually or in combination, on growth and C and N metabolisms of tobacco (Nicotiana tabacum L.). Application of IAA or GA3, at low concentrations had a promising effect in terms of promoting the yield and quality of tobacco. The key enzymes' activities were also enhanced by low PGRs concentrations, which is known to be involved in the C and N metabolisms. The combined treatment of the two PGRs was more effective than the PGRs applied individually in improving the activities of nitrate reductase (NR), invertase (INV) and amylase (AMY) finally resulting in improved soluble sugars, reducing sugars, starch, total C and N, soluble proteins and nicotine content. The optimum levels for improvement of C and N metabolites were found to be GA3 at 50 mg/L and IAA at 30 mg/L.

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Metabolism of indole-3-acetic acid in rice: Identification and characterization of N-β-d-glucopyranosyl indole-3-acetic acid and its conjugates

Cited by 24 publications

References 25 publications

Over‐expression of OsPIN2 leads to increased tiller numbers, angle and shorter plant height through suppression of OsLAZY1

Over‐expression of OsPIN2 leads to increased tiller numbers, angle and shorter plant height through suppression of OsLAZY1

Isolation of two rare N-glycosides from Ginkgo biloba and their anti-inflammatory activities

Exogenous application of indole acetic acid (IAA) and giberrelic acid (GA3) induces changes in carbon and nitrogen metabolisms that affect tobacco (Nicotiana tabacum L.) production

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