旱生香茶菜次生代谢产物的化学研究

	旱生香茶菜次生代谢产物的化学研究; Chemical studies on the secondary metabolites of Isodon xerophilus
	代家猛
导师	普诺·白玛丹增
摘要	This dissertation is composited of three chapters. Chapter 1 described the studies on chemical constituents and biological activities from the aerial parts and the rhizomes (one-year-old and four-year-old) of I. xerophilus. Chapter 2 described the studies on the biomimetic synthesis of xerophilines D and E analogues. Chapter 3 reviewed the phytochemical research progress on the diterpenoids from Isodon species in Yunnan Province, including their structures, bioactivities, and chemical synthesis. By means of chromatography methods, spectroscopic analysis, and single crystal X-ray diffraction method, 75 compounds, including 21 new ones, were isolated and identified from I. xerophilus. Their structures were classified into diterpenoids, novel meroditerpenoids, dimeric diterpenoids and so on. Biological evaluation of the selected diterpenoids showed their cytotoxic, anti-inflammatory, and anti-viral activities. In the biomimetic synthesis of 34 and 35 analogues, we took commercially available dehydroabietic acid as starting materials, which was subjected to reduction, and oxidative dearomatization. Then, treatment of the afforded diene intermediate with the expected ent-kauranoids via an intermolecular Diels-Alder reaction furnished the target molecules. Chapter 1. Chemical studies on the secondary metabolites of I. xerophilus 1.1. Phytochemical study on the aerial parts of I. xerophilus Thirty-two diterpenoids, including 10 new ones, were isolated and identified from the aerial parts of I. xerophilus. Among them, xerophilsins A and I were unusual meroditerpenoids derived from a hybrid of an ent-kauranoid and a long-chain aliphatic ester. Xerophilsin H (6) was a new 7,20-cyclo-ent-kauranoid, and xerophilsins B–D (25–27) and J (28) were dimeric ent-kauranoids. The absolute configurations of 6, 15 and 25 were established by single-crystal X-ray diffraction. Some compounds were evaluated for biological activities against five human tumor cell lines, against NO production in LPS-stimulated RAW264.7 cells, autophagy modulators and the functional study of antiviral activities. 1.2. Phytochemical study on the one-year-old rhizomes parts of I. xerophilus Phytochemical investigation on the one-year-old rhizomes of I. xerophilus led to the isolation of 32 diterpenoids, including seven new ones. Xerophilines A, D, E (33–35) were novel dimeric diterpenoids bearing two unprecedented skeletons. Based on the deduction from its plausible biogenetic pathway, 33 was derived from an ent-kauranoid and a semperviranoid via a [4+2] cycloaddition, while 34 and 35 were derived from an ent-kauranoid and an abietanoid via a [4+2] cycloaddition. The absolute structures of xerophilines A and D were determined by single-crystal X-ray diffraction analysis. Biological evaluation of 34 and 35 revealed their anti-tumor immune activity. 1.3. Phytochemical study on the four-year-old rhizomes parts of I. xerophilus Eleven compounds, including four new ones, were isolated and identif
	2021-05
文献类型	学位论文
条目标识符	http://ir.kib.ac.cn/handle/151853/74534
专题	昆明植物所硕博研究生毕业学位论文
推荐引用方式 GB/T 7714	代家猛. 旱生香茶菜次生代谢产物的化学研究, Chemical studies on the secondary metabolites of Isodon xerophilus[D],2021.

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