Terpenes From Two Genera Of Mangrove Plants

Chemical investigations of Xylocarpus granatum and Ceriops tagal were carried out in this thesis.TLC,HPLC-DAD,LC-MS and NMR were used to trace the terpenes.Forty-three compounds were obtained by normal-phase and reversed-phase silica gel column chromatography,high performance liquid chromatography,chemical derivation,and recrystallization.The structures of all compounds were established by UV,ORD,MS,NMR and single-crystal X-ray diffraction analysis.Twenty-five compounds were obtained from the seeds of X.granatum,among which twelve compounds were new,including nine limonoids(1~6,9~12)and three triterpenoids(13~15).Compounds 1~6,9 are a small group of limonoids containing a C1-O-C29 oxygen bridge.Compound 1 is a new limonoid with a(35)8,30 double bond and its absolute structure was determined by single-crystal X-ray diffraction analysis with Cu Kα radiation.Compounds 2~4,possessing conjugated(35)8,30 and(35)14,15 double bonds,are the first examples of this kind of limonoids isolated from the genus Xylocarpus.Compounds 5~6 are a pair of isomers separated and identified unambiguously by chemical derivation.Compound 9 is a limonoid with a γ-hydorcybutenolide ring at C-17,rather than the normal furan ring.Compounds 10~11 are new highly acetylated phragmalins while compound 12 is a phragmalin with a group of 8,9,30 orthoacetate.Compounds 13~15 are new triterpenes.Compound 13 contains three adjacent hydroxyl groups in the branched chain and its absolute configuration was determined by single-crystal X-ray diffraction analysis with Cu Kα radiation,while compounds 14~15 contain a substituent of tetrahydrofuran ring placing at C-22.The other thirteen known compounds includes: seven C1-C29 oxygen-bridged limoniods(7~8,16~20),including two derivatized products(7~8),two mexicanolides(21~22),two triterpenoids(23~24),and two glycerides(25~26).The absolute configuration of compound 18 was determined by single-crystal X-ray diffraction analysis with Cu Kα radiation for the first time.Another seventeen known compounds(T-1~T-17)were isolated from C.tagal,including fifteen dolabranes(T-1~T-15),one pimarane(T-16),and one artificial product of dolabrane(T-17).We also studied the anti-inflammatory(10~12)and anti-breast cancer(5,10~12)activity of some of new limoniods.Compounds 10~12 inhibited the expression of NF-KB reporter gene in RAW264.7 cells stimulated by LPS at the concentration of 10 μM and exhibited no cytotoxic effect on RAW264.7 cells.The results also suggested that compounds 10~12 may inhibit the production of inflammatory related factors by inhibiting NF-k B signaling pathway in RAW264.7 cells induced by LPS and thus play an anti-inflammatory effect.