Possible pharmaceutical applications can be developed from naturally occurring phenanthroindolizidine and phenanthroquin
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Possible pharmaceutical applications can be developed from naturally occurring phenanthroindolizidine and phenanthroquinolizidine alkaloids Xian-hui Jia . Huan-xin Zhao . Cheng-lin Du . Wen-zhao Tang Xiao-jing Wang
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Received: 13 March 2020 / Accepted: 14 September 2020 Ó Springer Nature B.V. 2020
Abstract Naturally occurring phenanthroindolizidine and phenanthroquinolizidine alkaloids (PIAs and PQAs) are two small groups of herbal metabolites sharing a similar pentacyclic structure with a highly oxygenated phenanthrene moiety fused with a saturated or an unsaturated N-heterocycle (indolizidine/quinolizidine moieties). Natural PIAs and PQAs only could be obtained from finite plant families (such as Asclepiadaceae, Lauraceae and Urticaceae families, etc.). Up to date, more than one hundred natural PIAs, while only nine natural PQAs had been described. PIA and PQA analogues have been applied to the development of potent anticancer agents all along because of their excellent cytotoxic activity. However, in the last two decades, other great biological properties, such as anti-inflammatory and antiviral activities were revealed successively by different pharmacological assays. Especially because of their potent antiviral activity against coronavirus (TGEV, SARS CoV and MHV) and tobacco mosaic virus, PIA and PQA analogues have attracted much pharmaceutical attention again, some of them have been used to present interesting targets for total or semi synthesis, and structure–activity relationship (SAR) study for the development of antiviral agents.
X. Jia H. Zhao C. Du W. Tang (&) X. Wang Institute of Materia Medica, Shandong First Medical University and Shandong Academy of Medical Sciences, Jinan 250062, People’s Republic of China e-mail: [email protected]
In this review, natural PIA and PQA analogues obtained in the last two decades with their herbal origins, key spectroscopic characteristics for structural identification, biological activity with possible SARs and application prospects were systematically summarized. We hope this paper can stimulate further investigations on PIA and PQA analogues as an important source for potential drug discovery. Keywords Phenanthroindolizidine and Phenanthroquinolizidine alkaloids Phytochemistry Biological properties Structure–activity relationships Application prospects
Introduction Phenanthroindolizidine and phenanthroquinolizidine alkaloids (PIAs and PQAs) are two small groups of natural bioactive products with similar molecular skeletons, belonging to indolizidine and quinolizidine alkaloid family, respectively. They commonly possess a pentacyclic structure with a phenanthrene moiety fused by a saturated or an unsaturated indolizidine/ quinolizidine group (Fig. 1). Natural PIAs and PQAs only could be obtained from few plant families, such as Asclepiadaceae, Lauraceae and Urticaceae families, etc. (Tables 1 and 2). The first isolation of PIAs was (R)-tylophorine (1) from Tylophora indica (Asclepiadaceae family), an
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