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. 2023 Nov 29;9(12):e22957. doi: 10.1016/j.heliyon.2023.e22957

Table 1.

Plant origin, extraction, detection and content of representative phthalides.

No. Compound Molecular formula Plant source Herbal part Extraction Detection Content (w/w) Reference
1 Z-ligustilide C12H14O2 Angelica acutiloba (Siebold & Zucc.) Kitag. Roots MeOH HPLC 0.08–0.22 % [29]
Angelica sinensis (Oliv.) Diels and Ligusticum chuanxiong Hort. Roots Water distillation GC-MS 1.077 % and 2.048 % [30]
Cnidium officinale Makino and Ligusticum chuanxiong Hort. Roots Water extraction HPLC-UVD 0.06–0.36 mg/g and 0.1–0.43 mg/g [31]
2 E-ligustilide C12H14O2 Angelica sinensis (Oliv.) Diels and Ligusticum chuanxiong Hort. Roots Water distillation GC-MS 0.027 % and 0.048 % [30]
3 Senkyunolide A C12H16O2 Angelica sinensis (Oliv.) Diels and Ligusticum chuanxiong Hort. Roots Water distillation GC-MS 0.002 % and 0.444 % [30]
Cnidium officinale Makino and Ligusticum chuanxiong Hort. Roots Water extraction HPLC-UVD 0.54–2.22 mg/g and 0.59–2.9 mg/g [31]
4 4,5-dihydro-3-butylphthalide C12H16O2 Angelica sinensis (Oliv.) Diels and Ligusticum chuanxiong Hort. Roots MeOH 2D-LC / [32]
5 Validene-4,5-dihydrophthalide C13H16O2 Levisticum officinale W. D. J. Koch Roots Water distillation TLC, GC-MS 1.3–4.7 % [33]
6 Z-iso-butylidene-3a,4-dihydrophthalide C12H14O2 Ligusticum canbyi J.M. Coult & Rose Roots 70 % EtOH TOF-MS / [34]
7 Z-validene-3a,4-dihydrophthalide C13H16O2 Apium graveolens L. Seeds Water distillation GC, IR / [35]
8 Butylphthalide C12H14O2 Angelica sinensis (Oliv.) Diels and Ligusticum chuanxiong Hort. Roots Water distillation GC-MS 0.007 % and 0.096 % [30]
Apium graveolens L. Seeds Water distillation LC-DAD-MS 13.10 % [21]
9 Z-butylidenephthalides C12H12O2 Angelica sinensis (Oliv.) Diels and Ligusticum chuanxiong Hort. Roots Water distillation GC-MS 0.03 % and 0.16 % [30]
Angelica sinensis (Oliv.) Diels Roots Pressurized liquid extraction GC-MS 0.08–0.15 % [59]
Ligusticum chuanxiong Hort. Roots Supercritical fluid extraction GC-MS 0.4–0.51 mg/g [36]
10 E-butylidenephthalides C12H12O2 Angelica sinensis (Oliv.) Diels and Ligusticum chuanxiong Hort. Roots Water distillation GC-MS 0.005 % [30]
Angelica sinensis (Oliv.) Diels Roots Pressurized liquid extraction GC-MS 0.04–0.05 % [59]
11 Propylidene-phthalide C11H10O2 Levisticum officinale W. D. J. Koch Matrix, leaves, stems, seeds Supercritical fluid extraction GC-MS / [38]
12 3-(3-Methylbutylidene)phthalide C13H14O2 Apium graveolens L. Leaves, stalks, roots Water distillation GC-MS / [39]
13 Sedanolide C12H18O2 Apium graveolens L. Seeds Supercritical fluid extraction GC-MS 72.24 % [40]
14 3-butylhexahydro-phthalide C12H16O2 Petroselinum crispum (Mill.) Nyman ex A. W. Hill Roots High-speed countercurrent chromatography GC-MS 1.1–4.2 % [41]
15 Hexahydro-3-butylphthalide C12H20O2 Seseli pallasii Besser Roots, stems, fruits Water distillation GC-MS 0.10 % [42]
16 Sedanonic acid lactone C12H16O2 Meum athamanticum Ext. Aerial parts Water distillation GC-MS 0.50 % [43]
17 Neoligustilide C12H14O2 Angelica sinensis (Oliv.) Diels Roots Water distillation GC-MS / [44]
18 Cnidilide C12H18O2 Ligusticum chuanxiong Hort. Roots MeOH HPLC-DAD-MS / [45]
19 10-angeloyl-3-butylphthalide C17H20O4 Angelica sinensis (Oliv.) Diels Roots MeOH UV, IR, NMR / [46]
20 10-Angeloylbutylphthalide C17H20O4 Angelica sinensis (Oliv.) Diels Roots MeOH UV, IR, NMR / [46]
21 11-Angeloylsenkyunolide F C17H20O4 Angelica acutiloba (Siebold & Zucc.) Kitag. Roots Hexane-MeOH extraction HPLC-MS, IR, UV, MS, NMR / [47]
22 Angeloyl ester of senkyunolide F C17H20O4 Angelica acutiloba (Siebold & Zucc.) Kitag. Roots Hexane-MeOH extraction HPLC-MS, IR, UV, MS, NMR / [47]
23 Celephthalide A C18H24O8 Apium graveolens L. Seeds MeOH HPLC, NMR / [48]
24 7-hydroxy-3-butylidenephthalide 7-O-glucoside C18H22O8 Petroselinum crispum (Mill.) Fuss Roots MeOH HPLC, GC-MS, NMR / [49]
25 Z-6,7-epoxyligustilide C12H14O3 Angelica sinensis (Oliv.) Diels
Angelica sinensis (Oliv.) Diels		 Roots
Roots		 Pressurized liquid extraction
MeOH		 GC-MS
LC-MS		 0.12–0.13 %
/		 [59]
[50]
26 7-methoxy-3-propylidenephthalide C12H12O3 Levisticum officinale W. D. J. Koch Roots n-hexane and ethyl acetate UHPLC-MS,
NMR		 / [51]
27 5,7-dimetoxy-6-(3-methylbut-2-enyl)-isobenzofuran-1(3H)-one C15H18O4 Peperomia nivalis Miq. Aerial parts / HR-TOF-MS,
NMR		 / [52]
28 Senkyunolide B C12H12O3 Angelica sinensis (Oliv.) Diels
Angelica sinensis (Oliv.) Diels		 Roots
Roots		 Pressurized liquid extraction
MeOH		 GC-MS
LC-MS		 0.13–0.14 %
/		 [59]
[50]
29 Senkyunolide C C12H12O3 Levisticum officinale W. D. J. Koch
Ligusticum chuanxiong Hort.		 Roots
Roots		 Ethyl acetate
60 % EtOH		 UHPLC-MS
HPLC, HR-ESI-MS, UV, IR, NMR		 /
/		 [54]
[53]
30 Senkyunolide E C12H12O3 Angelica acutiloba (Siebold & Zucc.) Kitag.
Angelica sinensis (Oliv.) Diels		 Roots
Roots		 Hexane-MeOH extraction
MeOH		 HPLC-MS, IR, UV, MS, NMR
LC-MS		 /
/		 [47]
[50]
31 3-butylidene-7-hydroxyphthalide C12H12O3 Ligusticum sinense Oliv. Roots Column chromatography MS / [55]
32 3-butylidene-4,5-dihydroxyphthalide C12H12O4 Angelica acutiloba (Siebold & Zucc.) Kitag. Roots ET2O extraction IR / [56]
33 4-hydroxy-3-butylphthalide C12H14O3 Ligusticum chuanxiong Hort.
Ligusticum chuanxiong Hort.		 Roots
Roots		 Column chromatography
MeOH		 NMR, MS
HPLC		 /
/		 [58]
[57]
34 3-hydroxy-3-butylphthalide C12H14O3 Ligusticum chuanxiong Hort. Roots Column chromatography NMR, MS / [58]
35 4,7-dihydroxy-3-butylphthalide C12H14O4 Ligusticum chuanxiong Hort. Roots Column chromatography NMR, MS / [58]
36 Senkyunolide F C12H14O3 Angelica sinensis (Oliv.) Diels Roots Pressurized liquid extraction GC-MS 0.13–0.14 % [59]
37 3,9-dihydroxy-ligustilide C12H16O4 Angelica sinensis (Oliv.) Diels Roots 80 % EtOH NMR / [60]
38 Senkyunolide G C12H16O3 Angelica sinensis (Oliv.) Diels Roots MeOH LC-MS / [50]
39 Senkyunolide K C12H16O3 Ligusticum striatum DC. Roots MeOH MS, UV, NMR / [61]
40 3-butylidene-6-hydroxy-5,6-dihydrophthalide C12H14O3 Ligusticum chuanxiong Hort. Roots 70 % MeOH HRMS / [62]
41 3-butylidene-6-hydroxy-5,6-dihydro-butylphthalide C12H16O3 Ligusticum chuanxiong Hort. Roots 70 % MeOH HRMS / [62]
42 Senkyunolide H C12H16O4 Angelica sinensis (Oliv.) Diels Roots Pressurized liquid extraction GC-MS 0.13–0.18 % [59]
43 Senkyunolide I C12H16O4 Angelica sinensis (Oliv.) Diels Roots Pressurized liquid extraction GC-MS 0.15–0.45 % [59]
44 Senkyunolide J C12H18O4 Apium graveolens L. Seeds MeOH NMR / [63]
45 Senkyunolide N C12H18O4 Apium graveolens L. Seeds MeOH NMR / [63]
46 3,6,7-trihydroxy-4,5,6,7-tetrahydro-3-butylphthalide C12H18O5 Ligusticum chuanxiong Hort. Roots 70 % MeOH HRMS / [62]
47 Senkyunolide R C12H16O5 Ligusticum chuanxiong Hort. Roots MeOH UV, IR, NMR / [64]
48 Senkyunolide S C12H16O5 Ligusticum chuanxiong Hort. Roots MeOH UV, IR, NMR / [64]
49 Senkyunolide L C12H15ClO3 Ligusticum chuanxiong Hort. Roots 70 % MeOH HRMS / [62]
50 Senkyunolide M C16H22O4 Ligusticum chuanxiong Hort. Roots 70 % MeOH HRMS / [62]
51 Senkyunolide Q C16H22O4 Ligusticum chuanxiong Hort. Roots 70 % MeOH HRMS / [62]
52 (3S, 3aR, 6S)-(−)-6-hydroxysedanolide C12H18O3 Ligusticum sinense Oliv cv. Chaxiong Aerial parts 95 % EtOH HR-ESI-MS, UV, IR, NMR / [65]
53 (3S, 3aR, 4R)-(−)-4-hydroxysedanolide C12H18O3 Ligusticum sinense Oliv cv. Chaxiong Aerial parts 95 % EtOH HR-ESI-MS, UV, IR, NMR / [65]
54 (3S, 3aR, 10R)-(−)-10-hydroxysedanolide C12H18O3 Ligusticum sinense Oliv cv. Chaxiong Aerial parts 95 % EtOH HR-ESI-MS, UV, IR, NMR / [65]
55 (3S, 3aR)-3-hydroxyethyl-3a, 4, 5,6-tetrahydrophthalide C10H14O3 Ligusticum sinense Oliv cv. Chaxiong Aerial parts 95 % EtOH HR-ESI-MS, UV, IR, NMR / [65]
56 (3S, 3aR, 6S)-(−)-6-hydroxysedanolide-10-one C12H16O4 Ligusticum sinense Oliv cv. Chaxiong Aerial parts 95 % EtOH HR-ESI-MS, UV, IR, NMR / [65]
57 (3S, 3aR)-3-(2-carboxyl) ethyl-3a, 4, 5,6-tetrahydrophthalide C10H12O4 Ligusticum sinense Oliv cv. Chaxiong Aerial parts 95 % EtOH HR-ESI-MS, UV, IR, NMR / [65]
58 (3R, 6R)-3-butyl-6-hydroxy-4, 5, 6, 7-tetrahydrophthalide C12H18O3 Ligusticum sinense Oliv cv. Chaxiong Aerial parts 95 % EtOH HR-ESI-MS, UV, IR, NMR / [65]
59 6-hydroxy-7-methoxydihydro-ligustilide C13H18O4 Angelica sinensis (Oliv.) Diels Roots MeOH LC-MS / [50]
60 (S)-3-ethyl-7-hydroxy-6-methoxyphthalide C11H12O4 Pittosporum illicioides Makino Roots MeOH UV, IR, NMR / [66]
61 (Z)-3-ethylidene-7-hydroxy-6-methoxyphthalide C11H10O4 Pittosporum illicioides Makino Roots MeOH UV, IR, NMR / [66]
62 (Z)-3-ethylidene-6,7-dimethoxyphthalide C12H12O4 Pittosporum illicioides Makino Roots MeOH UV, IR, NMR / [66]
63 (S)-3-ethyl-5,6,7-trimethoxyphthalide C13H16O5 Pittosporum illicioides Makino Roots MeOH UV, IR, NMR / [66]
64 (S)-3-ethyl-7-hydroxy-5,6-dimethoxyphthalide C12H14O5 Pittosporum illicioides Makino Roots MeOH UV, IR, NMR / [66]
65 6-formyl-7-hydroxy-5-methoxy-4-methylphthalide C11H10O5 Pittosporum illicioides Makino Roots MeOH UV, IR, NMR / [66]
66 1,3-Dihydro-3-oxo-1-isobenzofuranacetic acid C10H8O4 Ligusticum chuanxiong Hort. Roots 70 % MeOH HRMS / [62]
67 4,6-dimethoxy-phthalide C10H10O4 Asarum heterotropoides F. Schmidt Roots Water distillation MS / [67]
68 Arenophthalide B C19H24O9 Helichrysum arenarium (L.) Moench Whole plant 70 % EtOH IR, UV, NMR / [68]
69 Arenophthalide C C19H24O9 Helichrysum arenarium (L.) Moench Whole plant 70 % EtOH IR, UV, NMR / [68]
70 Senkyunolide D C12H14O4 Angelica sinensis (Oliv.) Diels Roots MeOH LC-MS / [50]
71 3,7-dihydroxyligustilide C12H16O4 Angelica sinensis (Oliv.) Diels Roots Pressurized liquid extraction GC-MS 0.13–0.14 % [59]
72 Neophathalide A C12H16O4 Ligusticum chuanxiong Hort. Roots 80 % EtOH IR, UV, NMR / [11]
73 Neophathalide B C12H14O4 Ligusticum chuanxiong Hort. Roots 80 % EtOH IR, UV, NMR / [11]
74 7-hydroxy-3-butylidenephthalide-7-O-(6′-malonylglucoside) C21H24O11 Petroselinum crispum (Mill.) Fuss Roots MeOH HPLC, GC-MS, NMR / [49]
75 Celephthalide B C23H32O12 Apium graveolens L. Seeds MeOH HPLC, NMR / [48]
76 3-butylidene-6α-hydroxy-7α-ethoxy-phthalide C14H21O4 Ligusticum chuanxiong Hort. Roots EtOH HR-ESI-MS,
NMR		 / [69]
77 Ligusticoside A C19H30O8 Ligusticum chuanxiong Hort. Roots Water MS, IR, UV, NMR / [5]
78 Celephthalide C C18H28O8 Apium graveolens L. Seeds MeOH HPLC, NMR / [48]
79 ligusticosides C C18H28O8 Cnidium officinale Makino Roots EtOH MS, IR, NMR / [70]
80 ligusticosides E C23H37O12 Cnidium officinale Makino Roots EtOH MS, IR, NMR / [70]
81 ligusticosides D C23H37O12 Cnidium officinale Makino Roots EtOH MS, IR, NMR / [70]
82 Senkyunolide O C24H28O4 Angelica sinensis (Oliv.) Diels Roots Column chromatography IR, MS, NMR / [71]
83 Senkyunolide P C24H30O4 Ligusticum chuanxiong Hort. Roots MeOH HPLC-DAD-MS / [72]
84 Levistolide A C24H28O4 Ligusticum chuanxiong Hort. Roots MeOH HPLC-DAD-MS 0.0468–0.0928 mg/g [72]
85 3,8-dihydro-diligustilide C24H30O4 Ligusticum chuanxiong Hort. Roots EtOH LC-MS / [73]
86 Chuanxiongdiolide A C24H32O4 Ligusticum chuanxiong Hort. Roots 95 % EtOH UV, IR, NMR, HR-ESI-MS / [74]
87 Chuanxiongnolide A C24H28O5 Ligusticum chuanxiong Hort. Roots 90 % EtOH HR-ESI-MS, NMR / [6]
88 Chuanxiongnolide B C24H28O5 Ligusticum chuanxiong Hort. Roots 90 % EtOH HR-ESI-MS, NMR / [6]
89 Tokinolide B C24H28O4 Ligusticum chuanxiong Hort. Roots MeOH HPLC-DAD-MS / [72]
90 Z-ligustilide dimer E−232 C24H28O4 Ligusticum chuanxiong Hort. Roots MeOH HPLC-DAD-MS / [72]
91 Angeolide C24H28O4 Ligusticum sinense Oliv. Roots 95 % EtOH UV, ECD, IR, NMR / [75]
92 Gaobennolide A C24H30O4 Ligusticum sinense Oliv. Roots 95 % EtOH UV, ECD, IR, NMR / [75]
93 Gaobennolide B C24H30O4 Ligusticum sinense Oliv. Roots 95 % EtOH UV, ECD, IR, NMR / [75]
94 Ansaspirolide C24H26O4 Angelica sinensis (Oliv.) Diels Roots MeOH UV, IR, NMR / [46]
95 Angesinenolide F C24H26O4 Ligusticum sinense Oliv. Roots 95 % EtOH UV, ECD, IR, NMR / [75]
96 (3′Z)-(3S,8S,3a′S,6′R)-4,5-dehydro-3.3a′,8.6′-diligustilide C24H26O4 Ligusticum chuanxiong Hort. Roots 95 % EtOH NMR, HR-ESI-MS / [77]
97 (3′Z)-(3S,8R,3a′S,6′R)-4,5-dehydro-3.3a′,8.6′-diligustilide C24H26O4 Ligusticum chuanxiong Hort. Roots 95 % EtOH NMR, HR-ESI-MS / [77]
98 4,5-Dehydro-diligustilide C24H26O4 Ligusticum chuanxiong Hort. Roots EtOH LC-MS / [73]
99 Chuanxiongdiolide R1 C25H31O5 Ligusticum chuanxiong Hort. Roots 95 % EtOH NMR, HR-ESI-MS / [77]
100 Chuanxiongdiolide R3 C25H31O5 Ligusticum chuanxiong Hort. Roots 95 % EtOH NMR, HR-ESI-MS / [77]
101 Z,Z′-3.3′a, 7.7′a-diligustilide C24H28O4 Angelica sinensis (Oliv.) Diels Roots MeOH MS / [78]
102 Z,Z′-3a.7a′,7a.3a′-dihydroxyligustilide C24H28O4 Angelica sinensis (Oliv.) Diels Roots MeOH LC-MS, NMR / [79]
103 Chuanxiongdiolide R6 C24H30O4 Ligusticum chuanxiong Hort. Aerial parts 95 % EtOH UV, ECD, IR, HR-ESI-MS, NMR / [80]
104 Angesinenolides C C24H28O4 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH HRMS, NMR / [76]
105 Angesinenolides D C24H28O4 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH HRMS, NMR / [76]
106 Tokinolide A C24H28O4 Angelica sinensis (Oliv.) Diels Roots Supercritical fluid extraction HPLC, NMR / [81]
107 Tokinolide C C24H28O4 Angelica sinensis (Oliv.) Diels Roots Supercritical fluid extraction HPLC, NMR / [81]
108 Neodiligustilide C24H28O4 Angelica sinensis (Oliv.) Diels Roots MeOH FT-IR, UV, NMR / [82]
109 Tokiaerialide C24H28O4 Ligusticum chuanxiong Hort. Aerial parts 95 % EtOH UV, ECD, IR, HR-ESI-MS, NMR / [80]
110 Riligustilide C24H28O4 Ligusticum chuanxiong Hort. Roots MeOH HPLC-DAD-MS / [72]
111 Gelispirolide C24H26O4 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH LC-HR-ESI-MS / [10]
112 3,3′Z-6.7′,7.6′-diligustilide C24H28O4 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH NMR / [83]
113 3′,8′,3′a,7′a-tetrahydro-6.3′,7.7′a-diligustilide-8′-one C24H30O4 Angelica sinensis (Oliv.) Diels Roots Column chromatography IR, MS, NMR / [71]
114 Sinaspirolide C24H26O4 Angelica sinensis (Oliv.) Diels Roots MeOH UV, IR, NMR / [46]
115 Chuanxiongdiolide B C24H32O4 Ligusticum chuanxiong Hort. Roots 95 % EtOH UV, IR, NMR, HR-ESI-MS / [74]
116 Wallichilide C25H33O5 Ligusticum striatum DC. Roots Water UV, IR, NMR, MS / [3]
117 E,E′-3,3':8,8′-Diligustilide C24H28O4 Ligusticum chuanxiong Hort. Roots MeOH HPLC-DAD-MS / [72]
118 Angesinenolides E C24H24O4 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH HRMS, NMR / [76]
119 Diangeliphthalide A C24H26O4 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH LC-HR-ESI-MS / [10]
120 Chuanxiongdiolide R4 C25H33O5 Ligusticum chuanxiong Hort. Aerial parts 95 % EtOH UV, ECD, IR, HR-ESI-MS, NMR / [80]
121 Chuanxiongdiolide R5 C24H32O4 Ligusticum chuanxiong Hort. Aerial parts 95 % EtOH UV, ECD, IR, HR-ESI-MS, NMR / [80]
122 Methyl ester of angeolide C25H33O5 Ligusticum chuanxiong Hort. Aerial parts 95 % EtOH UV, ECD, IR, HR-ESI-MS, NMR / [80]
123 (+)-6-3′a,7–6′-Isowallichilide C25H32O5 Ligusticum chuanxiong Hort. Roots MeOH HR-ESI-MS,
NMR		 / [84]
124 (−)-6-3′a,7–6′-Isowallichilide C25H32O5 Ligusticum chuanxiong Hort. Roots MeOH HR-ESI-MS,
NMR		 / [84]
125 1″,3′-seco-1′-ethoxy-3,3a′, 8,6′-diligustilide C26H33O5 Ligusticum chuanxiong Hort. Roots EtOH HR-ESI-MS,
NMR		 / [69]
126 Spiroligustolides A C24H26O6 Ligusticum chuanxiong Hort. Roots CH2Cl2–MeOH HR-ESI-MS, IR, NMR / [85]
127 Spiroligustolides B C24H26O6 Ligusticum chuanxiong Hort. Roots CH2Cl2–MeOH HR-ESI-MS, IR, NMR / [85]
128 Triangeliphthalides A C36H40O6 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH LC-HR-ESI-MS / [10]
129 Triangeliphthalides B C36H40O6 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH LC-HR-ESI-MS / [10]
130 Triligustilides A C36H42O6 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH HR-ESI-MS / [9]
131 Triligustilides B C36H44O6 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH HR-ESI-MS / [9]
132 Triangeliphthalides C C36H40O6 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH LC-HR-ESI-MS / [10]
133 Triangeliphthalides D C36H38O6 Angelica sinensis (Oliv.) Diels Roots 95 % EtOH LC-HR-ESI-MS / [10]