scholarly journals The 7[prime]-Methyl Group of Abscisic Acid Is Critical for Biological Activity in Wheat Embryo Germination

1994 ◽  
Vol 106 (4) ◽  
pp. 1279-1284 ◽  
Author(s):  
M. K. Walker-Simmons ◽  
P. A. Rose ◽  
A. C. Shaw ◽  
S. R. Abrams
Keyword(s):  
Biological Activity ◽  
Abscisic Acid ◽  
Embryo Germination ◽  
Wheat Embryo ◽  
Methyl Group

Chiral synthesis of (+)-8′-demethyl abscisic acid

1996 ◽  
Vol 74 (10) ◽  
pp. 1836-1843 ◽  
Author(s):  
Patricia A. Rose ◽  
Bo Lei ◽  
Angela C. Shaw ◽  
Suzanne R. Abrams ◽  
M. K. Walker-Simmons ◽  
...  
Keyword(s):  
Biological Activity ◽  
Abscisic Acid ◽  
Enantioselective Synthesis ◽  
Phenol Oxidation ◽  
Germination Inhibition ◽  
Embryo Germination ◽  
Chiral Synthesis ◽  
Wheat Embryo ◽  
Methyl Group ◽  
Key Words Abscisic Acid

An enantioselective synthesis of (+)-8′-demethyl ABA (2) is described. The chiral intermediate 7 was prepared by yeast reduction of a substituted monoprotected cyclohexa-2,5-dien-1,4-dione (9) synthesized through a phenol oxidation. The scope and limitations of the phenol oxidation is described. 8′-Demethyl ABA shows ABA-like activity in wheat embryo germination inhibition, showing that the 8′-methyl group is not essential for biological activity. Key words: abscisic acid, phenol oxidation, yeast reduction.

scholarly journals Transcriptome Reveals Roles of Lignin-Modifying Enzymes and Abscisic Acid in the Symbiosis of Mycena and Gastrodia elata

2021 ◽  
Vol 22 (12) ◽  
pp. 6557
Author(s):  
Li-Ying Ren ◽  
Heng Zhao ◽  
Xiao-Ling Liu ◽  
Tong-Kai Zong ◽  
Min Qiao ◽  
...  
Keyword(s):  
Biological Activity ◽  
Abscisic Acid ◽  
Lignin Degradation ◽  
Molecular Mechanisms ◽  
Receptor Protein ◽  
Gastrodia Elata ◽  
Upregulated Genes ◽  
Aba Biosynthesis ◽  
Seed Coats

Gastrodia elata is a well-known medicinal and heterotrophic orchid. Its germination, limited by the impermeability of seed coat lignin and inhibition by abscisic acid (ABA), is triggered by symbiosis with fungi such as Mycena spp. However, the molecular mechanisms of lignin degradation by Mycena and ABA biosynthesis and signaling in G. elata remain unclear. In order to gain insights into these two processes, this study analyzed the transcriptomes of these organisms during their dynamic symbiosis. Among the 25 lignin-modifying enzyme genes in Mycena, two ligninolytic class II peroxidases and two laccases were significantly upregulated, most likely enabling Mycena hyphae to break through the lignin seed coats of G. elata. Genes related to reduced virulence and loss of pathogenicity in Mycena accounted for more than half of annotated genes, presumably contributing to symbiosis. After coculture, upregulated genes outnumbered downregulated genes in G. elata seeds, suggesting slightly increased biological activity, while Mycena hyphae had fewer upregulated than downregulated genes, indicating decreased biological activity. ABA biosynthesis in G. elata was reduced by the downregulated expression of 9-cis-epoxycarotenoid dioxygenase (NCED-2), and ABA signaling was blocked by the downregulated expression of a receptor protein (PYL12-like). This is the first report to describe the role of NCED-2 and PYL12-like in breaking G. elata seed dormancy by reducing the synthesis and blocking the signaling of the germination inhibitor ABA. This study provides a theoretical basis for screening germination fungi to identify effective symbionts and for reducing ABA inhibition of G. elata seed germination.

Hitting a Moving Target: How Does anN-Methyl Group Impact Biological Activity?

ChemMedChem ◽  
2016 ◽  
Vol 11 (8) ◽  
pp. 881-892 ◽  
Author(s):  
Yen Chin Koay ◽  
Nicole L. Richardson ◽  
Samantha S. Zaiter ◽  
Jessica Kho ◽  
Sheena Y. Nguyen ◽  
...  
Keyword(s):  
Biological Activity ◽  
Moving Target ◽  
Methyl Group

ChemInform Abstract: Ring Conformational Requirement for Biological Activity of Abscisic Acid Probed by the Cyclopropane Analogues.

ChemInform ◽  
2010 ◽  
Vol 27 (38) ◽  
pp. no-no
Author(s):  
Y. TODOROKI ◽  
S. NAKANO ◽  
N. HIRAI ◽  
H. OHIGASHI
Keyword(s):  
Biological Activity ◽  
Abscisic Acid

Synthesis and biological activity of RS-abscisic acid and its analogs

1970 ◽  
Vol 6 (6) ◽  
pp. 741-744
Author(s):  
N. D. Livshits ◽  
Ch. Sh. Kadyrov ◽  
V. I. Kefeli
Keyword(s):  
Biological Activity ◽  
Abscisic Acid

scholarly journals Entomopathogenic Filamentous Fungi as Biocatalysts in Glycosylation of Methylflavonoids

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1148
Author(s):  
Agnieszka Krawczyk-Łebek ◽  
Monika Dymarska ◽  
Tomasz Janeczko ◽  
Edyta Kostrzewa-Susłow
Keyword(s):  
Biological Activity ◽  
Filamentous Fungi ◽  
Beauveria Bassiana ◽  
Biological Activities ◽  
Isaria Fumosorosea ◽  
Methyl Group ◽  
Group 2 ◽  
Pharmacological Application

Flavonoids are known for their numerous biological activities; however, their pharmacological application is limited by poor bioavailability. Glycosides are usually more stable and more soluble in water and in this form, flavonoids are present in nature. Likewise, the presence of the methyl group in the flavonoid skeleton results in facilitated absorption and greater bioavailability. Entomopathogenic filamentous fungi are effective in the biotransformation of flavonoids; they are known especially for efficient glycosylation. In the current study we used strains of Beauveria bassiana KCH J1.5 and Isaria fumosorosea KCH J2 to biotransform flavonoids with a single methyl group. 2′-Hydroxy-5′-methylchalcone was biotransformed by both strains into 2′-hydroxy-5′-methylchalcone 3-O-β-D-(4″-O-methyl)-glucopyranoside. In the culture of B. bassiana KCH J1.5 four products were obtained from 6-methylflavanone: 4′-hydroxy-6-methylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside; 4′-hydroxyflavanone 6-methylene-O-β-D-(4″-O-methyl)-glucopyranoside; 6-hydroxymethylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside and 4′-hydroxy-6-hydroxymethylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside. Biotransformation with I. fumosorosea KCH J2 as a biocatalyst resulted in the formation of 6-methylflavanone 4′-O-β-D-(4″-O-methyl)-glucopyranoside and 2-phenyl-6-methylchromane 4-O-β-D-(4″-O-methyl)-glucopyranoside. All of these flavonoids can be used in biological activity tests and can be useful in studies concerning structure—bioactivity relationships.

scholarly journals Synthesis, Biological Evaluation and Docking Studies of 13-Epimeric 10-fluoro- and 10-Chloroestra-1,4-dien-3-ones as Potential Aromatase Inhibitors

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1783 ◽  
Author(s):  
Rebeka Jójárt ◽  
Péter Traj ◽  
Édua Kovács ◽  
Ágnes Horváth ◽  
Gyula Schneider ◽  
...  
Keyword(s):  
Biological Activity ◽  
Inhibitory Action ◽  
Molecular Level ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Computational Simulations ◽  
Simultaneous Application ◽  
Methyl Group ◽  
Ic50 Values

Fluorination of 13-epimeric estrones and their 17-deoxy counterparts was performed with Selectfluor as the reagent. In acetonitrile or trifluoroacetic acid (TFA), 10β-fluoroestra-1,4-dien-3-ones were formed exclusively. Mechanistic investigations suggest that fluorinations occurred via SET in acetonitrile, but another mechanism was operative in TFA. Simultaneous application of N-chlorosuccinimide (NCS) and Selectfluor in TFA led to a 1.3:1 mixture of 10β-fluoroestra-1,4-dien-3-one and 10β-chloroestra-1,4-dien-3-one as the main products. The potential inhibitory action of the 10-fluoro- or 10-chloroestra-1,4-dien-3-one products on human aromatase was investigated via in vitro radiosubstrate incubation. The classical estrane conformation with trans ring anellations and a 13β-methyl group seems to be crucial for the inhibition of the enzyme, while test compounds bearing the 13β-methyl group exclusively displayed potent inhibitory action with submicromolar or micromolar IC50 values. Concerning molecular level explanation of biological activity or inactivity, computational simulations were performed. Docking studies reinforced that besides the well-known Met374 H-bond connection, the stereocenter in the 13 position has an important role in the binding affinity. The configuration inversion at C-13 results in weaker binding of 13α-estrone derivatives to the aromatase enzyme.

Metabolome and transcriptome analyses unravel the inhibition of embryo germination by abscisic acid in pear

2022 ◽  
Vol 292 ◽  
pp. 110652
Author(s):  
Qi Kai-Jie ◽  
Wu Xiao ◽  
Gao Xin ◽  
Li Lu-Fei ◽  
Xie Zhi-Hua ◽  
...  
Keyword(s):  
Abscisic Acid ◽  
Embryo Germination ◽  
Transcriptome Analyses
Sign in / Sign up

Export Citation Format

Share Document