Studies On The Chemical Constituents Of Croton Laevigatus And Hedychium Forrestii

In this paper,the chemical constituents of Croton laevigatus and Hedychium forrestii were studied.Sixty-eight compounds were obtained,and four of them are new compounds.At the same time,cembrane-type diterpenes in plants and their biological activities was reviewed,which provided reference for the research of these compounds in plants.The branches and leaves of C.laevigatus were extracted with methanol,and the extract was dissolved in water,after extracted with ethyl acetate.A variety of separation methods were applied（Silica gel 、 MCI 、 Sephadex LH-20 、 C18reversed-phase column chromatography and HPLC）to obtain 43 compounds.Their structures were identified by spectral analysis（IR,NMR and MS）.The structural types contained cembrane and pimarane diterpenes,sesquiterpenes,steroids and aromatic compounds.Compounds 1 and 2 were new cembrane diterpenes,named crolaevins A（1）and B（2）.The others were characterized as neocrotocembraneic acid（3）,crotocembraneic acid（4）,laevigatlactones A-F（5-10）,（-）-（R）-nephthenol（11）,sublylactones A（12）and B（13）,macrophypenes C（14）and D（15）,isopimara-7,15-dien-3β-ol（16）,EBC-346（17）,（3β,12α,13α）-3,12-dihydroxypimara-7,15-dien-2-one（18）,maniesculentin A（19）,laevigatbenzoate（20）,7-methoxydihydrosynapyl alcohol-9-O-benzoyl ester（21）,methyltessmannoate（22）,（7R）-opposit-4（15）-en-1β,7-diol（23）,isodaucene（24）,（6R）-hydroxy-humulene（25）,oplopanone（26）,aromadendrane-4β,10β-diol（27）,1αH,5βH-guai-10（14）-ene-4α,6β-diol（28）,3-（3’-methoxy-5’-phenylfuran-2’-yl）propan-1-ol（29）,（3R,6R,7E）-3-hydroxy-4,7-megastigmadien-9-one（30）,trans-β-coumaric acid（31）,dehydrovomifoliol（32）,loliolide（33）,3α-hydroxy-5,6-epoxy-7-megastigmen-9-one（34）,β-sitosterol（35）,stigmasterol（36）,ergost-5,22-diene-3β-ol-20,28-olide（37）,3β-hydroxystigmast-5,22-dien-7-one（38）,tigmast-5,22-dien-3β,7β-diol（39）,benzoic acid（40）,p-hydroxybenzoic acid（41）,p-hydroxybenzaldehyde（42）,isovanillin（43）.Compounds 11 and 23-25 were isolated from Croton for the first time,and compounds 4,12-13 and 16-19 were isolated from C.laevigatus originally.The rhizome of H.forrestii was extracted with methanol,and the extract was dissolved in water and extracted with petroleum ether and ethyl acetate in succession.Isolation of the ethyl acetate extracts in similar method as described for C.laevigatus provide 25 compounds.Two were identified as new labdane-diterpenes,named as hedyforresins A（1’）and B（2’）.The others were identified as hedychenone（3’）,coronarin A（4’）,hedyforrestins B（5’）,C（6’）,D（7’）、yunnancoronarins B（8’）,C（9’）,D（10’）,E（11’）,isocoronarin D（12’）,hedylongnoid A（13’）,pacovatinin A（14’）,villosin（15’）,forrestiin A（16’）,7-hydroxyl-hedychenone（17’）,6-shogaol（18’）,subamone（19’）,3,7-dimethyl-octa-1,7-diene-3,6-diol（20’）,asaricin B（21’）,4-hydroxy-3-methoxybenzaldehyde（22’）,isovanillin（23’）,3,4-dimethoxyphenol（24’）and β-sitosterol（25’）.Compounds 5’,8’,9’,12’-15’ and 17’were isolated from H.forrestii for the first time.Neocrotocembraneic acid（3）rich in C.laevigatus was tested for its inhibitory activity against Phytophthora infestans 88069,and the result showed that it possessed no activity.Compounds 3 and 5 isolated from C.Laevigatus were tested on the proliferation activity of primary chondrocytes of SD rat suckling mice,and both showed certain activities.The tumor cytotoxic activity test of some compounds is still in progress.