The chemistry of the gibberellins

Hanson, James R.

doi:10.1039/np9900700041

Cited by 14 publications

(6 citation statements)

References 113 publications

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“…It was envisaged that allylic bromination of this substrate with NBS would take place with rearrangement of the olefinic bond to afford the l-bromo-9-ene 161 which could then serve as an alternative substrate to 149 or its 3epimer. In any event, it was difficult to prevent further bromination to the 1,11-dibromide 162 and it was more efficient to carry out the intramolecular alkylation on this intermediate (giving 163) and then to remove the 11-bromo substituent at a later stage by base-induced elimination of HBr, followed by hydrogenation. The resulting sequence (Figure 49) afforded access to both 141 and 142.…”

Section: Second Generation Syntheses Of Fern Antheridiogens From Ga?mentioning

confidence: 99%

The chemistry of gibberellins: an overview

Mander¹

1992

Chem. Rev.

123

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Section: Second Generation Syntheses Of Fern Antheridiogens From Ga?mentioning

confidence: 99%

The chemistry of gibberellins: an overview

Mander¹

1992

Chem. Rev.

123

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“… 4 Mechanistically, terpenoids can target bacterial enzymes, 5 bacterial biofilms, 6 and bacterial pigment formation, 7 act as bacterial toxins 8 and bacterial surfactants, 9 inhibit the quorum sensing pathways, 10 and inhibit microbial mobility. 11 Diterpenes also have other significant biological activities around plant growth regulation, 12 antimicrobial activity, 13 antiviral activity, 14 and algicidal applications. 15 This diversity in diterpene biological activity is enabled by the diverse diterpene structures produced in nature.…”

Section: Introductionmentioning

confidence: 99%

Plant Terpenoid Permeability through Biological Membranes Explored via Molecular Simulations

et al. 2023

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Plants synthesize small molecule diterpenes composed of 20 carbons from precursor isopentenyl diphosphate and dimethylallyl disphosphate, manufacturing diverse compounds used for defense, signaling, and other functions. Industrially, diterpenes are used as natural aromas and flavoring, as pharmaceuticals, and as natural insecticides or repellents. Despite diterpene ubiquity in plant systems, it remains unknown how plants control diterpene localization and transport. For many other small molecules, plant cells maintain transport proteins that control compound compartmentalization. However, for most diterpene compounds, specific transport proteins have not been identified, and so it has been hypothesized that diterpenes may cross biological membranes passively. Through molecular simulation, we study membrane transport for three complex diterpenes from among the many made by members of the Lamiaceae family to determine their permeability coefficient across plasma membrane models. To facilitate accurate simulation, the intermolecular interactions for leubethanol, abietic acid, and sclareol were parametrized through the standard CHARMM methodology for incorporation into molecular simulations. To evaluate the effect of membrane composition on permeability, we simulate the three diterpenes in two membrane models derived from sorghum and yeast lipidomics data. We track permeation events within our unbiased simulations, and compare implied permeation coefficients with those calculated from Replica Exchange Umbrella Sampling calculations using the inhomogeneous solubility diffusion model. The diterpenes are observed to permeate freely through these membranes, indicating that a transport protein may not be needed to export these small molecules from plant cells. Moreover, the permeability is observed to be greater for plant-like membrane compositions when compared against animal-like membrane models. Increased permeability for diterpene molecules in plant membranes suggest that plants have tailored their membranes to facilitate low-energy transport processes for signaling molecules.

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“…Gibberellins (GAs), a class of natural tetracyclic diterpenoid PGRs, have been widely accepted by agricultural practitioners due to their ability to modulate stem elongation, seed germination, and flower and fruit development and mitigate the effects of citrus huanglongbing disease. − Natural products constitute the major sources of innovative chemicals due to their structural diversity. , The compound exo -16,17-dihydro-gibberellin A5-13-acetate (DHGA 5 ) represents a promising and potent gibberellin derivative for modulating plant growth regulation . It inhibits plant development under laboratory and field conditions, reduces the probability of crop lodging under adverse meteorological conditions, and adjusts turfgrass growth to maintain an overall uniform morphology. − It is clear that producing DHGA 5 from gibberellic acid (GA 3 ) constitutes a viable approach. ,,− …”

Section: Introductionmentioning

confidence: 99%

o-Nitrobenzyl-Based Caged exo-16,17-Dihydro-gibberellin A5-13-acetate for Photocontrolled Release of Plant Growth Regulators

Li,

Liang,

Gao

et al. 2023

J. Agric. Food Chem.

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Caged plant growth regulators (caged PGRs) that release bioactive molecules under irradiation are critical in enhancing the efficacy and mitigating the negative environmental effects of PGRs. The synthetically derived plant growth inhibitor exo-16,17-dihydro-gibberellin A5-13-acetate (DHGA5) regulates the development and stress resilience of plants. We report here the conception of novel caged DHGA5 derivatives wherein the photoremovable protecting groups (PRPGs) serve not only to enable light-controlled release but also to protect the carboxyl group during chemical synthesis. Three o-nitrobenzyl-based caged DHGA5 derivatives with different substituents on the nitrobenzyl moiety were obtained and evaluated for their properties in vitro and in vivo. The photolysis half-life values of caged DHGA5 derivatives 7a, 7b, and 7c under a UV lamp were 15.6 h, 1.2 h, and 28.2 h, respectively. Experiments in vivo showed that 0.2 mM of the caged compounds significantly inhibited the growth of the model plant Arabidopsis thaliana and important crop rice in a precise photoactivated form.

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The chemistry of the gibberellins

Cited by 14 publications

References 113 publications

The chemistry of gibberellins: an overview

The chemistry of gibberellins: an overview

Plant Terpenoid Permeability through Biological Membranes Explored via Molecular Simulations

o-Nitrobenzyl-Based Caged exo-16,17-Dihydro-gibberellin A5-13-acetate for Photocontrolled Release of Plant Growth Regulators

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