Table 3.
Phytochemical constituents of the genus Callicarpa
| Compound Type/Name | Species Studied | Plant Part | Reference |
|---|---|---|---|
| Amino Acids | |||
| Alanine | C. japonica Thunb. | Fruits | [60] |
| Aspartic acid | C. japonica Thunb. | Fruits | [60] |
| Glycine | C. japonica Thunb. | Fruits | [60] |
| Serine | C. japonica Thunb. | Fruits | [60] |
| Threonine | C. japonica Thunb. | Fruits | [60] |
| Benzenoids | |||
| Salicylic acid | C. integerrima Champ. ex Benth. | Entire plant | [87] |
| Syringic acid | C. integerrima Champ. ex. Benth | Entire plant | [87] |
| Vanillic acid | C. integerrima Champ. ex Benth. | Entire plant | [87] |
| Carbohydrates | |||
| D-Glucose | C. japonica Thunb. | Fruits | [60] |
| myo -Inositol | C. pedunculata R.Br. | Entire plant | [34] |
| Diterpenenoids [Fig. (1) and Fig. (2)] | |||
| Abieta-8,11,13,15-tetraen-18-oic acid (1) | C. pedunculata R.Br. | Entire plant | [34] |
| C. pedunculata R.Br. | Leaves | [33] | |
| Akhdarenol (2) | C. acuminata H.B.K. | Leaves | [3] |
| Callicarpone (3) | C. candicans (Burm. f.) Hochr. | Leaves | [40] |
| Calliphyllin (4) | C. macrophylla Vahl. | Leaves | [79] |
| C. pedunculata R.Br. | Leaves | [33] | |
| Callicarpenal (5) | C. americana L. | Leaf essential oil | [11] |
| C. japonica Thunb. | Leaf essential oil | [11] | |
| Calliterpenone (6) | C. americana L. | Fruits, leaves, and twigs | [36] |
| C. furfuracea Ridl. | Leaves | [70] | |
| C. longifolia Lam. | Leaves | [76] | |
| C. macrophylla Vahl. | Aerial parts | [13] | |
| C. macrophylla Vahl. | Leaves | [72, 76] | |
| C. macrophylla Vahl. | Seeds | [1] | |
| C. pedunculata R.Br. | Entire plant | [34] | |
| C. pedunculata R.Br. | Leaves | [33] | |
| Calliterpenone-17-acetate (7) | C. furfuracea Ridl. | Leaves | [70] |
| C. longifolia Lam. | Leaves | [76] | |
| C. macrophylla Vahl. | Aerial parts | [13] | |
| C. macrophylla Vahl. | Leaves | [72, 76] | |
| C. macrophylla Vahl. | Seeds | [1] | |
| 3β,12(S )-Dihydroxycleroda-4(18),13-dien-15,16-olide (8) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 3β,16ξ-Dihydroxycleroda-4(18),13-dien-15,16- olide (9) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 12(S ),16ξ-Dihydroxycleroda-3,13-dien-15,16- olide (10) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 2-Formyl-16ξ-hydroxy-3-A-norcleroda-2,13-dien-15,16-olide (11) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 12(S )-Hydroxycleroda-3,13-dien-15,16-olide (12) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 12(S )-Hydroxycleroda-3,13-dien-16,15-olide (13) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 12(S )-Hydroxy-16ξ-methoxycleroda-3,13-dien-15,16-olide (14) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 16ξ-Hydroxycleroda-3,13-dien-15,16-olide (15) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 16ξ-Hydroxycleroda-3,11(E ),13-trien-15,16-olide (16) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 6α-Hydroxynidorellol (17) | C. pedunculata R.Br. | Entire plant | [34] |
| C. pedunculata R.Br. | Leaves | [33] | |
| 3β-Hydroxyphyllocladan-17-oic acid (18) | C. furfuracea | Leaves | [70] |
| Isopimaric acid (19) | C. acuminata H.B.K. | Leaves | [3] |
| C. pedunculata R.Br. | Entire plant | [33] | |
| Isopimarol (20) | C. japonica Thunb. | Leaf essential oil | [42] |
| 16α,17-Isopropylideno-3-oxophyllocladane (21) | C. macrophylla Vahl. | Leaves | [72] |
| Maingayic acid (22) | C. maingayi King & Gamble | Leaves | [59] |
| 17-Norphyllocladane-3,16-dione (23) | C. furfuracea Ridl. | Leaves | [70] |
| Pentandralactone (24) | C. pentandra Roxb. | Leaves | [90] |
| Pentandranoic acid A (25) | C. pentandra Roxb. | Leaves | [90] |
| Pentandranoic acid B (26) | C. pentandra Roxb. | Leaves | [90] |
| Pentandranoic acid C (27) | C. pentandra Roxb. | Leaves | [90] |
| Phylloclad-15-en-3,17-dione (28) | C. furfuracea Ridl. | Leaves | [70] |
| 3β,16β-Phyllocladane-3,16,17-triol (29) | C. furfuracea Ridl. | Leaves | [70] |
| 3β,16β-Phyllocladane-3,16,17-triol-17-acetate (30) | C. furfuracea Ridl. | Leaves | [70] |
| Phytol (31) | C. japonica Thunb. | Leaves and twigs | [86] |
| Sandaracopimaradien-19-ol (32) | C. acuminata H.B.K. | Leaves | [3] |
| 16α,17,19-Trihydroxyphyllocladan-3-one (33) | C. furfuracea Ridl. | Leaves | [70] |
| 4,16α,17-Trihydroxy-3,4-secophyllocladan-3-oic acid (34) | C. furfuracea Ridl. | Leaves | [70] |
| 5β,16α-4,16,17-Trihydroxy-3,4-secophyllocladan-3-oic acid (35) | C. furfuracea Ridl. | Leaves | [70] |
| Flavonoids [Fig. (3)] | |||
| Apigenin (36) | C. longifolia Lam. | Leaves | [76] |
| C. macrophylla Vahl. | Leaves | [76] | |
| Apigenin-7-O -β-D-glucuronide (37) | C. longifolia Lam. | Leaves | [76] |
| C. macrophylla Vahl. | Leaves | [76] | |
| Chrysoeriol-4′-O -β-D-glucoside (38) | C. bodinieri H.Lév. | Entire plant | [66] |
| Cyanidin (39) | C. bodinieri H.Lév. | Fruits | [19] |
| C. purpurea Juss. | Fruits | [19] | |
| Cynaroside (40) | C. bodinieri H.Lév. | Entire plant | [66] |
| 5,4′-Dihydroxy-7-methoxyflavone (Genkwanin) (41) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 5,4′-Dihydroxy-3,7-dimethoxyflavone (42) | C. macrophylla Vahl. | Leaves | [79] |
| 7,4′-Dihydroxy-3,5-dimethoxyflavone (43) | C. pedunculata R.Br. | Entire plant | [34] |
| 5,4′-Dihydroxy-3,7,3′-trimethoxyflavone (44) | C. macrophylla Vahl. | Leaves | [14, 79] |
| 5-Hydroxy-7,4′-dimethoxyflavone (45) | C. americana L. | Fruits, leaves, and twigs | [36] |
| 5-Hydroxy-3,6,7,4′-tetramethoxyflavone (46) | C. bodinieri H.Lév. | Leaves | [67] |
| 5-Hydroxy-3,7,3′,4′-tetramethoxyflavone (47) | C. formosana Rolfe | Leaves | [15] |
| 5-Hydroxy-6,7,3′,4′-tetramethoxyflavone (48) | C. integerrima Champ. ex Benth. | Entire plant | [87] |
| 5-Hydroxy-3,7,4′-trimethoxyflavone (49) | C. formosana Rolfe | Leaves | [15] |
| C. pedunculata R.Br. | Entire plant | [34] | |
| 5-Hydroxy-6,7,4′-trimethoxyflavone (50) | C. acuminata H.B.K. | Leaves | [3] |
| C. americana L. | Fruits, leaves, and twigs | [36] | |
| Luteolin (51) | C. longifolia Lam. | Leaves | [76] |
| C. macrophylla Vahl. | Leaves | [76] | |
| Luteolin-4′-O -β-D-glucoside (52) | C. bodinieri H.Lév. | Entire plant | [66] |
| Luteolin-7-O -β-D-glucuronide (53) | C. longifolia Lam. | Leaves | [76] |
| C. macrophylla Vahl. | Leaves | [76] | |
| Paeonidin (54) | C. bodinieri H.Lév. | Fruits | [19] |
| C. purpurea Juss. | Fruits | [19] | |
| 3,5,7,3′,4′-Pentamethoxyflavone (55) | C. formosana Rolfe | Leaves | [15] |
| Petunidin (56) | C. purpurea Juss. | Fruits | [19] |
| 5,7,3′,4′-Tetramethoxyflavone (57) | C. formosana Rolfe | Leaves | [15] |
| 5,6,7-Trimethoxyflavone (58) | C. japonica Thunb. | Not stated | [29, 32] |
| Lignans [Fig. (4)] | |||
| Lariciresinol (59) | C. furfuracea Ridl. | Leaves | [70] |
| 9α-Methoxysesamin-2,2′-diol (60) | C. furfuracea Ridl. | Leaves | [70] |
| (+)-Sesamin (61) | C. furfuracea Ridl. | Leaves | [70] |
| (+)-Sesamin-2-ol (62) | C. furfuracea Ridl. | Leaves | [70] |
| Sesamin-2,2′-diol (63) | C. furfuracea Ridl. | Leaves | [70] |
| Lipids | |||
| Arachidic acid | C. japonica Thunb. | Fruits | [60] |
| (E )-2-Hexenal | C. americana L. | Leaf essential oil | [42, 82] |
| Lauric acid | C. japonica Thunb. | Fruits | [60] |
| Linoleic acid | C. japonica Thunb. | Fruits | [60] |
| Myristic acid | C. japonica Thunb. | Fruits | [60] |
| 1-Octen-3-ol | C. americana L. | Leaf essential oil | [42, 82] |
| Oleic acid | C. japonica Thunb. | Fruits | [60] |
| Palmitic acid | C. japonica Thunb. | Fruits | [60] |
| Pentatetracontanoic acid | C. bodinieri H.Lév. | Leaves | [67] |
| N -Pentatriacontane | C. bodinieri H.Lév. | Leaves | [67] |
| Stearic acid | C. japonica Thunb. | Fruits | [60] |
| N -Triacontane | C. integerrima Champ. ex Benth. | Entire plant | [87] |
| Monoterpenoids | |||
| Nopinone | C. americana L. | Leaf essential oil | [82] |
| α-Pinene | C. americana L. | Leaf essential oil | [42, 82] |
| β-Pinene | C. americana L. | Leaf essential oil | [42, 82] |
| Phenylpropanoids and Phenylethanoids [Fig. (4)] | |||
| 2′-Acetylverbascoside (2′-acetylacteoside) (64) | C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] |
| Brandioside (65) | C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] |
| Calceolarioside A (66) | C. bodinieri H.Lév. | Leaves | [80] |
| Cistanoside H (67) | C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] |
| Echinacoside (68) | C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] |
| Eugenol (69) | C. japonica Thunb. | Leaf essential oil | [42] |
| Forsythoside B (70) | C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] |
| Isoverbascoside (isoacteoside) (71) | C. bodinieri H.Lév. | Leaves | [80] |
| C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] | |
| Poliumoside (72) | C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] |
| E -Tubuloside E (73) | C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] |
| Z -Tubuloside E (74) | C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] |
| Verbascoside (acteoside) (75) | C. bodinieri H.Lév. | Leaves | [80] |
| C. tomentosa b | Leaves | [80] | |
| C. purpurea Juss. (C. dichotoma Raeusch.)a | Leaves and twigs | [43] | |
| Sesquiterpenoids | |||
| Bicyclogermacrene | C. japonica Thunb. | Leaf essential oil | [42] |
| α-Cadinol | C. americana L. | Leaf essential oil | [42, 82] |
| Camphor (juniper camphor) | C. japonica Thunb. | Leaf essential oil | [42] |
| Caryophyllene oxide | C. americana L. | Leaf essential oil | [82] |
| Curcuphenol | C. japonica Thunb. | Leaf essential oil | [42] |
| β-Elemene | C. japonica Thunb. | Leaf essential oil | [42] |
| γ-Elemene | C. japonica Thunb. | Leaf essential oil | [42] |
| δ-Elemene | C. japonica Thunb. | Leaf essential oil | [42] |
| 7-epi -α-Eudesmol | C. americana L. | Leaf essential oil | [42, 82] |
| Germacrene B | C. japonica Thunb. | Leaf essential oil | [42] |
| Germacrene D | C. japonica Thunb. | Leaf essential oil | [42] |
| Globulol | C. japonica Thunb. | Leaf essential oil | [42] |
| α-Guaiene | C. japonica Thunb. | Leaf essential oil | [42] |
| α-Humulene | C. americana L. | Leaf essential oil | [11, 42, 82] |
| C. japonica Thunb. | Leaf essential oil | [11] | |
| Humulene epoxide II | C. americana L. | Leaf essential oil | [11, 42, 82] |
| C. japonica Thunb. | Leaf essential oil | [11] | |
| Intermediol | C. americana L. | Leaf essential oil | [11] |
| C. japonica Thunb. | Leaf essential oil | [11] | |
| Khusinol | C. americana L. | Leaf essential oil | [82] |
| Ledol | C. japonica Thunb. | Leaf essential oil | [42] |
| Selin-11-en-4-α-ol | C. japonica Thunb. | Leaf essential oil | [42] |
| α-Selinene | C. americana L. | Leaf essential oil | [42, 82] |
| 7-epi -α-Selinene | C. americana L. | Leaf essential oil | [42, 82] |
| Seychellene | C. japonica Thunb. | Leaf essential oil | [42] |
| Spathulenol | C. japonica Thunb. | Leaf essential oil | [11, 42] |
| Valencene | C. americana L. | Leaf essential oil | [42, 82] |
| Viridiflorol | C. japonica Thunb. | Leaf essential oil | [42] |
| Phytosterols [Fig. (5)] | |||
| Campesterol (76) | C. japonica Thunb. | Fruits | [60] |
| β-Sitosterol (77) | C. arborea b | Bark | [68] |
| C. arborea b | Leaves | [14, 69] | |
| C. bodinieri H.Lév. | Entire plant | [66] | |
| C. formosana Rolfe | Leaves | [15] | |
| C. integerrima Champ. ex Benth. | Entire plant | [87] | |
| C. japonica Thunb. | Fruits | [60] | |
| C. macrophylla Vahl. | Leaves | [79] | |
| C. pedunculata R.Br. | Entire plant | [34] | |
| β-Sitosterol-d-glucoside (78) | C. formosana Rolfe | Leaves | [15] |
| Stigmasterol (79) | C. bodinieri H.Lév. | Leaves | [67] |
| C. formosana Rolfe | Leaves | [15] | |
| C. japonica Thunb. | Fruits | [60] | |
| Stigmasterol-D-glucoside (80) | C. formosana Rolfe | Leaves | [15] |
| Triterpenoids [Fig. (5)] | |||
| α-Amyrin (81) | C. acuminata H.B.K. | Leaves | [3] |
| C. bodinieri H.Lév. | Leaves | [67] | |
| β-Amyrin (82) | C. pedunculata R.Br. | Fruits | [23] |
| C. pedunculata R.Br. | Entire plant | [34] | |
| Bauerenol (83) | C. arborea b | Bark | [68] |
| Betulinic acid (84) | C. arborea b | Bark | [68] |
| C. bodinieri H.Lév. | Entire plant | [66] | |
| C. macrophylla Vahl. | Leaves | [79] | |
| Corosolic acid (85) | C. bodinieri H.Lév. | Entire plant | [65] |
| C. pentandra Roxb. | Leaves | [90] | |
| 2α,3α-Dihydroxyurs-12-en-28-oic acid (86) | C. bodinieri H.Lév. | Entire plant | [65] |
| C. formosana Rolfe | Leaves | [15] | |
| C. pentandra Roxb. | Leaves | [90] | |
| Epilupeol (87) | C. arborea b | Leaves | [69] |
| Euscaphic acid (88) | C. americana L. | Fruits, leaves, and twigs | [36] |
| C. bodinieri H.Lév. | Entire plant | [65] | |
| Oleanolic acid (89) | C. macrophylla Vahl. | Seeds | [1] |
| Pomolic acid (90) | C. pentandra Roxb. | Leaves | [90] |
| 2α,3α,24-Trihydroxyolean-12-en-28-oic acid (91) | C. bodinieri H.Lév. | Entire plant | [65] |
| Ursolic acid (92) | C. arborea b | Leaves | [14, 69] |
| C. bodinieri H.Lév. | Entire plant | [66] | |
| C. formosana Rolfe | Leaves | [15] | |
| C. longifolia Lam. | Leaves | [76] | |
| C. pedunculata R.Br. | Fruits | [23] | |
| C. pedunculata R.Br. | Entire plant | [34] | |
| C. pentandra Roxb. | Leaves | [90] |
a
The botanical binomial in parentheses is listed as a synonym for the preceding species name listed in the “International Plant Names Index” online database.
b
The taxonomic authority was not stated in the cited publication.