Chlomultiols A-L, sesquiterpenoids from Chloranthus multistachys and their anti-inflammatory activities

Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers

“…The D 4(5) double bond can be oxidized, forming the characteristic hydroxyl or peroxy-hydroxyl at C-4 or C-5 and migrating D 4(5) to D 5 (6) and D 15(4) (210)(211)(212)(213). Chlorahololides A (188), 151 C (189) 140 and spicachlorantin J (190) 152 possess a D 15 ′ (4 ′ ) double bond, and spicachlorantins E-F (191)(192), 153 sarcandrolide E (193), 107 chlorajaponilide E (194), 87 spicachlorantin G (195), 152,154 chlorasessilifol A (196), 155 fortunilides D-F (197)(198)(199), 49 chololactone B (200), 75 multistalide A (201), 141 chlomultiol B (202), 145 and sarcaglabrin B ( 203) feature an additional chiral center at C-4 ′ . 156 The migration of D 7 (11) affords a rare D 11 (13) , which is the characteristic of multistalide A (201), 141 chlomultiol B (202), 145 and sarcaglabrin B (203).…”

“…Chlorahololides A (188), 151 C (189) 140 and spicachlorantin J (190) 152 possess a D 15 ′ (4 ′ ) double bond, and spicachlorantins E-F (191)(192), 153 sarcandrolide E (193), 107 chlorajaponilide E (194), 87 spicachlorantin G (195), 152,154 chlorasessilifol A (196), 155 fortunilides D-F (197)(198)(199), 49 chololactone B (200), 75 multistalide A (201), 141 chlomultiol B (202), 145 and sarcaglabrin B ( 203) feature an additional chiral center at C-4 ′ . 156 The migration of D 7 (11) affords a rare D 11 (13) , which is the characteristic of multistalide A (201), 141 chlomultiol B (202), 145 and sarcaglabrin B (203). 156 The substituent groups at C-13 ′ and C-15 ′ form an 18-membered macrolide through their esterication reaction in compounds 204-209.…”

“…The active Δ 15′(4′) and allyl Me-13 undergo oxidation, esterification and rearrangement to form diverse homo-[4 + 2] dimers, including shizukaol N ( 119 ), 138 shizukaol M ( 120 ), 138 shizukaol I ( 121 ), 139 chlorahololide D ( 122 ), 140 shizukaol K ( 123 ), 138 multistalide B ( 124 ), 141 sarcandrolide A ( 125 ), 107 shizukaol C ( 126 ), 142 shizukaol L ( 127 ), 138 sarcandrolide B ( 128 ), 61 13′- O -methyl succinylshizukaol C ( 129 ), 50 chololactones E–F ( 130–131 ), 75 sarglabolides H–K ( 132–135 ), 143 fortunilide M ( 136 ), 90 chlojapolide A ( 137 ), 137 fortunilides A–C ( 138–140 ), 65 chlorahupetol F ( 141 ), 144 shizukaol O ( 142 ), 138 sarcandrolide J ( 143 ), 116 chlomultiol A ( 144 ), 145 sarcanolide E ( 145 ), 146 and shizukaols D–E ( 146–147 ). 139,142 Chlorahololide D ( 122 ) was also reported by Luo's group as henriol D in the same year.…”

“…Regarding their macrolides, chlorahololide B ( 229 ), 151 chloramultilide B ( 230 ), 160 and yinxiancaol ( 234 ) 161 contain methyl groups at the C-3′′ position. Conversely, the methyl group of chloramultilide C ( 231 ), 160 tianmushanol ( 232 ), 162 8- O -methyltianmushanol ( 233 ), 162 spicachlorantin A ( 235 ), 163 chlorajaponilide D ( 236 ), 87 237 , 40 sarcandrolide I ( 238 ), 116 chlomultiol C ( 239 ) 145 and 240 (ref. 40) is situated at the C-2′′ position.…”