Chemical Constituents from the style of <I>Zea mays</I> 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 – 40 ), 25 sesquiterpenes ( 41 – 65 ), 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‐3‐thujanol ( 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‐15‐en‐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 ); [51] 2 triterpenes ursolic acid ( 100 ), [52] acacic acid lactone ( 101 ) [51] . After Schmelz found ent ‐kaurane type diterpenes: kauralexin A1–A3, kauralexin B1–B3, [46] a series of these types of compounds were found in recent years′ bumper researches of CS for anti‐AD potential and exerted neuroprotective effects [45,48,51,53] .…”

“…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 ),…”

“…Very few kinds of steroids, including 15 steroids (102-116) (Table 1, Figure 3), have been identified from CS. The type of steroids isolated and identified in CS mainly include 8 stigmasterols: stigmast-4-ene-3β,6βdiol (102), [52] stigmast-4,22-diene-3β,6β-diol (103), [52] stigmast-4-ene-3β,7α-diol (104), [52] stigmast-4,22diene-3β,7α-diol (105), [52] stigmasterol (111), [35] stigmast-4-en-3-one (112), [35] stigmastone (113), [35] and stigmasterol-3-O-β-D-glucopyranoside (115); [52] 5 sitosterols: β-sitosterol (106), [55,56] 7α-hydroxysitosterol (107), [57] 7β-hydroxysitosterol (108), [57] β-sitosterol-3-O-β-D-glucopyranoside (114), [52] 7α-hydroxysitosterol-3-O-β-D-glucopyranoside (116), [57] and 2 ergosterols: ergosta-7,22-diene-3β,5α,6β-triol (109), [57] ergosterol peroxide (110). [58]…”

A New Cycloartane-Type Triterpenoid from the Stigma of Zea Mays L

“…3,4 Previous phytochemical studies showed that the secondary metabolites from the stigma of Zea mays L. were mainly terpenoids, steroids, and flavonoids. 1,2,[5][6][7] A recent NMR detection technique which we have used showed that an EtOH extract of the stigma of Zea mays L. contained cycloartane triterpenoids. Since there were no reports of such triterpenoids from the stigma of Zea mays L., we performed an NMR-guided fractionation to yield a new cycloartane-type triterpenoid, cycloart-24-ene-2α, 3β-diol (1) (Fig.…”