Sileneoside H, a New Phytoecdysteroid from Silene brahuica

Abstract

Sileneoside H (1), a new phytoecdysteroid, has been isolated from the roots of Silene brahuica and identified as 22-O-alpha-D-galactosylintegristerone A 25-acetate by MS and NMR analysis.

Ecdysteroid Glycosides from Sida rhombifolia L.

“…This could be accounted by the presence of a 25-AcO group, with signals at d(C) 22.7 and a 170.7. Due to the above AcO group, the signals for Me(26) and Me(27) appeared as two individual singlets, instead of one, as observed for ecdysone (4) 1 ) and 20-hydroxyecdysone (5) [11]. C-NMR spectra of 2 (Table) revealed an ecdysteroid glycoside.…”

Rapid Characterization of Components in Bolbostemma paniculatum by UPLC/LTQ-Orbitrap MSn Analysis and Multivariate Statistical Analysis for Herb Discrimination

“…At last, the fragment m/z 233 dehydrated at C 1 to generate the fragment ion m/z 215 [M − 200 + H] + . In this way, other 14 sterols were identified or tentatively identified, including stigmasta-7,16,25-triene-3-ol (peak 20) [ 19 ], stigmasta-7,22,25-triene-3-ol (peak 23) [ 20 , 21 ], uzarigenin-3-β-sophoroside (peak 43) [ 22 ], sileneoside H (peak 45) [ 23 ], daucosterol (peak 46) [ 20 ], frugoside (peak 47) [ 24 ], stigmasta-7,22,25-triene-3- O -β- d -glucopyranoside (peak 48) [ 20 , 21 ], integristerone A-25-acetate (peak 50) [ 25 ], 24(28)-dehydromakisterone A (peak 51) [ 26 ], β-sitosterol palmitate (peak 53) [ 18 ], stigmasta-7,22,25-triene-3- O -β- d -(6′-palmitoyl) glucopyranoside (peak 54) [ 27 ], stigmasta-7,22,25-triene-3- O -nonadecanoic acid ester (peak 55) [ 21 , 27 ], (3β,22E)-stigmasta-7,22,25-trien-3-yl-β- d -glucopyranoside (peak 59) [ 20 , 21 ] and 3-oxo-androsta-1,4-dien-17a′-spiro-2′-3′-oxo-oxetane (peak 60) [ 28 ], respectively. Among them, uzarigenin-3-β-sophoroside, sileneoside H, frugoside, integristerone A-25-acetate, 24(28)-dehydromakisterone A and 3-oxo-androsta-1,4-dien-17a′-spiro-2′-3′-oxo-oxetane were identified from the genus of Bolbostemma for the first time.…”

The phytochemical, biological, and medicinal attributes of phytoecdysteroids: An updated review

“…Thirty-six new ecdysteroids have been reported from the Caryophyllaceae family. The new ecdysteroids are integristerone A 25-acetate ( 93 ), isolated from Silene brahuica 81 , japonicone (22,25-epoxy-24-methylene-2,3,14,20-tetrahydroxycholest-7 - en - 6-one) ( 94 ), isolated from Sagina japonica 82 , 2-dehydroxyecdysterone-3- O -benzoate ( 95 ) 83 , 2-deoxyecdysterone-25-acetate ( 96 ) 84 , isolated from Silene wallichiana , 5 α -2-deoxy-20-hydroxyecdysone 20,22-acetonide ( 97 ) 85 , makisterone C 2,3; 20,22-diacetonide ( 98 ) 85 isolated from Silene viridiflora , (11 α )-11-hydroxyshidasterone [(2 β ,3 β ,5 β ,11 α ,22 R )-22,25-epoxy-2,3,11,14,20-pentahydroxycholest-7-en-6-one] ( 99 ), (2 β ,3 β ,5 β ,14 β ,22 R )-2,3,20,22,25-pentahydroxycholest-7-en-6-one ( 100 ), (2 β ,3 α ,5 β ,14 α ,22 R )-2,3,20,22,25-pentahydroxycholest-7-en-6-one ( 101 ), 22-dehydro-20-deoxy ajugasterone C ( 102 ), 1-hydroxy-22-deoxy-20,21-didehydro ecdysone ( 103 ), 22-deoxy-20,21-didehydro ecdysone ( 104 ), ponasterone A-22-apioside (2 β ,3 β ,14 α ,20 R -tetrahydroxy-22-{[3,4-dihydroxy-4-(hydroxymethyl)-tetrahydrofuran-2-yl]oxy}-5 β -cholest-7-en-6-one) ( 105 ), 3- epi -shidasterone [22,25-epoxy-2 β ,3 α ,14 α ,20 R )-tetrahydroxy-5 β -cholest-7-en-6-one] ( 106 ), isolated from S. wolffii 86 , 87 , 88 , 26-hydroxyintegristerone A ( 107 ), isolated from Silene frivaldszkyana 89 , 2-deoxy-20-hydroxyecdysone 25-glucoside ( 108 ), isolated from Silene gigantean 89 , 2-deoxy-5,20,26-trihydroxy ecdysone ( 109 ), 5,20,26-trihydroxyecdysone 20,22-acetonide ( 110 ), 2-deoxy-5,20,26-trihydroxyecdysone 20,22-acetonide ( 111 ), 20,26-dihydroxyecdysone 20,22-acetonide ( 112 ), 20-hydroxyecdysone 20,22-monoacetonide-25-acetate ( 113 ), 2,22-diacetate-20,26-dihydroxyecdysone ( 114 ), 3,22-diacetate-20,26-dihydroxyecdysone ( 115 ), isolated from S. viridiflora 90 , 91 , 92 , 22- O - α - d -galactosylintegristerone A 25-acetate (sileneoside H) ( 116 ), isolated from S. brahuica 93 , 9 α ,20-dihydroxyecdysone ( 117 ), 9 β ,20-dihydroxyecdysone ( 118 ), isolated from Silene italic ssp. n emoralis 94 , 95 , 3 -O-β - d -glucopyra...…”