Figures (5)  Tables (9)

    • Figure 1. 

      The chemical composition of Euodia rutaecarpa is diverse and includes alkaloids, limonoids, flavonoids, and volatile oils. The major bioactive compounds are: indole quinazolinone alkaloids, quinolone alkaloids, and limonoids.

    • Figure 2. 

      Skeleton types of quinazoline alkaloids in Euodia plants.

    • Figure 3. 

      The skeleton types of quinolone alkaloids in Euodia plants.

    • Figure 4. 

      Pharmacological effects of Euodia rutaecarpa: cardioprotective activity, neuroprotective activity, reproductive system activity, anti-tumor effect, insecticide activity, anti-obesity activity, antioxidant activity, digestive system activity, anti-inflammatory effect.

    • Figure 5. 

      Anti-tumor effect of E. rutaecarpa.

    • No. Indole quinazoline alkaloids Molecular formula Relative molecular mass Structure type Ref.
      1 Evodiamine (EVO) C19H17N3O 303 I [20−25]
      2 Hydroxyevodiamine C19H17N3O2 319 I [26]
      3 13β-acetongl hydroxyl evodiamine C22H21N3O2 359 I [27]
      4 Carboxyevodiamine C20H17N3O3 347 I [28]
      5 13,14-dihydrorutaecarpine C18H15N3O 289 I [29]
      6 14-N-formyldihydrorutaecarpine C19H15N3O2 317 I [22,23]
      7 13β-hydroxymethylevodiamine C20H19N3O2 333 I [30]
      8 Rutaecarpine (RUT) C18H13N3O 287 I [21−25]
      9 Hortiacine C19H15N3O2 317 I [31]
      10 1-hydroxyrutaecarpine C18H13N3O2 303 I [32]
      11 3-hydroxyrutaecarpine C18H13N3O2 303 I [29]
      12 7β-hydroxyrutaecarpine C18H13N3O2 303 I [22,23,25,33,34]
      13 10-hydroxyrutaecarpine C18H13N3O2 303 I [35]
      14 (7R,8S)-7,8-hydroxyrutaecarpine C18H13N3O3 319 I [32]
      15 (7R,8S)-7-hydroxy-8-methoxy-rutaecarpine C19H15N3O3 333 I [32]
      16 (7R,8S)-7-hydroxy-8-ethoxy-rutaecarpine C20H17N3O3 347 I [32]
      17 N13-methyl rutaecarpine C19H15N3O 301 I [36]
      18 1-O-β-D-glucopyranosylrutaecarpine C24H23N3O7 465 I [37]
      19 Rutaecarpine-2-O-β-D-glucopyranoside C24H23N3O7 465 I [37]
      20 Rutaecarpine-10-O-β-D-glucopyranoside C24H23N3O7 465 I [38]
      21 Rutaecarpine-10-O-β-D-rutinoside C30H33N3O11 611 I [38]
      22 13-methyl-13H-indolo [2',3':3,4] pyrido[2,1b] quinazolin-5-one C19H13N3O 299 I [39]
      23 7,8-dehydrorutaecarpine C18H11N3O 285 I [30]
      24 Pseudorutaecarpine C18H13N3O 287 I [32]
      25 Dehydroevodiamine C19H15N3O 301 I [22,23,40]
      26 Hortiamine C20H17N3O2 331 I [41]
      27 Dehydroevodiamine chloride C19H16N3OCl 337 I [31]
      28 Evodianinine C19H13N3O 299 I [20]
      29 Wuzhuyurutine A C17H11N3O2 289 I [36]
      30 Evodiagenine C19H13N3O 299 I [42]
      31 Evodiaxinine C20H15N3O 313 I [20,43]
      32 (+) evodiakine C19H17N3O3 335 I [44]
      33 (−) evodiakine C19H17N3O3 335 I [44]
      34 Dievodiamine C38H30N6O2 602 I, II [42]
      35 Wuchuyuamide I C19H17N3O4 351 II [21,22,25,31]
      36 Wuchuyuamide II C19H17N3O3 335 II [45]
      37 Evollionines B C20H19N3O5 381 II [46]
      38 Goshuyuamide-II C19H17N3O2 319 II [25,47]
      39 13-hydroxymethyl goshuyuamide-II C20H19N3O3 349 II [48]
      40 10-methoxygoshuyuamide-II C20H19N3O3 349 II [29]
      41 Wuzhuyurutine C C18H13N3O3 319 II [30]
      42 Wuzhuyurutine D C17H11N3O3 305 II [30]
      43 (s)-7-hydroxysecorutaecarpine C18H15N3O3 321 II [25,37]
      44 Wuzhuyurutine B C17H11N3O3 305 II [30]
      45 Bouchardatine C17H11N3O2 289 II [30]
      46 Evodiamide A C20H19N3O5 381 II [40]
      47 Evodiamide B C19H16N4O2 332 II [40]
      48 Evodiamide C C37H32N6O6 656 II, IV [40]
      49 Goshuyuamide-I C19H19N3O 305 III [23,25,47]
      50 Rhetsinine C19H17N3O2 319 III [49]
      51 Evollionines A C19H15N3O2 317 III [46]
      52 Evodiamide C19H21N3O 307 IV [23,27]
      53 Dimethyl evodiamide C18H19N3O 293 IV [47]
      54 Nb-demethylevodiamide C18H19N3O 293 IV [50]
      55 Wuchuyuamide III C18H17N3O3 323 V [40,51]
      56 Wuchuyuamide IV C19H17N3O4 351 V [51]
      57 Wuchuyuamide V C20H19N3O5 381 V [21]
      58 Evodamide A C19H15N3O2 317 VI [29]

      Table 1. 

      Quinazoline alkaloids isolated from Euodia plants.

    • No. Quinolone alkaloids Molecular formula Relative molecular mass Structure type Ref.
      1 2-ethyl-1-methyl-4(1H)-quinolone C12H13NO 187 I [52]
      2 Quinolone A C14H15NO3 245 I [53]
      3 1-methyl-2-pentyl-4(1H)-quinolone C15H19NO 229 I [52]
      4 Methyl 5-(1,4-dihydro-1-methyl-4-oxoquinolin-2-yl) pentanoate C16H19NO3 273 I [46]
      5 1-methyl-2-heptyl-4(1H)-quinolone C17H23NO 257 I [52]
      6 1-methyl-2-octyl-4(1H)-quinolone C18H25NO 271 I [52]
      7 1-methyl-2-nonyl-4(1H)-quinolone C19H27NO 285 I [25,52]
      8 1-methyl-2-[(Z)-4-nonenyl]-4(1H)-quinolone C19H25NO 283 I [54]
      9 1-methyl-2-decyl-4(1H)-quinolone C20H29NO 299 I [52]
      10 1-methyl-2-undecyl-4(1H)-quinolone C21H31NO 313 I [25,52]
      11 1-methyl-2-[(E)-1-undecenyl]-4(1H)-quinolone C21H29NO 311 I [54]
      12 1-methyl-2-[(Z)-5-undecenyl]-4(1H)-quinolone C21H29NO 311 I [30]
      13 1-methyl-2-[(Z)-6-undecenyl]-4(1H)-quinolone C21H29NO 311 I [30]
      14 1-methyl-2-[6-carbonyl-(E)-4-undecenyl]-4(1H)-quinolone C21H27NO2 325 I [30]
      15 1-methyl-2-[7-carbonyl-(E)-5-undecenyl]-4(1H)-quinolone C21H27NO2 325 I [54]
      16 1-methyl-2-[(1E,5Z)-1,5-undecadienyl]-4(1H)-quinolone C21H27NO 309 I [54]
      17 1-methyl-2-[(Z)-1-undecenyl]-4(1H)-quinolone C21H29NO 311 I [55]
      18 1-methyl-2-[6-carbonyl-(E)-7-undecenyl]-4(1H)-quinolone C21H27NO2 325 I [54]
      19 1-methyl-2-dodecyl-4(1H)-quinolone C22H33NO 327 I [25,52]
      20 1-methyl-2-[(Z)-5’-dodecenyl]-4(1H)-quinolone C22H31NO 311 I [52]
      21 1-methyl-2-tridecyl-4(1H)-quinolone or Dihydroevocarpine C23H35NO 341 I [52]
      22 Evocarpine C23H33NO 339 I [56].
      23 1-methyl-2-[(Z)-4-tridecenyl]-4(1H)-quinolone C23H33NO 339 I [57]
      24 1-methyl-2-[(Z)-7-tridecenyl]-4(1H)-quinolone C23H33NO 339 I [30]
      25 1-methyl-2-[(Z)-8-tridecenyl]-4(1H)-quinolone C23H33NO 339 I [30]
      26 1-methyl-2-[12-tridecenyl]-4(1H)-quinolone C23H33NO 339 I [58]
      27 1-methyl-2-[(4Z,7Z)-4,7-tridecadienyl]-4(1H)-quinolone C23H31NO 337 I [54]
      28 1-methyl-2-[6-carbonyl-(E)-7-tridecenyl]-4(1H)-quinolone C23H31NO2 353 I [30]
      29 1-methyl-2-[7-carbonyl-(E)-8-tridecenyl]-4(1H)-quinolone (correct)
      1-methyl-2-[7-carbonyl (E)-9-tridecenyl]-4(1H)-quinolone (reference)      		 C23H31NO2 353 I [30]
      30 1-methyl-2-[8-carbonyl-(E)-9-tridecenyl]-4(1H)-quinolone C23H31NO2 353 I [30]
      31 1-methyl-2-[9-carbonyl-(E)-7-tridecenyl]-4(1H)-quinolone C23H31NO2 353 I [52]
      32 1-methyl-2-[7-hydroxy-(E)-8-tridecenyl]-4(1H)-quinolone (correct)
      1-methyl-2-[7-hydroxy-(E)-9-tridecenyl]-4(1H)-quinolone (reference)      		 C23H33NO2 355 I [54]
      33 1-methyl-3-[(7E,9E,12Z)-7,9,12-pentadecadienyl]-4(1H)-quinolone C25H33NO 363 I [59]
      34 1-methyl-3-[(7E,9E,11E)-7,9,11-Pentadecadienyl]-4(1H)-quinolone C25H33NO 363 I [59]
      35 1-methyl-2-(13-hydroxy-tridecenyl)-4(1H)-quinolone C23H35NO2 357 I [30]
      36 1-methyl-2-tetradecyl-4(1H)-quinolone C24H37NO 355 I [52]
      37 1-methyl-2-[13-tetradecenyl]-4(1H)-quinolone C24H35NO 353 I [58]
      38 1-methyl-2-pentadecyl-4(1H)-quinolone C25H39NO 369 I [52,60]
      39 1-methyl-2-[(Z)-5-pentadecenyl]-4(1H)-quinolone C25H37NO 367 I [52]
      40 1-methyl-2-[(Z)-6-pentadecenyl]-4(1H)-quinolone C25H37NO 367 I [54]
      41 1-methyl-2-[(Z)-9-pentadecenyl]-4(1H)-quinolone C25H37NO 367 I [56]
      42 1-methyl-2-[(Z)-10-pentadecenyl]-4(1H)-quinolone C25H37NO 367 I [56]
      43 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone C25H35NO 365 I [30,39]
      44 1-methyl-2-[12-hydroxy-tridecyl]-4(1H)-quinolone C25H35NO2 381 I [58]
      45 1-methyl-2-[(6Z,9Z,12Z)-6,9,12-pentadecatriene]-4(1H)-quinolone C25H33NO 363 I [55]
      46 1-methyl-2-(15-hydroxy-pentadecenyl)-4(1H)-quinolone C25H39NO2 385 I [30]
      47 1-methyl-2-hexadecyl-4(1H)-quinolone C26H41NO 383 I [58].
      48 2-nonyl-4(1H)-quinolone C18H25NO 271 I [61]
      49 2-undecyl-4(1H)-quinolone C20H29NO 299 I [61]
      50 2-tridecyl-4(1H)-quinolone C22H33NO 327 I [56]
      51 1-methyl-2-[(6Z,9Z,12E)-pentadecatriene]-4(1H)- quinolone C25H33NO 363 I [58]
      52 1-methyl-2-[(9E,13E)-9,13-heptadecadienyl]-4(1H)- quinolone C27H39NO 393 I [58]
      53 2-hydroxy-4-methoxy-3-(3’-methyl-2’-butenyl)- quinolone C15H17NO2 243 I [62]
      54 4-hydroxy-1-methyl-2-nonyl-quinolinium C19H27NO 285 I [63]
      55 Atanine I C15H17NO2 243 II [33]
      56 4-methoxy-3-(3-methylbut-2-en-1-yl)-2-quinolone-8-O-β-D-glucopyranoside C21H27NO8 421 II [53]
      57 Quinolone B C21H27NO8 421 II [53]
      58 3-Dimethylallyl-4-methoxy-2-quinolone C15H17NO2 244 II [64]
      59 Edulinine C16H21NO4 291 II [65]
      60 Dictamnine C12H9NO4 199 III [33,66,67]
      61 6-methoxydictamnine C13H11NO3 229 III [33]
      62 Evolitrine C13H11NO3 229 III [33,67]
      63 Confusameline C12H13NO3 215 III [67]
      64 Kokusaginine C14H13NO4 259 III [66]
      65 Skimmianine C14H13NO4 259 III [23,25,33,67]
      66 Haplophine C13H11NO3 229 III [68,69]
      67 Robustine C12H9NO3 215 III [69]
      68 7-isopentenyl-γ-fagarine C18H19NO4 313 III [65]
      69 Melineurine C18H19NO4 313 III [70]
      70 Leptanoine A C17H15NO3 281 III [71]
      71 Leptanoine B C18H17NO4 311 III [71]
      72 Leptanoine C C18H19NO4 313 III [71]
      73 Evodine C18H19NO5 329 III [72]
      74 Roxiamine A C18H19NO5 329 III [73]
      75 Roxiamine B C18H17NO5 327 III [73]
      76 Roxiamine C C16H27NO4 287 III [73]
      77 Evoxoidine C18H19NO5 329 III [74]
      78 Ribalinine C15H17NO3 259 IV [65]
      79 1-hyddroxy-2,3-dimetoxy-10-methylacridone C16H15NO4 285 V [65]
      80 2,3-Dimethoxy-4-hydroxy-10-methylacridone C16H15NO4 285 V [75]
      81 2,3,4-trimethoxy-10-methylacridone C17H17NO4 299 V [76]
      82 Xanthoxoline C15H13NO4 271 V [77]
      83 Evoxanthidine C15H11NO4 269 V [77]
      84 Xanthevodine C16H13NO5 299 V [77]
      85 Melicopidin C17H15NO5 313 V [68]

      Table 2. 

      Quinolone alkaloids isolated from Euodia plants.

    • No. Limonoids Molecular formula Relative molecular mass Ref.
      1 Limonin C26H30O8 470 [69,78−82]
      2 12α-hydroxylimonin C26H30O9 486 [83−85]
      3 6α-acetoxy-5-epilimonin (glaucin B) C28H32O10 528 [82,86]
      4 6β-acetoxy-5-epilimonin C28H32O10 528 [87]
      5 Jangomolide C26H28O10 500 [88]
      6 Limonin diosphenol C26H28O9 484 [82−84]
      7 Evodol (graucin C) C26H28O11 516 [78,80]
      8 12α-hydroxyevodol C26H28O10 500 [80,89]
      9 12α-hydroxyrutaevin (glaucinA) C26H30O10 502 [82]
      10 Rutaevin C26H30O9 486 [80,82,90]
      11 7β-acetoxy-5-epilimonin (ruteavine acetate) C27H32O10 516 [91]
      12 Isolimonexic acid C26H30O10 502 [81]
      13 Shihulimonin A1 C26H30O10 502 [78]
      14 Evorubodinin C27H32O10 516 [59]
      15 Evolimorutanin C28H36O11 548 [79]
      16 Evodirutaenin A C26H29O11 517 [92]
      17 Euodirutaecins A C26H28O11 516 [92]
      18 Euodirutaecins B C26H28O11 516 [92]
      19 Graucin A C26H30O10 502 [83]

      Table 3. 

      Ring-integrating limonoids isolated from Euodia.

    • No. Limonoids Molecular formula Relative molecular mass Ref.
      20 Obacunone C26H30O7 454 [91]
      21 7-deacetylproceranone C25H29O5 409 [87]
      22 Nomilin C29H38O9 530 [87]
      23 Clauemargine L C26H34O7 458 [91]
      24 19-hydroxy methyl isoobacunoate diosphenol C28H36O10 532 [91]
      25 Obacunonsaeure C26H32O8 472 [91]

      Table 4. 

      Rearranged limonoids isolated from Euodia.

    • No. Degradable limonoids Molecular formula Relative molecular mass Ref.
      26 9α-methoxyl dictamdiol C16H20O5 292 [91]
      27 Hiiranlactone E C16H28O2 252 [91]

      Table 5. 

      Degradable limonoids isolated from Euodia.

    • Activities Signaling pathway Ref.
      Inhibiting the expression of COX-2 genes NF-κB [154−157]
      Inhibited NO production IFN-γ/LPS- [158]
      Against gastric ulceration P2X(4)R [161,162]

      Table 6. 

      Anti-inflammatory activity.

    • Activities Mechanism of action Signaling pathway Ref.
      Protective effect of gastric mucosa injury Stimulation of CGRP release TRPV1 [163]
      Reducing the inflammatory response [164]
      Effects on gastrointestinal transit Inhibiting gastrointestinal transit and gastric emptying CKK, CKK1 receptor [165]
      Increasing normal jejunal contractility [13]

      Table 7. 

      Effects on the digestive system.

    • Activities Mechanism of action Signaling pathway Ref.
      The positive inotropic and chronotropic effects Vanilloid receptors, the calcitonin gene related peptide antagonist [166,168]
      Anti-hypertensive Attenuation of VSMC migration PPAR [170,171]
      Regulating endothelial to mesenchymal transition The transforming growth factor-beta1/Smd [173]
      Anti-platelet and anti-thrombotic activities Inhibiting HUVECs tube formation and invasion VEGF, p44/p42, MAPK, ERK [174]
      Inhibiting thromboxane formation and phosphoinositide breakdown [11,166]
      The vasodiatory effect Endothelium, receptor-mediated Ca2+ channels [176]
      Anti-arrhythmic Decreasing the Na+ and Ca2+ currents [177]
      Vascular disease Attenuate the phosphorylation of mitogen-activated protein kinase promote the reverse transport of cholesterol VSMCs

      ABCA1      		 [179]

      [180]
      Protective effect against valvular heart disease Decrease the expression of phosphate cotransporter PiT-1 [181]

      Table 8. 

      Effects on the cardiovascular system.

    • Activities Mechanism of action Ref.
      Anti-Alzheimer's disease Beta-secretase inhibitor [182,183]
      Selectivity over AChE, strong neuroprotection [184]
      Inhibited tau phosphorylation on Ser202/Thr205, Ser262, and Ser396 and downregulated tau aggregation and neuronal cell apoptosis. [185]
      Anti-anoxic and
      anti-cerebral ischemia activities      		 Equivalent to vinpocetine [153]
      Upregulation of pGSK3b, pAkt, and claudin-5, and downregulation of NF-kB expression [187]
      Analgesic effect The activation and subsequent desensitization of TRPV1 [16]
      Antidepressant effect Monoamine emitters and hippocampal BDNF-TrkB signaling [189]

      Table 9. 

      Effect on the central nervous system.