苦木茎的化学成分

林清华; 徐健; 冯锋

doi:10.11665/j.issn.1000-5048.20170607

苦木茎的化学成分

中国药科大学天然药物化学教研室

基金项目: 国家自然科学基金资助项目(No.81703382)

计量
- 文章访问数: 961
- HTML全文浏览量: 1
- PDF下载量: 1417
出版历程
- 刊出日期: 2017-12-24

Chemical constituents from the stems of Picrasma quassioides Bennet

摘要

摘要: 采用硅胶、ODS和凝胶等柱色谱方法对苦木(Picrasma quassioides Bennet)干燥茎的化学成分进行分离纯化，通过NMR、MS等波谱技术鉴定了17个化合物，包括6个β-咔巴啉类生物碱:1-methoxycarbonyl-β-carboline( 1 )，1-carbamoyl-β-carbolin( 2 )，4-methoxy-β-carboline-1-carboxylic acid methyl ester( 3 )，1-ethoxycarbonyl-β-carboline( 4 )，1-ethyl-β-carboline( 5 )，cordysinin C( 6 )，5个铁屎米-6-酮类生物碱:4，5-dimethoxycanthin-6-one( 7 )，11-hydroxycanthin-6-one( 8 )，5-hydroxycanthin-6-one( 9 )，5-hydroxy-4-methoxycanthin-6-one( 10 )，canthin-6-one( 11 )；2个铁屎米-5，6-二酮类生物碱:3-methyl-4-methyoxycanthin-5，6-dione( 12 )，3-methylcanthin-5，6-dione( 13 )；3个倍半萜类化合物:10α-hydroxycadin-4-en-al( 14 )，canangaterpenes III( 15 )，15-oxo-T-cadinol( 16 )，1个甾体类化合物androsta-1，4-diene-3，17-dione( 17 )。其中化合物 16 为新的天然产物，化合物 5 、 6 和 14 ~ 17 为首次从苦木中分离鉴定。
- 苦木科 /
- 苦木 /
- 化学成分 /
- 结构鉴定
Abstract: The phytochemical studies on the stems of Picrasma quassioides Bennet led to the isolation of seven β-carboline alkaloids( 1 - 6 ), five cantin-6-one alkaloids( 7 - 11 ), two canthin-5, 6-dione( 12 , 13 ), three sesquiterpenes( 14 - 16 ), and one steroids( 17 ). Their structures were elucidated by the combination of spectroscopic analyses(ESI-MS, ¹H NMR and ¹³C NMR)and the comparisons with the reference. Compound 16 is a new natural product, and this is the first report for compounds 5 , 6 , 14 - 17 from the species P. quassioides.
- Simarubaceae /
- Picrasma quassioides Bennet /
- chemical constituents /
- structural identification

HTML全文

参考文献(26)

[1]	Zeng JF.Flora of China(中国植物志)[M].Beijing:Science Press,1997,43:7.
[2]	Chines Pharmacopoeia Commission.Chines Pharmacopoeia(中华人民共和国药典)[S].Beijng:Chinese Medical Science and Technology Press,2010:186.
[3]	Jiao WH.Studies on anti-inflammatory constituents of Picrasma quassioides Bennt[D].Shenyang:Shengyang Pharmaceutical University,2010.
[4]	Xu J,Xiao D,Lin QH,et al.Cytotoxic tirucallane and apotirucallane triterpenoids from the stems of Picrasma quassioides[J].J Nat Prod,2016,79:1899-1910.
[5]	Xu J,Xiao D,Song WW,et al.Quassinoids from the stems of Picrasma quassioides and their cytotoxic and NO production-inhibitory activities[J].Fitoterapia,2016,110:13-19.
[6]	Zhao F,Gao ZT,Jiao WH,et al.In vitro anti-inflammatory effects of β-carboline alkaloids,isolated from Picrasma quassioides,through inhibition of the iNOS pathway[J].Planta Med,2012,78(8):1906-1911.
[7]	Fan HY,Qi D,Yang MG,et al.In vitro and in vivo anti-inflammatory effects of 4-methoxy-5-hydroxycanthin-6-one,a natural alkaloid from Picrasma quassioides[J].Phytomedicine,2013,20(3/4):319-323.
[8]	Ma SD,Xie RM,Miao AR,et al.The effects of Picrasma quassioides on cardiovascular system[J].Acta Pharm Sin(药学学报),1982,17(5):327-330.
[9]	Yujiro N,Katsuyosh IM,Koike K,et al.Gastric antiulcer components from the woods of Picrasma quassioides(Simaroubaceae)[J].Nat Med,1994,48(2):116-121.
[10]	Gong GY,Lin QH,Xu J,et al.In vivo SAR and STR analyses of alkaloids from Picrasma quassioides identify 1-hydroxymethyl-8-hydroxy-β-carboline as a novel natural angiogenesis inhibitor[J].RSC Adv,2016,6(12):9484-9494.
[11]	Kondo Y,Takemoto T.The structure of a new β-carboline alkaloid from Picrasma ailanthoides Planchon[J].Chem Pharm Bull,1973,21(4):837-839.
[12]	Lai ZQ,Liu WH,Ip SP,et al.Seven alkaloids from Picrasma quassioides and their cytotoxic activities[J].Chem Nat Compd,2014,50(5):884-888.
[13]	Ohmoto T,Koike K.Studies on the constituents of Ailanthus altissima Swingle.III.The alkaloidal constituents[J].Chem Pharm Bull,1984,32(1):170-173.
[14]	Chen M,Fan HY,Dai SJ,et al.Alkaloids from twigs and leaves of Picrasma quassioides[J].China Tradit Herb Drugs(中草药),2007,38(6):807-810.
[15]	Lumonadio L, Vanhaelen M. Indole alkaloids from Hannoa klaineana roots[J].Phytochemistry,1984,23(2):453-455.
[16]	Yang ML,Kuo PC,Hwang TL,et al.Anti-inflammatory principles from Cordyceps sinensis[J].J Nat Prod,2011,74(9):1996-2000.
[17]	Clarke PJ,Jewers K,Jones HF.Crystal and molecular structure of amarorine monohydrate,a new phenolic alkaloid from Amaroria soulameoides[J].J Chem Soc Perk T ,1980:1614-1617.
[18]	Lassak E V,Polonsky J,Jacquemin H.5-Hydroxycanthin-6-one from Simarouba amara[J].Phytochemistry,1977,16(7):1126-1127.
[19]	Kondo Y,Takemoto T.The structure of a new β-carboline alkaloid from Picrasma ailanthoides Planchon[J].Chem Pharm Bull,1973,21(4):837-839.
[20]	Ohmoto T,Koike K.Studies on the constituents of Picrasma quassioides Bennet.II.On the alkaloidal constituents[J].Chem Pharm Bull,1983,31(9):3198-3204.
[21]	Ohmoto T,Koike K.Studies on the alkaloids from Picmsma quassioides Bennet.VI.Structures of picrasidines N,O,and Q[J].Chem Pharm Bull,1985,33(11):4901-4905.
[22]	Ohmoto T,Koike K.Studies on the alkaloids from Picrasma quassioides Bennet.V.Structures of picrasidines L,M,and P[J].Chem Pharm Bull,1985,33(9):3847-3851.
[23]	Iijima T,Yaoita Y,Kikuchi M.Five new sesquiterpenoids and a new diterpenoid from Erigeron annuus(L.)PERS.,Erigeron philadelphicus L.and Erigeron sumatrensis Retz[J].Chem Pharm Bull,2003,51(5):545-549.
[24]	Matsumoto T,Nakamura S,Nakashima S,et al.Lignandicarboxylates and terpenoids from the flower buds of Cananga odorata and their inhibitory effects on melanogenesis[J].J Nat Prod,2014,77(4):990-999.
[25]	Wu CL,Chien SC,Wang SY,et al.Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi[J].Holzforschung,2005,59(6):620-627.
[26]	Chen K,Liu C,Deng L,et al.A practical Δ 1-dehydrogenation of Δ 4-3-keto-steroids with DDQ in the presence of TBDMSCl at room temperature[J].Steroids,2010,75(7):513-516.

施引文献

资源附件(0)

计量

文章访问数: 961
HTML全文浏览量: 1
PDF下载量: 1417
被引次数: 0

苦木茎的化学成分

计量

出版历程

Chemical constituents from the stems of Picrasma quassioides Bennet

计量

出版历程

目录