Configuration at C‐24 of 24‐methyl and 24‐ethylcholesterol in tracheophytes

Nes, William R.; Krevitz, Kenneth; Behzadan, Shamideh

doi:10.1007/bf02532661

Cited by 85 publications

(27 citation statements)

References 15 publications

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“…While the Asteraceae (aster) and Fabaceae (pea) are similar to the above four families (3), at least one species in each biosynthesizes exclusively A7-sterols (9,10), Among the angiosperms in which more than one species within a genus was carefully examined, production of A s-versus A7-sterols in the photosynthetic tissue is consistent within a genus (1 1-13). In addition, the presence of A s-sterols from the seed oils of various species within the Brassicaceae also are consistent with that reported for the leaves (14,15).…”

Section: Introductionsupporting

confidence: 87%

“…The configuration at C-24 for the epimeric 24c~-and 24/3-alkylsterols was determined through the use of proton nuclear magnetic resonance spectra and comparison with authentic standards run concurrently (7,8,t 5,29-31). The use of this technique provides consistently reproducible and distinctly different spectra for individual epimers as well as for mixtures of the C-24 epimers as previously reported (15,31). Avenasterol [ 24-ethyl-5a-cholesta-7,24(28) Z-dien-3/3-ol] isolated from these chenopods had an RRTon SE-30 of 1.87 + 0.01, on XE-60 of 1.88 + 0.02 and an a c of 0.93 + 0.01.…”

Section: Resultssupporting

confidence: 57%

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Diversity of sterol composition in the family chenopodiaceae

Salt

Adler

1985

Lipids

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The predominant 4‐desmethylsterols from the leaves of 13 species in eight genera of the family Chenopodiaceae are 24α‐ethylsterols. In four species,Chenopodium ambrosioides L.,C. rubrum L.,Salicornia europaea L. andS. bigelovii Torr., the C‐22(23) double bond is introduced into more than 70% of the 24α‐ethylsterols producing spinasterol (24α‐ethylcholesta‐7,22E‐dien‐3β‐ol) in the first two species and mixtures of spinasterol and stigmasterol (24α‐ethylcholesta‐5,22E‐dien‐3β‐ol) in the latter species. The saturated side chain analogues predominate with more than 70% of the 24α‐ethylsterols in eight species.Salsola kali L.,Suaeda linearis (Ell.) Moq.,Kochia scoparia (L.) Roth., andBassia hirsute (L.) Aschers. synthesize sitosterol (24α‐ethylcholest‐5‐en‐3β‐ol), andAtriplex arenaria Nutt.,C. album L.,C. urbicum L. andC. leptophyllum Nutt. possess mixtures of sitosterol and 22‐dihydrospinasterol (24α‐ethylcholest‐7‐en‐3β‐ol). Sitostanol (24α‐ethyl‐5α‐cholestan‐3β‐ol) was isolated fromSuaeda linearis as an 18% component of the total 4‐desmethylsterol and in lesser amounts from four other species. In all species synthesizing 24‐ethyl‐Δ5‐sterols, a 24ξ‐methylcholest‐5‐en‐3β‐ol was also present at 1.0–20% of the total 4‐desmethylsterol. Avenasterol [24‐ethylcholesta‐7,24(28)Z‐dien‐3β‐ol], isofucosterol [24‐ethylcholesta‐5,24(28)Z‐dien‐3β‐ol), cholesterol (cholest‐5‐en‐3β‐ol) and 24ξ‐methyl‐5α‐cholestan‐3β‐ol also were isolated from several species. Species in the family Chenopodiaceae and the type genusChenopodium may be categorized into one of three groups based on sterol biosynthesis: the Δ7‐sterol producers; the Δ5‐sterol producers, and those producing mixtures of both Δ7‐ and Δ5‐sterols in relatively fixed percentage compositions.

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Section: Introductionsupporting

confidence: 87%

Section: Resultssupporting

confidence: 57%

Diversity of sterol composition in the family chenopodiaceae

Salt

Adler

1985

Lipids

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“…Sitosterol (∆ 5 ) and stigmasterol (∆ 5,22 ) were purchased from Sigma Chemical (St. Louis, MO, U.S.A.). Sitosterol, derived from soybean, was a mixture of 60% sitosterol, 27% campesterol (∆ 5 ) and 13% dihydrobrassicasterol (∆ 5 ); the profile and ratio of sterols from soybean are similar to those found in the Brassicaceae (Nes et al, 1976). Stigmasterol was µ 99% pure.…”

Section: Sterolsmentioning

confidence: 90%

“…The diamondback moth, P. xylostella, is a specialist on plants in the Brassicaceae, a family with a sterol profile dominated by the ∆ 5 phytosterols, sitosterol and campesterol (Nes et al, 1976). Stigmasterol comprises a very small fraction of the total phytosterol pool of plants in this family.…”

Section: Sterolsmentioning

confidence: 99%

Impact of dietary sterols on life‐history traits of a caterpillar

Behmer

Grebenok

1998

Physiological Entomology

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Although lepidopteran larvae have been shown to metabolise a number of different phytosterols, their life‐history traits in response to these different phytosterols may vary with the species. Using the specialist moth, Plutella xylostella (Linaeus) (Lepidoptera), growth, development and fecundity on artificial diets containing host and non‐host phytosterols were measured over two generations. Because of the nature of the experimental design, maternal effects linked to dietary sterol could be assessed. In both generations, survival was highest on diets containing sitosterol as the primary phytosterol. A significant decrease in survival on stigmasterol, a non‐host phytosterol, was observed between generations. As expected, survival on a control diet with only trace‐sterols decreased between generations. Larval duration and pupal duration in both generations was longest on the diets containing the non‐host phytosterols, stigmasterol and spinasterol, and on the trace‐sterol diet. Finally, fecundity was affected by dietary sterol. In the first generation, fewer viable eggs were produced on the stigmasterol and trace‐sterol diets than on wheatgerm control diet. In both generations, dietary sterol significantly influenced percentage egg viability. Overall, these results indicate that differences in phytosterol structure can have pronounced effects on life‐history traits, especially when they are projected to the population level. The implications of these results are discussed with respect to phytosterol use by phytophagous insects and their host plant affiliations.

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“…Addition of alkyl groups in the side chain results in the substituted carbon becoming asymmetric 10 . Generally the α-configuration is more common in higher plants, whereas the β-configuration predominates in algae 7 .…”

Section: Structurementioning

confidence: 99%

Untitled

2013

IJPSR

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Foods and nutrients play a vital role in normal functioning of the body. They are helpful in maintaining the health of the individual and in reducing the risk of various diseases. Worldwide acceptance of this fact formed a recognition link between "nutrition" and "health" and the concept of "nutraceuticals" has evolved. More than any other disease, the etiology of cardiovascular disease reveals many risk factors that are amenable to nutraceutical intervention. The scientific literature shows that there are several bioactive ingredients that are present in small amounts in plants that can affect mammalian biological processes relevant to cardiovascular disease and other common human diseases.

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Configuration at C‐24 of 24‐methyl and 24‐ethylcholesterol in tracheophytes

Cited by 85 publications

References 15 publications

Diversity of sterol composition in the family chenopodiaceae

Diversity of sterol composition in the family chenopodiaceae

Impact of dietary sterols on life‐history traits of a caterpillar

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