Antiproliferative ent-kaurane diterpenoids isolated from the roots of Zea mays L.

By‐Products of Zea mays L.: A Promising Source of Medicinal Properties with Phytochemistry and Pharmacological Activities: A Comprehensive Review

“…More than 66 terpenoids (36-101) (Table 1, Figure 2), including 5 monoterpenoids (36)(37)(38)(39)(40), 25 sesquiterpenes , 34 diterpenes (66-99), and 2 triterpenes (100, 101) were isolated from by-products of Z. mays, and play a significant role in CS. Monoterpenoids including: trans-pinocamphone (36), [42] citronellol (37), [42] cis-sabinene hydrate (38), [42] neo-iso-3thujanol (39), [42] and cis-α-terpineol (40) [42] were present in CS; 25 sesquiterpenes: 6,11-oxidoacor-4-ene (41), [42] (6R)-7,8-dihydro-3-oxoionone (42), [43] (6R,9R)-7,8-dihydro-3-oxoionol (43), [43] zealexin A1-A4 (44-47), [5,6,44] zealexin B1 (48), [5] stigmene A-I (49-57), [35,44,45] 3-(4-hydroxyphenyl)-5,5-dimethyl-2-cyclohexen-1-one (58), [44] (E)-β-caryophyllene (59), [46] α-humulene (60), [46] zeasesquiterpene A-E (61-65); [3] 34 diterpenes kauralexin A1-A3 (66-68), [7] kauralexin B1-B3 (69-71), [7] epoxydolabrene (72), [47] epoxydolabranol (73), [47] trihydroxydolabrene (74), [47] stigmaydene A-L (75-86), [48] ent-rosane-5β,15,16-triol (87), [49] ent-kaur-15-en-17,19-dioic acid (88), [50] 19-hydroxy-ent-kaur-15en-17-oic acid (89), [50] 17-hydroxy-ent-kaur-15-en-19-oic acid (90), [50] 3α-hydroxy-ent-kaur-15-en-17,19-dioic acid 19-methyl ester (91), [50] maizediterpenes A-D (92-95), [4] stigmane A-D (96-99);…”

“…[45,48,51,53] Moreover, with the medicinal properties of Z. mays, five sesquiterpenes and four diterpenes, which have anti-cancer activity, were identified and separated in RM. [3,4] To conclude, terpenoids, which play a significant role in by-products of Z. mays, are embedded in a new or potential medicinal effect with antioxidant, neuroprotective effects, and antitumor activities. Further research needs to explore terpenoids in RM, stems, and leaves compared to CS.…”

“…More than 41 phenylpropanoids (117 -157) (Table 1, Figure 4), including 16 simple phenylpropanoids (117-132) and 25 lignans were isolated from Z. mays. Compared with the simple structures and rare kinds of phenylpropanoids in CS and RM: p-coumaric acid (117), [55] 4-methoxycinnamic acid (118), [4] sinapic aldehyde (119), [4] chlorogenic acid (129), [38] 1-O-pcoumaroylglyceride (130), [4] eugenol (132), [42] syringar- esinol (152), [4] ciwujiatone (153), [4] 7S,8R-syringylglycerol-8-O-4'-(sinapyl alcohol) ether ( 154), [4] dehydrodiconiferyl alcohol (155), [4] and icariol (156), [4] the bran and stems of Z. mays contain more complex and variable phenylpropanoids, including dimer, trimer, tetramer, and glycoside: methyl (E)-p-coumarate (120), [14] methyl trans-ferulate (121), [14] 5-O-(trans-feruloyl)-L-arabinofuranoside ( 122), [16] p-coumaroylated-Larabinofuranoside( 123), [23] 124), [16] α- 125), [23] O-L-galactopyranosyl- 126), [16] α-D-galactopyranosyl- 127), [23] 128), [23] methyl (Z)-p-coumarate ( 131), [14] 1,3-O-diferuloyl glycerol (133), [14] 8-8(cyclic)-dehydrodiferulic acid (134), [20] 8-8(tetrahydrofuran)-dehydrodiferulic acid (135), [22] 5-5-dehydrodiferulic acid (136), [18] 8-O-4-dehydrodiferulic acid (137), [18] 8-5(noncyclic)-dehydrodiferulic acid (138), [22] (2E)-3-{4-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)acetyl]-5-methoxyphenyl}acrylic acid (139),…”

“…More than 41 phenylpropanoids ( 117 – 157 ) ( Table 1, Figure 4), including 16 simple phenylpropanoids ( 117 – 132 ) and 25 lignans ( 133 – 157 ) were isolated from Z. mays . Compared with the simple structures and rare kinds of phenylpropanoids in CS and RM: p‐ coumaric acid ( 117 ), [55] 4‐methoxycinnamic acid ( 118 ), [4] sinapic aldehyde ( 119 ), [4] chlorogenic acid ( 129 ), [38] 1‐O‐ p‐ coumaroylglyceride ( 130 ), [4] eugenol ( 132 ), [42] syringaresinol ( 152 ), [4] ciwujiatone ( 153 ), [4] 7S,8R‐syringylglycerol‐8‐O‐4′‐(sinapyl alcohol) ether ( 154 ), [4] dehydrodiconiferyl alcohol ( 155 ), [4] and icariol ( 156 ), [4] the bran and stems of Z. mays contain more complex and variable phenylpropanoids, including dimer, trimer, tetramer, and glycoside: methyl (E)‐ p‐ coumarate ( 120 ), [14] methyl trans‐ ferulate ( 121 ), [14] 5‐O‐( trans‐ feruloyl)‐L‐arabinofuranoside ( 122 ), [16] p‐ coumaroylated‐L‐arabinofuranoside( 123 ), [23] O‐ β ‐D‐xylopyranosyl‐(1→2)‐[5‐O‐( trans‐ feruloyl)‐L‐arabinofuranoside ( 124 ), [16] α ‐L‐galactopyranosyl‐(1→2)‐ β ‐D‐xylopyranosyl‐(1→2)‐5‐O‐transferuloyl‐L‐arabinofuranoside ( 125 ), [23] O‐L‐galactopyranosyl‐(1→4)‐O‐D‐xylopyranosyl‐(1→2)‐[5‐O‐( trans‐ feruloyl)‐L‐arabinofuranoside] ( 126 ), [16] α ‐D‐galactopyranosyl‐(1→3)‐ α ‐L‐galactopyranosyl‐(1→2)‐ β ‐D‐xylopyranosyl‐(1→2)‐5‐O‐transferuloyl‐L‐arabinofuranoside ( 127 ), [23] α ‐D‐xylopyranosyl‐(1→3)‐ α ‐L‐galactopyranosyl‐(1→2)‐ β ‐D‐xylopyranosyl‐(1→2)‐5‐O‐transferuloyl‐L‐arabinofuranoside ( 128 ), [23] methyl (Z)‐ p‐ coumarate ( 131 ), [14] 1,3‐O‐diferuloyl glycerol ( 133 ), [14] 8‐8(cyclic)‐dehydrodiferulic acid ( 134 ), [20] 8‐8(tetrahydrofuran)‐dehydrodiferulic acid ( 135 ), [22] 5‐5‐dehydrodiferulic acid ( 136 ), [18] 8‐O‐4‐dehydrodiferulic acid ( 137 ), [18] 8‐5(noncyclic)‐dehydrodiferulic acid ( 138 ), [22] (2E)‐3‐{4‐hydroxy‐3‐[(4‐hydroxy‐3‐methoxyphenyl)acetyl]‐5‐methoxyphenyl}acrylic acid ( 139 ), [21] 5‐5‐vanillin‐ferulic acid ( 140 ), [21] arabinofuranosyl‐ferulic acid‐(5‐5)‐ferulic acid‐(xylopyranosyl)‐arabinofuranoside ( 141 ), [19] arabinofuranosyl‐ferulic acid‐(8‐O‐4)‐ferulic acid‐arabinofuranoside ( 142 ), [19] 4‐O‐8′, 5′‐5′′‐dehydrotriferulic acid ( 143 ),…”

Design, Synthesis and Evaluation of Novel 1,4-Disubstituted Piperazine-2,5-dione Derivatives as Antioxidants against H2O2-Induced Oxidative Injury via the IL-6/Nrf2 Loop Pathway

“…Among these compounds, sesamin, syringaresinol, terminaloside K and pinoresinol showed significant antioxidant activities [ 12 ]. In our previous study, we also isolated and identified several known bisepoxylignans, including syringaresinol, from the roots of Zea mays L. (maize) and found that they protected SH-SY5Y cells against H 2 O 2 -induced cell apoptosis [ 13 ]. Therefore, bisepoxylignans are considered a good source of natural antioxidants [ 14 ].…”