Studies On The Terpenes Of Caesalpinia Minax Hance

Caesalpinia minax Hance,belonging to the genus Caesalpinia(family Fabaceae),was mainly distributed in Guangxi,Guangdong,Sichuan,Yunnan and Guizhou of China.This plant is rich in production,and its seeds are named as ’Ku Shi Lian’ in China.It has been widely used in folk medicine of Zhuang and Yao ethnic minority.It is bitter in flavour,cool in nature,which has the functions of clearing heat and removing toxicity,scattered stasis pain and dissipating dampness.The treatments of C.minax are common cold with wind-heat syndrome,traumatic injury,dysentery and stranguria with turbid discharge.The early phytochemical investigations on C.minax reported occurrences of diterpenes,triterpenes,flavonoids,sterols,etc,in which cassane-type diterpenes are the main chemical constituents and also the main active ingredients.Such cassane-type diterpenes have been proven to have strong anti-viral,anti-tumor or anti-inflammatory activities.In this thesis,the recent advances in the chemical composition,pharmacological activity,quality control and clinical application of C.minax are reviewed.In order to further clarify its chemical constituents,develop and enrich the medicinal resources of Caesalpinia minax,we carried out a phytochemical investigation on "Ku Shi Lian".The MeOH extract of the seeds of C.minax was chromatographed on silica gel,ODS,sephadex LH-20 and semi-preparation HPLC to yield 37 compounds.Their structures were determined on the basis of IR,NMR(1H-NMR,13C-NMR,1H-1H COSY,HSQC,HMBC,NOESY),HR-ESI-MS and X-ray crystallographic analysis.These compounds were elucidated as caesalminaxin O(1),caesalminaxin P(2),caesalminaxin Q(3),caesalminaxin R(4),caesalminaxin S(5),14-deoxy-ε-caesalpin(6),caesalmin E3(7),caesalmin E(8),caesalmin H(9),caesalpinin M1(10),7-O-acetyl-bonducellpin C(11),caesalpine A(12),bonducellpin C(13),caesalpinin M2(14),caesalpinin MB(15),bonducellpin G(16),caesalmin M(17),caesall C(18),ξ-caesalmin(19),caesalpinin MK(20),caesalmin C(21),caesalpinin P(22),norcaesalpinin E(23),caesalpine C(24),norcaesalpinin A(25),caesalmin J(26),caesalpinin F1(27),neocaesalpin AB(28),caesalpinolide G(29),neocaesalpin L(30),3-deacetoxy-6-acetoxy caesaldekarin E(31),neocaesalpin AH(32),spirocaesalmin B(33),spirocaesalmin(34),minaxin B(35),β-amyrine(36),β-sitosterol(37).Among them,caesalminaxins O-S(1-5)were new compounds.Compounds(22 and 31)were firstly isolated from the plant.There are 35 diterpenes(1-35),one triterpene(36)and one sterol(37).These diterpenes are mainly casane-type diterpenes,and there are twenty-six furan casane-type diterpenes(2-27),and three butenolide diterpenes(28-30).