7α-alkylation, 7,7-bisalkylation, and reduction of the 20-oxo group of poststerone in reactions with alkyl halides in lithium–ammonia solution

Galyautdinov, I. V.; Sadretdinova, Z. R.; Mozgovoi, Oleg S.; Gibadullina, G. G.; Халилов, Л. М.; Muslimov, Z. S.; Odinokov, V. N.

doi:10.1134/s1070428017010201

Cited by 2 publications

(1 citation statement)

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“…Reaction of excess halide with poststerone gives a diastereomeric mixture of 20-hydroxy-7,7-bis-alkyl EC derivatives. Therefore, alkylation of ECs can lead to a few medicinally potent compounds [ 130 , 131 , 132 ].…”

Section: Structure Of Phytoecdysteroidsmentioning

confidence: 99%

Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones

Arif

Singh

Bajguz

et al. 2022

IJMS

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Phytoecdysteroids (PEs) are naturally occurring polyhydroxylated compounds with a structure similar to that of insect molting hormone and the plant hormone brassinosteroids. PEs have a four-ringed skeleton composed of 27, 28, 29, or 30 carbon atoms (derived from plant sterols). The carbon skeleton of ecdysteroid is known as cyclopentanoperhydrophenanthrene and has a β-sidechain on C-17. Plants produce PEs via the mevalonate pathway with the help of the precursor acetyl-CoA. PEs are found in algae, fungi, ferns, gymnosperms, and angiosperms; more than 500 different PEs are found in over 100 terrestrial plants. 20-hydroxyecdysone is the most common PE. PEs exhibit versatile biological roles in plants, invertebrates, and mammals. These compounds contribute to mitigating biotic and abiotic stresses. In plants, PEs play a potent role in enhancing tolerance against insects and nematodes via their allelochemical activity, which increases plant biological and metabolic responses. PEs promote enzymatic and non-enzymatic antioxidant defense systems, which decrease reactive oxygen species in the form of superoxide radicals and hydroxyl radicals and reduce malondialdehyde content. PEs also induce protein biosynthesis and modulate carbohydrate and lipid synthesis. In humans, PEs display biological, pharmacological, and medicinal properties, such as anti-diabetic, antioxidant, anti-microbial, hepatoprotective, hypoglycemic, anti-cancer, anti-inflammatory, antidepressant, and tissue differentiation activity.

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Section: Structure Of Phytoecdysteroidsmentioning

confidence: 99%