“…The known isolates, i.e., xanthyletin (3) [50], umbelliferone (4) [51], scopoletin (5) [51], and (þ)-(S)-marmesin (6) [52], carpachromene (7) [53], parvisoflavone B (8) [54], alpinumisoflavone (9) [64], a mixture of 6b-hydroxystigmast-4-en-3-one (20) and 6b-hydroxystigmasta-4,22-dien-3-one (21) [65], a mixture of b-sitosterol (22) and stigmasterol (23) [66], and oleanolic acid (24) [67], were readily identified based on the data from the literature.…”
Section: Secondary Metabolites and Antimycobacterial Activities From mentioning
Bioassay-guided fractionation of the active AcOEt-soluble layer led to the isolation of two new pyranocoumarins, 3-hydroxyxanthyletin (1) and 3-methoxyxanthyletin (2), along with 22 known compounds including four simple coumarins, i.e., xanthyletin (3), umbelliferone (4), scopoletin (5), and (+)-(S)-marmesin (6); nine flavonoids, i.e., carpachromene (7), parvisoflavone B (8), alpinumisoflavone (9) genistein (10), 2'-hydroxygenistein (11), prunetin (12), cajanin (13), apigenin (14), and (2S)-naringenin (15); three benzenoids, i.e., 4-hydroxybenzaldehyde (16), vanillin (17), and (S)-lasiodiplodin (18); five steroids, i.e., ergosterol peroxide (19), a mixture of 6beta-hydroxystigmast-4-en-3-one (20) and 6beta-hydroxystigmasta-4,22-dien-3-one (21), and a mixture of beta-sitosterol (22) and stigmasterol (23); and one triterpenoid, i.e., oleanolic acid (24) from the roots of Ficus nervosa. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR as well as MS analyses. Among these isolates, 3-hydroxyxanthyletin (1), genistein (10), prunetin (12), and (2S)-naringenin (15) showed antimycobacterial activities against Mycobacterium tuberculosis H(37)R(V) in vitro with MIC values of 16, 35, 30, and < or =2.8 microg/ml, respectively.
“…The known isolates, i.e., xanthyletin (3) [50], umbelliferone (4) [51], scopoletin (5) [51], and (þ)-(S)-marmesin (6) [52], carpachromene (7) [53], parvisoflavone B (8) [54], alpinumisoflavone (9) [64], a mixture of 6b-hydroxystigmast-4-en-3-one (20) and 6b-hydroxystigmasta-4,22-dien-3-one (21) [65], a mixture of b-sitosterol (22) and stigmasterol (23) [66], and oleanolic acid (24) [67], were readily identified based on the data from the literature.…”
Section: Secondary Metabolites and Antimycobacterial Activities From mentioning
Bioassay-guided fractionation of the active AcOEt-soluble layer led to the isolation of two new pyranocoumarins, 3-hydroxyxanthyletin (1) and 3-methoxyxanthyletin (2), along with 22 known compounds including four simple coumarins, i.e., xanthyletin (3), umbelliferone (4), scopoletin (5), and (+)-(S)-marmesin (6); nine flavonoids, i.e., carpachromene (7), parvisoflavone B (8), alpinumisoflavone (9) genistein (10), 2'-hydroxygenistein (11), prunetin (12), cajanin (13), apigenin (14), and (2S)-naringenin (15); three benzenoids, i.e., 4-hydroxybenzaldehyde (16), vanillin (17), and (S)-lasiodiplodin (18); five steroids, i.e., ergosterol peroxide (19), a mixture of 6beta-hydroxystigmast-4-en-3-one (20) and 6beta-hydroxystigmasta-4,22-dien-3-one (21), and a mixture of beta-sitosterol (22) and stigmasterol (23); and one triterpenoid, i.e., oleanolic acid (24) from the roots of Ficus nervosa. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR as well as MS analyses. Among these isolates, 3-hydroxyxanthyletin (1), genistein (10), prunetin (12), and (2S)-naringenin (15) showed antimycobacterial activities against Mycobacterium tuberculosis H(37)R(V) in vitro with MIC values of 16, 35, 30, and < or =2.8 microg/ml, respectively.
“…The previously described − diols 3 and 4 have been obtained by catalytic osmium oxidation of 1 and 2 , respectively, using N -methylmorpholine N -oxide to regenerate the oxidizing agent (Scheme ). Treatment of cis diols 3 and 4 with excess Ac 2 O in pyridine afforded the corresponding diesters − 5 and 6 . 1 …”
Section: Resultsmentioning
confidence: 99%
“…(()-trans-4′-Hydroxy-3′-bromo-3′,4′-dihydroseselin ( 7) and (()-trans-4′-hydroxy-3′-bromo-3′,4′-dihydroxanthyletin (8) were obtained by treatment of 1 and 2, respectively, with NBS in aqueous THF solution. 11 The bromohydrins 7 and 8 were smoothly debrominated with tributyltin hydride, 11 to 9 and 10, respectively.…”
The synthesis of known (3-6) and new (7-10 and 14-22) coumarins in the seselin and xanthyletin series is described. The cytotoxic activity of compounds 3-22 was carried out in vitro on L-1210 cells. The most active compounds were 9, 16, 18, and 20 in the seselin series and 10, 17, and 19 in the xanthyletin series. Structure-activity relationships are discussed.
Das aus dem Kernholz von Chloroxylon swietenia isolierte Xanthyletin (I) liefert bei der Osmiumtetroxid‐Oxidation in Dioxan das cis‐Dihydroxydihydroxanthyletin perbenzoesäure (III) und Acetanhydrid gewonnenen Derivates (IV) entsteht.
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