Studies On The Chemical Constituents From Ilex Asprella And Psychotria Serpens Linn

This dissertation consists of two parts:one is our study of chemical constituts of Ilex asprella (Hook, et Arn) Champ, ex Benth., psychotria serpens linn and Chonemorpha valvata Chatt.; another is previous studies on Ilex asprella (Hook, et Arn) Champ, ex Benth. and psychotria serpens linn. ObejectiveScreening bio-active nature products, clarifying material foundation of medicinal effectiveness are the purpose of nature product research. China is rich in natural medicine resource, and traditional medicinal scriptures play a guide role on nature product research. In that case, three traditional medicinal plants, Aquifoliaceae, Ilex, Ilex asprella (Hook, et Arn) Champ, ex Benth.;Rubiaceae, Psychotria L, psychotria serpens linn and Apocynaceae, Chonemorpha, Chonemorpha valvata Chatt., were selected for phytochemistry investigations.The plant Ilex asprella (Hook, et Arn.) sourse of Aquifoliaceae, Ilex, Ilex asprella (Hook, et Arn) Champ, ex Benth dried root, also known as Cheng Xing tree, fake Chengxing tree (Dongguan), Roots, leaves used as medicine, is mainly distributed in Southern China, such as in Guangdong province and the Guangxi Zhuang autonomous region[1]. The roots of I. asprella have been widely used in Chinese medicine for the treatment of amygdalitis, laryngopharyngitis, racheitis, and pertussis, increase coronary blood flow in guinea pigs, and strengthen the role of myocardial contractility [2],This crude drug is also a major ingredient of’Wang-Lao-Ji Herbal Tea’which was formulated in1828and is widely accepted as a popular healthy beverage by Chinese people and Shaxi herbal tea, Lingnan folk also widely used Gang Mei homemade herbal tea tea. The less chemical research at home and abroad on the Ilex asprella, separation is mainly concentrated in parts of ethyl acetate and n-butanol large polarity in view of the of its multifaceted important bioactive, its potential medicinal prospects increasingly great potential caused by the extensive attention of the chemist, pharmacologist, development, in order to fully understand the chemical composition of the Ilex asprella its chloroform part of the research.psychotria serpens linn is a plants of Psychotria L. of Rubiaceae, medicinal part is dry leaves and stems. About700species of this genus in the worldwide, widespread in tropical and subtropical regions, China has15kinds of production from southwest to Taiwan, located in Guangxi, Guangdong, Fujian, Zhejiang, Taiwan and Hainan provinces. The medicinal function Dispelling wind and relieving pain and stimulate the circulation of the blood and cause the muscles and joints to relax. For rheumatoid arthritis, lumbar and leg pain, limb pain, bruises, malnutrition product Through literature retrieval, foreign scholars on more separation section Psychotria, many alkaloids, but not so much research on the chemical constituents of Psychotria serpens L. in China, all previous to study the chemical constituents of psychotria serpens are less, and not the system. In view of the many important biological activity, and its potential prospect in medicine and more attentions chemists, pharmacologists, development potential is very great, so this paper made a research on its chemical constituents.Chonemorpha friffithii hook(former name as Chonemorpha valvata Chat., Apocynaceae), is woody climber plant indigenous to Yunnan Province of China, Myanmar and thailang. its roots and rhizomes have a long history as folk medicine for the treatment of fracture and rheumatism arthritis in the Dai national area. However, no any report for C. griffithii was found thus far.A continuing interest in Chinese national folks prompted us to conduct an investigation on the chemical constituents of the title plant.MethodsIsolation and identification of chemical constituents of Ilex asprella (Hook.et Arn) Champ, ex Benth. And psychotria serpens1Extraction and separation of Ilex asprella The dry roots of Ilex asprella extracted with70%ethanol under reflux, and concentrated until no alcohol flavor, dissolved in water, and the partitioned successively with petroleum ether, chloroform, ethyl acetate, the chloroform fraction(55g) sample enrichment process to produce a lot of yellow insolubles,400g sample to obtain a precipitate after centrifugation. Defatting with petroleum ether, and then followed by using chloroform, ethyl acetate, n-butanol, wherein the chloroform extracts of55g samples, enrichment process produces a lot of yellow insoluble, centrifugation to get400g sediment samples.We use a variety of separation techniques (n, anti-column chromatography on silica gel chromatography, preparative thin layer chromatography, MCI column chromatography, Sephadex LH-20gel column chromatography, preparative-HPLC, etc.) to separate the chemical composition of parts of the system of the chloroform extracts of Ilex asprella, using a variety of analytical tools (ESI-MS, EI-MS, IR,’H NMR spectra,13C NMR spectra, DEPT spectra, HMQC, HMBC, ROESY, etc.) for the structural identification of the compounds, combined with spectroscopic data, and reported data comparing the structure of the compounds were identified. We are part of a large amount of the compound of the in vitro antibacterial activity screening.2Extraction and separation of psychotria serpenspsychotria serpens3Kg, crushed, extracted3times with methanol, respectively extracted with petroleum ether, chloroform and n-butanol, and then get petroleum ether fraction43g, chloroform fraction31.8g (foaming state), n-butanol fraction240g.The chloroform fraction using normal phase silica gel column chromatography, reversed phase silica gel column chromatography, Sephadex LH-20gel column and preparative HPLC and other methods of separation; n-butanol fraction using macroporous resin, MCI, reversed phase silica gel column chromatography, low-voltage preparative liquid equal other methods of separation; petroleum ether fraction using normal phase silica gel, Sephadex LH-20gel column method of separation. Share of compounds with nuclear magnetic resonance (NMR), infrared (IR), ultraviolet (UV),’H NMR spectra,13C NMR spectra, DEPT spectra, HMQC, HMBC, ROESY, etc. spectral technology, combined with the spectroscopic data and data reported in the literature comparing the structures of the compounds were elucidated.3Extraction and separation of Chonemorpha friffithii hookThe dried aerial part of C. griffithii (3.0kg) was extracted at r. t. three times with95%EtOH. The extract was concentrated under reduced pressure to2L, and then partitioned successively with petroleum ether, CHC13, and n-BuOH. The CHCl3-soluble fraction (33g).We use a variety of separation techniques (n, anti-column chromatography on silica gel chromatography, preparative thin layer chromatography, MCI column chromatography, Sephadex LH-20gel column chromatography, preparative-HPLC, etc.) to separate the chemical composition of parts of the system of the chloroform extracts of Ilex asprella, using a variety of analytical tools (ESI-MS, EI-MS, IR,’H NMR spectra,"C NMR spectra, DEPT spectra, HMQC, HMBC, ROESY, etc.) for the structural identification of the compounds, combined with spectroscopic data, and reported data comparing the structure of the compounds were identified. We are part of a large amount of the compound of the in vitro antibacterial activity screening.ResultDetailed chemical investigation of the roots of Ilex asprella70%ethanol extract chloroform fraction led to the isolation of25compounds by various chromatographic methods. The structure of23compounds were fully determined on the basis of spectroscopic analysis, including triterpenoids, sterols, lignans, phenylpropanoids, et al. Among them3compounds were identified as new compounds, and a known similar compound, identified asll,12-epoxy-2,6β-dihydroxy-24-norolean-1,4,20-dien-3-on-(28â†'13)-olide (Gm-1-1),11,12-epoxy-2,6β,20-trihydroxy-24-norursa-1,4-dien-3-on-(28â†'13)-olide (Gm-4),11,12-epoxy-2,6β-dihydroxy-24-norursa-1,4,20(30)-trien-3-on-(28â†'13)-olide (Gm-12),11,12-epoxy-2,6β-dihydroxy-24-norursa-1,4,20-dien-3-on-(28â†'13)-olide (Gm-13),15compounds which were identified as the known properties are Syringaresinol(Gm-2),β-hydroxypropiovanillone(Gm-2-1), Stigmast-erol-5,25(27)-diene-3-0-(6’-0-palmitoyl)-β-D-glucoside (Gm-2-1-8-5), Cerebroside(2S,3S,4R,82)-1-0-(b-D-Glucopyranosyl)-2-[(R)-2’-hydroxydocosan-oyl] amino-8-octadecene-1,3,4-triol(Gm-9),3-hydrox y-1-(4-hydroxy-3,5-dimethoxyphenyl) propan-1-one (Gm-14), Medioresinol (Gm-15),22-dehyclerosterol(Gm-17-1), Clerosterol(Gm-17-2), α-glucose (Gm-18), Urs-12-ene-3a,24-diol3-Acetate(Gm-19), sucrose(Gm-20), Ursolic Acid(Gm-21),24-R-stigmasterol-5,25(27)-diene-3-0-β-D glucoside(Gm-22), daucosterol(Gm-23),3,5-dimethoxy-4-methyl benzoic acid (Gm-197), diasyringaresinol(Ca-1-2), Syringaresinol-4’-0-beta-the D-glucoside(Ca-2-1), diasyringaresinol-4’-O-beta-the D-glucoside(Ca-2-2).To study the chemical constituents of the leaves and stems of psychotria serpens lin for reveal the active components for their further development. The compounds were isolated by normal phase silica gel column chromatography, reversed phase silica gel column chromatography, Sephadex LH-20gel column and preparative HPLC and other methods of separation and identified on the nuclear magnetic resonance (NMR), infrared (IR), ultraviolet (UV),’H NMR spectra,13C NMR spectra, DEPT spectra, HMQC, HMBC, ROESY, etc.32compounds were obtained and eighteen compounds were identified.18compounds which were identified as the known properties are rel-(3S,7R,10R)-3,11-dihydroxy-7,10-epoxy-3,7,11-trimethyldodeca-1,5-diene(Lstl-1), rel-(3S,7S,10R)-3,11-dihydroxy-7,10-epoxy-3,7,11-trimethyldodeca-1,5-diene (Lstl-2),7-hydroxylcoumarin(Lst-3), dehydrovomifoliol (Lst5-1), Loliolide (Lst5-2),(E)-4-(r-1’, t-2’, c-4’-trihydroxy-2’,6’,6’ trimethyl-cyclohexyl)but-3-en-2-one(Lst5-3),1-(4-hydroxy-3-methox yphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyp henoxyl]-propane-1,3-d-iol(Lst5-4), Cerebroside(2S,3S,4R,8Z)-1-0-(b-D-Glucopyranosyl)-2-[(R)-2’-hydroxydocosan-oyl] amino-8-octadecene-1,3,4-triol (Lst-6), Daphylloside(Lst-7-3), β-sitosterol (Lst-8),33,6β,23-trihydroxy-urs-12-en-28-oic acid(Lst-9-3-4), Syringaresinol (Lst-11), Loliolide (Lst-13),3-Hydroxy-12-ursen-28-oic acid(Lst-21), daucosterol(Lst-23), Hydroxybenzoate(Lst-24),33-Hydroxyolean-12-en-28-oic acid(Lst-p-1), Fatty alcohol (Lst-p-9), Kaempferol3-0-3-D-glucopyranosyl (1â†'2)-β-D-rhamnosidase(Lst-n-1).To study the chemical constituents of the leaves and stems of psychotria serpens lin for reveal the active components for their further development. The compounds were isolated by normal phase silica gel column chromatography, reversed phase silica gel column chromatography, Sephadex LH-20gel column and preparative HPLC and other methods of separation and identified on the.nuclear magnetic resonance (NMR), infrared (IR), ultraviolet (UV),’H NMR spectra,13C NMR spectra, DEPT spectra, HMQC, HMBC, ROESY, etc.8compounds were obtained and identified, Among them1compound were identified as new compound,5’-methoxy-7’-oxomatairesinol (Mz-1),7compounds which were identified as the known properties are(+)-(7R,8R,7’R)-lyoniresinol (Mz-2), balanophoni(Mz-3), β-sitosterol(Mz-4),(+)-lariciresinol(Mz-5),(+)-syringaresinol (Mz-6),(-)-(7R,8S)-dihydrodehydrodiconiferyl alcohol(Mz-7), daucosterol(Mz-8).ConclusionIn the Ilex asprella:A total of25final compounds obtained from Ilex asprella, and indentified23compounds,11,12-epoxy-2,6β-dihydroxy-24-norolean-1,4,20-dien-3-on-(28â†'13)-olide(Gm-1-1),11,12-epoxy-2,6β,20-trihydroxy-24-norursa-1,4-dien-3-on-(28â†'13)-olide(Gm-4),11,12-epoxy-2,6β-dihydroxy-24-norursa-1,4,20(30)-trien-3-on-(28â†'13)-olide(Gm-12) three new compounds, β-hydroxypropiovanillone (Gm-2-1), Stigmasterol-5,25(27)-diene-3-0-(6’-0-palmitoyl)-β-D-glucoside (Gm-2-1-8-5), Cerebroside,(2S,3S,4R,8Z)-1-0-(b-D-Glucop yranosyl)-2-[(R)-2’-hydroxydocosan-oyl]amino-8-octadecene-1,3,4-triol(Gm-9),11,12-epoxy-2,6β-dihydroxy-24-norursa-1,4,20-dien-3-on-(28â†'13)-olide(Gm-13),3-hydroxy-1-(4-hydroxy-3,5-dimethoxy phenyl)propan-1-one(Gm-14), Medioresinol(Gm-15),22-dehyclerosterol (Gm-17-1), α-glucose (Gm-18), Urs-12-ene-3a,24-diol3-Acetate(Gm-19), sucrose (Gm-20),24-R-stigmasterol-5,25(27)-diene-3-0-β-D glucoside (Gm-22),3,5-dimethoxy-4-methyl-benzoic acid (Gm-197), diasyringaresinol (Ca-1-2), diasyringaresinol-4’-0-beta-the D-glucoside (Ca-2-2). thirteen compounds isolated from this plant for the first time.In the psychotria serpens:A total of32final compounds obtained from Ilex asprella, and indentified18compounds. rel-(3S,7R,10R)-3,11-dihydroxy-7,10-epoxy-3,7,11-trimethyldodeca-1,5-diene(Lstl-1), rel-(3S,7S,10R)-3,11-dihydroxy-7,10-epoxy-3,1,11-trimethyldodeca-1,5-diene(Lstl-2),7-hydroxylcoumarin(Lst-3), dehydrovomifoliol(Lst5-1), Loliolide(Lst5-2),(E)-4-(r-1’, t-2’, c-4’-trihydroxy-2’,6’,6’ trimethyl-cyclohexyl)but-3-en-2-one(Lst5-3),1-(4-hydroxy-3-met hoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyp henoxyl]-propane-1,3- diol.(Lst5-4), Cerebroside,(2S,3S,4R,8Z)-1-0-(β-D-Glucop yranosyl)-2-[(R)-2’-hydroxydocosan-oyl] amino-8-octadecene-1,3,4-triol(Lst-6), Daphylloside(Lst-7-3),33,60,23-trihydroxy-urs-12-en-28-oic acid(Lst-9-3-4), Syringaresinol(Lst-11), Loliolide (Lst-13), Hydroxybenzoate(Lst-24), thirteen compounds isolated from this plant for the first time.In Chonemorpha friffithii hook:A total of8final compounds obtained from Ilex asprella, and indentified8compounds.and5’-methoxy-7’-oxomatairesinol (Mz-1) is new compound, Mz2-8seven compounds isolated from this plant for the first time.