Two New Nortriterpenoid Glycosides and a New Phenylpropanoid Glycoside from the Bulbs of <i>Scilla scilloides</i>

Abstract

Two new norlanostane-type triterpenoid glycosides and a new phenylpropanoid glycoside were isolated from the bulbs of Scilla scilloides DRUCE (Liliaceae), along with two known alkaloids. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.

Inhibitory effects of the ethyl acetate extract from bulbs ofScilla scilloideson lipoxygenase and hyaluronidase activities

“…The obtained plant was subsequently identified by Professor Dr. Toshihiro Nohara (Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto Prefecture, Japan) where the voucher specimen (SCK2005) was deposited at the laboratory of Natural Products Chemistry, School of Agriculture, Tokai University, Kumamoto, Japan. This batch (SCK2005, same as the identification reference) has been used for chemical analyses (Nishida et al, 2008;Ono et al, 2011Ono et al, , 2012Ono et al, , 2013 and further bioassays. Lipoxygenase type I-B, nordihydroguaiaretic acid (NDGA), hyaluronidase from bovine testis type IV-S, compound 48/80, and lipopolysaccharide (LPS) from Escherichia coli were purchased from Sigma-Aldrich Co. (St. Louis, MO).…”

“…Using a same batch of S. scilloides (SCK2005), we have previously separated and isolated nine homoisoflavones and other compounds from the bulbs of this plant by methanol (MeOH) extraction (Nishida et al, 2008;Ono et al, 2011Ono et al, , 2012Ono et al, , 2013. All the chemicals previously isolated and nine homoisoflavones (1-9) used in this study are compiled in Table 1.…”

Chemical Constituents of the Bulbs of Scilla peruviana and Their Pancreatic Lipase Inhibitory Activity

“…The MeOH-eluted fraction was passed through column chromatography (CC) on silica gel and octadecylsilanized (ODS) silica gel, producing 4 – 11 and 14 – 17 . Compounds 4 – 11 and 14 – 17 were identified as peruvianoside A ( 4 ) [ 7 ], peruvianoside B ( 5 ) [ 7 ], (23 S ,25 R )-3β,31-dihydroxy-17α,23-epoxy-5α-lanost-8-en-23,26-olactone3β- O -[ O -α- l -rhamnopyranosyl-(1→2)- O -β- d -gluco-pyranosyl-(1→2)- O -α- l -arabinopyranosyl-(1→6)- O -β- d -glucopyranoside] (scillascilloside D-2) ( 6 ) [ 10 ], (23 S ,25 R )-3β,30,31-trihydroxy-17α,23-epoxy-5α-lanost-5-en-23,26-olactone3- O -[ O -α- l -rhamno-pyranosyl-(1→2)- O -β- d -glucopyranosyl-(1→2)- O -α- l -arabinopyranosyl-(1→6)- O -β- d -glucopyranoside] ( 7 ) [ 10 ], (23 S ,25 R )-3β,31-dihydroxy-17α,23-epoxy-5α-lanost-8-en-23,26-olactone 3β- O -[ O -β- d -glucopyranosyl-(1→3)- O -[α- l -rhamnopyranosyl-(1→2)]- O -β- d -glucopyranosyl-(1→2)- O -α- l -arabinopyranosyl-(1→6)- O -β- d -glucopyranoside] (scillanoside L-2) ( 8 ) [ 17 ], 15-deoxy-eucosterol3β-[ O -β- d -glucopyranosyl-(1→3)- O -[α- l -rhamnopyranosyl-(1→2)]-β- d -glucopyranosyl-(1→2)- O -α- l -arabinopyranosyl-(1→6)- O -β- d -glucopyranoside] (scillascilloside E-1) ( 9 ) [ 9 ], 15-deoxy-30-hydroxyeucosterol3β-[ O- β- d -glucopyranosyl-(1→3)- O -[α- l -rhamnopyranosyl-(1→2)]-β- d -glucopyranosyl-(1→2)- O -α- l -arabinopyranosyl-(1→6)- O -β- d -glucopyranoside] (scillanoside L-1) ( 10 ) [ 17 ], scillanostaside G ( 11 ) [ 18 ], (3 R )-5,7-dihydroxy-6-methoxy-3-(4′-methoxybenzyl)-chroman-4-one ( 14 ) [ 19 ], (3 R )-5,7-dihydroxy-3-(4′-hydroxybenzyl)-6-methoxy-chroman-4-one ( 15 ) [ 20 ], and (3 S )-6,7-dimethoxy-5-hydroxy-3-(4′-hydroxybenzyl)-chroman-4-one ( 16 ) [ 21 ], and (3 R )-5,7-dihydroxy-3-(4′-methoxybenzyl)-chroman-4-one ( 17 ) [ 22 ] ( Figure 1 ). This is the first report on the isolation of 8 , 10 , 11 , and 14 – 17 from S. peruviana .…”

Biophysical characterization of antibacterial compounds derived from pathogenic fungi Ganoderma boninense

“…In nature, 27-norlanostane triterpenes are rare. Examples include eight 27-norlanostane saponins from Muscari paradoxam and 14 and 10 norlanostane saponins from Scilla scilloides (Kuroda et al, 2004;Ono et al, 2012Ono et al, , 2013. Previously, Ma et al (2014) isolated a similar compound with consider- Compound class Note 1,5,5′-Trimethyl-4,8-dioxo-6-isopropenyl-8′-ethyl-5′,8′epoxy-4a,8a-didehydro-1,4′-ethanospiro[decalin-2,3′oxocane]-5-propionic acid methyl ester 3,4-seco-27-norlanostane triterpene Ma et al (2014) had done NMR analysis of almost similar compound (based on NMR spectroscopy analysis), with proposed name Ganoboninketal a The highest three possible-optimized conformers (based on 2a configuration in Fig.…”