Study On The Chemical Constituents Of Pinus Koraiensis Pinecones And Their Biological Activity

Pinus koraiensis(Pinaceae),also known as Korean pine,is widely distributed from the Xiaoxing’anling region to the Changbai Mountains,and it is a unique tree with both fruit and wood in Northeast of China.Pinecones,a globular fruit without seeds of pines,has the effects of expectorant,relieving cough and asthma,dispelling wind and moistening intestines,and it contains various bioactive substances such as anti-tumor,antibacterial,anti-virus,and antioxidant activities.In this study,we describe the analysis of chemical constituents from pinecones of P.koraiensis,and the antitumor activities of obtained compounds were preliminarily evaluated,which further enriched the pharmacodynamic material basis of P.koraiensis pinecones and provided a scientific basis for the full development and utilization of this plant.In this study,twenty compounds were isolated from petroleum ether and dichloromethane fractions of P.koraiensis pinecones by means of various separation and purification technology such as silica gel column chromatography,recrystallization,preparative high performance liquid chromatography and Sehadex LH-20 column chromatography.The chemical structures of isolated compounds were identified as β-sitosterol(1),daucosterol(2),dehydroabietal(3),cis-abienol(4),dehydroabietic acid(5),isopimaric acid(6),alusenone(7),17-nor-7,15-dion-8,11,13-abietatrien-18-oic acid(8),15-hydroxydehydroabietic acid(9),inonotusic acid(10),entisopimara-8,15-dien-7-oxo-18-oic acid(11),7α-methoxy-dehydroabietic acid(12),8(14)-podocarpen-13-on-18-oic acid(13),pinmassin B(14),abieta-7,13-diene-12α-methoxy-18-oic acid(15),8(14)-podocarpen-7,13-dion-18-oic acid(16),7β-hydroxydehydroabietic acid(17),and 7α-hydroxydehydroabietic acid 18)on the basis of NMR spectroscopic analysis.Among them,compounds 8,10,12 and 15 were isolated from this plant for the first time.In this study,the isolated compounds were tested for their inhibitory effects on HIF-1α activation in He La cells using the luciferase reporter gene assay system to evaluate their antitumor activities in vitro,and the cytotoxicity of the compounds was detected by MTT assay.As a result,none compound exhibited significant HIF-1αinhibitory activity,and all of the compounds did not show obvious cytotoxicity.