王阳;范潇晓;杨军;王梓琴;王宁;陈佳琪;刘长鑫;马晓静;高小力;屠鹏飞;柴兴云;
WANG Yang;FAN Xiao-xiao;YANG Jun;WANG Zi-qin;WANG Ning;CHEN Jia-qi;LIU Chang-xin;MA Xiao-jing;GAO Xiao-li;TU Peng-fei;CHAI Xing-yun;School of Chinese Materia Medica, Beijing University of Chinese Medicine;

• 1:北京中医药大学中药学院

摘要(Abstract)：

木香原产于印度,现主产于我国云南、四川等地,是我国藏族等少数民族地区常用药材之一,具有行气止痛、健脾消食之功效,临床主要用于脾胃气滞证、泻痢、里急后重等肠胃疾病。从木香中报道了萜类、苯丙素类、木脂素类、黄酮类等化合物200余个,萜类尤其倍半萜类成分受重点关注,从化合物的数量上看,桉烷型为主,愈创木烷型、吉马烷型等也多有报道;药理活性研究涉及到提取物、挥发油和以去氢木香内酯为首要代表的单体成分,在抗肿瘤、抗炎、作用于消化系统、抗菌等方面多受关注。然而,木香来源复杂,临床应用广泛,相关化学成分和药理活性研究进展较为缺乏,该文针对木香中的萜类成分与木香的药理作用做系统总结,为进一步研究和临床应用提供参考。
Saussurea lappa originates in India, and now mainly grow in Yunnan, Sichuan and other places in China. It is one of the commonly used traditional herbal medicines in Tibet and other minority regions, with effects in regulating qi to relieve pain and invigo-rating spleen to promote food. It has been used in clinic for gastrointestinal diseases, such as Qi stagnation syndrome of spleen and stomach, diarrhea and tenesmus. More than 200 compounds have been identified from S. lappa. Among them, sesquiterpenoids attracted much attention. In terms of the number of compounds, eudesmanetype is dominant, guaiane and germacranetypes have also been reported frequently. Pharmacological studies have involved extracts, volatile oils and monomeric components represented by dehydrocostus lactone. Anti-tumor, anti-inflammatory and anti-bacterial effects on digestive system have attracted great attention. However, due to the complex sources of S. lappa and widely used in clinical practice, there is few research progress on relevant chemical constituents and pharmacological activities. This paper systematically summarizes terpenes and the pharmacological effects of S. lappa, in order to provide basis for further studies and clinical applications.

关键词(KeyWords)： 木香;风毛菊属;化学成分;药理作用;综述
Saussurea lappa;Saussurea;chemical constituent;pharmacological effect;review

Abstract:

Keywords:

基金项目(Foundation): 中国民族医药学会科研项目(2019KYXM-M202-112);; 国家自然科学基金项目(81473426)

作者(Author): 王阳;范潇晓;杨军;王梓琴;王宁;陈佳琪;刘长鑫;马晓静;高小力;屠鹏飞;柴兴云;
WANG Yang;FAN Xiao-xiao;YANG Jun;WANG Zi-qin;WANG Ning;CHEN Jia-qi;LIU Chang-xin;MA Xiao-jing;GAO Xiao-li;TU Peng-fei;CHAI Xing-yun;School of Chinese Materia Medica, Beijing University of Chinese Medicine;

Email:

DOI: 10.19540/j.cnki.cjcmm.20200903.601

参考文献(References)：

• [1] 杨宪,刘筱琴,张雪,等.HPLC一测多评法用于木香及3种含木香中药复方制剂的质量评价 [J].中国药房,2014,25(11):1030.
• [2] 包桂花,玉华,包同力嘎.HPLC法测定蒙药清咽六味散中甘草酸的含量及 TLC 鉴别 [J].中华中医药学刊,2013,31(2):402.
• [3] 魏华,彭勇,马国需,等.木香有效成分及药理作用研究进展 [J].中草药,2012,43(3):613.
• [4] SINGH R,CHANHAL K,SINGLA N.Chemical composition and pharmacological activities of Saussurea lappa:a review [J].J Pharmacogn Phytochem,2017,6(4):1298.
• [5] 杨辉,谢金伦,孙汉董.云木香化学成分研究Ⅰ[J].云南植物研究,1997,19(1):85.
• [6] YIN H Q,FU H W,HUA H M,et al.Two new sesquiterpene lactones with the sulfonic acid group from Saussurea lappa [J].Chem Pharm Bull,2005,53(7):841.
• [7] 尹宏权,齐秀兰,华会明,等.云木香化学成分研究 [J].中国药物化学杂志,2005,15(4):217.
• [8] 梁晟,梁逸曾,李雅文,等.木香挥发性化学成分的气相色谱-质谱分析 [J].广州化学,2007,32(4):12.
• [9] CHANG K M,KIM G H.Comparison of volatile aroma components from Saussurea lappa C.B.Clarke root oils [J].Food Sci Nutr,2008,13(2):128.
• [10] ZHAO F,XU H,HE E Q,et al.Inhibitory effects of sesquiterpenes from Saussurea lappa on the overproduction of nitric oxide and TNF-α release in LPS-activated macrophages [J].J Asian Nat Prod Res,2008,10(11/12):1045.
• [11] 尹宏权,付红伟,华会明,等.云木香的化学成分 [J].沈阳药科大学学报,2006,23(10):641.
• [12] CHOI J Y,NA M,HWANG I H,et al.Isolation of betulinic acid,its methyl ester and guaiane sesquiterpenoids with protein tyrosine phosphatase 1B inhibitory activity from the roots of Saussurea lappa C.B.Clarke.[J].Molecules,2009,14(1):266.
• [13] ROBINSON A,SUNKARA Y,SURESH B K R J M,et al.Isolation of α-amyrin eicosanoate,a triterpenoid from the roots of Saussurea lappa Clarke--differential solubility as an aid [J].J Pharmaceu Sci Tech,2010,2(4):207.
• [14] 陈飞龙,谭晓梅,汤庆发,等.几种“木香”挥发油成分的GC-MS比较研究 [J].中药材,2011,34(3):395.
• [15] 陈飞龙,谭晓梅,汤庆发,等.不同产地木香挥发油成分的GC-MS分析比较 [J].中国药房,2011,22(23):2187.
• [16] 张婷,马林,吴丰,等.云木香乙醇提取物化学成分研究 [J].中国中药杂志,2012,37(9):1232.
• [17] 张婷,杨燕,杜冠华,等.云木香化学成分研究Ⅱ [J].中国中药杂志,2011,36(12):1620.
• [18] 娄方明,李群芳,张倩茹.固相微萃取-气相色谱-质谱联用分析云木香挥发油成分 [J].药物分析杂志,2011,31(3):513.
• [19] WANG F,XIE Z H,GAO Y,et al.Sulfonated guaianolides from Saussurea lappa [J].Chem Pharm Bull,2008,56(6):864.
• [20] ROBINSON A,KUMAR T,SREEDHAR E,et al.A new sesquiterpene lactone from the roots of Saussurea lappa:structure-anticancer activity study [J].Bioorgan Med Chem,2018,18(14):4015.
• [21] DUAN J A,HOU P,TANG Y,et al.A new sesquiterpene and other constituents from Saussurea lappa root [J].Nat Prod Commun,2010,5(10):1531.
• [22] CAO K,QIAN W,XU Y,et al.A new sesquiterpenoid from Saussurea lappa roots [J].Nat Prod Res,2016,30(19):2160.
• [23] 包玉敏,张力,马莹莹,等.木香挥发油化学成分分析 [J].光谱实验室,2011,28(1):121.
• [24] GILANI A H,SHAH A J,YAEESH S.Presence of cholinergic and calcium antagonist constituents in Saussurea lappa explains its use in constipation and spasm [J].Phytother Res,2007,21(6):541.
• [25] 侯影,张旭,尹丽波,等.木香生品、麸煨品及活性单体对小鼠胃肠运动的影响 [J].中国实验方剂学杂志,2011,17(24):132.
• [26] ZHANG T Y,WANG P W,WANG Q,et al.Saussurea lappa modulates gastrointestinal motility,motilin and cholecystokinin expression in ulcer rats [J].J Gastroenterol Hepatol Res,2016,5(2):2021.
• [27] YANG X,ZHANG X,YANG S,et al.Evaluation of Aucklandia lappa Decne extracts as antiulcer activity in animals [J].Pak J Pharm Sci,2016,29(5):1695.
• [28] 王永兵,王强,毛福林,等.木香的药效学研究 [J].中国药科大学学报,2001,32(2):146.
• [29] PENG Z X,WANG Y,GU X,et al.Metabolic transformation of breast cancer in a MCF-7 xenograft mouse model and inhibitory effect of volatile oil from Saussurea lappa Decne treatment [J].Metabolomics,2015,11(3):636.
• [30] KIM H R,KIM J M,KIM M S,et al.Saussurea lappa extract suppresses TPA-induced cell invasion via inhibition of NF-κB-dependent MMP-9 expression in MCF-7 breast cancer cells [J].BMC Complem Altern M,2014,14(170):1.
• [31] PENG Z,WANG Y,FAN J,et al.Costunolide and dehydrocostuslactone combination treatment inhibit breast cancer by inducing cell cycle arrest and apoptosis through c-Myc/p53 and AKT/14-3-3 pathway [J].Sci Rep-UK,2017,7:41254.
• [32] CHOI Y K,CHO S G,WOO S M,et al.Saussurea lappa clarke-derived costunolide prevents TNFα-induced breast cancer cell migration and invasion by inhibiting NF-κB activity [J].Evid-Based Compl Alt,2013(12):936257.
• [33] LIN X,PENG Z,LIU C,et al.Volatile oil from Saussurea lappa exerts antitumor efficacy by inhibiting epithelial growth factor receptor tyrosine kinasemediated signaling pathway in hepatocellular carcinoma [J].Oncotarget,2016,7(48):79761.
• [34] KIM E J,LIM S S,PARK S Y,et al.Apoptosis of DU145 human prostate cancer cells induced by dehydrocostus lactone isolated from the root of Saussurea lappa [J].Food Chem Toxicol,2008,46(12):3651.
• [35] KIM E J,HONG J E,LIM S S,et al.The hexane extract of Saussurea lappa and its active principle,dehydrocostus lactone,inhibit prostate cancer cell migration [J].J Med Food,2012,15(1):24.
• [36] TIAN X,SONG H S,CHO Y M,et al.Anticancer effect of Saussurea lappa extract via dual control of apoptosis and autophagy in prostate cancer cells [J].Medicine,2017,96(30):e7606.
• [37] HASSON S S,AI-SHUBI A S H,AL-BUSAIDI J Z,et al.Potential of Aucklandia lappa Decne ethanolic extract to trigger apoptosis of human T47D and Hela cells [J].Asian Pac J Cancer P,2018,19(7):1917.
• [38] CHOI E J,KIM G H.Evaluation of anticancer activity of dehydrocostuslactone in vitro [J].Mol Med Rep,2010,3(1):185.
• [39] 郝立杰,赵烽,高治廷,等.木香倍半萜对血管内皮细胞生长因子的抑制作用 [J].天然产物研究与开发,2010,22(4):687.
• [40] MOON S M,YUN S J,KOOK J K,et al.Anticancer activity of Saussurea lappa extract by apoptotic pathway in KB human oral cancer cells [J].Pharm Biol,2013,51(11):1372.
• [41] LIM H S,HA H,LEE M Y,et al.Saussurea lappa alleviates in?ammatory chemokine production in HaCaT cells and house dust mite-induced atopic-like dermatitis in Nc/Nga mice [J].Food Chem Toxicol,2014,63:212.
• [42] LIM H Y,HA H,SHIN H K,et al.The genome-wide expression profile of Saussurea lappa extract on house dust mite-induced atopic dermatitis in Nc/Nga mice [J].Mol Cells,2015,38(9):765.
• [43] YANG H J,KIM M J,KANG S,et al.Topical treatments of Saussurea costus root and Thuja orientalis L.synergistically alle-viate atopic dermatitis-like skin lesions by inhibiting protease-activated receptor-2 and NF-κB signaling in HaCaT cells and Nc/Nga mice [J].J Ethnopharmacol,2017,199:97.
• [44] PARK E J,PARK S W,KIM H J,et al.Dehydrocostuslactone inhibits LPS-induced in?ammation by p38MAPK-dependent induction of hemeoxygenase-1 in vitro and improves survival of mice in CLP-induced sepsis in vivo [J].Int Immunopharmacol,2014,22(2):332.
• [45] TAG H M,KHALED H E,LSMMAIL H A A,et al.Evaluation of anti-inflammatory potential of the ethanolic extract of the Saussurea lappa root (costus) on adjuvant-induced monoarthritis in rats [J].J Basic Clin Physiol Pharmacol,2016,27(1):71.
• [46] PYUN H,KANG U,SEO E K,et al.Dehydrocostus lactone,a sesquiterpene from Saussurea lappa Clarke,suppresses allergic airway in?ammation by binding to dimerized translationally controlled tumor protein [J].Phytomedicine,2018,43:46.
• [47] QURESHI A S,ENBERGS H.Effects of Saussurea lappa roots extract in ethanol on leukocyte phagocytic activity,lymphocyte proliferation and interferon-gamma (IFN-γ) [J].Pak J Pharm Sci,2007,20(3):175.
• [48] LIM H S,Jin S E,Kim O S,et al.Alantolactone from Saussurea lappa exerts antiinflammatory effects by inhibiting chemokine production and STAT1 phosphorylation in TNF-α and IFN-γ-induced in HaCaT cells [J].Phytother Res,2015,29(7):1088.
• [49] SEO C S,LIM H S,JEONGS S J,et al.Anti-allergic effects of sesquiterpene lactones from the root of Aucklandia lappa Decne [J].Mol Med Rep,2015,12(5,Pt.B):7789.
• [50] SHIN M S,KIM S B,LEE J,et al.Beneficial effect of herbal formulation KM1608 on inflammatory bowl diseases:a preliminary experimental study [J].Molecules,2018,23(8):2068.
• [51] YU H H,LEE J S,LEE K H,et al.Saussurea lappa inhibits the growth,acid production,adhesion,and water-insoluble glucan synthesis of streptococcus mutans [J].J Ethnopharmacol,2007,111(2):413.
• [52] QIU J,WANG J,LUO H,et al.The effects of subinhibitory concentrations of costus oil on virulence factor production in staphylococcus aureus [J].J Appl Microbiol,2011,110(1):333.
• [53] Negi J,Bisht V,Bhandari A,et al.Chemical fingerprinting and antibacterial activity of Saussurea lappa Clarke [J].Appl Biochem Micro,2014,50(6):588.
• [54] NEJI J S,BISHT V K,BHANDARI A K,et al.Evaluation of anti-resistant activity of auklandia(Saussurea lappa) root against some human pathogens [J].Asian Pac J Trop Bio,2013,3(7):557.
• [55] MOHAMED A,ALDAW M,ISMAIL E,et al.Evaluation of antimicrobial activity of different solvent extracts of Saussurea lappa [J].J Pharm Pharm Sci,2017,6(9):12.
• [56] TRIVEDI S,DIXIT J.Clinical effects of irrigation with Saussurea lappa extract in the treatment of chronic periodontitis:a pilot randomized trial [J].J Orofac Sci,2015,7(2):80.
• [57] JEONG G,PAE H,JEONG S,et al.The α-methylene-γ-butyrolactone moiety in dehydrocostus lactone is responsible for cytoprotective heme oxygenase-1 expression through activation of the nuclear factor E2-related factor 2 in HepG2 cells [J].Eur J Pharmacol,2007,565(1/3):37.
• [58] SADIK I,ALLAH A A,ABDULHAMEED M,et al.Antioxidant activity and in vitro potential inhibition of Nigella sativa and Saussurea lappa against LDL oxidation among Sundance [J].Indian J Med Res,2017,6(3):22.
• [59] GARG R,SHARMA A K.Antioxidant activities of Saussurea lappa (root),Ficus bengallensis (root),Flacourtria romantchi (stem bark and root),and Oroxyllum indicum (root) in Swiss Albino Mice [J].Int J Pharm Pharmaceu Res,2016,6(3):274.
• [60] SALEEM T S M,PRASANTHI N L A,MALLIKA M M G,et al.Aqueous extract of Saussurea lappa root ameliorate oxidative myocardial injury induced by isoproterenol in rats [J].J Adv Pharm Technol Res,2013,4(2):94.
• [61] AKHTAR M S,BASHIR S,MALIK M N H,et al.Cardiotonic activity of methanolic extract of Saussurea lappa Linn roots [J].Pak J Pharm Sci,2013,26(6):1197.
• [62] YAEESH S,JAMAL Q,SHAH A J,et al.Antihepatotoxic acti-vity of Saussurea lappa extract on D-galactosamine and lipopolysaccharide-induced hepatitis in mice [J].Phytother Res,2010,24(2):229.
• [63] ANSARI S,SIDDIQUI M A,MAAZ M.Hepatocurative effect of Saussurea lappa C.B Clarke and Artemisia absinthium,Linn in chronic hepatitis B [J].J Young Pharm,2018,10(3):354.
• [64] CHOI E M.Dehydrocostus lactone prevents mitochondrial dysfunction in osteoblastic MC3T3-E1 cells [J].Eur J Pharmacol,2011,664(1/3):1.
• [65] JANI D P,PATEL B R.A clinical evaluation of kushtha (Saussurea lappa.C.B.Clarke.) on shukradushti w.s.r.to seminal par.h parameters [J].Int J Ayu Pharm Chem,2015,3(2):223.
• [66] ELDAIM A A M,TOUSSON E,SAYED I E T E,et al.Ameliorative effects of Saussurea lappa root aqueous extract against ethephon-induced reproductive toxicity in male rats [J].Environ Toxicol,2019,34(2):150.
• [67] LIU Z L,HE Q,CHU S S,et al.Essential oil composition and larvicidal activity of Saussurea lappa roots against the mosquito Aedes albopictus (Diptera:Culicidae) [J].Parasitol Res,2012,110(6):2125.
• [68] 赵勤实,从玉文.迈克尔反应受体分子化学生物学研究[J].化学进展,2007,19(12):1972.
• [69] 王佳铭,曹境洳,高小力,等.八味沉香散的化学和药理研究进展[J].中国中药杂志,2020,45(9):2063.