Synthesis of lesquerella-based bisphosphonates

IF 1.9 4区 农林科学 Q3 CHEMISTRY, APPLIED Journal of the American Oil Chemists Society Pub Date : 2023-11-24 DOI:10.1002/aocs.12760
Laurelee M. Boon, Sierra R. Bamert, Effrat L. Fayer, Chelsea L. Coley, Shannon M. Henry, Diana M. Cermak, Steven C. Cermak
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Abstract

Hydroxy fatty acids (HFAs) have found wide use in today's market, ranging from industrial materials to pharmaceuticals. Castor oil, which is obtained from castor seeds, has served as a primary source of the most common HFA, ricinoleic acid, but also contains several undesirable compounds which pose severe health risks, the most notable being ricin, an unusually stable, toxic protein. A promising HFA alternative is lesquerella oil, an oil obtained from seeds of the Lesquerella fendleri species. Lesquerella oil is mainly comprised of lesquerolic acid, an HFA that is structurally similar to ricinoleic acid, the only difference being that lesquerolic acid possesses two additional methylene groups on the carboxyl end of the molecule. In addition, the bisphosphonate moiety has been shown to display interesting biological activities, primarily as osteoporosis drugs and anti-cancer therapeutics. The synthesis of lesquerella-based bisphosphonates, both an unsaturated and saturated series, have been produced in high yields and high purity and are reported here.

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lesquerella基双膦酸盐的合成
羟基脂肪酸(hfa)在今天的市场上有广泛的用途,从工业材料到药品。从蓖麻籽中提取的蓖麻油是最常见的HFA蓖麻油酸的主要来源,但也含有几种对健康构成严重威胁的不良化合物,其中最显著的是蓖麻毒素,这是一种异常稳定的有毒蛋白质。一种很有前途的HFA替代品是lesquerella油,一种从lesquerella fendleri物种的种子中获得的油。lesquerolic acid lesquerolic acid lesquerolic oil lesquerolic油主要由lesquerolic酸组成,这是一种结构类似于蓖麻油酸的HFA,唯一的区别是lesquerolic酸在分子的羧基端具有两个额外的亚甲基。此外,双膦酸盐部分已显示出有趣的生物活性,主要作为骨质疏松症药物和抗癌药物。本文报道了以lesquerella为基础的不饱和系列和饱和系列双膦酸盐的高收率和高纯度合成。
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来源期刊
CiteScore
4.10
自引率
5.00%
发文量
95
审稿时长
2.4 months
期刊介绍: The Journal of the American Oil Chemists’ Society (JAOCS) is an international peer-reviewed journal that publishes significant original scientific research and technological advances on fats, oils, oilseed proteins, and related materials through original research articles, invited reviews, short communications, and letters to the editor. We seek to publish reports that will significantly advance scientific understanding through hypothesis driven research, innovations, and important new information pertaining to analysis, properties, processing, products, and applications of these food and industrial resources. Breakthroughs in food science and technology, biotechnology (including genomics, biomechanisms, biocatalysis and bioprocessing), and industrial products and applications are particularly appropriate. JAOCS also considers reports on the lipid composition of new, unique, and traditional sources of lipids that definitively address a research hypothesis and advances scientific understanding. However, the genus and species of the source must be verified by appropriate means of classification. In addition, the GPS location of the harvested materials and seed or vegetative samples should be deposited in an accredited germplasm repository. Compositional data suitable for Original Research Articles must embody replicated estimate of tissue constituents, such as oil, protein, carbohydrate, fatty acid, phospholipid, tocopherol, sterol, and carotenoid compositions. Other components unique to the specific plant or animal source may be reported. Furthermore, lipid composition papers should incorporate elements of year­to­year, environmental, and/ or cultivar variations through use of appropriate statistical analyses.
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Issue Information Issue Information Microfluidization outperforms homogenization: Optimizing stability and bioaccessibility in krill oil emulsions Issue Information JAOCS special issue on advancement in plant protein-based emulsions
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