“…Known compounds 3 , 4 , 14 – 35 , and 37 were identified by NMR and MS analyses, compared with reference data, and identified as the following: (7 R , 8 S )-4,7,9,3′,9′-pentahydroxy-3-methoxyl-8-4′-oxyneolignan-4- O -β- d -glucopyranoside ( 3 ), (7 R , 8 R )-4,7,9,3′,9′-pentahydroxy-3-methoxyl-8-4′-oxyneolignan-4 - O -β- d -glucopyranoside ( 4 ), (7 R , 8 R )-threo-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8- O -4′-neolignan-4- O -β- d -glucopyranoside ( 14 ), (+)-cycloolivil-4′- O -β- d -glucopyranoside ( 15 ), (+)-isolarisiresinol ( 16 ), (+)-isolarisiresinol-4′- O -β- d -glucopyranoside ( 17 ), (+)-isolarisiresinol-4- O -β- d -glucopyranoside ( 18 ), (+)-isolarisiresinol-9- O -β- d -xylopyranoside ( 19 ), (7 S , 8 R )-dihydrodehydrodiconiferyl alcohol-3′- O -β- d -glucopyranoside ( 20 ), (7 R , 8 S )-dihydrodehydrodiconiferyl alcohol-4- O -β- d -glucopyranoside ( 21 ), (7 S , 8 R )-dihydrodehydrodiconiferyl alcohol-9- O -α- l -rhamnopyranoside ( 22 ), olivil-4- O -β- d -glucopyranoside ( 23 ), gallic acid ( 24 ), 3- O -methyl gallic acid ( 25 ), 4- O -β- d -glucopyranosyloxy-3,5-dimethoxy-benzoic acid ( 26 ), protocatechuic acid ( 27 ), vanillic acid ( 28 ), vanillic acid 4- O -β- d -glucopyranoside ( 29 ), tyrosol ( 30 ), salidroside( 31 ), 4-hydroxybenzoic acid ( 32 ), 4-hydroxybenzoic acid 4- O -β- d -glucopyranoside ( 33 ), rhodiocyanoside A ( 34 ), sarmentosin ( 35 ), and EGCG ( 37 )…”
Rhodiola crenulata L. is an important species in genus Rhodiola widely used as a health food to reinforce immunity, improve memory and learning, scavenge active-oxygen species, and relieve altitude sickness. Eleven new lignans and a new benzonitrile compound, crenulatanoside A, were isolated from the roots of R. crenulata L. along with 25 known compounds, including 12 lignans. The structures of these compounds were elucidated by spectroscopic data and chemical evidence. Among them, compounds 1-4 and 5-7 were determined to be optical isomers of two 8-O-4' neolignan glycosides. Compounds 8-11 were aryl tetralin type lignans, and compounds 12 and 13 were dihydrobenzofuran neolignans. All of the isolated compounds were evaluated for their inhibitory activity against α-glucosidase. From the data obtained, compound 37 showed strong inhibitory activity against α-glucosidase with an IC(50) value of 96.8 μM.
“…Known compounds 3 , 4 , 14 – 35 , and 37 were identified by NMR and MS analyses, compared with reference data, and identified as the following: (7 R , 8 S )-4,7,9,3′,9′-pentahydroxy-3-methoxyl-8-4′-oxyneolignan-4- O -β- d -glucopyranoside ( 3 ), (7 R , 8 R )-4,7,9,3′,9′-pentahydroxy-3-methoxyl-8-4′-oxyneolignan-4 - O -β- d -glucopyranoside ( 4 ), (7 R , 8 R )-threo-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8- O -4′-neolignan-4- O -β- d -glucopyranoside ( 14 ), (+)-cycloolivil-4′- O -β- d -glucopyranoside ( 15 ), (+)-isolarisiresinol ( 16 ), (+)-isolarisiresinol-4′- O -β- d -glucopyranoside ( 17 ), (+)-isolarisiresinol-4- O -β- d -glucopyranoside ( 18 ), (+)-isolarisiresinol-9- O -β- d -xylopyranoside ( 19 ), (7 S , 8 R )-dihydrodehydrodiconiferyl alcohol-3′- O -β- d -glucopyranoside ( 20 ), (7 R , 8 S )-dihydrodehydrodiconiferyl alcohol-4- O -β- d -glucopyranoside ( 21 ), (7 S , 8 R )-dihydrodehydrodiconiferyl alcohol-9- O -α- l -rhamnopyranoside ( 22 ), olivil-4- O -β- d -glucopyranoside ( 23 ), gallic acid ( 24 ), 3- O -methyl gallic acid ( 25 ), 4- O -β- d -glucopyranosyloxy-3,5-dimethoxy-benzoic acid ( 26 ), protocatechuic acid ( 27 ), vanillic acid ( 28 ), vanillic acid 4- O -β- d -glucopyranoside ( 29 ), tyrosol ( 30 ), salidroside( 31 ), 4-hydroxybenzoic acid ( 32 ), 4-hydroxybenzoic acid 4- O -β- d -glucopyranoside ( 33 ), rhodiocyanoside A ( 34 ), sarmentosin ( 35 ), and EGCG ( 37 )…”
Rhodiola crenulata L. is an important species in genus Rhodiola widely used as a health food to reinforce immunity, improve memory and learning, scavenge active-oxygen species, and relieve altitude sickness. Eleven new lignans and a new benzonitrile compound, crenulatanoside A, were isolated from the roots of R. crenulata L. along with 25 known compounds, including 12 lignans. The structures of these compounds were elucidated by spectroscopic data and chemical evidence. Among them, compounds 1-4 and 5-7 were determined to be optical isomers of two 8-O-4' neolignan glycosides. Compounds 8-11 were aryl tetralin type lignans, and compounds 12 and 13 were dihydrobenzofuran neolignans. All of the isolated compounds were evaluated for their inhibitory activity against α-glucosidase. From the data obtained, compound 37 showed strong inhibitory activity against α-glucosidase with an IC(50) value of 96.8 μM.
An efficient stereoselective synthesis of a pivotal intermediate, a cyclic allyl alcohol derivative containing two methoxy groups [(±)-22], using for the preparation of (±)-trans-dihydronarciclasine analogues was elaborated starting from easily available and inexpensive methyl gallate. This new synthetic route consists of 17 reaction steps, and provides an opportunity to obtain the wanted alkaloid derivative containing an additional methoxy group at position 11, in the ring A of the phenanthridone scaffold.
“…Azasteganes 257 − 263 (Scheme ), the aza-analogues of steganone , and dibenzoazepins 264 and 265 , stegane analogues, have also been prepared. − The hetero analogues of lignans will likely be an area of medicinal chemistry that continues to expand as the interest in the lignan natural products as therapeutic agents progresses. 40 Synthesis of Heterocyclic Lignans…”
Section: 2 Research Perspectives Of Heterocyclic
Lignansmentioning
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