Studies On The Chemical Constituents Of Hedychium Villosum

The genus Hedychium belongs to Zingiberaceae,with about 50 species in the world,and distributed in Southeast Asia and Brazil.This genus is mainly growing in the southwestern regions in China,such as Yunnan,Guangxi,and Sichuan,and is widely used in the production of insect repellent and tobacco flavor.Phytochemical studies showed that their rhizome contains a large number of diterpenoids,and some of the labdane diterpenoids have novel skeleton and biological activities.In order to search for more diterpenoids with good biological activities from the genus Hedychium,the chemical constituents of H.villosum were studied in this paper.The rhizome of H.villosum were extracted repeatedly with methanol.After removal of the solvents under reduced pressure,the residual was partitioned between Et OAc and H₂O.A variety of separation techniques were used to isolate compounds and their structures were identified by spectral methods,inclouding NMR,MS and IR.As a result,50 compounds were isolated and identified from the ethyl acetate extract,among which 5 were new diterpenoid compounds,named hedyvillosins A-E（1-5）.1was labdane norditerpenoid.Others were identified as hedychenone（6）,coronarin A（7）,coronarin E（8）,yunnancoronarin A（9）,yunnancoronarin E（10）,yunnancoronarin D（11）,hedyyunnanin C（12）,7-hydroxyl-hedychenone（13）,yunnancoronarin B（14）,hedyforrestin B（15）,chinensine B（16）,7-hydroxy-6-oxo-7,11,13-labdatrien-16,15-olide（17）,hedyforrestin C（18）,hedycoronarin B（19）,hedycoronarin C（20）,hedycoronarin E（21）,yunnancoronarin C（22）,hedyforrestin D（23）,hedychenoid B（24）,spicatanol（25）,hedychilactone B（26）,hedychilactone A（27）,coronarin H（28）,15,16-bisnorlabda-7,11-diene-6,13-dione（29）,hedychiumin（30）,hedyunchene A（31）,9-oxonerolidol（32）,aromadendrane-4β,10β-diol（33）,10,11-dihydro-10,11-dihydroxynerolidol（34）,kaempferol-3,4’,7-O-trimethylether（35）,3,5-dihydroxy-7,4’-dimethoxyflavone（36）,（-）-sakuranetin（37）,aromadendrin-7,4’-dimethyl ether（38）,4’,5,7-trimethoxyflavonol（39）,3,5,7,4’-tetramethoxyflavone（40）,8-hydroxy-p-menth-1-en-7-al（41）,（4R,6S）-6-hydroxypiperitone（42）,1,5-octadien-3-hydroxy-3-methyl-7-one（43）,（4E,6E）-1,7-bis（4-hydroxy-3-methoxyphenyl）hepta-4,6-dien-3-one（44）,4-hydroxy-benzaldehyde（45）,4-methoxybenzoic acid（46）,vanillic acid（47）,pyrocatechol（48）,β-sitosterol（49）,daucosterol（50）.43 and 48 were isolated from the genus Hedychium for the first time;compounds 6-7,9-42 and 44-47 were obtained from H.villosum for the first time.Besides,hedychenone（6）,a large amount of labdane diterpenoid from H.villosum and alisol B 23-acetate from Alisma plantago-aquatica（Alismataceae）,were structurally modified to give 4 new hedychenone derivatives and alisol B 23-acetate phenylhydrazine condensate,a alisol B 23-acetate derivative.The screening results of antitriple negative breast cancer activity in vitro showed that hedyyunanin C（24）had significant inhibition activity againist MDA-MB-231,with IC₅₀value of 12.42±2.28μM(positive control cisplatin,IC₅₀:9.95±2.90μM).However,compounds 17-19,51 and 55 showed no inhibition activity.Compounds17-19,24,51 and 55 exhibited no activity againist HCC1806,IC₅₀ value>20μM(positive control cisplatin,IC₅₀:1.13±0.56μM).Other diterpene compounds 10,12,16,19-21,24-25,27-28,30,51-53 and 55were also screened for activity,and the results showed that compounds 16(IC₅₀values of 19.87 and 22.28μM)and 25(IC₅₀ values of 13.10 and 11.60μM,respectively)showed cytotoxic activity against human breast cancer cell lines（MDA-MB-231）and human colon cancer cell lines（HCT-116）.