Studies On The Chemical Constituents & Bioactivity Of Uvaria Kurzii & Polyalthia Nemoralis

In order to discover bio-active compounds from rich Chinese plant sources and make full use of them,the chemical constituents of Uvaria kurzii(King) P.T.and Polyalthia nemoralis A.DC.were systematically separated with various chromatographic techniques and the structures were elucidated by means of spectra and chemical methods.Furthermore,the isolates were screened for biological activities.34 compounds were isolated,purified and identified from the EtOH extract of Uvaria kurzii(King) P.T.branches and leaves,including 5 ent-kaurane diterpenoids,5 aporphine alkaloids,4 anthraquinones,3 flavonoids,9 steroids,and 7 other type compounds.These compounds are identified as follows:bis(4-octanoylphenyl)methane (1),ent-kaur-16-en-19-oic acid(2),grandifloric acid(3), ent-kaur-15-en-17-ol-19-oic acid(4),ent-16a,17-dihydroxykauran-19-oic acid(5), ent-16β,17-dihydroxykauran-19-oic acid(6),bidebiline A(7),annobraine(8), oxoputerine(9),atherospermidine(10),liriodenine(11),allantoin(12),physcion (13),questin(14),rubiadin 3-methyl ether(15),emodin(16),kaempferol-3-O-β-D-(6"-O-p-coumaryoyl)galactopyrannoside(17),kaempferol-3-O-rutinoide (18),rutin(19),vanillic acid(20),protocatechuic acid(21),N-(p-trans-coumaroyl) tyramine(22),β-sitosterol hexadecanoate(23),stigmasterol hexadecanoate(24),β-acetylsitosterol(25),13-acetylstigmasterol(26),13-sitosterol(27),stigmasterol (28),5a-stigmast-3,6-dione(29),5a-stigmast-22-ene-3,6-dione(30),daucosterol (31),L-quebrachitol(32),tetratriacontanol(33),dotdacontanoic.Among them, 1 is a new compound,and 12-16,22-26,29,30,32-34 were isolated from Annonaceae for the first time,2-10,17-19 were firstly found from genus Uvaria,as well as 11,20,21,27,28,31 firstly found from Uvaria kurzii(King) P.T..38 compounds were isolated from the EtOH extract of Polyalthia nemoralis A.DC. branches and leaves,including 8 aporphine alkaloids,7 2-thiopyridines,3 quaternary benzyltetrahydronisoquinolines,4 simple phenols,4 polyols,2 steroids,and 10 other type compounds.These compounds were identified as follows:polynemoraline A (35),polynemoraline B(36),polynemoraline C(37),polynemoraline D(38), zincpolyanemine(39),nickel bis(pyridine-N-oxide-2-thiolate)(40),cupric bis-(pyridine-N-oxide-2thiolate) (41),2-methanesulfonyl-pyridine(42), 2-pyridinethiolate N-oxide(43),2-thiohydroxy-pyridin-N-oxide-2-S-β-D-glucopyranoside (44),2,2'-dithiodipyridine(45),bidebiline A(46),annobraine (47),lanuginosine(48),liriodenine(49),oxostephanosine(50),(+)-magnoflorine (51),(+)-xylopinidine(52),(+)-oblongine(53),(+)-tembetarine(54), stepharanine(55),pyridine-N-oxide(56),syringic acid(57),3-methoxy-4-hydroxycinnamic acid(58),vanillic acid(59),4-hydroxybenzoic acid(60), mauritianin(61),3-amino-3-deoxy-D-glucose(62),eythritol(63),D-mannitol (64),ethyl-β-D-glucopyranoside(65),myo-inositol(66),glycerol(67),β-sitosterol(68),daucosterol(69),(2S,4R)-4-hydroxy-2-piperidinecarboxylic acid(70),stearic acid(71)。Among them,35-38 are identified to be novel compounds,40,42,43,45,56 were new natural products,50,53-55,61,62, 70were isolated for the first time from Annonaceae,47,51,52,57-59,60,63, 64,65were isolated for the first time from genus Polyalthia,and 46,48,49,71 are found from Polyalthia neraoralis A.DC.。Bio-activity test in vitro against human tumor cell lines with MTT method showed potent cytotoxic activity of 39-,40,41,43(IC₅₀ 0.05μg/ml),which were isolated from Polyalthia nemoralis A.DC.In addition,the oxoaporphines isolated from these two plants showed moderate cytotoxic activity(IC₅₀ 1μg/ml).The new compound,bis(4-octanoylphenyl)methane(1),showed significantly to increase the coronary flow and the contractile force.Thus 9 analogues of 1 were designed and synthesized for the bioactivity test and the QSR study,among them,2 compounds were new.