Studies On The Chemical Constituents From Garcinia Multiflora Fruits And Their Bioactivities

In this paper,thirty one compounds（1-28）were isolated and purified from Garcinia multiflora fruits,and their structures were identified by modern spectroscopies,quantum chemical calculations and other methods,including twenty new compounds（1,2,4-6,8-12,17,20-26）,compounds 7,8 and 25 are keto-enol tautomeric mixtures,it was the first time that NMR calculations and DP4+analysis based on ¹³C and ¹H-NMR calculation data were used to determine the relative configurations of PPAPs with flexible isogeranyl chain,and the absolute configuration of this type of compound was determined by ECD calculation method.Compounds 1-25 are all PPAPs derivatives,including eight type A BPAPs compounds（1-7）,two type B BPAPs compounds（8）,five caged homoadamantane-type PPAPs compounds（9-14）,two caged adamantane-type PPAPs compounds（15,16）,three complicated PPAPs compounds（17-19）,one seco-homoadamantane-type new skeleton PPAPs（20）,five monocyclic polyprenylated acylphloroglucinol derivatives（MPAPs,21-25）.26 is tocotrienol derivative,27-28 are xanthones compounds.The new compounds were named:garcimultinone D（1）,garcimultinone E（2）,garcimultinone F（4）,garcimultinone G（5）,garcimultinone H（6）,garcimultinone I（8a）,garcimultinone J（8b）,iso-hookerione J（9）,iso-sampsonione（10）,epi-garcimultiflorone P（11）,iso-garcimultiflorone G（12）,garmultinone D（17）,garcimultinone K（20）,garcimultinone L（21）,garcimultinone M（22）,norgarmultinone B（23）,garcimultinone N（24）,garcimultinone O（25a）,garcimultinone P（25b）;2Z,6E,10E-13-（6-acetyl-2,8-dimethyl-3,4-dihydro-2H,2-chromenyl）-2,6,10-trimethyl-2,6,10-tridecatrien-1-ol（26）.Compounds 8a and 8b are a pair of BPAPs with keto-enol tautomeric mixtures,the content ratio is about 2:1.17 is the first example of tricyclo[4.3.1.0^3,7]decane PPAPs with the 2,2-dimethyl-3-isopropenylcyclopentyl in nature.20 is the second exampleofseco-homoadamantane-typePPAPswith5-oxotricyclic[7.3.1.0^3,7]tridecane skeleton and a unique 5/7/6 tricyclic system.23 is cyclized by isogeranyl side chain to form the first example of natural cyclohexanone-monocyclic polyprenylated acylphloroglucinol（C-MPAP）derivatives with tetrahydropyran ring.Compounds 25a and 25b are a pair of keto-enol tautomeric MPAPs with a content ratio of 1:2.Their anti-proliferative activities of all compounds were measured against three tumor cell lines（T98,Hep G2,MCF-7）by CCK-8 method,compounds 2 and 6showed strong anti-proliferative activities against three tumor cell lines.The IC50values of compound 2 are 13.23±4.24,13.53±0.17 and 9.81±1.56μM,and the IC50values of compound 6 are 17.00±2.75,12.84±1.59 and 15.68±1.65μM,respectively,its IC50 value is smaller than or equivalent to cisplatin.Among ten BPAPs compounds（1-8）,only 2 and 6 have better anti-proliferative activity.Therefore,it is speculated that the 3,4-dihydroxybenzoyl of 2 and 6 are pharmacophores that exert anti-tumor activity.The anti-inflammatory activities of 25 compounds were tested by Griess method.The results showed that all test compounds were in the concentration range from 1.25to 20μM,the survival rate of macrophages RAW264.7 was more than 80%,the inhibition rate of NO production was less than 50%,and the IC50 values were all more than 20μM.Compared with the positive drug dexamethasone,the inhibitory rate of all compounds against NO production is less than that of positive drugs,and did not show significant anti-inflammatory activity.