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Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Review Article

Occurrence and Biological Activities of Phenylpropionyl Iridoids

Author(s): Jiaoxian Cao, Hanchuan Yu, Yingchun Wu* and Xinhong Wang*

Volume 19, Issue 4, 2019

Page: [292 - 309] Pages: 18

DOI: 10.2174/1389557518666181026091449

Price: $65

Abstract

As noteworthy members of the terpenoid family, iridoids are a group of natural compounds that have a cyclopentane ring and hemiacetal structural features. Among them, phenylpropionyl iridoids— widely present in Bignoniaceae, Rubiaceae, Scrophulariaceae, Verbenaceae, and Oleaceae— were discovered and extracted from plants mainly between the 1980s and 2000s. Because of their unique structural features and complex stereo configurations, these compounds exhibit numerous desirable biological activities such as neuroprotective, anti-inflammatory, antimicrobial, and antitumour activities; they have received increasing interest recently. This review summarises progress in research on phenylpropionyl iridoids, including their occurrence and biological activities.

Keywords: Phenylpropionyl iridoids, neuroprotective activity, anti-inflammatory, antitumour, antimicrobial, antioxidant.

Graphical Abstract
[1]
Liu, J.; Liang, J.Y.; Xie, T. Development of iridoids in rencent years. Strait. Pharm. J., 2004, 16, 14-19.
[2]
Dinda, B.; Debnath, S.; Harigaya, Y. Naturally Occurring Iridoids. A Review. Part 1. Chem. Pharm. Bull. , 2007, 55, 159-222.
[3]
Lichti, H.; Von Wartburg, A. Die Struktur des Harpagosids. 2. Mitteilung über Iridoide. Helv. Chim. Acta, 1966, 49(5), 1552-1580.
[4]
Kim, Y.; Park, E.J.; Kim, Y.; Kim, S.; Kim, Y. Neuroprotective constituents from Hedyotis diffusa. J. Nat. Prod., 2001, 64(1), 75-78.
[5]
Kim, S.R.; Lee, K.Y.; Koo, K.A.; Sung, S.H.; Lee, N.G.; Kim, J.; Kim, Y.C. Four new neuroprotective iridoid glycosides from Scrophularia buergeriana roots. J. Nat. Prod., 2002, 65(11), 1696.
[6]
Ding, B.; Ma, W.W.; Dai, Y.; Gao, H.; Yang, Y.; Ye, T.; Zhong, Y.; Yao, X.S. Biologically active iridoids from Hedyotis diffusa. Helv. Chim. Acta, 2011, 93(12), 2488-2494.
[7]
Jeong, E.J.; Lee, K.Y.; Kim, S.H.; Sung, S.H.; Kim, Y.C. Cognitive-enhancing and antioxidant activities of iridoid glycosides from Scrophularia buergeriana in scopolamine-treated mice. Eur. J. Pharmacol., 2008, 588(1), 78-84.
[8]
Lu, J.H.; Pu, X.P.; Tu, G.Z.; Zhao, Y.Y. Iridoid Glycosides from Buddleja lindeyana. J. Chin. Pharm. Sci., 2004, 13(3), 151-154.
[9]
Ouitas, N.A.; Heard, C.M. A novel ex vivo skin model for the assessment of the potential transcutaneous anti-inflammatory effect of topically applied Harpagophytum procumbens extract. Int. J. Pharm., 2009, 376(1-2), 63-68.
[10]
Qi, J.; Chen, J.J.; Cheng, Z.H.; Zhou, J.H.; Yu, B.Y.; Qiu, S.X. Iridoid glycosides from Harpagophytum procumbens D.C. (devil’s claw). Phytochemistry, 2006, 67(13), 1372-1377.
[11]
Ching, F.P.; Falodun, A.; Omogbai, E.K.I.; Okpo, S.O.; Ozolua, R.I.; Iqbal, C.M. Evaluation of analgesic and anti-inflammatory compounds from Stereospermum kunthianum (Bignoniaceae). Int. J. Pharm. Res, 2009, 1(4), 1065-1068.
[12]
Ahmed, B.; Alrehaily, A.J.; Alhowiriny, T.A.; Elsayed, K.A.; Ahmad, M.S. Scropolioside-D2 and harpagoside-B: two new iridoid glycosides from Scrophularia deserti and their antidiabetic and antiinflammatory activity. Biol. Pharm. Bull., 2003, 26(4), 462.
[13]
Cao, J.X.; An, R.; Tang, Y.; Yu, H.C.; Wu, Y.C.; Wang, X.H. Three new iridoid glycosides isolated from the traditional herb Siphonostegia chinensis with NF-κB inhibitory activity. Phytochemistry . Lett., 2017, 22, 261-265.
[14]
Shukla, A.K.; Patra, S.; Dubey, V.K. Iridoid glucosides from Nyctanthes arbortristis result in increased reactive oxygen species and cellular redox homeostasis imbalance in Leishmania parasite. Eur. J. Med. Chem., 2012, 54, 49-58.
[15]
Khan, Z.K.; Manglani, A.; Shukla, P.K.; Puri, A.; Saxena, R.P.; Tandon, J.S. Immunomodulatory effect of plant extracts and iridoid glucosides from Nyctanthes arbortristis against systemic Candidiasis in mice. Pharm. Biol., 1995, 33(4), 297-304.
[16]
Li, M.; Jiang, R.W.; Hon, P.M.; Cheng, L.; Li, L.L.; Zhou, J.R.; Shaw, P.C.; But, P.P.H. Authentication of the anti-tumor herb Baihuasheshecao with bioactive marker compounds and molecular sequences. Food Chem., 2010, 119(3), 1239-1245.
[17]
Shi, J.; Li, C.J.; Yang, J.Z.; Ma, J.; Wang, C.; Tang, J.; Li, Y.; Chen, H.; Zhang, D.M. Hepatoprotective coumarins and secoiridoids from Hydrangea paniculata. Fitoterapia, 2014, 96(96), 138-145.
[18]
Yadav, D.; Masood, N.; Luqman, S.; Brindha, P.; Gupta, M.M. Antioxidant furofuran lignans from Premna integrifolia. Ind. Crops Prod., 2013, 41(1), 397-402.
[19]
Kil, Y.S.; Kim, S.M.; Kang, U.; Chung, H.Y.; Seo, E.K. Peroxynitrite-Scavenging Glycosides from the Stem Bark of Catalpa ovata. J. Nat. Prod., 2017, 80(8), 2240.
[20]
Mishra, V.; Shukla, A.; Pandeti, S.; Barthwal, M.K.; Pandey, H.; Palit, G.; Narender, T. Arbortristoside-A and 7-O-trans-cinnamoyl-6β-hydroxyloganin isolated from Nyctanthes arbortristis possess anti-ulcerogenic and ulcer-healing properties. Phytomedicine, 2013, 20(12), 1055-1063.
[21]
Gupta, P.P.; Srimal, R.C.; Srivastava, M.; Singh, K.L.; Tandon, J.S. Antiallergic activity of arbortristosides from Nyctanthus arbortristis. Pharm. Biol., 1995, 33(1), 70-72.
[22]
Hua, J.; Qi, J.; Yu, B.Y. Iridoid and phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl. and their α-Glucosidase inhibitory activities. Fitoterapia, 2014, 93(3), 67.
[23]
Xu, G.H.; Kim, Y.H.; Chi, S.W.; Choo, S.J.; Ryoo, I.J.; Ahn, J.S.; Yoo, I.D. Evaluation of human neutrophil elastase inhibitory effect of iridoid glycosides from Hedyotis diffusa. Bioorg. Med. Chem. Lett., 2010, 20(2), 513-515.
[24]
Shukla, V.; Yadav, D.; Phulara, S.C.; Gupta, M.M.; Saikia, S.K.; Pandey, R. Longevity-promoting effects of 4-hydroxy-E-globularinin in Caenorhabditis elegans. Free Radic. Biol. Med., 2012, 53(10), 1848-1856.
[25]
Asthana, J.; Yadav, A.K.; Pant, A.; Pandey, S.; Gupta, M.M.; Pandey, R. Specioside ameliorates oxidative stress and promotes longevity in Caenorhabditis elegans. Comp. Biochem. Phys. C, 2015, 169, 25-34.
[26]
Kaewkongpan, C.; Sahakitpichan, P.; Ruchirawat, S.; Kanchanapoom, T. Iridoid and phenylethanoid glycosides from Heterophragma sulfureum. Phytochemistry . Lett., 2015, 12, 277-281.
[27]
Falodun, A.; Qadir, I.M.; Poh, C.F.; Eric, K.I.O.; Choudhary, M.I. Bioactive chemical constituents of Stereospermum kunthianum (Bignoniaceae). Res. J. Phytochem., 2009, 3(2), 35-43.
[28]
Kanchanapoom, T.; Noiarsa, P.; Otsuka, H.; Ruchirawat, S. Lignan, phenolic and iridoid glycosides from Stereospermum cylindricum. Phytochemistry, 2006, 67(5), 516-520.
[29]
Ramsay, K.S.; Wafo, P.; Ali, Z.; Khan, A.; Oluyemisi, O.O.; Marasini, B.P.; Khan, I.A.; Bonaventure, N.T.; Choudhary, M.I. AttaurRahman Chemical constituents of Stereospermum acuminatissimum and their urease and α-chymotrypsin inhibitions. Fitoterapia, 2012, 83(1), 204-208.
[30]
Sampath, K.U.; Tiwari, A.K.; Reddy, S.V.; Aparna, P.; Rao, R. Jaga.; Ali, A. Z.; Rao, J.M., Free-radical-scavenging and xanthine oxidase inhibitory constituents from Stereospermum personatum. J. Nat. Prod., 2005, 68(11), 1615-1621.
[31]
Dal Piaz, F.; Vassallo, A.; Temraz, A.; Cotugno, R.; Belisario, M.A.; Bifulco, G.; Chini, M.G.; Pisano, C.; De Tommasi, N.; Braca, A. A chemical-biological study reveals C9-type iridoids as novel heat shock protein 90 (Hsp90) inhibitors. J. Med. Chem., 2013, 56(4), 1583-1595.
[32]
Compadre, C.M.; Jáuregui, J.F.; Nathan, P.J.; Enríquez, R.G. Isolation of 6-O-(p-coumaroyl)-catalpol from Tabebuia rosea. Planta Med., 1982, 46(1), 42.
[33]
Warashina, T.; Nagatani, Y.; Noro, T. Constituents from the bark of Tabebuia impetiginosa. Phytochemistry, 2004, 65(13), 2003-2011.
[34]
Maksudov, M.S.; Umarov, R.U.; Saatov, Z. Iridoids from Catalpa bignonioides. Chem. Nat. Compd., 1995, 31(5), 632-633.
[35]
Elnaggar, S.A.F.; Doskotch, R. Specioside: A new iridoid glycoside from Catalpa speciosa. J. Nat. Prod., 1980, 43(4), 524-526.
[36]
Rivière, C.; Goossens, L.; Guerardel, Y.; Maes, E.; Garénaux, E.; Pommery, J.; Pommery, N.; Désiré, O.; Lemoine, A.; Telliez, A. Chemotaxonomic interest of iridoids isolated from a Malagasy species: Perichlaena richardii. Biochem. Syst. Ecol., 2011, 39(4-6), 797-825.
[37]
Han, X.H.; Oh, J.H.; Hong, S.S.; Lee, C.; Park, J.I.; Lee, M.K.; Hwang, B.Y.; Lee, M.S. Novel iridoids from the flowers of Campsis grandiflora. Arch. Pharm. Res., 2012, 35(2), 327-332.
[38]
Guiso, M.; Marra, C.; Piccioni, F.; Nicoletti, M. Iridoid and phenylpropanoid glucosides from Tecoma capensis. Phytochemistry, 1997, 45(1), 193-194.
[39]
Alvarez, L.; Núñez, M.; Del, C.P.M.; Villarreal, M.L.; Delgado, G. Chemical and biological study of Astianthus viminalis. Planta Med., 1994, 6(1), 98-98.
[40]
Gouda, Y.G.; Abdel-Baky, A.M.; Darwish, F.M.; Mohamed, K.M.; Kasai, R.; Yamasaki, K. Iridoids from Kigelia pinnata DC. fruits. Phytochemistry, 2003, 63(8), 887.
[41]
Costa, R.; Albergamo, A.; Pellizzeri, V.; Dugo, G. Phytochemical screening by LC-MS and LC-PDA of ethanolic extracts from the fruits of Kigelia africana (Lam.) Benth. Nat. Prod. Res., 2017, 31(12), 1397-1402.
[42]
Iwagawa, T.; Asai, H.; Hase, T.; Sako, S.; Su, R.; Hagiwara, N.; Kim, M. Monoterpenoids from Radermachia sinica. Phytochemistry, 1990, 29(6), 1913-1916.
[43]
Guiso, M. Pondraneoside, A New Iridoid Glucoside From Pondranea ricasoliana. J. Nat. Prod., 1982, 45(4), 462-465.
[44]
Harinantenaina, L.; Kasai, R.; Rakotovao, M.; Yamasaki, K. Iridoid glucosides from a malagasy medicinal Plant, Ophiocolea floribunda (Natural Medicine Note); Natural Medicines, 2002, p. 56.
[45]
Harinantenaina, L.R.R.; Kasai, R.; Rakotovaob, M.; Yamasaki, K. New Iridoid and phenethyl glycosides from Malagasy medicinal plant, Phyllarthron madagascariense. Nat. Med., 2001, 1(1), 187-192.
[46]
Yang, X.D.; Mei, S.X.; Zhao, J.F.; Li, G.P.; Zhang, H.B.; Li, L. A New Iridoid Glucoside from Lagotisyunnanensis. Chinese . Chem. Lett., 2003, 14(9), 936-938.
[47]
Liu, Y.F.; Liang, D.; Luo, H.; Hao, Z.Y.; Wang, Y.; Zhang, C.L.; Zhang, Q.J.; Chen, R.Y.; Yu, D.Q. Hepatoprotective iridoid glycosides from the roots of Rehmannia glutinosa. J. Nat. Prod., 2012, 75(9), 1625-1631.
[48]
Li, X.; Zhou, M.; Shen, P.; Zhang, J.; Chu, C.; Ge, Z.; Yan, J. Chemical constituents from Rehmannia glutinosa. Chin. J. Chin. Mater. Med, 2011, 36(22), 3125-3129.
[49]
Nishimura, H.; Sasaki, H.; Morota, T.; Mitsuhashi, H. Six iridoid glycosides from Rehmannia glutinosa. Phytochemistry. Phytochemistry, 1989, 28(10), 2705-2709.
[50]
Tomassini, L.; Serafini, M.; Foddai, S.; Ventrone, A.; Nicoletti, M. Iridoid glycosides from Alonsoa meridionalis. Nat. Prod. Res., 2014, 28(15), 1187.
[51]
Hussain, H.; Aziz, S.; Miana, G.A.; Ahmad, V.U.; Anwar, S.; Ahmed, I. Minor chemical constituents of Verbascum thapsus. Biochem. Syst. Ecol., 2009, 37(2), 124-126.
[52]
Warashina, T.; Miyase, T.; Ueno, A. Iridoid Glycosides from Verbascum thapsus L. Chem. Pharm. Bull., 1991, 39(12), 3261-3264.
[53]
Klimek, B. Hydroxycinnamoyl ester glycosides and saponins from flowers of Verbascum phlomoides. Phytochemistry, 1996, 43(6), 1281-1284.
[54]
Stavri, M.; Mathew, K.T.; Gibbons, S. Antimicrobial constituents of Scrophularia deserti. Phytochemistry, 2006, 67(14), 1530-1533.
[55]
Li, Y.M.; Jiang, S.H.; Gao, W.Y.; Zhu, D.Y. Iridoid glycosides from Scrophularia ningpoensis. Phytochemistry, 1999, 50(1), 101-104.
[56]
Chen, X.; Liu, Y.H.; Chen, P. Iridoid glycosyl esters from Scrophularia ningpoensis. Nat. Prod. Res., 2007, 21(13), 1187-1190.
[57]
Wu, Q.; Yuan, Q.; Liu, E.H.; Qi, L.W.; Bi, Z.M.; Li, P. Fragmentation study of iridoid glycosides and phenylpropanoid glycosides in Radix Scrophulariae by rapid resolution liquid chromatography with diode‐array detection and electrospray ionization time‐of‐flight mass spectrometry. Biomed. Chromatogr., 2010, 24(8), 808-819.
[58]
Zhu, L.J.; Qiao, C.; Shen, X.Y.; Zhang, X.; Yao, X.S. Iridoid glycosides from the roots of Scrophularia ningpoensis Hemsl. Chin. Chem. Lett., 2014, 25(10), 1354-1356.
[59]
Zhang, L.; Zhu, T.; Qian, F.; Xu, J.; Dorje, G.; Zhao, Z.; Guo, F.; Li, Y. Iridoid glycosides isolated from Scrophularia dentata Royle ex Benth. and their anti-inflammatory activity. Fitoterapia, 2014, 98, 84-90.
[60]
Fernandez, L.; Diaz, A.M.; Ollivier, E.; Faure, R.; Balansard, G. An iridoid diglycoside isolated from Scrophularia scorodonia. Phytochemistry, 1995, 40(5), 1569-1571.
[61]
Fernandez-Matellano, L.; Ollivier, E.; Diaz-Lanza, A.M.; Faure, R.; Balansard, G. Iridoids from Scrophularia scorodonia. Planta Med., 1995, 61(1), 93.
[62]
Belofsky, G.N.; Stermitz, F.R. 10-trans-Cinnamoylmelittoside and Other Iridoids from Castilleja wightii. J. Nat. Prod., 1988, 51(3), 614-616.
[63]
Gousiadou, C.; Kokubun, T.; Gotfredsen, C.H.; Jensen, S.R. Unexpected Secoiridoid Glucosides from Manulea corymbosa. J. Nat. Prod., 2014, 77(3), 589-595.
[64]
Xu, Y.; Xu, Q.; Zhao, W.; Li, W.; Guo, G.; Li, Z.; Ou, W.; Zheng, L.; Bao, Y.; Sun, L. A New Flavonoid Glycoside from Dodartia orientalis and Antitumor Activity Evaluation of Its Constituents. Chem. Nat. Compd., 2016, 5(5), 798-801.
[65]
Li, C.; Liu, Y.; Abdulla, R.; Aisa, H.A.; Suo, Y. Characterization and identification of chemical components in Neopicrorhiza scrphulariiflora roots by liquid chromatography-electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Anal. Methods, 2014, 6(11), 3634-3643.
[66]
Cao, X.; Qiao, J.; Wang, L.; Ye, X.; Zheng, L.; Jiang, N.; Mo, W. Screening of glycoside isomers in P. scrophulariiflora using ionic liquid-based ultrasonic-assisted extraction and ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Rapid Commun. Mass Sp., 2012, 26(7), 740-748.
[67]
Ilieva, E.I.; Handjieva, N.V.; Popov, S.S. Iridoid glucosides from Linaria vulgaris. Phytochemistry, 1992, 31(31), 1040-1041.
[68]
Zhang, H.F.; Zhang, H.Y.; Li, Y.; Guo, X.J. Determination of four components in Hedyotis diffusa oral solution by reversed-phase HPLC. Chin. J. Chin. Mater. Med, 2008, 33(20), 2329.
[69]
Liang, Z.; Jiang, Z.; Ho, H.; Zhao, Z. Comparative analysis of Oldenlandia diffusa and its substitutes by high performance liquid chromatographic fingerprint and mass spectrometric analysis. Planta Med., 2007, 73(14), 1502-1508.
[70]
Otsuka, H.; Yoshimura, K.; Yamasaki, K.; Cantoria, M.C. Isolation of 10-O-acyl iridoid glucosides from a Philippine medicinal plant, Oldenlandia corymbosa L. (Rubiaceae). Chem. Pharm. Bull., 1991, 39(8), 2049-2052.
[71]
Yuan, Q.M.; Yang, H. Zhao, J.; Liang, L.I. One New Iridoid Glycoside from Hedyotis tenelliflora. Chin. Herb. Med., 2011, 3(2), 87-89.
[72]
Ahn, D.; Kim, D.K. Iridoid glycosides from the aerial parts of Galium spurium L. Nat. Prod. Sci., 2012, 18(3), 195-199.
[73]
Wu, Z.J.; Wang, J.H.; Fang, D.M.; Zhang, G.L. Analysis of iridoid glucosides from Paederia scandens using HPLC-ESI-MS/MS. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2013, 924(4), 54-64.
[74]
Suzuki, S.; Endo, K. Studies on the constituents of Paederia scandens Fruits: Isolation and structure determination of paederinin. Ann. Rep. Tohoku Coll. Pharm, 1993, 40, 73-78.
[75]
Ling, S.K.; Tanaka, T.; Kouno, I. Iridoids from Rothmannia macrophylla. J. Nat. Prod., 2001, 64(6), 796-798.
[76]
Raju, B.L.; Lin, S.J.; Hou, W.C.; Lai, Z.Y.; Liu, P.C.; Hsu, F.L. Antioxidant iridoid glucosides from Wendlandia formosana. Nat. Prod. Lett., 2004, 18(4), 357-364.
[77]
Shi, X.J.; Hai-Ning, Y.U.; Zhan, Z.J.; Shan, W.G. Studies on the glycosides constituents from the rhizome of Gardenia jasminoides. J. Zhejiang Univ. Technol, 2010, 38, 142-143.
[78]
Atsuko, I.; Kanako, F.; Sumie, T.; Chika, T.; Takao, T.; Naotaka, N.A.; Chen, C.C. Six Secoiridoid Glucosides from Adina racemosa. J. Nat. Prod., 2003, 66(9), 1212-1216.
[79]
Hui, Y.; Bei, J.; Zhi, N.A.; Yun, P.G.; Han, D.S. Two New Iridoid Glucosides from Clerodendrum serratum. Chin. Chem. Lett., 2000, 11(3), 231-234.
[80]
Chen, J.C.; Zhu, Q.X. Two new terpenoid glucosides from Clerodendrum serratum. Pharm. Die, 2001, 56(3), 270-271.
[81]
Sudo, H.; Ide, T.; Otsuka, H.; Hirata, E.; Takushi, A.; Takeda, Y. Iridoid glucosides with different acyl moieties from globularinin and globularimin from leaves of Premna subscandens. Phytochemistry, 1998, 49(3), 783-786.
[82]
Yadav, D.; Gupta, M.M. Isolation and HPTLC analysis of iridoids in Premna integrifolia, an important ingredient of Ayurvedic drug Dashmool. J. Planar Chromatogr. , 2013, 26(3), 260-266.
[83]
Shaker, K.H.; Elgama, M.H.; Seifert, K. Iridoids from Avicennia marina. Zeitschrift Für Naturforschung C, 2001, 56(11-12), 965.
[84]
Feng, S.X.; Bo, Y.; Min, Z.; Jing, X.; Hai, L.; Xu, W.T. Iridoid glycosides from Callicarpa nudiflora Hook. Nat. Prod. Res., 2017, 31(2), 181-189.
[85]
Zheng, D.K.; Chen, W.K.; Ma, S.C.; Wang, J.; Luo, C.X.; Luo, Y.H. Study on HPLC fingerprint of Callicarpa nudiflora and determination of ten components. Chin. J. Chin. Mater. Med, 2015, 40(9), 1776.
[86]
Wang, Y.M.; Xiao, H.; Liu, J.K.; Wang, F. New iridoid glycosides from the twigs and leaves of Callicarpa formosana var. formosana. J. Asian Nat. Prod. Res., 2010, 12(3), 220-226.
[87]
Ayers, S.; Sneden, A.T. Caudatosides A-F: New iridoid glucosides from Citharexylum caudatum. J. Nat. Prod., 2002, 65(11), 1621-1626.
[88]
Shen, Y.C.; Lin, S.L.; Chein, C.C. Three secoiridoid glucosides from Jasminum lanceolarium. Planta Med., 1997, 62(6), 515-518.
[89]
Ya, C.S.; Shao, L.L.; Chyh, C.C. Three secoiridoid glucosides from Jasminum lanceolarium. Phytochemistry, 1997, 44(5), 891-895.
[90]
Ning, K.Q.; Meng, D.L.; Lou, L.L.; Li, X. Chemical constituents from the Jasminum lanceolarium Roxb. Biochem. Syst. Ecol., 2013, 51, 297-300.
[91]
Shen, Y.C.; Lin, T.T.; Lu, T.Y.; Hung, S.E.; Sheu, J.H. Secoiridoids glycosides from Jasminum amplexicaule. J. Chin. Chem. Soci. Taip., 1999, 46(2), 197-200.
[92]
José, A.P.; José, M.H.; Hermelo, L.; Juan, M.T. Secoiridoid glucosides and iridoids from jasminum odoratissimum. Nat. Prod. Lett., 1999, 13(4), 247-254.
[93]
Lpez, H.; Prez, J.A.; Hernndez, J.M. Secoiridoids from Jasminum odoratissimum. J. Nat. Prod., 1997, 60(12), 1334-1337.
[94]
Inoue, K.; Tanahashi, T.; Inouye, H.; Murai, F.; Tagawa, M. A secoiridoid glucoside of Jasminum humile var. revolutum. Phytochemistry, 1982, 21(2), 359-361.
[95]
Shen, Y.C.; Hsieh, P.W. Secoiridoid glucosides from Jasminum urophyllum. Phytochemistry, 1997, 46(7), 1197-1201.
[96]
Tanahashi, T.; Shimada, A.; Nagakura, N.; Inoue, K.; Ono, M.; Fujita, T.; Chen, C.C. Structure elucidation of six acylated iridoid glucosides from Jasminum hemsleyi. Chem. Pharm. Bull. , 1995, 43(5), 729-733.
[97]
Luo, Y.; Liu, Y.; Qi, H.; Wu, Z.; Zhang, G. Steryl esters and phenylethanol esters from Syringa komarowii. Steroids, 2006, 71(8), 700.
[98]
Deng, R.X.; Hua, Y.; Pu, L.; Yin, W.P.; Wang, X.S.; Zhao, T.Z. Chemical constituents from Syringa pubescens Turcz. Biochem. Syst. Ecol., 2010, 38(4), 813-815.
[99]
Gousiadou, C.; Kokubun, T.; Martins, J.; Gotfredsen, C.H.; Jensen, S.R. Iridoid glucosides in the endemic Picconia azorica (Oleaceae). Phytochemistry, 2015, 115, 171-174.
[100]
Stuppner, H.; Müller, E.P.; Mathuram, V.; Kundu, A.B. Iridoid glycosides from Nyctanthes arbortristis. Phytochemistry, 1993, 32(2), 375-378.
[101]
Kanchanapoom, T.; Noiarsa, P.; Ruchirawat, S.; Kasai, R.; Otsuka, H. Phenylethanoid and iridoid glycosides from the Thai medicinal plant, Barleria strigosa. Chem. Pharm. Bull. , 2004, 52(5), 612.
[102]
Lai, G.F.; Wang, X.Y.; Wang, Y.F.; Cao, J.X.; Luo, S.D.; Ju, P. Diterpenes and Diterpene Glucosides from Phlogacanthus curviflorus. Helv. Chim. Acta, 2009, 92(3), 470-480.
[103]
Xu, C.; Chou, G.X.; Wang, C.H.; Wang, Z.T. Rare noriridoids from the roots of Andrographis paniculata. Phytochemistry, 2012, 77(77), 275-279.
[104]
Kikuchi, T.; Matsuda, S.; Kubo, Y.; Namba, T. New Iridoid Glucosides from Harpagophytum procumbens DC. Chem. Pharm. Bull. , 2008, 31(7), 2296-2301.
[105]
Bae, Y.H.; Cuong, T.D.; Hung, T.M.; Kim, J.A.; Woo, M.H.; Byeon, J.S.; Choi, J.S.; Min, B.S. Cholinesterase inhibitors from the roots of Harpagophytum procumbens. Arch. Pharm. Res., 2014, 37(9), 1124.
[106]
Potterat, O.; Saadou, M.; Hostettmann, K. Iridoid glucosides from Rogeria adenophylla. Planta Med., 1989, 55(07), 630-630.
[107]
Potterat, O.; Saadou, M.; Hostettmann, K. Iridoid glucosides from Rogeria adenophylla. Phytochemistry, 1991, 30(3), 889-892.
[108]
Narukawa, Y.; Shimizu, N.; Takeda, T. Studies on the constituents of Leonotis nepetaefolia. Nat. Med., 2001, 55(2), 79-82.
[109]
Murata, T.; Arai, Y.; Miyase, T.; Yoshizaki, F. An alkaloidal glycoside and other constituents from Leucosceptrum japonicum. J. Nat. Med., 2009, 63(4), 402-407.
[110]
Kirmizibekmez, H.; Ariburnu, E.; Masullo, M.; Festa, M.; Capasso, A.; Yesilada, E.; Piacente, S. Iridoid, phenylethanoid and flavonoid glycosides from Sideritis trojana. Fitoterapia, 2012, 83(1), 130.
[111]
Alipieva, K.I.; Kostadinova, E.P.; Evstatieva, L.N.; Stefova, M.; Bankova, V.S. An iridoid and a flavonoid from Sideritis lanata L. Fitoterapia, 2009, 80(1), 51-53.
[112]
Shi, J.; Li, C.J.; Yang, J.Z.; Yuan, Y.H.; Chen, N.H.; Zhang, D.M. Coumarin glycosides and iridoid glucosides with neuroprotective effects from Hydrangea paniculata. Planta Med., 2012, 78(17), 1844-1850.
[113]
Yamamoto, A.; Nitta, S.; Miyase, T.; Ueno, A.; Wu, L.J. Phenylethanoid and lignan-iridoid complex glycosides from roots of Buddleja davidii. Phytochemistry, 1993, 32(2), 421-425.
[114]
Miyase, T.; Akahori, C.; Kohsaka, H.; Ueno, A. Acylated Iridoid Glycosides from Buddleja japonica HEMSL. Chem. Pharm. Bull. , 2008, 39(11), 2944-2951.
[115]
Li, C.; Zhang, C.; Yao, H. Iridoids from Fountain Butterflybush (Buddleja alternifolia). Chin. .Tradition. Herb.Drug, 1994, 5, 227-228.
[116]
Huang, X.Z.; Wang, Y.H.; Yu, S.S.; Fu, G.M.; Hu, Y.C.; Liu, Y.; Fan, L.H. Iridoid Glycosides and Grayanane Diterpenoids from the Roots of Craibiodendron henryi. J. Nat. Prod., 2005, 68(11), 1646-1650.
[117]
Bai, H.; Hu, L. Study on the Chemical Constituents of Daphniphyllum angustifolium. Helv. Chim. Acta, 2006, 8(5), 884-894.
[118]
Kwak, J.H.; Kim, H.J.; Lee, K.H.; Kang, S.C.; Zee, O.P. Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina. Arch. Pharm. Res., 2009, 32(2), 207-213.
[119]
Jensen, S.R.; Gotfredsen, C.H.; Grayer, R.J. Unusual iridoid glycosides in Veronica sects. Hebe and Labiatoides. Biochem. Syst. Ecol., 2008, 36(3), 207-215.
[120]
Arslanian, R.L.; Anderson, T.; Stermitz, F.R. Iridoid glucosides of Penstemon ambiguus. J. Nat. Prod., 1990, 53(6), 1485-1489.
[121]
Deyama, T.; Kobayashi, H.; Nishibe, S.; Tu, P. Isolation, Structure Elucidation and Bioactivities of Phenylethanoid Glycosides from Cistanche, Forsythia and Plantago Plants. Stud. Nat. Prod. Chem, 2006, 33(5), 645-674.
[122]
Amessis-Ouchemoukh, N.; Abu-Reidah, I.M.; Quirantes-Piné, R.; Rodríguez-Pérez, C.; Madani, K.; Fernández-Gutiérrez, A.; Segura-Carretero, A. Tentative characterisation of iridoids, phenylethanoid glycosides and flavonoid derivatives from Globularia alypum L. (Globulariaceae) leaves by LC-ESI-QTOF-MS. Phytocheml. Analy., 2014, 25(5), 389.
[123]
Es-Safi, N.E.; Khlifi, S.; Kollmann, A.; Kerhoas, L.; El Abbouyi, A.; Ducrot, P-H. Iridoid Glucosides from the Aerial Parts of Globularia alypum L. (Globulariaceae). Chem. Pharm. Bull. , 2006, 54(1), 85-88.
[124]
Chaudhuri, R.K.; Sticher, O. new iridoid glucosides and a lignan diglucoside from Globularia alypum L. Helv. Chim. Acta, 1981, 64(1), 3-15.
[125]
Hasan, K.X.; Bekmez, X.; Hhsan, C.X.; Piacente, S.; Piacente, S.; Pizza, C. Iridoid and phenylethyl glycosides from Globularia sintenisii. Helv. Chim. Acta, 2004, 87(5), 1172-1179.
[126]
Ochi, M.; Matsunami, K.; Otsuka, H.; Takeda, Y. new iridoid glycoside and NO production inhibitory activity of compounds isolated from Russelia equisetiformis. J. Nat. Med., 2012, 66(1), 227-232.
[127]
Pennacchio, M.; Syah, Y.M.; Ghisalberti, E.L.; Alexander, E. Cardioactive iridoid glycosides from Eremophila species. Phytomedicine, 1997, 4(4), 325-330.
[128]
Ren, F.C.; Wang, L.X.; Wang, F.; Li, B.C. Chemical constituents from Scilla scilloides. Chin.Trad. Herb. Drug., 2014, 45(14), 1984-1988.
[129]
Kosuge, K.; Mitsunaga, K.; Koike, K.; Ohmoto, T. Studies on the constituents of Ailanthus integrifolia. Chem. Pharm. Bull., 1994, 42(8), 1669-1671.
[130]
Nie, T.T.; Zhao, H.X.; Bai, H. Chemical Constituents of Pittosporum glabratum. Chin. J. Nat. Med., 2011, 9(3), 180-184.
[131]
Şöhretoğlu, D.; Masullo, M.; Piacente, S.; Kirmizibekmez, H. Iridoids, monoterpenoid glucoindole alkaloids and flavonoids from Vinca major. Biochem. Syst. Ecol., 2013, 49(2), 69-72.
[132]
Mananjarasoa, E.; Ochi, H.; Harinantenaina, L.; Kasai, R.; Yamasaki, K. A new secoiridoid glucoside from a malagasy medicinal plant, Cassinopsis chapieleri. Nat. Med., 2002, 56, 204-207.
[133]
Kuwajima, H.; Hagiwara, S.; Fujino, E.; Takaishi, K.; Tachibana, Y.; Inoue, K. Iridoid glucosides from Curtia tenuifolia. Planta Med., 1996, 62(1), 91-92.
[134]
Bergeron, C.; Marston, A.; Gauthier, R.; Hostettmann, K. Iridoids and secoiridoids from Gentiana linearis. Phytochemistry, 1997, 44(4), 633-637.
[135]
Das, S.; Barua, R.N.; Sharma, R.P.; Baruah, J.N.; Kulanthaivel, P.; Herz, W. Secoiridoids from Exacum tetragonum. Phytochemistry, 1984, 23(4), 908-909.
[136]
Houghton, P.J.; Lian, L.M. Iridoids, iridoid-triterpenoid congeners and lignans from Desfontainia spinosa. Phytochemistry, 1986, 25(8), 1907-1912.
[137]
Ganzera, M.; Orsi, H.; Zidorn, C.; Khan, I.A.; Stuppner, H. Occurrence of grandifloroside-11-methyl ester in Nyssa ogeche (Nyssaceae). Biochem. Syst. Ecol., 2005, 33(3), 327-329.
[138]
Zhao, J.Q.; Wang, Y.M.; Wang, D.; Yang, C.R.; Xu, M.; Zhang, Y.J. Five new sucrose esters from the whole plants of Phyllanthus cochinchinensis. Nat. Prod. Bio, 2013, 3(2), 61-65.

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