角果木属植物的二萜类化学成分研究进展
|
摘要
自2005年以来,通过对角果木属植物的化学成分研究,分离鉴定了多种类型的二萜类化合物和结构新颖的二聚二萜。研究表明,角果木属植物中的二萜类化合物具有抗菌、防污、杀虫、抗肿瘤等多种药理作用。本文以国内外发表的文献作为依据,对从角果木属中分离得到的99个二萜类化合物进行分析和总结,包括它们的结构、分类、生源关系、生物活性和构效分析,为角果物木属植物的进一步开发利用提供借鉴和参考。
Since 2005,due to the chemical research on the Ceriops plants,a number of diterpenoids and dimeric diterpenes with novel structure have been isolated and identified. At the same time,these newly reported diterpenoids with diverse structures have led to new findings on their biological properties,including the antibacterial,antifouling,insecticidal and antitumor activities.In this review,we summarize the 99 diterpenoids reported in the Ceriops plants,including their structures,classifications,biogenetic relationship,bioactivities and structure-activity relationship,to provide reference for further research and utilization of Ceriops plants.
Since 2005,due to the chemical research on the Ceriops plants,a number of diterpenoids and dimeric diterpenes with novel structure have been isolated and identified. At the same time,these newly reported diterpenoids with diverse structures have led to new findings on their biological properties,including the antibacterial,antifouling,insecticidal and antitumor activities.In this review,we summarize the 99 diterpenoids reported in the Ceriops plants,including their structures,classifications,biogenetic relationship,bioactivities and structure-activity relationship,to provide reference for further research and utilization of Ceriops plants.
引文
[1] Wu J,Xiao Q,Xu J,et al. Natural products from true mangrove flora:source,chemistry and bioactivities[J]. Nat Prod Rep,2008,40(23):955-981.
[2] Tsai CC,Li SJ,Su YY,et al. Molecular phylogeny and evidence for natural hybridization and historical introgression between Ceriops species(Rhizophoraceae)[J]. Biochem Syst Ecol,2012,43(4):178-191.
[3]廖宝文,张乔民.中国红树林的分布、面积和树种组成[J].湿地科学,2014,12(4):435-440.
[4] Zhang Y,Deng Z,Gao T,et al. Tagalsins A-H,dolabrane-type diterpenes from the mangrove plant,Ceriops tagal[J]. Org Lett,2005,36(49):1465-1471.
[5] Fun HK,Pakhathirathien C,Chantrapromma S,et al. 7-Ethenyl-1-[(Z)-hydroxy-methyl-idene]-4b,7,10a-trimethyl-perhydro-phenanthren-2-one[J]. Acta Crystallogr,2006,62(12):o5539-o5541.
[6] Ouyang XW,Wang XC,Yue QX,et al. A new dolabrane-type diterpene from Ceriops tagal[J]. Nat Prod Commun,2010,5(1):9-12.
[7] Hu WM,Li MY,Li J,et al. Dolabranes from the Chinese mangrove,Ceriops tagal[J]. Nat Prod,2010,73(10):1701-1705.
[8] Chen Y,Wang WJ,Wu J. Two new dolabranes from the Chinese mangrove Ceriops tagal[J]. J Asian Nat Prod Res,2016,18(1):41-45.
[9] Wu X,Liao H,Lu H,et al. A new dolabrane dinorditerpene from Ceriops tagal[J]. OALib J,2016,3(8):1-6.
[10] Yang Y,Zhang Y,Liu D,et al. Dolabrane-type diterpenes from the mangrove plant Ceriops tagal with antitumor activities[J]. Fitoterapia,2015,103:277-282.
[11] Peng Y,Ni SJ,Li J,et al. Three new dolabrane diterpenes from the Chinese mangrove plant of Ceriops tagal[J]. Phytochem Lett,2017,21:38-41.
[12] Ni SJ,Li J,Li MY. Two new dolabrane diterpenes from the Chinese mangrove Ceriops tagal[J]. Chem Biodivers,2018,15(3).
[13]刘喜苹,申丽,吴军.角果木的dolabrane型二萜类化合物研究[J].中草药,2016,47(13):2226-2231.
[14]彭媛,李敏一.海南红树植物角果木的二萜类化学成分研究[J].天然产物研究与开发,2016,(12):1870-1874.
[15]张晓慧,申丽,吴军.角果木中两个新的dolabrane型二萜类化合物[J].天然产物研究与开发,2017,(4):549-552.
[16] Zhang X,Li W,Shen L,et al. Four new diterpenes from the mangrove Ceriops tagal and structure revision of four dolabranes with a 4,18-epoxy group[J]. Fitoterapia,2017,124:1-7.
[17] Zhang X,Yang Y,Liu J,et al. Tagalide A and Tagalol A,naturally occurring 5/6/6/6-and 5/6/6-fused cyclic dolabrane-type diterpenes:a new insight into anti-breast cancer activity of the dolabrane scaffold[J]. Org Chem Front,2018,5(7):1176-1183.
[18] Chantrapromma S,Karalai C,Fun HK,et al. 7-Glycoloyl-2-hydr-oxy-1,4b,7,10a-tetra-methyl-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-phenanthren-3(4H)-one[J]. Acta Crystallogr,2007,63(2):o459-o461.
[19]王慧,吴军.十雄角果木树皮的二萜类化学成分研究[J].中草药,2013,44(5):532-536.
[20] Anjaneyulu ASR,Rao VL. Ceriopsins AD,diterpenoids from Ceriops decandra[J]. Phytochemistry,2002,60(8):777-782.
[21] Anjaneyulu ASR,Rao VL. Ceriopsins F and G,diterpenoids from Ceriops decandra[J]. Phytochemistry,2003,62(8):1207.
[22] Chacha M,Mapitse R,Afolayan AJ,et al. Antibacterial diterpenes from the roots of Ceriops tagal[J]. Nat Prod Commun,2008,3(1):17-20.
[23] Chen JD,Feng DQ,Yang ZW,et al. Antifouling metabolites from the mangrove plant Ceriops tagal[J]. Molecules,2008,13(2):212-219.
[24] Fun H-K,Chantrapromma S,Pakhathirathien C,et al. ent-(15S)-Pimar-8(14)-ene-15,16-diol[J]. Acta Crystallogr E,2012,68(Pt 2):o520-o521.
[25]胡格华,吴军.十雄角果木树皮的乙酸乙酯萃取部位化学成分的研究[J].三峡大学学报(自然科学版),2013,35(3):95-97.
[26] Wang H,Li MY,Satyanandamurty T,et al. New diterpenes from a Godavari mangrove,Ceriops decandra[J]. Planta Med,2013,79(8):666-672.
[27] Wang H,Li MY,Katele FZ,et al. Decandrinin,an unprecedented C9-spiro-fused 7,8-seco-ent-abietane from the Godavari mangrove Ceriops decandra[J]. Beils J Org Chem,2014,10(1):276-281.
[28] Simlai A,Mukherjee K,Mandal A,et al. Partial purification and characterization of an antimicrobial activity from the wood extract of mangrove plant Ceriops decandra[J]. Excli J,2016,15:103-112.
[29] Anjaneyulu SR,Rao VL,Lobkovskya E,et al. Ceriopsin E,a new epoxy ent-kaurene diterpenoid from Ceriops decandra[J]. J Nat Prod,2002,65(4):592-594.
[30] Chantrapromma S,Razak IA,Karalai C,et al. 14-Hydroxy-14-hydroxymethyl-5,5,9-trimethyl-tetracyclo-[11.2.1.0 1,10.0 4,9]hexa-decane hemihydrate[J]. Acta Crystallogr,2006,62(5):o1742-o1744.
[31] Zhang Y,Lu Y,Mao L,et al. Tagalsins I and J,two novel tetraterpenoids from the mangrove plant,Ceriops tagal[J]. Org Lett,2005,36(47):3037-3040.
[32] Chen JD,Qiu Y,Yang ZW,et al. Dimeric diterpenes from the roots of the mangrove plant Ceriops tagal[J]. Helv Chim Acta,2008,91(12):2292-2298.
[33] Chen JD,Yi RZ,Lin YM,et al. Characterization of terpenoids from the root of Ceriops tagal with antifouling activity[J]. Int J Mol Sci,2011,12(10):6517-6528.
[34] Nebula M,Harisankar HS,Chandramohanakumar N. Metabolites and bioactivities of Rhizophoraceae mangroves[J]. Nat Prod Bioprosp,2013,3(5):207-232.
[35] Peters RJ. Two rings in them all:the labdane-related diterpenoids[J]. Nat Prod Rep,2010,27(11):1521-1530.
[36]孙汉董.二萜化学[M].第2版.北京:化学工业出版社,2012:1054-1060.
[37] Nagahama S,Tajima M. Diterpene hydrocarbons from the leaf oil of Thujopsis dolabrata var. dolabrata[J]. Biochem Syst Ecol,1996,24(1):49-52.
[38] Fang LQ,Ito A,Chai HB. Cytotoxic constituents from the stem bark of Dichapetalum gelonioides collectedin the Philippines[J]. J Nat Prod,2006,69(3):332-337.
[39] Chacha M. Terpenoids from the roots of Ceriops tagal induces apoptosis through activation of caspase-3 enzyme[J]. Int J Biol Chem Sci,2011,5(2):2193-2196.
[40] Chacha M. Comparative anticancer activity of dolaborane diterpenes from the roots of Ceriops tagal(Rhizophoraceae)[J]. Int J Biol Chem Sci,2012,6(2):913-919.
[41]冯龄鑫,刘淑萍,丁爱萍,等.中国红树科植物角果木中Dolabrane型二萜的抗肿瘤作用[J].齐鲁医学杂志,2010,25(3):198-201.
[42]宋修岐,邢智远,郭云良,等.角果木提取物Tagalsin对H22荷瘤小鼠Survivin和Caspase-3表达的影响[J].中国临床研究,2010,23(9):748-751.
[43]孙蓓,王秀美,邱文生,等.角果木dolabrane型二萜对Lewis荷瘤小鼠的抗肿瘤作用[J].临床肿瘤学杂志,2010,15(2):127-131.
[44] Neumann J,Yang Y,K?hler R,et al. Mangrove dolabrane-type of diterpenes tagalsins suppresses tumor growth via ROS-mediated apoptosis and ATM/ATR-Chk1/Chk2-regulated cell cycle arrest[J]. Int J Cancer,2015,137(11):2739-2748.
[45] Du SS,Wang CF,Li J,et al. Antifeedant diterpenoids against Tribolium castaneum from the stems and twigs of Ceriops tagal(Rhizophoraceae)[J]. Molecules,2011,16(7):6060-6067.
[2] Tsai CC,Li SJ,Su YY,et al. Molecular phylogeny and evidence for natural hybridization and historical introgression between Ceriops species(Rhizophoraceae)[J]. Biochem Syst Ecol,2012,43(4):178-191.
[3]廖宝文,张乔民.中国红树林的分布、面积和树种组成[J].湿地科学,2014,12(4):435-440.
[4] Zhang Y,Deng Z,Gao T,et al. Tagalsins A-H,dolabrane-type diterpenes from the mangrove plant,Ceriops tagal[J]. Org Lett,2005,36(49):1465-1471.
[5] Fun HK,Pakhathirathien C,Chantrapromma S,et al. 7-Ethenyl-1-[(Z)-hydroxy-methyl-idene]-4b,7,10a-trimethyl-perhydro-phenanthren-2-one[J]. Acta Crystallogr,2006,62(12):o5539-o5541.
[6] Ouyang XW,Wang XC,Yue QX,et al. A new dolabrane-type diterpene from Ceriops tagal[J]. Nat Prod Commun,2010,5(1):9-12.
[7] Hu WM,Li MY,Li J,et al. Dolabranes from the Chinese mangrove,Ceriops tagal[J]. Nat Prod,2010,73(10):1701-1705.
[8] Chen Y,Wang WJ,Wu J. Two new dolabranes from the Chinese mangrove Ceriops tagal[J]. J Asian Nat Prod Res,2016,18(1):41-45.
[9] Wu X,Liao H,Lu H,et al. A new dolabrane dinorditerpene from Ceriops tagal[J]. OALib J,2016,3(8):1-6.
[10] Yang Y,Zhang Y,Liu D,et al. Dolabrane-type diterpenes from the mangrove plant Ceriops tagal with antitumor activities[J]. Fitoterapia,2015,103:277-282.
[11] Peng Y,Ni SJ,Li J,et al. Three new dolabrane diterpenes from the Chinese mangrove plant of Ceriops tagal[J]. Phytochem Lett,2017,21:38-41.
[12] Ni SJ,Li J,Li MY. Two new dolabrane diterpenes from the Chinese mangrove Ceriops tagal[J]. Chem Biodivers,2018,15(3).
[13]刘喜苹,申丽,吴军.角果木的dolabrane型二萜类化合物研究[J].中草药,2016,47(13):2226-2231.
[14]彭媛,李敏一.海南红树植物角果木的二萜类化学成分研究[J].天然产物研究与开发,2016,(12):1870-1874.
[15]张晓慧,申丽,吴军.角果木中两个新的dolabrane型二萜类化合物[J].天然产物研究与开发,2017,(4):549-552.
[16] Zhang X,Li W,Shen L,et al. Four new diterpenes from the mangrove Ceriops tagal and structure revision of four dolabranes with a 4,18-epoxy group[J]. Fitoterapia,2017,124:1-7.
[17] Zhang X,Yang Y,Liu J,et al. Tagalide A and Tagalol A,naturally occurring 5/6/6/6-and 5/6/6-fused cyclic dolabrane-type diterpenes:a new insight into anti-breast cancer activity of the dolabrane scaffold[J]. Org Chem Front,2018,5(7):1176-1183.
[18] Chantrapromma S,Karalai C,Fun HK,et al. 7-Glycoloyl-2-hydr-oxy-1,4b,7,10a-tetra-methyl-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-phenanthren-3(4H)-one[J]. Acta Crystallogr,2007,63(2):o459-o461.
[19]王慧,吴军.十雄角果木树皮的二萜类化学成分研究[J].中草药,2013,44(5):532-536.
[20] Anjaneyulu ASR,Rao VL. Ceriopsins AD,diterpenoids from Ceriops decandra[J]. Phytochemistry,2002,60(8):777-782.
[21] Anjaneyulu ASR,Rao VL. Ceriopsins F and G,diterpenoids from Ceriops decandra[J]. Phytochemistry,2003,62(8):1207.
[22] Chacha M,Mapitse R,Afolayan AJ,et al. Antibacterial diterpenes from the roots of Ceriops tagal[J]. Nat Prod Commun,2008,3(1):17-20.
[23] Chen JD,Feng DQ,Yang ZW,et al. Antifouling metabolites from the mangrove plant Ceriops tagal[J]. Molecules,2008,13(2):212-219.
[24] Fun H-K,Chantrapromma S,Pakhathirathien C,et al. ent-(15S)-Pimar-8(14)-ene-15,16-diol[J]. Acta Crystallogr E,2012,68(Pt 2):o520-o521.
[25]胡格华,吴军.十雄角果木树皮的乙酸乙酯萃取部位化学成分的研究[J].三峡大学学报(自然科学版),2013,35(3):95-97.
[26] Wang H,Li MY,Satyanandamurty T,et al. New diterpenes from a Godavari mangrove,Ceriops decandra[J]. Planta Med,2013,79(8):666-672.
[27] Wang H,Li MY,Katele FZ,et al. Decandrinin,an unprecedented C9-spiro-fused 7,8-seco-ent-abietane from the Godavari mangrove Ceriops decandra[J]. Beils J Org Chem,2014,10(1):276-281.
[28] Simlai A,Mukherjee K,Mandal A,et al. Partial purification and characterization of an antimicrobial activity from the wood extract of mangrove plant Ceriops decandra[J]. Excli J,2016,15:103-112.
[29] Anjaneyulu SR,Rao VL,Lobkovskya E,et al. Ceriopsin E,a new epoxy ent-kaurene diterpenoid from Ceriops decandra[J]. J Nat Prod,2002,65(4):592-594.
[30] Chantrapromma S,Razak IA,Karalai C,et al. 14-Hydroxy-14-hydroxymethyl-5,5,9-trimethyl-tetracyclo-[11.2.1.0 1,10.0 4,9]hexa-decane hemihydrate[J]. Acta Crystallogr,2006,62(5):o1742-o1744.
[31] Zhang Y,Lu Y,Mao L,et al. Tagalsins I and J,two novel tetraterpenoids from the mangrove plant,Ceriops tagal[J]. Org Lett,2005,36(47):3037-3040.
[32] Chen JD,Qiu Y,Yang ZW,et al. Dimeric diterpenes from the roots of the mangrove plant Ceriops tagal[J]. Helv Chim Acta,2008,91(12):2292-2298.
[33] Chen JD,Yi RZ,Lin YM,et al. Characterization of terpenoids from the root of Ceriops tagal with antifouling activity[J]. Int J Mol Sci,2011,12(10):6517-6528.
[34] Nebula M,Harisankar HS,Chandramohanakumar N. Metabolites and bioactivities of Rhizophoraceae mangroves[J]. Nat Prod Bioprosp,2013,3(5):207-232.
[35] Peters RJ. Two rings in them all:the labdane-related diterpenoids[J]. Nat Prod Rep,2010,27(11):1521-1530.
[36]孙汉董.二萜化学[M].第2版.北京:化学工业出版社,2012:1054-1060.
[37] Nagahama S,Tajima M. Diterpene hydrocarbons from the leaf oil of Thujopsis dolabrata var. dolabrata[J]. Biochem Syst Ecol,1996,24(1):49-52.
[38] Fang LQ,Ito A,Chai HB. Cytotoxic constituents from the stem bark of Dichapetalum gelonioides collectedin the Philippines[J]. J Nat Prod,2006,69(3):332-337.
[39] Chacha M. Terpenoids from the roots of Ceriops tagal induces apoptosis through activation of caspase-3 enzyme[J]. Int J Biol Chem Sci,2011,5(2):2193-2196.
[40] Chacha M. Comparative anticancer activity of dolaborane diterpenes from the roots of Ceriops tagal(Rhizophoraceae)[J]. Int J Biol Chem Sci,2012,6(2):913-919.
[41]冯龄鑫,刘淑萍,丁爱萍,等.中国红树科植物角果木中Dolabrane型二萜的抗肿瘤作用[J].齐鲁医学杂志,2010,25(3):198-201.
[42]宋修岐,邢智远,郭云良,等.角果木提取物Tagalsin对H22荷瘤小鼠Survivin和Caspase-3表达的影响[J].中国临床研究,2010,23(9):748-751.
[43]孙蓓,王秀美,邱文生,等.角果木dolabrane型二萜对Lewis荷瘤小鼠的抗肿瘤作用[J].临床肿瘤学杂志,2010,15(2):127-131.
[44] Neumann J,Yang Y,K?hler R,et al. Mangrove dolabrane-type of diterpenes tagalsins suppresses tumor growth via ROS-mediated apoptosis and ATM/ATR-Chk1/Chk2-regulated cell cycle arrest[J]. Int J Cancer,2015,137(11):2739-2748.
[45] Du SS,Wang CF,Li J,et al. Antifeedant diterpenoids against Tribolium castaneum from the stems and twigs of Ceriops tagal(Rhizophoraceae)[J]. Molecules,2011,16(7):6060-6067.