Study On Chemical Constituents Of Rubus Delavayi And The Branches And Leaves Of Pyrus Pashia And The Transformation Between Cis- And Trans-cinnamic Acid Deprivatives

Rosaceae plants (124 genus,3300 specis) are mainly distributed in north temperate zone. Rosaceae plants are widely distributed in China and the amount of these plants exceeds 1000 specia (51 genuses). Firstly,141 compounds including 16 new ones were isolated from Rubus delavayi and Pyrus pashia (Rosaceae). The cytotoxic and antioxidant activities of some isolated compounds were evaluated. Secondly, based on "previous phytochemical studies, a highly efficient method that utilizes iodine to entirely convert cis-cinnamic acid derivatives into their trans-forms was developed for the first time. Lastly, the structures and biological activities of cinnamic acid derivatives from plant, as well as the transformation method between cis- and trans- cinnamic derivatives were summarized.R. delavayi which grows in hillside and gully at 1600～3000 m altitude is disturbed in Midu, Weishan, Jianchuan, Eryuan, Yangbi countries in Yunnan Province, is common herb to treat tonsillitis, common cold, acute conjunctivitis, dysentery, furuncles and rheumatoid arthritis for Lisu and Nu nationalities, and t is also used as a kind of cool tea in Dali city of Yunnan province. It is reported that R delavayi showed some obvious bio activities, such as anti-inflammatory, cytotoxic and enhance the function of nonspecific immunity in mice. In this work, eleven new compounds and sixty-four known ones, including monoterpene, triterpene, steroid, flavonoid and phenolic acid were isolated from this plant. And compounds 59-61 possessing bromine atom were isolated from Rubus genus for the first time.The flower of P. pashia is a favorite health-giving food in the Yunnan Province of China. Its fruit is effective in the treatment of dyspepsia and dysmenorrhea. Its branches and leaves are used as antidiarrheal in the Chinese folk. In previous researches, fourty-seven compounds, including the triterpenoids,phenolic compounds and two cyclic peptides, were isolated from the flowers and the branches and leaves of P. pashia. During our further phytochemical investigation on the branches and leaves of this plant, five new compounds (1,13,36,47 and 49), together with sixty-one known ones were isolated from this plant It’s worthy to note that (4a)-3-(5,5-dimethyltetrahydrofuranyl)-1-buten-3-ol 3-O-β-D-glucopyranoside (1) and (4β)-3-(5,5-dimethyltetrahydrofuranyl) -1-buten-3-ol 3-O-β-D-glucopyranoside (2) were the first isolation of monoterpenoids from Pyrus genus.Cinnamic acid derivatives (CAs) composed of one phenylpropane (C6-C3) unit have proven to be versatile components, are present in abundant biologically active natural products, and widely used as intermediates for the manufacture of pharmaceuticals and chemicals. The mixture of cis-and trans-CAs can make some difficulties to the structure identification of natural products and organic synthetic studies. Based on CAs isolated from Pyrus pashia, photoisomersion phenomenon of trans-CAs was investigated. A highly efficient method that utilizes iodine to entirely convert cis-CAs into their trans- forms was developed. The mechanism study revealed this conversion occurred via an anti-diioodo intermediate.In the end of this thesis, the structural types and bioactivities of CAs isolated from plants were reviewed. The transformation methods between cis-and trans-CAs were also summarized.