Studies on the Chemical Constituents of the Stems of Celastrus Paniculatus Willd
|School||Peking Union Medical College , China|
|Keywords||Celastrus paniculatus Willd. Celastrus L. Celastraceae triterpene diterpene β-dihydroagarofuran-sesquiterpene alkaloid flanvoniods|
Celastrus paniculatus Willd. belongs to the Celastraceae family and is distributed in the South of China including Tanwan, Guangdong, Hainan, Guangxi, Guizhou and Yunnan provinces. This plant grows in the bushland at the altitude of 200～2000 metre. It was recorded in the "Chinese herb" that this plant was bitter and acrid in taste, neutral in nature, slightly poisonous, and it was traditionally used for the treatment of rheumatic arthralgia, constipation, and abdominal distention, so it is meaningful to investigate its chemical constitute. In the last twenty years, many compounds had been isolated from the Celastreae plants. Some of them exhibited the activities of antifeedant and antitumor, and most of which wereβ-dihydroagarofuran-sesquiterpenes. Beside of theβ-dihydroagarofuran sesquiterpenes, triterpenes, diterpenes and flanvoniods had also been found in the Celastrus plants. In order to make full use of the medicinal plant in our country, and to develop medicine from Celastrus paniculatus Willd., it was necessary to make the chemical component clear. As a result, the main aim of the present studay was to find active compounds from the stems of Celastrus paniculatus Willd. collected from Yunnan province.Phytochemical studies in the present study had led to the isolation of 61 compounds using different chromatographic techniques and subsequently the structures were elucidated by using spectrometric approaches, including IR, UV, 1D and 2D NMR, EI-MS, FAB-MS, ESI etc., and classical chemical methods. Of the 61 compounds identified, 13 were found to be new compounds, 33 to be isolated from the Celastrus plants for the first time. Except forβ-amyrin,α-amyrin,β-sterol and daucosterol, the others were all isolated from this species for the first time.The new compounds consisted of one diterpene named as 11-hydroxy- 14-methoxy-8, 11, 13-abietatrien- 19-acid (cp13), and twelveβ-dihydroagarofuran sesquiterpene alkaloids named as paniculatine A (cp16)、paniculatine B (cp17)、paniculatine C (cp18)、paniculatine D (cp21)、paniculatine E (cp22)、paniculatine F (cp25)、paniculatine G (cp26)、paniculatine H (cp30)、paniculatine I (cp33)、paniculatine G (cp34)、paniculatine K (cp35)、paniculatine L(cp36)。The forty eight known compounds including ten triterpenes, they areβ-amyrin (cp1)、3β-hydroxyolean-12-en-11-one (cp2)、β-amyrin palmitate (cp3)、α-amyrin acetate (cp4)、α-amyrin (cpS)、3β-hydroxyurs-12-en-11-one(cp6)、α-amyrin palmitate (cp7)、wilforlide A (cp8)、3β, 22β-dihydroxy-olean- 22en-28 acid (cp9)、2α-hydroxy-lupeol (cp10): two known diterpens, they are 13, 14-dihydroxy-8, 11, 13-podocarpatrien-7-one (cp11)、8, 12-abietadien-11, 14-dione-19-acid (cp12): elevenβ-dihydroagarofuran sesquiterpene alkaloids, such as euonymin (cp14)、wifomines F (cp15)、euojaponine I (cp19)、mayteine (cp20)、hyponines D(cp23)、2-Desacetylevonin(cp24)、8-(acetyloxy)-O~2-deacetyl-8-deoxo-evonine(cp27)、peritassines A(cp28)、8-(isobutyloxy)-8-deacetyl-peritassines A(cp29)、euonnie(cp31)、euojaponine F(cp32); three sitosterols, they areβ-sitosterol (cp37)、daucosterol (cp38)、7-oxo-β-sitosterol (cp39); ten small aromatic molecules, they are 4-hydroxybenzoic acid (cp40)、salicylic acid (cp41)、vanillic acid (cp42)、4-hydroxy-benzaldehyde (cp43)、1, 4-benzene diol (cp44)、syfingic acid (cp45)、1, 3, 5-trimethoxy-benzene (cp46)、3, 4-dihydroxy benzoic acid (cp47)、3-methoxy-4-hydroxy-benzoic acid-4-β-D-glucoside (cp48)、3, 5-dimethoxy-4-hydroxy-benzoic acid-4-β-D-glucoside (cp49); eight flavonoids, such as kaempferol (cp50)、quercetin (cp51)、(-)-epigallocatechin (cp52)、(+)-gallocatechin (cp53)、phlofizin (cp54)、(-)-3, 5, 7-trihydroxyflavan (cp55)、(+)-3, 5, 7, 4’-tetrahydroxyfiavan (cp56)、(-)-epicatechin (cp57): and four other types of compounds, such as glucose (cp58)、n-butyl-β-D-glucopyranoside (cp59)、adenosine (cp60)、palmitic acid (cp61)。Some of the sesquiterpene alkaloids isolated from Celastrus paniculatus Willd. were tested their effects of antitumor, but the result was not good. The principle between structure and antitumor activity of sesquiterpene alkaoids was concluded primarily in this paper.In addition, the isolation method and strcture elucidation of the sesquterpene alkaloids has also been concluded in detail, it would be useful for the research in this type of compounds.Finally, this study had also systemically summaries the advances in the research of chemical constituents and their pharmacological activities of Celastrus plants.