Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

The Chemical Structure and Bioactivity of Cycloartane-type Compounds

Author(s): Wenyan Gao , Xiaoyan Dong, Taiming Wei and Wenmin Xing*

Volume 23, Issue 25, 2019

Page: [2848 - 2872] Pages: 25

DOI: 10.2174/1385272823666191203113221

Price: $65

Abstract

For decades now, compounds in the cycloartane-type series have been shown to have versatile pharmacological activities. However, no extensive review has been written to summarize these health-beneficial activities. Therefore, the purpose of this paper is to systematically highlight the biological activities of these compounds, including their antitumor and anti-osteoporosis effects, their effects on receptors, cytokine release, and chronic renal failure, as well as their tyrosinase inhibitory, anticomplement, anti-parasite, anti-HIV, and antituberculosis activities. In this review, we have summarized the structures of over 200 compounds based on their characteristics and described their structureactivity relationships (SARs), and potential mechanisms of action.

Keywords: Cycloartane, structure-activity relationships, tetracyclic triterpene, biological activities, antitumor effect, anti-inflammatory activity.

Graphical Abstract
[1]
Piegang, B.N.; Tigoufack, I.B.; Ngnokam, D.; Achounna, A.S.; Watcho, P.; Greffrath, W.; Treede, R.D.; Nguelefack, T.B. Cycloartanes from Oxyanthus pallidus and derivatives with analgesic activities. BMC Complement. Altern. Med., 2016, 16, 97.
[http://dx.doi.org/10.1186/s12906-016-1075-3] [PMID: 26956043]
[2]
Ayatollahi, A.M.; Zarei, S.M.; Memarnejadian, A.; Ghanadian, M.; Heydarian Moghadam, M.; Kobarfard, F. Triterpene constituents of euphorbia erythradenia bioss. and their anti-HIV activity. Iran. J. Pharm. Res., 2016, 15(Suppl.), 19-27.
[PMID: 28228800]
[3]
Benabdelaziz, I.; Gómez-Ruiz, S.; Benkhaled, M.; Carralero, S.; Schenker, P.; Salm, A.; Gertsch, J.; Haba, H. New cycloartane-type ester triterpenes from Euphorbia pterococca and biological evaluation. Fitoterapia, 2018, 127, 271-278.
[http://dx.doi.org/10.1016/j.fitote.2018.02.027] [PMID: 29524564]
[4]
Nguyen, V.T.; Do, L.Q.; Nguyen, T.A.; Nguyen, T.T.; Tran, V.L.; Ho, N.A.; Tran, V.C.; Tran, V.S.; Tran, T.P.T. New cycloartanes and new iridoids from Dolichandrone spathacea collected in the mangrove forest of Soc Trang province, Vietnam. J. Asian Nat. Prod. Res., 2018, 20(9), 889-896.
[http://dx.doi.org/10.1080/10286020.2017.1406927] [PMID: 29182020]
[5]
Wang, N.; Gao, J.; Yue, Z.G.; Huang, W.J.; Li, B.; Tang, Z.S.; Song, Z.X. Responses of seed germination of Astragalus membranaceus to light and temperature conditions accompanied with drought and salt stresses. Zhongguo Zhong Yao. Za. Zhi., 2019, 44(12), 2444-2451.
[PMID: 31359709]
[6]
Lu, J.; Peng, X.R.; Li, D.S.; Shi, Q.Q.; Qiu, M.H. Cytotoxic cycloartane triterpenoid saponins from the rhizomes of Cimicifuga foetida. Nat. Prod. Bioprospect., 2019, 9(4), 303-310.
[http://dx.doi.org/10.1007/s13659-019-0214-1] [PMID: 31214880]
[7]
Shi, Q.Q.; Lu, J.; Peng, X.R.; Li, D.S.; Zhou, L.; Qiu, M.H. Cimitriteromone a-g, macromolecular triterpenoid-chromone hybrids from the rhizomes of Cimicifuga foetida. J. Org. Chem., 2018, 83(17), 10359-10369.
[http://dx.doi.org/10.1021/acs.joc.8b01466] [PMID: 30044102]
[8]
Wang, Y.P.; Ma, D.; Cheng, X.T.; Zhang, S.J.; Xue, W.; Deng, Y.; Wang, Y.F.; Sun, A.J. Comparison of Cimicifuga foetida extract and different hormone therapies regarding in causing breast pain in early postmenopausal women. Gynecol. Endocrinol., 2019, 35, 160-164.
[http://dx.doi.org/10.1080/09513590.2018.1505845]
[9]
Georgieva, K.; Trusheva, B.; Uzunova, V.; Stoyanova, T.; Valcheva, V.; Popova, M.; Tzoneva, R.; Bankova, V. New cycloartane triterpenes from bioactive extract of propolis from Pitcairn Island. Fitoterapia, 2018, 128, 233-241.
[http://dx.doi.org/10.1016/j.fitote.2018.05.024] [PMID: 29800610]
[10]
Hill, R.A.; Connolly, J.D. Triterpenoids. Nat. Prod. Rep., 2018, 35(12), 1294-1329.
[http://dx.doi.org/10.1039/C8NP00029H] [PMID: 29993074]
[11]
Sarraj-Laabidi, A.; Lacaille-Dubois, M-A.; Semmar, N. Structural organization of cycloartane-based saponins in the genus astragalus (fabaceae). Phytochem. Rev., 2017, 17, 431-452.
[http://dx.doi.org/10.1007/s11101-017-9541-1]
[12]
Bai, S.T.; Zhu, G.L.; Peng, X.R.; Dong, J.R.; Yu, M.Y.; Chen, J.C.; Wan, L.S.; Qiu, M.H. Cytotoxicity of triterpenoid alkaloids from buxus microphylla against human tumor cell lines. Molecules, 2016, 21(9), 1125.
[http://dx.doi.org/10.3390/molecules21091125] [PMID: 27571056]
[13]
Ngo, T.N.; Phan, N.M.; Bui, T.D.; Dang, V.S.; Tran, C.L.; Mai, D.T.; Nguyen, T.P. Cytotoxic cycloartane triterpenoids from the leaves of markhamia stipulata var. Canaense. Phytochem. Lett., 2017, 22, 251-254.
[http://dx.doi.org/10.1016/j.phytol.2017.10.020]
[14]
Fang, Z.Z.; Nian, Y.; Li, W.; Wu, J.J.; Ge, G.B.; Dong, P.P.; Zhang, Y.Y.; Qiu, M.H.; Liu, L.; Yang, L. Cycloartane triterpenoids from Cimicifuga yunnanensis induce apoptosis of breast cancer cells (MCF7) via p53-dependent mitochondrial signaling pathway. Phytother. Res., 2011, 25(1), 17-24.
[http://dx.doi.org/10.1002/ptr.3222] [PMID: 20564500]
[15]
Gaube, F.; Wolfl, S.; Pusch, L.; Kroll, T.C.; Hamburger, M. Gene expression profiling reveals effects of Cimicifuga racemosa (L.) NUTT. (black cohosh) on the estrogen receptor positive human breast cancer cell line MCF-7. BMC Pharmacol., 2007, 7, 11.
[http://dx.doi.org/10.1186/1471-2210-7-11] [PMID: 17880733]
[16]
Ionkova, I.; Momekov, G.; Proksch, P. Effects of cycloartane saponins from hairy roots of Astragalus membranaceus Bge., on human tumor cell targets. Fitoterapia, 2010, 81(5), 447-451.
[http://dx.doi.org/10.1016/j.fitote.2009.12.007] [PMID: 20060881]
[17]
Sun, L.R.; Qing, C.; Zhang, Y.L.; Jia, S.Y.; Li, Z.R.; Pei, S.J.; Qiu, M.H.; Gross, M.L.; Qiu, S.X. Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells. Beilstein J. Org. Chem., 2007, 3, 3.
[http://dx.doi.org/10.1186/1860-5397-3-3] [PMID: 17266751]
[18]
Tian, Z.; Xu, L.; Chen, S.; Zhou, L.; Yang, M.; Chen, S.; Xiao, P.; Wu, E. Cytotoxic activity of schisandrolic and isoschisandrolic acids involves induction of apoptosis. Chemotherapy, 2007, 53(4), 257-262.
[http://dx.doi.org/10.1159/000102582] [PMID: 17496413]
[19]
Gao, J.; Huang, F.; Zhang, J.; Zhu, G.; Yang, M.; Xiao, P. Cytotoxic cycloartane triterpene saponins from Actaea asiatica. J. Nat. Prod., 2006, 69(10), 1500-1502.
[http://dx.doi.org/10.1021/np060113h] [PMID: 17067171]
[20]
Tian, Z.; Si, J.; Chang, Q.; Zhou, L.; Chen, S.; Xiao, P.; Wu, E. Antitumor activity and mechanisms of action of total glycosides from aerial part of Cimicifuga dahurica targeted against hepatoma. BMC Cancer, 2007, 7, 237.
[http://dx.doi.org/10.1186/1471-2407-7-237] [PMID: 18166137]
[21]
Nuanyai, T.; Sappapan, R.; Teerawatananond, T.; Muangsin, N.; Pudhom, K. Cytotoxic 3,4-seco-cycloartane triterpenes from Gardenia sootepensis. J. Nat. Prod., 2009, 72(6), 1161-1164.
[http://dx.doi.org/10.1021/np900156k] [PMID: 19456120]
[22]
Gan, L.S.; Ren, G.; Mo, J.X.; Zhang, X.Y.; Yao, W.; Zhou, C.X. Cycloartane triterpenoids from Kleinhowia hospita. J. Nat. Prod., 2009, 72, 1102-1105.
[23]
Thanesuan, N.S. Vilaivan. T.; Pudhom, K. Cytotoxic 3,4-seco-cycloartane triterpenes from the exudate of Gardenia tubifera. J. Nat. Prod., 2010, 73, 51-54.
[http://dx.doi.org/10.1021/np900658t]
[24]
Nian, Y.; Zhang, Y.L.; Chen, J.C.; Lu, L.; Qiu, M.H.; Qing, C. Cytotoxic chemical constituents from the roots of Cimicifuga fetida. J. Nat. Prod., 2010, 73, 93-98.
[http://dx.doi.org/10.1021/np9003855]
[25]
Zhang, L.S.; Wang, Y.L.; Liu, Q.; Zhou, C.X.; Mo, J.X.; Lin, L.G.; Gan, L.S. Three new 3,4-seco-cycloartane triterpenoids from the flower of Gardenia jasminoides. Phytochem. Lett., 2018, 23, 172-175.
[http://dx.doi.org/10.1016/j.phytol.2017.11.006]
[26]
Nian, Y.; Zhang, X.M.; Li, Y.; Wang, Y.Y.; Chen, J.C.; Lu, L.; Zhou, L.; Qiu, M.H. Cycloartane triterpenoids from the aerial parts of Cimicifuga foetida Linnaeus. Phytochemistry, 2011, 72(11-12), 1473-1481.
[http://dx.doi.org/10.1016/j.phytochem.2011.03.022] [PMID: 21565371]
[27]
Chen, J.Y.; Li, P.L.; Tang, X.L.; Wang, S.J.; Jiang, Y.T.; Shen, L.; Xu, B.M.; Shao, Y.L.; Li, G.Q. Cycloartane triterpenoids and their glycosides from the rhizomes of Cimicifuga foetida. J. Nat. Prod., 2014, 77(9), 1997-2005.
[http://dx.doi.org/10.1021/np500249v] [PMID: 25136911]
[28]
Yang, X.W.; Li, S.M.; Wu, L.; Li, Y.L.; Feng, L.; Shen, Y.H.; Tian, J.M.; Tang, J.; Wang, N.; Liu, Y.; Zhang, W.D. Abiesatrines A-J. Anti-inflammatory and antitumor triterpenoids from Abies georgei Orr. Org. Biomol. Chem., 2010, 8(11), 2609-2616.
[http://dx.doi.org/10.1039/c001885f] [PMID: 20372737]
[29]
Tian, Z.S. Jianyong; Wang, T.; Yang, M.; Han, R.; Xiao, P. Cytotoxicity and mechanism of 24-o-acetycimigenol -3-o-beita-d-xylopyranoside on hepg2 cells. Chung Kuo Yao Hsueh Tsa Chih, 2007, 42, 505-507.
[30]
Yokosuka, A.; Sato, K.; Yamori, T.; Mimaki, Y. Triterpene glycosides from Curculigo orchioides and their cytotoxic activity. J. Nat. Prod., 2010, 73(6), 1102-1106.
[http://dx.doi.org/10.1021/np100111s] [PMID: 20524638]
[31]
Bao, N.M.; Nian, Y.; Zhu, G.L.; Wang, W.H.; Zhou, L.; Qiu, M.H. Cytotoxic 9,19-cycloartane triterpenes from the aerial parts of Cimicifuga yunnanensis. Fitoterapia, 2014, 99, 191-197.
[http://dx.doi.org/10.1016/j.fitote.2014.05.019] [PMID: 24887699]
[32]
Bo, Li. Yunheng, Shen.; Hu, Yuan.; Rongcai, Yue.; Yiren, He.; Lu, Lu.; Huiliang, Li.; Ji, Ye.; Xianwen, Yang.; Juan, Su.; Runhui, Liu.; Weidong, Zhang. Pseudolaridimers a and b, hetero-cycloartane labdane diels alder adducts from the cone of Pseudolarix amabilis. Org. Lett., 2012, 42, 5432-5435.
[33]
Shen, T.; Wan, W.; Yuan, H.; Kong, F.; Guo, H.; Fan, P.; Lou, H. Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells. Phytochemistry, 2007, 68(9), 1331-1337.
[http://dx.doi.org/10.1016/j.phytochem.2007.01.013] [PMID: 17343886]
[34]
Shen, T.Y.H.Q.; Wan, W.Z.; Wang, X.L.; Ji, M.; Lou, H.X. Cycloartane-type triterpenes from the resinous exudates of Commiphora opobalsamum. J. Nat. Prod., 2008, 71, 81-86.
[http://dx.doi.org/10.1021/np070442p] [PMID: 18177010]
[35]
Gao, W.; Su, X.; Dong, X.; Chen, Y.; Zhou, C.; Xin, P.; Yu, C.; Wei, T. Cycloartan-24-ene-1α,2α,3β-triol, a cycloartane-type triterpenoid from the resinous exudates of Commiphora myrrha, induces apoptosis in human prostatic cancer PC-3 cells. Oncol. Rep., 2015, 33(3), 1107-1114.
[http://dx.doi.org/10.3892/or.2015.3725] [PMID: 25591732]
[36]
Li, F.; Awale, S.; Zhang, H.; Tezuka, Y.; Esumi, H.; Kadota, S. Chemical constituents of propolis from Myanmar and their preferential cytotoxicity against a human pancreatic cancer cell line. J. Nat. Prod., 2009, 72(7), 1283-1287.
[http://dx.doi.org/10.1021/np9002433] [PMID: 19572611]
[37]
Zhang, X.T.; Ma, S.W.; Jiao, H.Y.; Zhang, Q.W. Two new saponins from Thalictrum fortunei. J. Asian Nat. Prod. Res., 2012, 14(4), 327-332.
[http://dx.doi.org/10.1080/10286020.2011.653684] [PMID: 22375870]
[38]
Sashidhara, K.V.; Singh, S.P.; Kant, R.; Maulik, P.R.; Sarkar, J.; Kanojiya, S.; Ravi Kumar, K. Cytotoxic cycloartane triterpene and rare isomeric bisclerodane diterpenes from the leaves of Polyalthia longifolia var. pendula. Bioorg. Med. Chem. Lett., 2010, 20(19), 5767-5771.
[http://dx.doi.org/10.1016/j.bmcl.2010.07.141] [PMID: 20732814]
[39]
Liu, Q.; Chen, C.J.; Shi, X.; Zhang, L.; Chen, H.J.; Gao, K. Chemical constituents from Aphanamixis grandifolia. Chem. Pharm. Bull. (Tokyo), 2010, 58(11), 1431-1435.
[http://dx.doi.org/10.1248/cpb.58.1431] [PMID: 21048332]
[40]
Fan, Y.S.; Yao, Z.; Zhang, Y.W.; Duan, H.Q. Six new cycloartane triterpene glycosides from Actaea asiatica. J. Asian Nat. Prod. Res., 2009, 11(7), 588-596.
[http://dx.doi.org/10.1080/10286020902819848] [PMID: 20183295]
[41]
Li, F.; Awale, S.; Tezuka, Y.; Kadota, S. Cytotoxic constituents of propolis from Myanmar and their structure-activity relationship. Biol. Pharm. Bull., 2009, 32(12), 2075-2078.
[http://dx.doi.org/10.1248/bpb.32.2075] [PMID: 19952433]
[42]
Wong, Y.H.; Abdul Kadir, H.; Ling, S.K. Bioassay-guided isolation of cytotoxic cycloartane triterpenoid glycosides from the traditionally used medicinal plant leea indica. Evid. Based Complement. Alternat. Med., 2012, 2012 164689
[http://dx.doi.org/10.1155/2012/164689] [PMID: 22203865]
[43]
Thanesuan, N. Sappapan, R.; Vilaivan, T.; Pudhom, K.; Gardenoins, E-H. Cycloartane triterpenes from the apical buds of Gardenia obtusifolia. Chem. Pharm. Bull. (Tokyo), 2011, 59, 385-387.
[http://dx.doi.org/10.1248/cpb.59.385]
[44]
Awang, K.; Loong, X.M.; Leong, K.H.; Supratman, U.; Litaudon, M.; Mukhtar, M.R.; Mohamad, K. Triterpenes and steroids from the leaves of Aglaia exima (Meliaceae). Fitoterapia, 2012, 83(8), 1391-1395.
[http://dx.doi.org/10.1016/j.fitote.2012.10.004] [PMID: 23098876]
[45]
Khan, M.T.; Khan, S.B.; Ather, A. Tyrosinase inhibitory cycloartane type triterpenoids from the methanol extract of the whole plant of Amberboa ramosa Jafri and their structure-activity relationship. Bioorg. Med. Chem., 2006, 14(4), 938-943.
[http://dx.doi.org/10.1016/j.bmc.2005.09.010] [PMID: 16202612]
[46]
Marrero-Ponce, Y.; Khan, M.T.; Casañola Martín, G.M.; Ather, A.; Sultankhodzhaev, M.N.; Torrens, F.; Rotondo, R. Prediction of tyrosinase inhibition activity using atom-based bilinear indices. ChemMedChem, 2007, 2(4), 449-478.
[http://dx.doi.org/10.1002/cmdc.200600186] [PMID: 17366651]
[47]
Su, S.L.; Duan, J.A.; Tang, Y.P.; Zhang, X.; Yu, L.; Jiang, F.R.; Zhou, W.; Luo, D.; Ding, A.W. Isolation and biological activities of neomyrrhaol and other terpenes from the resin of Commiphora myrrha. Planta Med., 2009, 75(4), 351-355.
[http://dx.doi.org/10.1055/s-0028-1112214] [PMID: 19101885]
[48]
Lee, I.; Kim, J.; Kim, Y.S.; Yoo, N.H.; Kim, C.S.; Jo, K.; Kim, J.H.; Bach, T.T.; Kim, J.S. Cycloartane-type triterpenes from the leaves of Homonoia riparia with VEGF-induced angiogenesis inhibitory activity. J. Nat. Prod., 2012, 75(7), 1312-1318.
[http://dx.doi.org/10.1021/np300224k] [PMID: 22731844]
[49]
Pudhom, K.; Nuanyai, T.; Matsubara, K.; Vilaivan, T. Antiangiogenic activity of 3,4-seco-cycloartane triterpenes from Thai Gardenia spp. and their semi-synthetic analogs. Bioorg. Med. Chem. Lett., 2012, 22(1), 512-517.
[http://dx.doi.org/10.1016/j.bmcl.2011.10.128] [PMID: 22142538]
[50]
Pudhom, K.; Nuanyai, T.; Matsubara, K. Cytotoxic and anti-angiogenic properties of minor 3,4-seco-cycloartanes from Gardenia sootepensis exudate. Chem. Pharm. Bull. (Tokyo), 2012, 60(12), 1538-1543.
[http://dx.doi.org/10.1248/cpb.c12-00699] [PMID: 23207634]
[51]
Graziani, V.; Esposito, A.; Scognamiglio, M.; Chambery, A.; Russo, R.; Ciardiello, F.; Troiani, T.; Potenza, N.; Fiorentino, A.; D’Abrosca, B. Spectroscopic characterization and cytotoxicity assessment towards human colon cancer cell lines of acylated cycloartane glycosides from Astragalus boeticus l. Molecules, 2019, 24(9), 1725.
[http://dx.doi.org/10.3390/molecules24091725] [PMID: 31058835]
[52]
Toume, K.; Nakazawa, T.; Ohtsuki, T.; Arai, M.A.; Koyano, T.; Kowithayakorn, T.; Ishibashi, M. Cycloartane triterpenes isolated from Combretum quadrangulare in a screening program for death-receptor expression enhancing activity. J. Nat. Prod., 2011, 74(2), 249-255.
[http://dx.doi.org/10.1021/np100784t] [PMID: 21265555]
[53]
Serhat, S. Cicek.; Sophia, Khom.; Barbara, Taferner.; Steffen, Hering.; Hermann, Stuppner. Bioactivity-guided isolation of gabaa receptor modulating constituents from the rhizomes of Actaea racemosa. J. Nat. Prod., 2010, 73, 2024-2028.
[http://dx.doi.org/10.1021/np100479w]
[54]
Toume, K.; Nakazawa, T.; Hoque, T.; Ohtsuki, T.; Arai, M.A.; Koyano, T.; Kowithayakorn, T.; Ishibashi, M. Cycloartane triterpenes and ingol diterpenes isolated from Euphorbia neriifolia in a screening program for death-receptor expression-enhancing activity. Planta Med., 2012, 78(12), 1370-1377.
[http://dx.doi.org/10.1055/s-0032-1314975] [PMID: 22700046]
[55]
Zou, J.; Jiang, J.; Diao, Y.Y.; Yang, L.B.; Huang, J.; Li, H.L.; Du, X.; Xiao, W.L.; Pu, J.X.; Sun, H.D. Cycloartane triterpenoids from the stems of Schisandra glaucescens and their bioactivity. Fitoterapia, 2012, 83(5), 926-931.
[http://dx.doi.org/10.1016/j.fitote.2012.04.007] [PMID: 22537642]
[56]
Khan, M.T.; Choudhary, M.I. Atta-ur-Rahman; Mamedova, R.P.; Agzamova, M.A.; Sultankhodzhaev, M.N.; Isaev, M.I. Tyrosinase inhibition studies of cycloartane and cucurbitane glycosides and their structure-activity relationships. Bioorg. Med. Chem., 2006, 14(17), 6085-6088.
[http://dx.doi.org/10.1016/j.bmc.2006.05.002] [PMID: 16716596]
[57]
Casañola-Martín, G.M.; Khan, M.T.; Marrero-Ponce, Y.; Ather, A.; Sultankhodzhaev, M.N.; Torrens, F. New tyrosinase inhibitors selected by atomic linear indices-based classification models. Bioorg. Med. Chem. Lett., 2006, 16(2), 324-330.
[http://dx.doi.org/10.1016/j.bmcl.2005.09.085] [PMID: 16275084]
[58]
Long, C.; Beck, J.; Cantagrel, F.; Marcourt, L.; Vendier, L.; David, B.; Plisson, F.; Derguini, F.; Vandenberghe, I.; Aussagues, Y.; Ausseil, F.; Lavaud, C.; Sautel, F.; Massiot, G. Proteasome inhibitors from Neoboutonia melleri. J. Nat. Prod., 2012, 75(1), 34-47.
[http://dx.doi.org/10.1021/np200441h] [PMID: 22168134]
[59]
Mu, L.H.; Zhao, J.Y.; Zhang, J.; Liu, P. Cycloartane triterpenes from Beesia calthaefolia and their anticomplement structure-activity relationship study. J. Asian Nat. Prod. Res., 2016, 18(11), 1101-1107.
[http://dx.doi.org/10.1080/10286020.2016.1174698] [PMID: 27140685]
[60]
Mpetga, J.D.; Shen, Y.; Tane, P.; Li, S.F.; He, H.P.; Wabo, H.K.; Tene, M.; Leng, Y.; Hao, X.J. Cycloartane and friedelane triterpenoids from the leaves of Caloncoba glauca and their evaluation for inhibition of 11β-hydroxysteroid dehydrogenases. J. Nat. Prod., 2012, 75(4), 599-604.
[http://dx.doi.org/10.1021/np200831c] [PMID: 22360639]
[61]
Lowe, H.I.; Watson, C.T.; Badal, S.; Toyang, N.J.; Bryant, J. Cycloartane-3,24,25-triol inhibits MRCKα kinase and demonstrates promising anti prostate cancer activity in vitro. Cancer Cell Int., 2012, 12, 46.
[http://dx.doi.org/10.1186/1475-2867-12-46]
[62]
Ramírez-Cisneros, M.A.; Rios, M.Y.; Ríos-Gómez, R.; Aguilar-Guadarrama, A.B. Cycloartanes from Krameria pauciflora and their in vitro PLA2, COX-1, and COX-2 enzyme inhibitory activities. Planta Med., 2012, 78(18), 1942-1948.
[http://dx.doi.org/10.1055/s-0032-1327882] [PMID: 23161426]
[63]
Yesilada, E.; Bedir, E.; Caliş, I.; Takaishi, Y.; Ohmoto, Y. Effects of triterpene saponins from Astragalus species on in vitro cytokine release. J. Ethnopharmacol., 2005, 96(1-2), 71-77.
[http://dx.doi.org/10.1016/j.jep.2004.08.036] [PMID: 15588652]
[64]
Mai, H.L.; Grellier, P.; Prost, E.; Lemoine, P.; Poullain, C.; Dumontet, V.; Deguin, B.; Vo, T.B.H.; Michel, S.; Grougnet, R. Triterpenes from the exudate of Gardenia urvillei. Phytochemistry, 2016, 122, 193-202.
[http://dx.doi.org/10.1016/j.phytochem.2015.11.001] [PMID: 26608669]
[65]
Althaus, J.B.; Jerz, G.; Winterhalter, P.; Kaiser, M.; Brun, R.; Schmidt, T.J. Antiprotozoal activity of Buxus sempervirens and activity-guided isolation of O-tigloylcyclovirobuxeine-B as the main constituent active against Plasmodium falciparum. Molecules, 2014, 19(5), 6184-6201.
[http://dx.doi.org/10.3390/molecules19056184] [PMID: 24838073]
[66]
Ozipek, M.; Dönmez, A.A.; Caliş, I.; Brun, R.; Rüedi, P.; Tasdemir, D. Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius. Phytochemistry, 2005, 66(10), 1168-1173.
[http://dx.doi.org/10.1016/j.phytochem.2005.04.019] [PMID: 15922377]
[67]
Lacroix, D.; Prado, S.; Deville, A.; Krief, S.; Dumontet, V.; Kasenene, J.; Mouray, E.; Bories, C.; Bodo, B. Hydroperoxy-cycloartane triterpenoids from the leaves of Markhamia lutea, a plant ingested by wild chimpanzees. Phytochemistry, 2009, 70(10), 1239-1245.
[http://dx.doi.org/10.1016/j.phytochem.2009.06.020] [PMID: 19679323]
[68]
Jan, S.; Abbaskhan, A.; Musharraf, S.G.; Sattar, S.A.; Resayes, S.I.; Al-Othman, Z.A.; Al-Majid, A.M.; Choudhary, M.I. Three new cycloartane triterpenoids from Astragalus bicuspis. Planta Med., 2011, 77(16), 1829-1834.
[http://dx.doi.org/10.1055/s-0030-1271196] [PMID: 21766268]
[69]
Chung, I.M.; Kim, M.Y.; Park, S.D.; Park, W.H.; Moon, H.I. In vitro evaluation of the antiplasmodial activity of Dendropanax morbifera against chloroquine-sensitive strains of Plasmodium falciparum. Phytother. Res., 2009, 23(11), 1634-1637.
[http://dx.doi.org/10.1002/ptr.2838] [PMID: 19367673]
[70]
Zhao, Z.; Matsunami, K.; Otsuka, H.; Shinzato, T.; Takeda, Y. Tareciliosides N-S: further cycloartane saponins from the leaves of Tarenna gracilipes, and cytotoxicity of saponins and triterpenes. J. Nat. Med., 2013, 67(3), 503-511.
[http://dx.doi.org/10.1007/s11418-012-0707-2] [PMID: 23015040]
[71]
Ali, Z.; Khan, S.I.; Khan, I.A. New cycloartane-type triterpene arabinosides from the roots of Actaea podocarpa and their biological study. Lett. Plant Med., 2007, 73(7), 699-703.
[72]
Qiu, M.; Kim, J.H.; Lee, H.K.; Min, B.S. Anticomplement activity of cycloartane glycosides from the rhizome of Cimicifuga foetida. Phytother. Res., 2006, 20(11), 945-948.
[http://dx.doi.org/10.1002/ptr.1982] [PMID: 16906637]
[73]
Aslanipour, B.; Gülcemal, D.; Nalbantsoy, A.; Yusufoglu, H.; Bedir, E. Cycloartane-type glycosides from Astragalus brachycalyx fischer and their effects on cytokine release and hemolysis. Phytochem. Lett., 2017, 21, 66-73.
[http://dx.doi.org/10.1016/j.phytol.2017.05.028]
[74]
Kuang, H.; Su, Y.; Wang, Q.; Wu, L.; Yang, B.; Wang, Z.; Xia, Y. Three new cycloartenol glycosides from the roots of Cimicifuga simplex. Planta Med., 2012, 78, 622-625.
[http://dx.doi.org/10.1055/s-0031-1298224]
[75]
Yan, J.; Zhou, Z.Y.; Zhang, M.; Wang, J.; Dai, H.F.; Tan, J.W. Cycloartane-type triterpene glycosides from the rhizomes of Cimicifuga heracleifolia and their anticomplementary activity. Planta Med., 2012, 78, 1387-1391.
[PMID: 22753038]
[76]
Sun, R.; Song, H.C.; Wang, C.R.; Shen, K.Z.; Xu, Y.B.; Gao, Y.X.; Chen, Y.G.; Dong, J.Y. Compounds from Kadsura angustifolia with anti-HIV activity. Bioorg. Med. Chem. Lett., 2011, 21(3), 961-965.
[http://dx.doi.org/10.1016/j.bmcl.2010.12.055] [PMID: 21232955]
[77]
Li, S.F.; Li, S.L. Cycloartane triterpenoid and its glucoside isolated from Cassia occidentalis. Chin. J. Nat. Med., 2017, 15(12), 950-954.
[http://dx.doi.org/10.1016/S1875-5364(18)30012-8] [PMID: 29329653]
[78]
Li, S.F.; Di, Y.T.; Luo, R.H.; Zheng, Y.T.; Wang, Y.H.; Fang, X.; Zhang, Y.; Li, L.; He, H.P.; Li, S.L.; Hao, X.J. Cycloartane triterpenoids from Cassia occidentalis. Planta Med., 2012, 78(8), 821-827.
[http://dx.doi.org/10.1055/s-0031-1298376] [PMID: 22411720]
[79]
Truong, N.B.; Pham, C.V.; Doan, H.T.; Nguyen, H.V.; Nguyen, C.M.; Nguyen, H.T.; Zhang, H.J.; Fong, H.H.; Franzblau, S.G.; Soejarto, D.D.; Chau, M.V. Antituberculosis cycloartane triterpenoids from Radermachera boniana. J. Nat. Prod., 2011, 74(5), 1318-1322.
[http://dx.doi.org/10.1021/np200022b] [PMID: 21469696]
[80]
Yoshihiro, M. Isao, Nadaoka.; Masaaki, Yasue.; Yasuyuki, Ohtake.; Mitsuo, Ikeda.; Kazuki, Watanabe.; Sashida, Y. Neocimicigenosides A and B, cycloartane glycosides from the rhizomes of Cimicifuga racemosa and their effects on CRF-stimulated ACTH secretion from AtT-20 cells. J. Nat. Prod., 2006, 69, 829-832.
[http://dx.doi.org/10.1021/np058127v]
[81]
Du, Q.; Chen, Z.; Zhou, L.F.; Zhang, Q.; Huang, M.; Yin, K.S. Inhibitory effects of astragaloside IV on ovalbumin-induced chronic experimental asthma. Can. J. Physiol. Pharmacol., 2008, 86(7), 449-457.
[http://dx.doi.org/10.1139/Y08-053] [PMID: 18641694]
[82]
Li, J.X.; Liu, J.; He, C.C.; Yu, Z.Y.; Du, Y.; Kadota, S.; Seto, H. Triterpenoids from Cimicifugae rhizoma, a novel class of inhibitors on bone resorption and ovariectomy-induced bone loss. Maturitas, 2007, 58(1), 59-69.
[http://dx.doi.org/10.1016/j.maturitas.2007.06.001] [PMID: 17658706]
[83]
Sevimli-Gür, C.; Onbaşılar, I.; Atilla, P.; Genç, R.; Cakar, N.; Deliloğlu-Gürhan, I.; Bedir, E. In vitro growth stimulatory and in vivo wound healing studies on cycloartane-type saponins of Astragalus genus. J. Ethnopharmacol., 2011, 134(3), 844-850.
[http://dx.doi.org/10.1016/j.jep.2011.01.030] [PMID: 21291980]
[84]
Yun, J.X.Z. Y.D.; Sun, S.; Shen, J.P.; Qiu, J.; Yin, X.X.; Yin, H.L.; Jiang, S.J. Inhibitory effects of astragaloside iv on diabetic peripheral neuropathy in rats. Canad. J. Physiol. Pharmacol., 2006, 84(6), 579-587.
[85]
Shang, N.; Guerrero-Analco, J.A.; Musallam, L.; Saleem, A.; Muhammad, A.; Walshe-Roussel, B.; Cuerrier, A.; Arnason, J.T.; Haddad, P.S. Adipogenic constituents from the bark of Larix laricina du Roi (K. Koch; Pinaceae), an important medicinal plant used traditionally by the Cree of Eeyou Istchee (Quebec, Canada) for the treatment of type 2 diabetes symptoms. J. Ethnopharmacol., 2012, 141(3), 1051-1057.
[http://dx.doi.org/10.1016/j.jep.2012.04.002] [PMID: 22542642]
[86]
Romero, J.C.; Martínez-Vázquez, A.; Herrera, M.P.; Martinez-Mayorga, K.; Parra-Delgado, H.; Pérez-Flores, F.J.; Martínez-Vázquez, M. Synthesis, anti-inflammatory activity and modeling studies of cycloartane-type terpenes derivatives isolated from Parthenium argentatum. Bioorg. Med. Chem., 2014, 22(24), 6893-6898.
[http://dx.doi.org/10.1016/j.bmc.2014.10.028] [PMID: 25456078]
[87]
Li, H.J.; Mu, L.H.; Dong, X.Z.; Ge, X.Y.; Liu, P. New cycloartane triterpene glycosides from Beesia calthaefolia. Nat. Prod. Res., 2013, 27(21), 1987-1993.
[http://dx.doi.org/10.1080/14786419.2013.811407] [PMID: 23815442]
[88]
Li, C.; Xi, F.; Mi, J.; Wu, Z.; Chen, W. Two new 3,4;9,10-seco-cycloartane type triterpenoids from Illicium difengpi and their anti-inflammatory activities. Evid. Based Complement. Alternat. Med., 2013, 2013942541
[PMID: 23762173]
[89]
Lee, D.Y.; Noh, H.J.; Choi, J.; Lee, K.H.; Lee, M.H.; Lee, J.H.; Hong, Y.; Lee, S.E.; Kim, S.Y.; Kim, G.S. Anti-inflammatory cycloartane-type saponins of Astragalus membranaceus. Molecules, 2013, 18(4), 3725-3732.
[http://dx.doi.org/10.3390/molecules18043725] [PMID: 23529032]
[90]
Jia, L.Y.; Wang, J.; Lv, C.N.; Xu, T.Y.; Jia, B.Z.; Lu, J.C. A new cycloartane nortriterpenoid from stem and leaf of Quercus variabilis. J. Asian Nat. Prod. Res., 2013, 15(9), 1050-1054.
[http://dx.doi.org/10.1080/10286020.2012.762911] [PMID: 23869388]
[91]
Fang, Z.J.; Zhang, T.; Chen, S.X.; Wang, Y.L.; Zhou, C.X.; Mo, J.X.; Wu, Y.J.; Xu, Y.K.; Lin, L.G.; Gan, L.S. Cycloartane triterpenoids from Actaea vaginata with anti-inflammatory effects in LPS-stimulated RAW264.7 macrophages. Phytochemistry, 2019, 160, 1-10.
[http://dx.doi.org/10.1016/j.phytochem.2019.01.003] [PMID: 30641334]
[92]
Nalbantsoy, A.; Nesil, T.; Yılmaz-Dilsiz, O.; Aksu, G.; Khan, S.; Bedir, E. Evaluation of the immunomodulatory properties in mice and in vitro anti-inflammatory activity of cycloartane type saponins from Astragalus species. J. Ethnopharmacol., 2012, 139(2), 574-581.
[http://dx.doi.org/10.1016/j.jep.2011.11.053] [PMID: 22155389]
[93]
Aslanipour, B.; Gülcemal, D.; Nalbantsoy, A.; Yusufoglu, H.; Bedir, E. Secondary metabolites from Astragalus karjaginii BORISS and the evaluation of their effects on cytokine release and hemolysis. Fitoterapia, 2017, 122, 26-33.
[http://dx.doi.org/10.1016/j.fitote.2017.08.008] [PMID: 28827003]
[94]
Ayatollahi, A.M.; Ghanadian, M.; Afsharypuor, S.; Mesaik, M.A.; Abdalla, O.M.; Shahlaei, M.; Farzandi, G.; Mostafavi, H. Cycloartanes from Euphorbia aellenii rech. F. and their antiproliferative activity. Iran. J. Pharm. Res., 2011, 10(1), 105-112.
[PMID: 24363688]
[95]
Guo, H.; Yao, S.; Yang, X.; Chen, Y.; Chen, Y.; Gong, F.; Tong, J.; Qian, J.; Zhang, A.; Cai, X. Oxidatively rearranged cycloartane triterpenoids from the seeds of Pseudolarix amabilis. Nat. Prod. Res., 2018, 32(15), 1817-1823.
[http://dx.doi.org/10.1080/14786419.2017.1405406] [PMID: 29171302]
[96]
Huong, P.T.; Diep, C.N.; Thanh, N.V.; Tu, V.A.; Hanh, T.H.; Cuong, N.T.; Thao, N.P.; Cuong, N.X.; Thao, T.; Thai, T.H.; Nam, N.H.; Ban, N.K.; Kiem, P.V.; Minh, C.V. A new cycloartane glucoside from Rhizophora stylosa. Nat. Prod. Commun., 2014, 9(9), 1255-1257.
[http://dx.doi.org/10.1177/1934578X1400900909] [PMID: 25918786]
[97]
Wang, X.Y.; Li, C.J.; Ma, J.; Li, C.; Chen, F.Y.; Wang, N.; Shen, C.J.; Zhang, D.M.; Naeem, R.U.; Izhar, A.; Wang, X.Y.; Li, C.J.; Ma, J.; Li, C.; Chen, F.Y.; Wang, N.; Shen, C.J.; Zhang, D.M. Cytotoxic 9,19-cycloartane type triterpenoid glycosides from the roots of Actaea dahurica. Phytochemistry, 2019, 160, 48-55.
[http://dx.doi.org/10.1016/j.phytochem.2019.01.004] [PMID: 30708138]
[98]
Kim, J.H.; Thao, N.P.; Han, Y.K.; Lee, Y.S.; Luyen, B.T.T.; Oanh, H.V.; Kim, Y.H.; Yang, S.Y. The insight of in vitro and in silico studies on cholinesterase inhibitors from the roots of Cimicifuga dahurica (Turcz.) Maxim. J. Enzyme Inhib. Med. Chem., 2018, 33(1), 1174-1180.
[http://dx.doi.org/10.1080/14756366.2018.1491847] [PMID: 30286669]
[99]
Mu, L.H.; Zhao, J.Y.; Liu, P. Anticomplement cycloartane triterpene glycosides from Beesia calthaefolia (maxim.). Phytochem. Lett., 2016, 16, 47-51.
[http://dx.doi.org/10.1016/j.phytol.2016.02.015]
[100]
Nian, Y.; Wang, H-Y.; Zhou, L.; Su, J.; Li, Y.; Qiu, M.H. Cytotoxic cycloartane triterpenes of the traditional chinese medicine “shengma” (Cimicifuga dahurica). Planta Med., 2013, 79(1), 60-69.
[PMID: 23225366]
[101]
Ito, M.; Nakagawa, T.; Higuchi, K.; Sugiyama, S. Dirhodium(ii)-catalyzed ortho C-H amination of sterically congested N, N-dialkylanilines. Org. Biomol. Chem., 2018, 16(38), 6876-6881.
[http://dx.doi.org/10.1039/C8OB01974F] [PMID: 30229789]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy