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Studies On The Chemical Constituents And Bioactivities Of Inula Racemosa And Saussurea Lappa. C.B. Clarke

Posted on:2012-01-27Degree:DoctorType:Dissertation
Country:ChinaCandidate:T ZhangFull Text:PDF
GTID:1114330335981910Subject:Medicinal chemistry
Abstract/Summary:PDF Full Text Request
"Muxiang" is a traditional Chinese medicine, including four kinds, all belonging to Compositae and three different genus:Saussurea lappa C.B. Clarke, Inula helenium L., Inula racemosa Hook. f., Vladimiria souliei (Franch.) Ling.There are about 100 species of the genus Inula widely found in Europe, Asia and Africa, mostly in Mediterranean, with more than 20 species being distributed in China. Many of them have long been used in Chinese folk medicine, most frequently employed for their peptic, relieving phlegm, detumescence, anti-inflammatory and vermifuge properties. Recently much attention has been paid to Inula species due to their diverse biological activities, which include anti-inflammation, antitumor and anti-bactericidal effects. Plants of Inula are rich sources of sesquiterpenes, such as eudesmanes, germacranes, guaianes and bis-sesquiterpenes. Inula racemosa are traditional Chinese drugs which have been used as antimicrobial agents for nearly a thousand years. The roots of Inula racemosa in our study were collected in Tibet, twenty-six compounds had been isolated from the extracts of roots of Inula racemosa, among which six ones (Ir-1-Ir-6) were new compounds, and compounds Ir-10-Ir-12, Ir-17-Ir-25 were isolated from this genus for the first time, and compounds Ir-8, Ir-9, Ir-13, Ir-14, Ir-16, Ir-26 were isolated from this plant for the first time. These compounds list as follows: (3S,4R,5Z,7R,8R,10R,11S)-3β-hydroxy-11 a,13-dihydroalantolactone (Ir-1), (4S,5Z,7S,8R,10R,11R)-11a-hydroxy-eudesm-5-en-8β,12-olide (Ir-2), (4R,5S,7R,8R,10R)-1-one-4-epi-alantolactone (Ir-3), (4R,5E,7Z,8S,10R)-4a,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide (Ir-4), (4S,5S,6Z,10R)-8-oxo-tri-nor-eudesm-6-en-5α-ol (Ir-5), (4S,5Z,7S,8R,10R)-tri-nor-eudesm-5-en-7,8-diol(Ir-6), isoalantolactone (Ir-7),11,13-dihydroisolantolactone (Ir-8),11,13-dihydroivalin (Ir-9),5-deoxy-5-hydroperoxytelekin (Ir-10),11a,13-dihydro-2α-hydroxy-alantolactone (Ir-11), septuplinolide (Ir-12), macrophyllilactone E (Ir-13), 13-acetyloxy-5,7(11)-eudesmadien-12,8-olide (Ir-14), alloalantolactone (Ir-15),8-epi-ivangustin (Ir-16), deacetyl-y-cycloepitulipinolide (Ir-17), clemaphnol A (Ir-18), dammara-20,24-dien-3/β-OAc (Ir-19), friedelin (Ir-20), ethyl trans-3,4-dihydroxy-cinnamate (Ir-21), syringic acid (Ir-22),5-hydroxymethyl-furaldehyde (Ir-23), n-butyl-β-D-fructopyranoside (Ir-24), ethyl-β-D-fructopyranoside (Ir-25), p-hydroxybenzldehyde (Ir-26).Nineteen compounds (Ir-1 Ir-5, Ir-7-Ir-20) were evaluated for cytotoxicity test against five human tumor cell lines (A549, Bel-7402, BGC-823, HCT-8 and A2780). Compounds Ir-7, Ir-9, Ir-11 and Ir-12 showed certain activities, and the best was compound Ir-7.Sixteen compounds (Ir-1-Ir-4, Ir-7-Ir-9, Ir-11-Ir-13, Ir-15-Ir-20) were tested for their anti-inflammatory activities in vitro by an assay to release ofβ-glucuronidase from rat PMNs induced by PAF. Only compounds Ir-7 and Ir-13 showed certain activities with the inhibitory ratios more than 50%(P<0.001) at concentration of 10-5 M.There are about 400 species of the genus Saussurea all over the world, with more than 300 species being distributed in China. Many of them have long been used in Chinese folk medicine. The roots of Saussurea lappa in our study were bought in Hebei province, forty-four compounds had been isolated from the extracts of roots of Saussurea lappa, among which two ones (SI-1 and Sl-2) were new compounds, and compounds SI-4, SI-11, SI-16, SI-17, SI-19, SI-20, SI-22, SI-26, SI-27, SI-28, SI-29, SI-31, SI-33, SI-35, SI-40, SI-44 were isolated from this genus for the first time, and compounds Sl-15, SI-39, SI-41, SI-42, SI-43 were isolated from this plant for the first time, compound SI-27 was isolated from natural pruoducts for the first time. These compounds list as follows: lappadimer A (SI-1), lappadimer B (SI-2), lappadilactone (SI-3),5a-hydroxy-β-costic acid (SI-4), ilicic alcohol (SI-5),β-cyclocostunolide (SI-6), reynosin (SI-7),11β,13-dihydroreynosin (SI-8), arbusculin A (SI-9), 1β-hydroxy-arbusculin A (SI-10), 1β-hydroxycolartin (SI-11), santamarine (SI-12), dehydrocostuslactone (SI-13), 11β,13-dihydro-3-epizaluzanin C (SI-14),8α-hydroxyl-11βH-11,13-dihydro-dehydrocostuslactone (SI-15),11a,13-dihydroxydehidrocostuslactone (SI-16), 11,13-dihydro-7,11-dehydro-13-hydroxy-3-desoxyzaluzanin C (SI-17), costunolide (SI-18), soulangianolide A (SI-19), syringaresinol (SI-20),8,8'-dihydroxypinoresinol (SI-21), scopoletin (SI-22), pregnenolone (SI-23), betulinic acid (SI-24), stigmasterol (SI-25),1,2-benzenedicarboxylic acid dibutyl ester (SI-26), ethyl 2-pyrrolidinone-5(s)-carboxylate (SI-27),5,7-dihydroxy-2-methylchromone (SI-28), 3,5-dimethoxy-4-hydroxyacetophenone (SI-29),3,5-dimethoxy-4-hydroxybenzaldehyde (SI-30), p-hydroxybenzaldehyde (SI-31),5-hydroxymethyl-furaldehyde (SI-32), palmitic acid (SI-33), succinic acid (SI-34), glucose (SI-35),β-sitosterol (SI-36), daucosterol (SI-37), (+)-1-hydroxypinoresinol-1-O-β-D-glucopyranoside (SI-38), (+)-1-hydroxypinoresinol-4"-O-β-D-glucopyranoside (SI-39), (+)-1-hydroxy-pinoresinol 4"-O-methyl ester-4'-β-D-glucopyranoside (SI-40), phenyl-β-D-glucopyranoside (SI-41). benzyl-β-D-glucopyranoside (SI-42), n-butyl-β-D- glucopyranoside (SI-43), ascleposide E (SI-44).Twenty-one compounds (SI-3-SI-21, SI-23, SI-24) were evaluated for cytotoxicity test against five human tumor cell lines (A549, Bel-7402, BGC-823, HCT-8 and A2780). Compounds Sl-3, Sl-7, SI-10, SI-12, SI-13, SI-18 and SI-24 showed certain activitives.Twenty-one compounds (SI-3-S1-21, SI-23, SI-24) were tested for their anti-inflammatory activities in vitro by an assay to release ofβ-glucuronidase from rat PMNs induced by PAF. Compounds SI-3, SI-9, SI-12, SI-18, SI-20, SI-21 and SI-23 showed activities with the inhibitiory ratios more than 50%(P<0.05) at concentration of 10-5 M, and their inhibitiory ratios were 95.5%,55.0%,59.7%,65.7%,53.9%, 66.9% and 58.8%, of which the best was SI-3.
Keywords/Search Tags:Compositae, Inula Racemosa, Saussurea lappa, Chemical constituents, Bioactivities
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