InChI=1S/C28H48O4/c1-15(2)16(3)25(31)26(32)17(4)20-7-8-21-19-14-24(30)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-23,25-26,29,31-32H,7-14H2,1-6H3/t16-,17-,18+,19-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1 |
SBSXXCCMIWEPEE-SELDZKRUSA-N |
CC(C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC(=O)[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
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Brassica juncea
(NCBI:txid3707)
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See:
PubMed
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Oryza sativa
(NCBI:txid4530)
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Found in
seed
(BTO:0001226).
See:
PubMed
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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View more via ChEBI Ontology
(3α,5α,22R,23R,24S)-3,22,23-trihydroxyergostan-6-one
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2-Deoxycastasterone
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HMDB
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typhasterol
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UniProt
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3629989
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Reaxys Registry Number
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Reaxys
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87734-68-7
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CAS Registry Number
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KNApSAcK
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Kanwar MK, Poonam, Bhardwaj R (2015) Arsenic induced modulation of antioxidative defense system and brassinosteroids in Brassica juncea L. Ecotoxicology and environmental safety 115, 119-125 [PubMed:25700090] [show Abstract] Brassica juncea (Indian mustard) L. plants were exposed to different concentrations (0.0, 0.1, 0.2 and 0.3mM) of arsenic (V) and harvested after 30 and 60 days of sowing for the analysis of growth parameters, metal uptake, brassinosteroids (BRs) synthesis and oxidative stress markers. As (V) significantly hampered the growth of B. juncea plants and triggered the modulations of various stress markers like proteins, antioxidative enzymes (SOD, CAT, POD, APX, GR, MDHAR and DHAR) and MDA content. Furthermore, As (V) induced the synthesis of 4 BRs, castasterone, teasterone, 24-epibrassinolide, and typhasterol, which were isolated and characterized by gas chromatography-mass spectrometry (GC-MS). The study further highlig5895hted the significant uptake of arsenic ions by mustard plants. | Joo SH, Jang MS, Kim MK, Lee JE, Kim SK (2015) Biosynthetic relationship between C₂₈-brassinosteroids and C₂₉-brassinosteroids in rice (Oryza sativa) seedlings. Phytochemistry 111, 84-90 [PubMed:25433632] [show Abstract] A crude enzyme solution was prepared from young rice seedlings, and the metabolism of C29-brassinosteroids identified from the seedlings was examined. When 28-homoteasterone was added as a substrate, 28-homotyphasterol, teasterone, and 26-nor-28-homoteasterone were characterized as enzyme products by GC-MS/SIM analysis. With 28-homotyphasterol, 28-homoteasterone, typhasterol, 28-homocastasterone, and 26-nor-28-homotyphasterol were formed and identified as products. When 28-homocastasterone was used, castasterone and 26-nor-28-homocastasterone were identified as products. Together with the reduced biological activity of C29-brassinosteroids and their metabolites in the rice lamina inclination assay, these metabolic studies suggest a biosynthetic sequence, 28-homoteasterone↔28-homotyphasterol→28-homocastasterone for C29-brassinosteroid biosynthesis is connected to the biosynthetic sequence teasterone↔typhasterol→castasterone for C28-brassinosteroids by C-28 demethylation, i.e., in order to increase biological activity in the rice plant. Additionally, the C29-brassinosteroids seem to bio-degrade their C-26 demethylated C28-brassinosteroid analogs to reduce brassinosteroid activity in planta. In conclusion, the biosynthesis of C29-brassinosteroids is a likely alternative route to the biologically-active brassinosteroid, castasterone, in rice. | Wang L, Duan C, Wu D, Guan Y (2014) Quantification of endogenous brassinosteroids in sub-gram plant tissues by in-line matrix solid-phase dispersion-tandem solid phase extraction coupled with high performance liquid chromatography-tandem mass spectrometry. Journal of chromatography. A 1359, 44-51 [PubMed:25092597] [show Abstract] A matrix solid-phase dispersion (MSPD)-tandem mixed mode anion exchange (MAX)-mixed mode cation exchange (MCX) solid phase extraction-high performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS) method was developed for quantification of six endogenous brassinosteroids (BRs) (24-epibrassinolide, 24-epicastasterone, 6-deoxo-24-epicastasterone, dolichosterone, teasterone and typhasterol) in rice plant tissues. Non-polar interferences were removed effectively by C8 dispersant used in MSPD, while the following tandem MAX-MCX process facilitated the elimination of polar and ionizable compounds. The weak reversed-phase retention feature of MAX-MCX leaded to good compatibility of the elution solvents in the in-line coupled MSPD-MAX-MCX system. This system was optimized for extraction and purification of BRs in plant samples. The effects of the type of solid phase, the elution solvent, the extraction temperature and the clean-up material were studied. Before HPLC separation, BRs purified were derivatized by m-aminophenylboronic acid to enhance the sensitivity of MS/MS to BRs. Compared with traditional liquid-liquid extraction and solid phase extraction (LLE-SPE), the proposed MSPD-MAX-MCX method showed higher extraction efficiency, lower matrix effect, and advantages of easy manipulation and time-saving. The in-line MSPD-MAX-MCX coupled with HPLC-MS/MS method provided a linear response over two orders of magnitude of BRs concentration with correlation coefficients above 0.9982, limits of detection between 0.008 and 0.04ngmL(-1), relative standard deviations (RSDs) below 29.4%, and recoveries above 77.8%. The proposed method has been successfully applied to analysis of endogenous BRs in rice plant at booting stage and maturity stage. | Asahina M, Tamaki Y, Sakamoto T, Shibata K, Nomura T, Yokota T (2014) Blue light-promoted rice leaf bending and unrolling are due to up-regulated brassinosteroid biosynthesis genes accompanied by accumulation of castasterone. Phytochemistry 104, 21-29 [PubMed:24856112] [show Abstract] In this study the relationship between blue light- and brassinosteroid-enhanced leaf lamina bending and unrolling in rice was investigated. Twenty-four hours (h) irradiation with white or blue light increased endogenous brassinosteroid levels, especially those of typhasterol and castasterone, in aerial tissues of rice seedlings. There was an accompanying up-regulation of transcript levels of CYP85A1/OsDWARF, encoding an enzyme catalyzing C-6 oxidation, after 6h under either white or blue light. These effects were not observed in seedlings placed under far-red or red light regimes. It was concluded that blue light up-regulates the levels of several cytochrome P450 enzymes including CYP85A1, thereby promoting the synthesis of castasterone, a biologically active brassinosteroid in rice. Based on these findings, it is considered that blue light-mediated rice leaf bending and unrolling are consequences of the enhanced biosynthesis of endogenous castasterone. In contrast to aerial tissues, brassinosteroid synthesis in roots appeared to be negatively regulated by white, blue and red light but positively controlled by far-red light. | Yamamoto R, Fujioka S, Demura T, Takatsuto S, Yoshida S, Fukuda H (2001) Brassinosteroid levels increase drastically prior to morphogenesis of tracheary elements. Plant physiology 125, 556-563 [PubMed:11161013] [show Abstract] As the first step toward understanding the involvement of endogenous brassinosteroids (BRs) in cytodifferentiation, we analyzed biosynthetic activities of BRs in zinnia (Zinnia elegans L. cv Canary Bird) cells differentiating into tracheary elements. The results of feeding experiments suggested that both the early and late C6-oxidation pathways occur during tracheary element differentiation. Gas chromatography-mass spectrometry analysis revealed that five BRs, castasterone, typhasterol, 6-deoxocastasterone, 6-deoxotyphasterol, and 6-deoxoteasterone, actually existed in cultured zinnia cells and culture medium. Quantification of endogenous BRs in each stage of tracheary element differentiation by gas chromatography-mass spectrometry exhibited that they increased dramatically prior to the morphogenesis, which was consistent with the idea that BRs are necessary for the initiation of the final stage of tracheary element differentiation. Moreover, the proportion of each BR in culture medium was quite different from that in cells, suggesting that specific BRs are selectively secreted into medium and may function outside the cells. |
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