Chemical Constituents From Morus Wittiorum And Ficus Microcarpa

Three new flavane glucosides, alonge with twenty-nine known compounds were isolated from the leaves of Morus wittiorum. In addition, twenty-eight known compounds were isolated from the aerial roots of the Ficus microcarpa. The structures of the new compounds were elucidated by means of spectroscopic methods (UV, IR, HR-ESI-MS, and NMR), and the absolute configurations were assigned by CD spectra. The structures of the known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literatures. Otherwise, a pair of configurationally unstable diastereomers were found could automatic isomeric interconvert in solution. A plausible racemization procedure of the C-2 stereocenter was also proposed in this thesis.1. Chemical constituents from the leaves of Morus wittiorumMulberry leaves had been used as a traditional Chinese medicine for the treatment of diabetes. Previous phytochemical studies had led to the isolation of flavonoids, polyhydroxylated alkaloids and benzofurans from some mulberry leaves. Moreover, two clinical drugs for diabetes, Miglitol and Emiglitate had been developed by Bayer Company based on 1-deoxynojirimycin, which was isolated from the leaves and stem barks of Morus alba. Thus, further investigation of the chemical constituents of Morus plants is significant.During our investigation on structurally and pharmacologically interesting secondary metabolites from Morus plant, thirty-six compounds were isolated from the leaves of M. wittiorum by various chromatographic methods. Among them, thirty-two compounds were identified as (2S)-7-hydroxyl-8-hydroxyethyl-4'-methoxylflavan-2'-O-β-D-glucopyranoside (MW-1), (2S)-7-methoxyl-8-hydroxy-ethyl-4'-hydroxylflavan-2'-O-β-D-glucopyranoside (MW-2), (2R)-7-meth-oxyl-8-hydr-oxyethyl-4'-hydroxylflavan-2'-O-β-D-glucopyranoside (MW-3),1-deoxynojirimycin (MW-4), fagomine (MW-5),4-O-β-D-glucopyranosyl-fagomine (MW-6),2-O-α-D-galacto-pyranosyl-1-deoxynojirimycin (MW-7), caffeic acid methyl ester (MW-8),7-hydroxycoumarin (MW-9), esculetin (MW-10), scopoletin (MW-11), esculetin-7-O-β-D-glucoside (MW-12), scopolin (MW-13), apigenin (MW-14), luteolin (MW-15), apigenin-7-O-β-D-glucoside (MW-16), luteolin-7-O-β-D-glucoside (MW-17), quercetin (MW-18), kaempferol-3-O-β-D-glucoside (MW-19), rutin (MW-20), quercetin-3-O-maltopyranoside (MW-21), quercetin-3-O-β-neohesperidin (MW-22), moracin D (MW-23), moracin C (MW-24), benzyl-β-glucopyranoside (MW-25), icariside D (MW-26), (6R,3E)-1-hydroxylinalool-6-O-β-D-glucopyranoside (MW-27), (6S,3E)-1-hydroxy-linalool-6-O-β-D-glucopyranoside (MW-28), betulalbuside A (MW-29), (6S,9R)-roseoside (MW-30), bridelionoside C (MW-31) and icariside B1 (MW-32) respectively. Compounds MW-1, MW-2 and MW-3 were new compounds. MW-8～MW-22 and MW-25～MW-32 were isolated from this plant for the first time. MW-2 and MW-3 as a pair of configurationally unstable diastereomers could interconvert in solution, the proposed mechanism was also discussed.2. Chemical constituents from the aerial roots of Ficus microcarpaFicus microcarpa belongs to Ficus genus of Moraeeae family. It is widely cultivated in Fujian, Guangdong, Hainan and Zhejiang provinces of China. Both aerial roots and leaves of F. microcarpa could be used for treatment of antitussive, influenz, and tonsillit, etc. Thus, further investigation on chemical constituents from F. microcarpa is necessary.During our investigation on structurally and pharmacologically interesting secondary metabolites from the aerial roots of F. microcarpa, thirty-two compounds were isolated by various chromatographic methods. Among them, twenty-eight compounds were identified as epi-friedelanol (FM-1), friedelin (FM-2), amyrin (FM-3), amyrolacetate (FM-4), ursolic acid (FM-5),3β-hydroxyl-11-oxours-12-ene (FM-6),3β-acetoxy-11-oxours-12-ene (FM-7), taraxerol (FM-8),3β-hydroxy-oleana-11,13(18)-dien-28-oic acid (FM-9), oleanic acid (FM-10), betulinic acid (FM-11), platanic acid (FM-12), pyracrenic acid (FM-13), citrostadienol (FM-14),β-Sitosterol (FM-15),3β-Hydroxysitost-5-en-7-one (FM-16), Stigmast-4-ene-6β-ol-3-one (FM-17), stigmast-4-ene-3,6-dione (FM-18),5a,8a-epidioxy-ergosta-6,22-dien-3β-ol (FM-19), caffeic acid methyl ester (FM-20), caffeic acid ethyl ester (FM-21), isowigtheone (FM-22), myrsininone A (FM-23), derrone (FM-24), alpinumisoflavone (FM-25),5,4'-dihydroxyl-3,7, 3'-trimethoxyflavon (FM-26), artemetin (FM-27), and 1-tricosanol (FM-28). Compounds FM-9, FM-13～FM-14, FM-16～FM-21 and FM-28 were isolated from this genus for the first time.