Reminiscences of research on the chemistry and biology of natural sterols in insects, plants and humans

Ikekawa, Nobuo; Fujimoto, Yoshinori; Ishiguro, Masaji

doi:10.2183/pjab.89.349

Cited by 12 publications

(7 citation statements)

References 79 publications

(73 reference statements)

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“…First, compound 1 possesses the 14β(H)17β(H) configuration expected for a synthetic compound; to the best of our knowledge, this is the first time such a steroid was isolated from a plant source. Natural sterols, the precursors in the biosynthesis of ecdysteroids in plants, typically have a 17β-oriented side chain, 21 as do all phytoecdysteroids isolated to date. It must be stressed that the total synthesis of ecdysteroids requires many stereoselective steps and is much less economical than their isolation from plants; 22 therefore, adulteration of the extract with synthetic analogues would be expensive and pointless.…”

Section: Results and Discussionmentioning

confidence: 99%

A Commercial Extract of Cyanotis arachnoidea Roots as a Source of Unusual Ecdysteroid Derivatives with Insect Hormone Receptor Binding Activity

Tóth

Herke

Gáti³

et al. 2021

J. Nat. Prod.

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Ecdysteroids act as molting hormones in insects and as nonhormonal anabolic agents and adaptogens in mammals. A wide range of ecdysteroid-containing herbal extracts are available worldwide as food supplements. The aim of this work was to study such an extract as a possible industrial source of new bioactive ecdysteroids. A large-scale chromatographic isolation was performed from an extract of Cyanotis arachnoidea roots. Ten ecdysteroids ( 1 – 10 ) including eight new compounds were isolated and characterized by extensive nuclear magnetic resonance studies. Highly unusual structures were identified, including a H-14β ( 1 , 2 , 4 , and 10 ) moiety, among which a 14β(H)17β(H) phytosteroid ( 1 ) is reported for the first time. Compounds with an intact side chain ( 4 – 10 ) and 11 other natural or semisynthetic ecdysteroids ( 11 – 21 ) were tested for insect ecdysteroid receptor (EcR) binding activity. Two new compounds, i.e., 14-deoxydacryhainansterone ( 5 ) and 22-oxodacryhainansterone ( 6 ), showed strong EcR binding activity (IC 50 = 41.7 and 380 nM, respectively). Six compounds were identified as EcR agonists and another two as antagonists using a transgenic ecdysteroid reporter gene assay. The present results demonstrate that commercial C. arachnoidea extracts are rich in new, unusual bioactive ecdysteroids. Because of the lack of an authentic plant material, the truly biosynthetic or artifactual nature of these compounds cannot be confirmed.

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Section: Results and Discussionmentioning

confidence: 99%

A Commercial Extract of Cyanotis arachnoidea Roots as a Source of Unusual Ecdysteroid Derivatives with Insect Hormone Receptor Binding Activity

Tóth

Herke

Gáti³

et al. 2021

J. Nat. Prod.

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“…Many phytophagous insects can convert plant sterols to cholesterol in their intestines. 19,20) While ecdysteroids are biosynthesized from the embryonic to the adult stage, 12,21) ecdysteroid biosynthesis has been intensively studied using larvae and pupae. This is because the most typical ecdysteroids, ecdysone (E) and its derivative 20-hydroxyecdysone (20E), were originally identified as the "molting hormones" that can induce drastic morphological and developmental changes in the processes of molting and metamorphosis.…”

Section: The Ecdysteroid Biosynthesis Pathway In Insectsmentioning

confidence: 99%

Enzymes for ecdysteroid biosynthesis: their biological functions in insects and beyond

Niwa

2014

Bioscience, Biotechnology, and Biochemistry

212

165

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Steroid hormones are responsible for the coordinated regulation of many aspects of biological processes in multicellular organisms. Since the last century, many studies have identified and characterized steroidogenic enzymes in vertebrates, including mammals. However, much less is known about invertebrate steroidogenic enzymes. In the last 15 years, a number of steroidogenic enzymes and their functions have been characterized in ecdysozoan animals, especially in the fruit fly Drosophila melanogaster. In this review, we summarize the latest knowledge of enzymes crucial for synthesizing ecdysteroids, the principal insect steroid hormones. We also discuss the functional conservation and diversity of ecdysteroidogenic enzymes in other insects and even non-insect species, such as nematodes, vertebrates, and lower eukaryotes.

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“…Cholesterol and 7dehydrocholesterol are formed during synthetic pathway. For example, the beetle Tenebrio molitor produces about 17% of 7-dehydrocholesterol and about 67% of cholesterol from sitosterol (Leclerq, 1948;Svoboda and Feldlaufer, 1991;Ikekawa et al, 1993;Svoboda and Lusby, 1994;Ikekawa et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Minor lipophilic compounds in edible insects

Sabolová

Adámková

Kouřimská

et al. 2016

Potr. S. J. F. Sci.

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Contemporary society is faced with the question how to ensure suffiecient nutrition (quantity and quality) for rapidly growing population. One solution can be consumption of edible insect, which can have very good nutritional value (dietary energy, protein, fatty acids, fibers, dietary minerals and vitamins composition). Some edible insects species, which contains a relatively large amount of fat, can have a potential to be a "good" (interesting, new) source of minor lipophilic compounds such as sterols (cholesterol and phytosterols) and tocopherols in our diet. For this reason, the objective of this work was to characterize the sterols and tocopherols composition of fat from larvae of edible insect Zophobas morio L. and Tenebrio mollitor L. Cholesterol and three phytosterols (campesterol, stigmasterol and β-sitosterol) were reliably identified and quantified after hot saponification and derivatization by GC-MS. Other steroid compounds, including 5,6-transcholecalciferol were identified only according to the NIST library. Cholesterol was the predominant sterol in all analysed samples. Both types of larvae also contained high amount of phytosterols. Different region of origin had a no significant impact on sterols composition, while the effect of beetle genus was crucial. Tocopherols were analysed by reverse phase HPLC coupled with amperometric detection. Tocopherols content in mealworm larvae was lower than content in edible oils, but important from the nutritional point of view. Change of tocopherols composition was not observed during the storage under different conditions. Larvae of edible insect can be a potential good dietary source of cholesterol, but also vitamin D3 isomers, phytosterols and tocopherols.

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Reminiscences of research on the chemistry and biology of natural sterols in insects, plants and humans

Cited by 12 publications

References 79 publications

A Commercial Extract of Cyanotis arachnoidea Roots as a Source of Unusual Ecdysteroid Derivatives with Insect Hormone Receptor Binding Activity

A Commercial Extract of Cyanotis arachnoidea Roots as a Source of Unusual Ecdysteroid Derivatives with Insect Hormone Receptor Binding Activity

Enzymes for ecdysteroid biosynthesis: their biological functions in insects and beyond

Minor lipophilic compounds in edible insects

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