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Progress in the Chemistry of Organic Natural Products 106 pp 241–304Cite as

Progress in the Chemistry of Naturally Occurring Coumarins

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Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 106))

Abstract

Coumarins are the largest group of 1-benzopyran derivatives found in plants. The initial member of this group of compounds, coumarin (2H-1-benzopyran-2-one), a fragrant colorless compound, was first isolated from the Tonka bean (Dipteryx odorata, family Fabaceae) in 1820. The name coumarin comes from a French term for the tonka bean, coumarou. Since the discovery of coumarin, several of its derivatives, with umbelliferone (7-hydroxycoumarin) being the most common one, have been reported from various natural sources. The families Apiaceae, Asteraceae, and Rutaceae are the three major plant sources of coumarins.

Generally, these plant secondary metabolites may be classified into simple, simple prenylated, simple geranylated, furano, pyrano, sesquiterpenyl and oligomeric coumarins. Using this standard classification, this chapter aims to present an account on the advances of the chemistry of naturally occurring coumarins, as reported in the literature during the period 2013–2015.

In Sect. 1, the coumarins are introduced and their generic biosynthetic route discussed briefly. In Sect. 2, the largest of the three sections, various classes of natural coumarins are detailed, with their relevant structures and the citation of appropriate references. In a concluding section, it is highlighted that during the last 3 years, more than 400 coumarins have been reported in the literature. Many of these coumarins have been re-isolations of known compounds from known or new sources, most often associated with various biological activities. However, a substantial number of coumarins bearing new skeletons, especially dimers, prenylated furanocoumarins, sesquiterpenyl, and some unusual coumarins were also reported during the period of 2013–2015.

Coumarin chemistry remains one of the major interest areas of phytochemists, especially because of their structural diversity and medicinal properties, along with the wide-ranging bioactivities of these compounds, inclusive of analgesic, anticoagulant anti-HIV, anti-inflammatory, antimicrobial, antineoplastic, antioxidant, and immunomodulatory effects. Despite significant advancements in the extraction, isolation, structure elucidation and bioactivity testing of naturally occurring coumarins, only a marginal advancement has been observed recently in relation to the study of their biosynthesis.

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References

  1. Murray RDH (1978) Naturally occurring plant coumarins. Prog Chem Org Nat Prod 35:199

    CAS  Google Scholar 

  2. Murray RDH (1991) Naturally occurring plant coumarins. Prog Chem Org Nat Prod 59:1

    Google Scholar 

  3. Murray RDH (1997) Naturally occurring plant coumarins. Prog Chem Org Nat Prod 72:121

    Google Scholar 

  4. Murray RDH (2002) Naturally occurring coumarins. Prog Chem Org Nat Prod 83:1

    CAS  Google Scholar 

  5. Sarker SD, Nahar L (2007) Chemistry for pharmacy students: general, organic and natural product chemistry. Wiley, London

    Book  Google Scholar 

  6. Olennikov SN, Kashchenko NI (2014) Componential profile and amylase inhibiting activity of phenolic compounds from Calendula officinalis L. leaves. Scientific World J 2014:1

    Article  CAS  Google Scholar 

  7. Li Y-Y, Di E, Baibado JT, Cheng Y-S, Huang Y-Q, Sun H, Cheung H-Y (2014) Identification of kukoamines as the novel markers for quality assessment of Lycii Cortex. Food Res Int 55:373

    Article  CAS  Google Scholar 

  8. Iyer D, Patil UK (2014) Evaluation of antihyperlipidemic and antitumor activities of isolated coumarins from Salvadora indica. Pharm Biol 52:78

    Article  CAS  Google Scholar 

  9. Li R, Liu S-K, Song W, Wang Y, Li Y-J, Qiao X, Liang H, Ye M (2014) Chemical analysis of the Tibetan herbal medicine Carduus acanthoides by UPLC/DAD/qTOF-MS and simultaneous determination of nine major compounds. Anal Methods 6:7161

    Article  CAS  Google Scholar 

  10. Wang J, Petrova V, S-B W, Zhu M, Kennelly EJ, Long C (2014) Antioxidants from Gerbera piloselloides: an ethnomedicinal plant from southwestern China. Nat Prod Res 28:2072

    Article  CAS  Google Scholar 

  11. Ghasemi S, Habibi Z (2014) A new dihydrofuranocoumarin from Opopanax hispidus (Friv.) Griseb. Nat Prod Res 21:1808

    Google Scholar 

  12. Shah MR, Shamim A, White LS, Bertino MF, Mes MA, Soomo S (2014) The anti-inflammatory properties of Au-scopoletin nanoconjugates. New J Chem 38:5566

    Article  CAS  Google Scholar 

  13. Yin HL, Li JH, Li B, Chen L, Li J, Tian Y, Liu SJ, Zhao YK, Xiao YH, Dong JX (2015) Two new coumarins from the seeds of Solanum indicum. J Asian Nat Prod Res 16:153

    Article  CAS  Google Scholar 

  14. Phakhodee W, Pattarawarapan M, Pongpam P, Laphookhieo S (2014) Naturally occurring prenylated coumarins from Micromelum integerrimum twigs. Phytochem Lett 7:165

    Article  CAS  Google Scholar 

  15. Yan ZW, Liu JP, Lu D, Narlawar R, Groundwater P, Li PY (2014) Two new ceramides from the fruit pulp of Acanthopanax senticosus (Rupr. et Maxim.) Harms. Nat Prod Res 28:144

    Article  CAS  Google Scholar 

  16. Kasaian J, Iranshahy M, Masullo M, Poacente S, Ebrahimi F, Iranshahi M (2014) Sesquiterpene lactones from Ferula oopoda and their cytotoxic properties. J Asian Nat Prod Res 16:248

    Article  CAS  Google Scholar 

  17. Lv H-N, Wang S, Zeng K-W, Li J, Guo X-Y, Ferreira D, Zjawiony JK, Tu P-F, Jiang Y (2015) Anti-inflammatory coumarin and benzocoumarin derivatives from Murraya alata. J Nat Prod 78:279

    Article  CAS  Google Scholar 

  18. Luo J, Zhou W, Cao S, Zhu H, Zhang C, Jin M, Li G (2015) Chemical constituents of Chroogomphus rutilus (Schaeff.) O.K. Mill. Biochem Syst Ecol 61:203

    Article  CAS  Google Scholar 

  19. Yang J-L, Dhodary B, Ha TKQ, Kim J, Kim E, Oh WK (2015) Three new coumarins from Saposhnikovia divaricata and their porcine epidemic diarrhea virus (PEDV) inhibitory activity. Tetrahedron 71:4651

    Article  CAS  Google Scholar 

  20. Chen J-J, Yang C-K, Kuo Y-H, Hwang T-L, Kuo W-L, Lim Y-P, Sung P-J, Chang T-H, Cheng M-J (2015) New coumarin derivatives and other constituents from the stem bark of Zanthoxylum avicennae: effects on neutrophil pro-inflammatory responses. Int J Mol Sci 16:9719

    Article  CAS  Google Scholar 

  21. Bousetla A, Zellagui A, Derouiche K, Rhouati S (2015) Chemical constituents of the roots of Algerian Bunium incrassatum and evaluation of its antimicrobial activity. Arabian J Chem 8:313

    Article  CAS  Google Scholar 

  22. Happi GM, Kouam SF, Yalontsi FM, Zuhlke S, Lamshoft M, Spiteller M (2015) Minor secondary metabolites from the bark of Entandrophragma congoense (Meliaceae). Fitoterapia 102:35

    Article  CAS  Google Scholar 

  23. Li X-N, Tong S-Q, Cheng D-P, Li Q-Y, Yan J-Z (2014) Coumarins from Edgeworthia chrysantha. Molecules 19:2042

    Article  CAS  Google Scholar 

  24. Tatuedom OK, Kouam SF, Yapna DB, Ngadjui BT, Green IR, Choudhary MI, Lantovololona JER, Spiteller M (2014) Spiroalkaloids and coumarins from the stem bark of Pauridiantha callicarpoides. Z Naturforsch B 69:747

    Article  CAS  Google Scholar 

  25. Rajachan OA, Kanokmedhakul S, Nasomjai P, Kanokmedhakul K (2014) Chemical constituents and biological activities from roots of Enkleia siamensis. Nat Prod Res 28:268

    Article  CAS  Google Scholar 

  26. Bashir S, Alam M, Adhikari A, Shrestha RL, Yousuf S, Ahmad B, Parveen S, Aman A, Choudhary MI (2014) New antileishmanial sesquiterpene coumarins from Ferula narthex Boiss. Phytochem Lett 9:46

    Article  CAS  Google Scholar 

  27. Shakeel-ur-Rahman FS, Dangroo NA, Priya D, Banday JA, Sangwan PL, Qurishi MA, Koul S, Saxena AK (2014) Isolation, cytotoxicity evaluation and HPLC-quantification of the chemical constituents from Prangos pabularia. PLoS One 9:e108703

    Article  CAS  Google Scholar 

  28. Huang W-H, Luo W, Wang C-Z, Yuan C-S, Nie M-K, Shi S-Y, Zhou H-H, Ouyang D-S (2014) Phenolic constituents from Oplopanax horridus. China J Chin Mat Med 39:1852

    CAS  Google Scholar 

  29. Kang YF, Liu CM, Kao CL, Chen CY (2014) Antioxidant and anticancer constituents from the leaves of Liriodendron tulipifera. Molecules 19:4234

    Article  CAS  Google Scholar 

  30. Liu JL, Wang XY, Zhang LL, Fang MJ, YL W, Wu Z, Qiu YK (2014) Two-dimensional countercurrent chromatography x high performance liquid chromatography with heart-cutting and stop-and-go techniques for preparative isolation of coumarin derivatives from Peucedanum praeruptorum Dunn. J Chromatogr A 1374:156

    Article  CAS  Google Scholar 

  31. Silva FL, Moreno PRH, Braz R, Tavares JF, Barbosa JM (2014) Chemical constituents of Cardiospermum corindum and their distribution in Sapindaceae. Biochem Syst Ecol 57:137

    Article  CAS  Google Scholar 

  32. Wang ZY, He WJ, Zhou WB, Zeng GZ, Yin ZQ, Zhao SX, Tan NH (2014) Two phenylpropanoids from Micromelum integerrimum. Chin J Nat Med 12:619

    CAS  Google Scholar 

  33. Znati M, Ben Jannet H, Cazaux S, Bouajila J (2014) Chemical composition, biological activities of plant extracts and compounds isolated from Ferula lutea. Molecules 19:2733

    Article  CAS  Google Scholar 

  34. Li B, Zhang X, Wang J, Zhang L, Gao BW, Shi SP, Wang XH, Li J, Tu PH (2014) Simultaneous characterisation of fifty coumarins from the roots of Angelica dahurica by off-line two dimensional high-performance liquid chromatography coupled with electrospray ionisation tandem mass spectrometry. Phytochem Anal 25:229

    Article  CAS  Google Scholar 

  35. Chen SQ, Wang LL, Zhang WQ, Wei YL (2015) Secondary metabolites from the root of Lindera reflexa Hemsl. Fitoterapia 105:222

    Article  CAS  Google Scholar 

  36. Yang XL, Huang L, Li HY, Yang DF, Li ZZ (2015) Two compounds from the plant endophytic fungus Pestalotiopsis versicolor. J Asian Nat Prod Res 17:333

    Article  CAS  Google Scholar 

  37. Wang Y, Liang H, Zhang Q, Cheng W, Sirong Y (2014) Phytochemical and chemotaxonomic study on Ficus tsiangii Merr. ex Corner. Biochem Syst Ecol 57:210

    Article  CAS  Google Scholar 

  38. Chang C-I, Hu W-C, Shen C-P, Hsu B-D, Lin W-Y, Sung P-J, Wang W-H, J-B W, Kuo Y-H (2014) 8-Alkylcoumarins from the fruits of Cnidium monierri protect against hydrogen peroxide induced oxidative stress damage. Int J Mol Sci 15:4608

    Article  CAS  Google Scholar 

  39. Zhao D-D, Zhao Q-S, Liu L, Chen Z-Q, Zeng W-M, Lei H, Zhang Y-L (2014) Compounds from Dryopteris fragrans (L.) Schott with cytotoxic activity. Molecules 19:3345

    Article  CAS  Google Scholar 

  40. Sruyatep T, Chakthong S, Leejae S, Voravuthikunchai SP (2014) Two lignans, one alkaloid, and flavone from the twigs of Feroniella lucida. Tetrahedron 70:1773

    Article  CAS  Google Scholar 

  41. Tran TVA, Malainer IC, Schwaiger S, Atanasov AG, Heiss EH, Dirsch VM, Stuppner H (2014) NF-κB inhibitors from Eurycoma longifolia. J Nat Prod 77:483

    Article  CAS  Google Scholar 

  42. Suthiwong J, Sriphana U, Thongsri Y, Promswan P, Prariyachatigul C, Yenjai C (2014) Coumarinoids from the fruits of Micromelum falcatum. Fitoterapia 94:134

    Article  CAS  Google Scholar 

  43. Lin T-T, Huang Y-Y, Tang G-H, Cheng Z-B, Liu X, Luo H-B, Yin S (2014) Prenylated coumarins: natural phosphodiesterase-5 inhibitors from Toddalia asiatica. J Nat Prod 77:955

    Article  CAS  Google Scholar 

  44. You X-X, Yang K, Wang C-F, Zhang W-J, Wang Y, Han J, Fan L, Du S-S, Geng Z-F, Deng Z-W (2014) Cytotoxic compounds isolated from Murraya tetramera Huang. Molecules 19:13225

    Article  CAS  Google Scholar 

  45. Shi J, Li C-J, Yang J-Z, Ma J, Wang C, Tang J, Li Y, Chen H, Zhang D-M (2014) Hepatoprotective coumarins and secoiridoids from Hydrangea paniculata. Fitoterapia 96:138

    Article  CAS  Google Scholar 

  46. Li W, Zhou W, Shim SH, Kim YH (2014) Chemical constituents of Zanthoxylum schinifolium (Rutaceae). Biochem Syst Ecol 55:60

    Article  CAS  Google Scholar 

  47. Rivere C, Krisa S, Pechamat L, Nassra M, Delaunay J-C, Marchal A, Badoc A, Waffo-Teguo P, Merillon J-M (2014) Polyphenols from the stems of Morus alba and their inhibitory activity against nitric oxide production by lipolysaccharide activated microglia. Phytochemistry 97:253

    Google Scholar 

  48. Mamoon-ur-Rashid, Ali S, Alamzeb M, Igoli J, Clements C, Shah SQ, Ferro VA, Gray AI, Khan MR (2014) Phytochemical and antitrypanosomal investigation of the compounds isolated from Artemisia elegantissima. Pharm Biol 52:983

    Google Scholar 

  49. Zeng YT, Jiang JM, Lao HY, Guo JW, Lun YN, Yang M (2015) Antitumor and apoptotic activities of the chemical constituents from the ethyl acetate extract of Artemisia indica. Mol Med Rep 11:2234

    CAS  Google Scholar 

  50. Erwin NA, Soekamto NH, Altena IV, Syah YM (2014) Waltherione C and cleomiscosin from Melochia umbellata var. degrabrata K. (Malvaceae), biosynthetic and chemotaxonomic significance. Biochem Syst Ecol 55:358

    Article  CAS  Google Scholar 

  51. Yim S-H, Jung D-W, Williams DR, Geckeler KE, Kim KK, Shin BA, Lee I-S, Kim HJ (2015) Antiproliferative effects of β-cyclodextrin inclusion complexes with coumarinolignans from Acer mono. Korean J Pharmacog 46:133

    Google Scholar 

  52. Yu M, Sun A, Zhang Y, Liu R (2014) Purification of coumarins from Cortex Fraxinus by adsorption chromatography. J Chromatogr Sci 52:1033

    Article  CAS  Google Scholar 

  53. Jeong SY, Nguyen PH, Zhao BT, Min BS, Ma ES, Woo MH (2015) Bioactive constituents from the leaves of Zanthoxylum schinifolium. Nat Prod Sci 21:1

    CAS  Google Scholar 

  54. Razavi SM, Janani M (2015) A new ester coumarin from Ferula persica Wild. indigenous to Iran. Nat Prod Res 29:717

    Article  CAS  Google Scholar 

  55. Perez-Vasquez A, Castillejos-Ramirez E, Cristian S, Mata R (2014) Develoment of a UHPLC-PDA method for the simultaneous quantification of 4-phenylcoumarins and chlorogenic acid in Exostema caribaeum stem bark. J Nat Prod 77:516

    Article  CAS  Google Scholar 

  56. Dang BT, Rouger C, Litaudon M, Richomme P, Seraphim D, Derbre S (2015) Identification of minor benzoylated 4-phenylcoumarins from a Mammea neurophylla bark extract. Molecules 20:17735

    Article  CAS  Google Scholar 

  57. Liu W, Wu J, Wang SJ, Kong WS, Qin YH, Yang GY, Chen YK (2014) A new coumarin from roots and stems of flue-cured tobacco and its anti-tobacco mosaic virus activity. Asian J Chem 26:2820

    CAS  Google Scholar 

  58. Tanemossu SAF, Franke K, Arnold N, Schmidt J, Wabo HK, Tane P, Wessjohann LA (2014) Rare biscoumarin derivatives and flavonoids from Hypericum riparium. Phytochemistry 105:171

    Article  CAS  Google Scholar 

  59. He J-W, Qin D-P, Gao H, Kuang R-Q, Yu Y, Liu X-Z, Yao X-S (2014) Two new coumarins from Talaromyces flavus. Molecules 19:20880

    Article  CAS  Google Scholar 

  60. Khan S, Fatima I, Kazmi MH, Malik A, Afza N, Iqbal L, Latif M (2015) Cashmins A and B, potent antioxidant coumarins from Sorbus cashmiriana. Chem Nat Compd 51:626

    Article  CAS  Google Scholar 

  61. Lei L, Xue Y-B, Liu Z, Peng S-S, He Y, Zhang Y, Fang R, Wang J-P, Luo Z-W, Yao G-M, Zhang J-W, Zhang G, Song H-P, Zhang Y-H (2015) Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity. Sci Rep 5:13544

    Article  CAS  Google Scholar 

  62. Faeilla L, Piaz FD, Bader A, Bracca A (2014) Diterpenes and phenolic compounds from Sideritis pullulans. Phytochemistry 106:164

    Article  CAS  Google Scholar 

  63. Li X-B, Li L, Zhu R-X, Chang W-Q, Zhang L-L, Wang X-N, Zhao Z-T, Lou H-X (2015) Tetramic acids and pyridone alkaloids from the endolichenic fungus Tolypocladium cylindrosporum. J Nat Prod 78:2155

    Article  CAS  Google Scholar 

  64. Sribuhom T, Sriphana U, Thongsri Y, Yenjao C (2015) Chemical constituents from the stems of Alyxia schlechteri. Phytochem Lett 11:80

    Article  CAS  Google Scholar 

  65. Lei C, Xu W, Wu J, Wang S, Sun J-Q, Chen Z, Yang G (2015) Coumarins from the roots and stems of Nicotiana tabacum and their anti-tobacco mosaic virus activity. Chem Nat Compd 51:43

    Article  CAS  Google Scholar 

  66. Lopes EV, Dias HB, Torres ZES, Chaves FCM, Siani AC, Pohlit AM (2015) Coumarins, triterpenes and a hemiterpene from Bonamia ferruginea (Choisy) Hallier f. Biochem Syst Ecol 61:67

    Article  CAS  Google Scholar 

  67. Yang XL, Huang L, Li HY, Yang DF, Li ZZ (2015) Two compounds from the plant endophytic fungus Pestalotiopsis versicolor. J Asian Nat Prod Res 17:333

    Article  CAS  Google Scholar 

  68. EA Y, Kim G-S, Jeong SW, Park S, Lee SJ, Kim JH, Lee WS, Bark K-M, Jin JS, Shin SC (2014) Flavonoid profile and biological activity of Korean citrus varieties (II): Pyunkuul (Citrus tangerina Hort. ex Tanaka) and overall contribution of its flavonoids to antioxidant effect. J Funct Foods 6:637

    Article  CAS  Google Scholar 

  69. Shokoohinia Y, Sajjadi SE, Gholamzade S, Fattahi A, Behbahani M (2014) Antiviral and cytotoxic evaluation of coumarins from Prangos ferulacea. Pharm Biol 52:1543

    Google Scholar 

  70. Fujimaki T, Saiki S, Tashiro E, Yamada D, Kitagawa M, Hattori N, Imoto M (2014) Identification of licopyranocoumarin and glycyruril from herbal medicies as neuroprotective compounds for Parkinsons’s disease. PLoS One 9:e100395

    Article  Google Scholar 

  71. Daud S-B, Ee GCL, Malek EA, Teh SS, See I (2014) A new coumarin from Calophyllum hosei. Nat Prod Res 28:1534

    Article  CAS  Google Scholar 

  72. Popova M, Stoyanova A, Valyovska-Popova N, Bankova V, Peev D (2014) A new coumarin and total phenolic and flavonoids content of Bulgarian celeriac. Bulg Chem Commun 46:88

    Google Scholar 

  73. Negi N, Abou-Dough AM, Kurosawa M, Kitaji Y, Saito K, Ochi A, Ushijima K, Kusakabe E, Kitaguchi Y, JGJ Y (2015) Coumarins from Murraya exotica collected in Egypt. Nat Prod Commun 10:617

    Google Scholar 

  74. Adianti M, Aoki C, Komoto M, Deng L, Shoji I, Wahyuni TS, Lusida MI, Soetjipto A, Fuchino H, Kawahara N (2014) Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. Microbiol Immunol 58:180

    Article  CAS  Google Scholar 

  75. Shi L-S, Kuo S-C, Sun H-D, Morris-Natschke SL, Lee K-H, Wu R-S (2014) Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria. Bioorg Med Chem 22:1889

    Article  CAS  Google Scholar 

  76. Cuong NM, Khanh PN, Duc HV, Huong TT, Tai BH, Binh NQ, Durante M, Fusi F (2014) Vasorelaxing activity of two coumarins from Murraya paniculata leaves. Biol Pharm Bull 37:694

    Article  CAS  Google Scholar 

  77. Watanabe A, Kumagai M, Mishima T, Ito J, Otoki Y, Harada T, Kato T, Yoshida M, Suzuki M, Yoshida I, Fujita K, Watai M, Nakagawa K, Miyazawa T (2015) Toddaculin, isolated from Toddalia asiatica (L.) Lam., inhibited osteoclastogenesis in RAW 264 cells and enhanced osteoblastogenesis in MC3T3-E1 cells. PLoS One 10:e127158

    Google Scholar 

  78. Lee T-H, Chen Y-C, Hwang T-L, Shu C-W, Sung P-J, Lim Y-P, Kuo W-L, Chen J-J (2014) New coumarins and anti-inflammatory constituents from the fruits of Cnidium monnieri. Int J Mol Sci 15:9566

    Article  CAS  Google Scholar 

  79. Shen DY, Chan YY, Hwang TL, Juang SH, Huang SC, Kuo PC, Thang TD, Lee EJ, Damu AG, Wu TS (2014) Constituents of the roots of Clausena lansium and their potential anti-inflammatory activity. J Nat Prod 77:1215

    Article  CAS  Google Scholar 

  80. Auranwiwat C, Laphookhieo S, Trisuwan K, Pyne SG, Ritthiwigrom T (2014) Carbazole alkaloids and coumarins from the roots of Clausena guillauminii. Phytochem Lett 8:113

    Article  CAS  Google Scholar 

  81. Kouloura E, Danika E, Kim S, Hoerle M, Cuendet M, Halabalaki M, Skaltsounis LA (2014) Rapid identification of coumarins from Micromelum falcatum by UPLC-HRMS/MS and targeted isolation of three new derivatives. Molecules 19:15042

    Article  CAS  Google Scholar 

  82. Watanabe A, Kato T, Ito Y, Yoshida I, Harada T, Mishima T, Fujita K, Watai M, Nakagawa K, Miyazawa T (2014) Aculeatin, a coumarin derived from Toddalia asiatica (L.) Lam., enhances differentiation and lipolysis of 3T3-L1 adipocytes. Biochem Biophys Res Commun 452:787

    Article  CAS  Google Scholar 

  83. Rammohan A, Munikishore R, Gunasekar D, Deville A, Bodo B (2015) A new di-C-prenylated coumarin from Sophora interrupta. Nat Prod Res 29:82

    Article  CAS  Google Scholar 

  84. Magadula JJ, Masimba PJ, Tarimo RB, Msengwa Z, Mbwambo ZH, Heydenreich M, Breard D, Richomme P (2014) Mammaea-type coumarins from Mammaea usambarensis Verdc. Biochem Syst Ecol 56:65

    Article  CAS  Google Scholar 

  85. Dang BT, Guitton Y, Freuze I, Grovel O, Litaudon M, Derbre S, Seraphin D, Derbre S (2015) Dereplication of Mammea neurophylla metabolites to isolate original 4-phenylcoumarins. Phytochem Lett 11:61

    Article  CAS  Google Scholar 

  86. Deng H-D, Mei W-L, Guo Z-K, Liu S, Zuo W-J, Dong W-H, Li S-P, Dai H-F (2014) Monoterpenyl coumarins from the peels of Clausena lansium. Planta Med 80:955

    Article  CAS  Google Scholar 

  87. Rocha MRE, de Souza JJ, Barcellos LT, Sant’Anna CMR, Braz-Filho R, Vieira IJC (2014) A novel 3,9-(1,2,3-trioxocine)-type steroid of Rauia nodosa (Rutaceae). Molecules 19:14637

    Article  CAS  Google Scholar 

  88. Adhami H-R, Fitz V, Lubich A, Kaehlig H, Zehl M, Krenn L (2014) Acetylcholinesterase inhibitors from galbanum, the oleogum resin of Ferula gummosa Boiss. Phytochem Lett 10:lxxxii

    Article  CAS  Google Scholar 

  89. Nhiem NX, Yen HT, Kiem PV, Minh CV, Tai BH, Anh HLT, Park S, Kim N, Kim SH (2015) 1H and 13C NMR assignments of tricanguinas A and B, coumarin monoterpenes from Trichosanthes anguina L. Magn Reson Chem 53:178

    Article  CAS  Google Scholar 

  90. Lee SE, Lee EK, Chun CS, Lee K-H, Jun M-Y, Sook H (2014) Psoralea corylifolia L. seed extract ameliorates streptozotocin-induced diabetes in mice by inhibition of oxidative stress. Oxid Med Cell Longev 2014:897296

    Google Scholar 

  91. Walasek M, Grzegorczyk A, Malm A, Skalicka-Wozniak K (2015) Bioactivity-guided isolation of antimicrobial coumarins from Heracleum mantegazzianum Sommier & Levier (Apiaceae) fruits by high-performance counter-current chromatography. Food Chem 186:133

    Article  CAS  Google Scholar 

  92. Gao Y, Liu Y, Wang ZG, Zhang HL (2014) Chemical constituents of Heracleum dissectum and their cytotoxic activity. Phytochem Lett 10:276

    Article  CAS  Google Scholar 

  93. Skalicka-Wozniak K, Zagaia M, Glowniak K, Liszczki JJ (2014) Purification and anticonvulsant activity of xanthotoxin (8-methoxypsoralen). Cent Eur J Biol 9:43

    Google Scholar 

  94. He F, Wang M, Gao M, Zhao M, Bai Y, Zhao C (2014) Chemical composition and biological activities of Gerbera anandria. Molecules 19:4046

    Article  CAS  Google Scholar 

  95. Song P-P, Ly Y, Xu Z-L, Wang Q, Wang N-H (2014) Chemical constituents of Angelica nitida roots. J Chin Med Mat 37:55

    CAS  Google Scholar 

  96. Liu H, Li F, Li C-J, Yang J-Z, Li L, Chen N-H, Zhang D-M (2014) Bioactive furanocoumarins from stems of Clausena lansium. Phytochemistry 107:141

    Article  CAS  Google Scholar 

  97. Deng G-G, Wei W, Yang X-W, Zhang Y-B, Xu W, Gong N-B, Lu Y, Wang F-F (2015) New coumarins from the roots of Angelica dahurica var. formosana cv. Chianbaixhi and their inhibition on NO production in LPS-activated RAW 264.7 cells. Fitoterapia 101:194

    Article  CAS  Google Scholar 

  98. Garcia-Beltran O, Areche C, Cassels BK, Suarez LEC (2014) Coumarins isolated from Esenbeckia alata (Rutaceae). Biochem Syst Ecol 52:38

    Article  CAS  Google Scholar 

  99. Wanchuk P, Pyne SG, Keller PA, Taweechotipatr M, Kamchonwongpaisam S (2014) Phenylpropanoids and furanocoumarins as antibacterial and antimalarial constituents of the Bhutanese medicinal plant Pleurospermum amabile. Nat Prod Commun 9:957

    Google Scholar 

  100. Znati M, Ben Jannet H, Cazaux S, Souchard JP, Skhiri FH, Bouajila J (2014) Antioxidant, 5-lipoxygenase inhibitory and cytotoxic activities of compounds isolated from the Ferula lutea flowers. Molecules 19:16959

    Article  CAS  Google Scholar 

  101. Razavi SM, Ravansalar A, Mirinejad S (2015) The investigation on phytochemicals from Ferulago angulata (Schlecht) Boiss. indigenous to central parts of Iran. Nat Prod Res 29:2037

    Article  CAS  Google Scholar 

  102. Jiang HY, Zhang WJ, You CX, Yang K, Fan L, Feng JB, Chen J, Yang YJ, Wang CF, Deng ZW, Yin H-B, Du S-S (2014) Two new cytotoxic constituents from Clausena lansium (Lour.) Skeels. Phytochem Lett 9:92

    Article  CAS  Google Scholar 

  103. Xu XY, Xie HH, Wei XY (2014) Jasmonoid glucosides, sesquiterpenes and coumarins from the fruit of Clausena lansium. LWT-Food Sci Technol 59:65

    Article  CAS  Google Scholar 

  104. Severino VGP, de Freitas SDL, Braga PAC, Forim MR, da Silva MFGF, Fernandes JB, Vieira PC, Venacio T (2014) New limonoids from Hortia oreadica and unexpected coumarin from H. superba using chromatography over cleaning Sephadex with sodium hypochlorite. Molecules 19:1203

    Article  CAS  Google Scholar 

  105. Severino VGP, Monteiro AF, da Silva MFDF, Luxarini R, Martins CHG (2015) Chemical study of Hortia superba (Rutaceae) and investigation of the antimyxobacterial activity of crude extracts and constituents isolated from Hortia species. Quim Nova 38:42

    CAS  Google Scholar 

  106. Hu F, Wang LF, Zhou XM, Luo K, Bai LY (2015) Two coumarins with safer activity from Rhizoma et Radix Notopterygii. Weed Technol 29:161

    Article  Google Scholar 

  107. Pavlovic I, Krunic A, Nikolic D, Radenkovic M, Brankovic S, Niketic M, Petrovic S (2014) Chloroform extract of underground parts of Ferula heuffelii: secondary metabolites and spasmolytic activity. Chem Biodiversity 11:1417

    Article  CAS  Google Scholar 

  108. Kim AH, Lee JI, Kong C-S, Choe JC, Oh K-S, Seo Y (2014) Antioxidant activity of dihydrofuranocoumarins from Corydalis heterocarpa. Biotechnol Bioprocess Eng 19:771

    Article  CAS  Google Scholar 

  109. Wahyuni TS, Widyawaruyanti A, Lusida MI, Fuad A, Soetjipto, Fuchino H, Kawahara N, Hayashi Y, Aoki C, Hotta H (2014) Inhibition of hepatitis C virus replication by chalepin and pseudane IX isolated from Ruta angustifolia leaves. Fitoterapia 99:276

    Google Scholar 

  110. Guo T, Tang XF, Zhang JB, Wei JQ, Wang Y, Li YH, Zhang Z (2014) Chemical constituents from the root and stem of Zanthoxylum avicennae. In: Materials, machines and development of technologies for industrial production, Vol 618. Trans Tech Zurich, p 428

    Google Scholar 

  111. Ramasamy D, Saraswathy A (2014) Vitiquinolone – a quinolone alkaloid from Hibiscus vitifolius Linn. Food Chem 145:970

    Article  CAS  Google Scholar 

  112. Bin Zakaria M, Vijayasekaran A, Ilham Z, Muhammad NA (2014) Anti-inflammatory activity of Calophyllum inophyllum fruit extracts. Procedia Chem 13:218

    Article  CAS  Google Scholar 

  113. Bai G, Xu J, Cao XL, Pei HR (2014) Preparative separation of luvangetin from Zanthoxylum ailanthoides Sieb. & Zucc. by centrifugal partition chromatography. J Liq Chromatogr Relat Technol 37:1819

    Article  CAS  Google Scholar 

  114. Song YL, Jing WH, Chen YG, Yuan YF, Yan R, Wang YT (2014) H-1 nuclear magnetic resonance based-metabolomic characterisation of Peucedani Radix and simultaneous determination of praeruptorin A and praeruptorin B. J Pharm Biomed Anal 93:86

    Article  CAS  Google Scholar 

  115. Nugara RN, Inafuku M, Takara K, Iwasaki H, Oku H (2014) Pteryxin: a coumarin in Peucedanum japonicum Thunb. leaves exerts antiobesity activity through modulation of adipogenic gene network. Nutrition 30:1177

    Article  CAS  Google Scholar 

  116. Lee JW, Lee C, Jin Q, Yeon TE, Lee D, Kim S-Y, Han SB, Hong JT, Lee MK, Hwang BY (2014) Pyranocoumarins from Glenhia littoralis inhibit the LPS-induced NO production in macrophage RAW 264.7 cells. Bioorg Med Chem Lett 24:2717

    Article  CAS  Google Scholar 

  117. Ghannadi A, Fattahian K, Shokoohinia Y, Behbahani M, Shahnoush A (2014) Anti-viral evaluation of sesquiterpene coumarins from Ferula assa-foetida against HSV-1. Iran J Pharm Res 13:523

    CAS  Google Scholar 

  118. Iranshahi M, Barthomeuf C, Bayet-Robert M, Chollet P, Davoodi D, Piacente S, Rezaee R, Aahebkar A (2014) Drimane-type sesquiterpene coumarins from Ferula gummosa fruits enhance doxorubicin uptake in doxorubicin-resistant human breast cancer cell line. J Tradit Complement Med 4:118

    Article  Google Scholar 

  119. Li G, Li X, Li C, Zhang L, Shen L, Zhu J, Wang J, Si J (2015) Sesquiterpene coumarins from seeds of Ferula sinkiangensis. Fitoterapia 103:222

    Article  CAS  Google Scholar 

  120. Dastan D, Salehi P, Ghanati F, Gohari AR (2014) Phytotoxicity and cytotoxicity of disesquiterpene and sesquiterpene coumarins from Ferula pseudalliacea. Ind Crops Prod 55:43

    Article  CAS  Google Scholar 

  121. Dastan D, Salehi P, Gohari AR, Ebrahami SN, Aliahmadi A, Hamburger M (2014) Bioactive sesquiterpene coumarins from Ferula pseudalliacea. Planta Med 80:1118

    Article  CAS  Google Scholar 

  122. Ghanem H, Haba H, Marcourt L, Benkhaled M, Wolfender JL (2014) Microphynolides A and B, new spiro-γ-lactone glycosides from Thymelaea microphylla. Nat Prod Res 28:1732

    Article  CAS  Google Scholar 

  123. Kerbab K, Mekhelfi T, Zaiter L, Benayache S, Benayache F, Picerno P, Mencherini T, Sansone F, Aquino RP, Rastrelli L (2015) Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. et Dur. Nat Prod Res 29:671

    Article  CAS  Google Scholar 

  124. Li Q, Gao W, Cao J, Bi X, Chen C, Zhang X, Xia X, Zhao Y (2014) New cytotoxic compounds from flowers of Lawsonia inermis L. Fitoterapia 94:148

    Article  CAS  Google Scholar 

  125. Yang WQ, Song YL, Zhu ZX, Su C, Zhang X, Wang J, Shi SP, Tu PF (2015) Anti-inflammatory dimeric furanocoumarins from the roots of Angelica dahurica. Fitoterapia 105:187

    Article  CAS  Google Scholar 

  126. Yang JH, Liu WY, Li SC, Ye HY, Tang H, Chen LJ, Peng AH (2014) Coumarinolignans isolated from the seeds of Brucea javanica. Helv Chim Acta 97:278

    Article  CAS  Google Scholar 

  127. Donfack ARN, Tala MF, Wabo HK, Jerz G, Zeng GZ, Winterhalter P, Tan NH, Tane P (2014) Two new anthraquinone dimers from the stem bark of Pentas schimperi (Rubiaceae). Phytochem Lett 8:55

    Article  CAS  Google Scholar 

  128. Su W, Zhao JP, Yang M, Yan HW, Pang T, Chen SH, Huang HY, Zhang SH, Ma XC, Guo DA (2015) A coumarin lignanoid from the stems of Kadsura heteroclita. Bioorg Med Chem Lett 25:1506

    Article  CAS  Google Scholar 

  129. Xu B, Liu S, Fan X-D, Deng L-Q, Ma W-H, Chen M (2015) Two new coumarin glycosides from Herpetospermum caudigerum. J Asian Nat Prod Res 17:738

    Article  CAS  Google Scholar 

  130. Xu W-H, Shen Y-H, Liang Q, Zhao P (2015) New coumarin derivative from Euphorbia wallichii. Nat Prod Res 29:1860

    Article  CAS  Google Scholar 

  131. Liu B-Y, Zhang C, Zeng K-W, Li J, Guo X-Y, Zhao M-B, Tu P-F, Jiang Y (2015) Exotines A and B, two heterodimers of isopentenyl-substituted indole and coumarin derivatives from Murraya exotica. Org Lett 17:4380

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Medicinal Chemistry and Natural Products Research Group, School of Pharmacy and Biomolecular Sciences, Faculty of Science, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK

    Satyajit D. Sarker & Lutfun Nahar

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  1. Satyajit D. Sarker
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  2. Lutfun Nahar
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Correspondence to Satyajit D. Sarker .

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Editors and Affiliations

  1. Division of Medicinal Chemistry & Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, USA

    A. Douglas Kinghorn

  2. Institute of Organic Chemistry, Johannes Kepler University Linz, Linz, Austria

    Heinz Falk

  3. Research Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, London, United Kingdom

    Simon Gibbons

  4. Graduate School of Pharmaceutical Science, Hokkaido University, Sapporo, Japan

    Jun'ichi Kobayashi

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Sarker, S.D., Nahar, L. (2017). Progress in the Chemistry of Naturally Occurring Coumarins. In: Kinghorn, A., Falk, H., Gibbons, S., Kobayashi, J. (eds) Progress in the Chemistry of Organic Natural Products 106. Progress in the Chemistry of Organic Natural Products, vol 106. Springer, Cham. https://doi.org/10.1007/978-3-319-59542-9_3

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