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Studies on the Chemical Constituents of the Solidago virgaurea Linn. with Their Pharmacological Activities

Author: LiTao
Tutor: YaoQingQiang
School: Jinan University
Course: Medicinal Chemistry
Keywords: Solidago virgaurea Linn. Chemical constituents Pharmacologicalactivities
CLC: R284.1
Type: Master's thesis
Year: 2013
Downloads: 29
Quote: 0
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Abstract


Solidago virgaurea Linn, a perennial herbaceous plant, is also known as Solidagocanadensis in Xinjiang. It mainly distributes under the trees and bushes in high altituderegion including the mountain Altai in Xinjiang, and also can be found in the northeastand north China, Soviet Union and Mongolia. S. virgaurea Linn is mainly used astraditional medicine to treat nephritis and cystitis, but the whole grass has hemolyticactivity, resulting chronic intestinal bleeding and other gastrointestinal symptoms in alarge doses, such as nausea, vomiting, etc. Prevoius phytochemical studies indicated itschemical composition mainly contained diterpene, flavonoids, saponins, volatile oil andphenylpropionic acid, etc. Its pharmacological activities include anti-bacterial andanti-inflammatory, diuresis, anti-tumor and so on.Objective: To study on the chemical composition of S. virgaurea Linn and to discussthe pharmacological activities and the mechanism in anti-inflammatory of somebioactive compounds isolated from this species.Mothod:95%ethanol extract of the whole dry grass was separated by polyamide, silicagel, Sephadex LH-20, ODS column chromatography and HPLC. Structures of isolatedcompounds were identified on the basis of their physical and chemical propertiescombining with the reference of ESI-MS and NMR. Furthermore, anti-inflammatoryactivity of benzyl benzoate compounds was explored by the method of Elisa.Result: Nineteen compounds were isolated from Solidago, and they are respectivelyelucidated as2′-Methoxybenzyl-2-methoxy-6-hydroxybenzoate,2′-Methoxybenzyl-2,6-dimethoxy-benzoate, solidagobenzofuran, β-amyrin acetate, α-spinasterol,stigmasta-7,22-dien-3-one, palmitic acid,2-Hydroxy-6-methoxybenzoic acid,3β-acetoxyolean-12-en-11-one-acetate, pedalitin, N-benzoylphen-ylalaninyl-N-benzoylphen-ylalaninate, quercecetin, kaemferol, protocatechuic acid, sakicylic acid,p-hydroxybenzoic acid, solidago virgaurea glycoside, kaempferol-3-O-β-D-rutinosideand rutin. Compound I (2′-Methoxybenzyl-2-methoxy-6-hydroxybenzoate) and compound Ⅱ (2′-Methoxybenzyl-2,6-dimethoxy-benzoate) showed obviousinhibition on the releasing TNF-α and IL-6ofmononuclear cells RAW264.7induced byLPS with obvious concentration dependence, while compound ⅩⅦ (solidago virgaureaglycoside)has no anti-inflammatory activity.Conclusion: Compounds Ⅲ and XⅦ are new compounds. Compound ⅩⅠ is isolatedfrom this family for the first time, and compounds Ⅵ, Ⅶ, IX, and ⅩⅣ are obtainedfrom this genus for the first time. Compounds I, Ⅱ, X are isolated from this specices forthe first time. Three alkaloids isolated from Solidago show no obvious growth inhibitionand cytotoxic activity to tumor cell lines. The ELISA anti-inflammatory activity ofbenzyl benzoate compounds isolated from Solidago is in progress. Elisa test indicatedCompound I (2′-Methoxybenzyl-2-methoxy-6-hydroxybenzoate) and compound Ⅱ(2′-Methoxybenzyl-2,6-dimethoxy-benzoate) possess good anti-inflammatory activity. As benzyl benzoate compounds occur in great quantity in S.virgaurea, they can be inferred as the main active ingredients for theanti-inflammatory activity of S. virgaurea.

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