Studies On The Chemical Constituents Of The Fruit Of Alpinia Oxyphylla Miq

Alpinia Oxyphylla is the dry ripe fruit of Alpinia oxyphylla Miq.(Zingiberaceae), which is distributed in Guangdong, Guangxi, Hainan, Yunnan, and Fujian provinces of China, named "YiZhi Ren" and "YiZhi Zi". It is a Geoherb of Hainan province, and also is one of the four famous Chinese traditional herbs in South China. Modern pharmacological research reveals that Alpinia Oxyphylla shows the activities in neuroprotection, anticancer, cardiotonic, vasodilator, immune-enhancing, antioxidant, gastrointestinal tract-protecting, antiulcer, pain relief, sedative, hypnotic, memorization-improving and so on.Currently, compounds isolated from Alpinia Oxyphylla are mainly terpenoids, flavonoids, diphenyl-heptanes, phenols, sterols, and other kinds of components, among which sesquiterpenes and diphenyl-heptanes are the important active ingredients. The main aim of this study is to find active ingredients, in order for the further evaluation of the medicinal application of Alpinia Oxyphylla.Totally26compounds have been isolated and identified from the w-butanol part of95%ethanol extract of Alpinia oxyphylla in this work. Their structures were elucidated by spectrometric approaches, including (ID and2D)NMR, MS, IR, UV, ORD, CD etc.. Among the26compounds,7of them were found to be new compounds,4to be new natural products and9isolated from the genus (Alpinia) for the first time,1isolated from the plant for the first time.The new compounds includes:3sesquiterpenes,named(1R,4R,10R)-1β,4a-dihydr-oxy-4β,10β-dimethyl-11,12,13-trinor-5,6-eudesmen-7-one (compoundl),3a,4a,8β-trihydroxy-3β-methyl-6β-isopropyl-14-nor-5,10-cadinane-9-one(compound23),3a,4a,7-trihydroxy-4β,1Oa-dimethyl-7-acetyl-13-nor-5,6-eudesmen-7-one(compound24);1organic acid, named5-hydroxy-6-(3’,4’-dihydroxy-4’-methyl-pentyl)pyridine-2-carboxylic acid (compound25);3monoterpenes, named (4Z)-3,7-dimethyl-4-octene-1,2,3,6,7-pentaol (compound20),(4E)-3,7-dimethyl-4-octene-1,2,3,6,7-pentaol (compound21),(3E)-3,7-dimethyl-3-octene-1,2,5,6,7-pentaol (compound22)。Four new natural products were determined as3β-D-pyranoside and1lactone, named2-O-β-D-Glucosyl-(1S)-phenylethylene Glycol(compound9)、(S)-1-Phenyleth-y1β-D-glucopyranoside (compound10),1-methyl butyl-β-D-glucopyranoside (comp-ound14),2-acetamido-2,3-dideoxy-D-threo-hex-2-enono-1,4-lactone(compoundl8). In addition,15known compounds were identified as4sesquiterpenes, named1β,4β-dihydroxy-11,12,13-trinor-8,9-eudesmen-7-one (compound2); oxyphyllenone A(co mpound3), oxyphyllenone B (compound4), Teucrenone (compound6);1flavonoid, named rhamnocitrin (compound5);7glycosides, named Staphylionoside D(compound7), Benzyl-l-O-β-D-glucopyranoside(compound8),β-D-Glucopyrano-side,[4-(1-hydroxy-l-methylethyl)phenyl]methyl(compound11), butylβ-D-fructopyr-anoside (compound13), uridine (compound15), thymidine (compound16), β-D-glucopyranoside,2-hydroxy-5-methoxyphenyl(compound17); and other kinds of compounds,β-sitosterol (compound12),(3E)-3,7-dimethyl-3-octene-1,2,6,7-tetraol (compound19), Levulinic acid(compound26).Compounds2,7,11,13,15,16,17,19,26were isolated from the genus (Alpinia) for the frist time; Compounds8was isolated from the plant for the first time.Finally, this study had also systemically summaried the advances in the research of chemical constituents and their pharmacological activities of the genus(Alpinia), which provided certain reference for the further development of the plant.