Three New Nortriterpene Glycosides and Two New Triterpene Glycosides from the Bulbs of Scilla scilloides

Abstract

Scilla scilloides DRUCE is a perennial herb belonging to the Liliaceae family. The bulb of this plant has been used as a foodstuff, a traditional medicine for promoting blood circulation, an anti-inflammatory agent, and an analgesic.1) With regard to the chemical constituents of this bulb, the presence of homoisoflavones, norlanostane-type triterpenes, and lanostane-type triterpenes has been reported. [2][3][4][5][6] In a previous paper, 7) we reported the isolation and structural elucidation of a new homostilbene and two new homoisoflavones from the methanol (MeOH) extract of fresh bulbs of S. scilloides along with 13 known compounds consisting of a homostilbene, seven homoisoflavones, a xanthone, a lignan, and three norlanostane-type triterpenes. As part of an ongoing study of this plant, we describe the isolation and structural characterization of three new norlanostane-type triterpene glycosides and two new lanostane-type triterpene glycosides along with one known norlanostane-type triterpene glycoside from the MeOH extract. 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan: and d Faculty of Pharmaceutical Sciences, Sojo University; 4-22-2 Ikeda, Kumamoto 860-0082, Japan. Received June 17, 2011; accepted August 18, 2011; published online August 23, 2011 Three new norlanostane-type triterpene glycosides, scillanostasides A, B, and C, and two new lanostane-type triterpene glycosides, scillanostasides D and E, were isolated from the bulbs of Scilla scilloides DRUCE (Liliaceae) along with one known norlanostane-type triterpene heptaglycoside, scillascilloside G-1. 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.…”

Five New Nortriterpenoid Glycosides from the Bulbs of <i>Scilla scilloides</i>

“…1). Furthermore, the assigned 13 C-NMR spectral data of Agl and the sugar moiety were considerably similar to those of scillanostaside C 8) and (23R)-17α,23-epoxy-3β,29-dihydroxy-27-nor-lanost-8-ene-15,24-dione 11) respectively. The structure of 1 was thus concluded to be 15-deoxyeucosterol…”

Scillapersicene: a new homoisoflavonoid with cytotoxic activity from the bulbs ofScilla persicaHAUSSKN

“…According to previous studies on Scilla species, they contain alkaloids (Kato et al 2007), cardiac glycosides (Kamano & Petit 1974), triterpenoids (Mimaki et al 1993;Nishida et al 2008), triterpenoid glycosides (Arjune & Klar 2011;Ono et al 2011), nortriterpenoid glycosides (Ono et al 2011(Ono et al , 2013, eucosterol oligoglycosides (Lee et al 2002), stilbenoids (Bangani et al 1999;Nishida et al 2008), xanthone, lignin and phenylpropanoid glycoside (Nishida et al 2008), as well as homoisoflavanones (Heller & Tamm 1981;Bangani et al 1999;Silayo et al 1999;Mutanyatta et al 2003;Shim et al 2004;Nishida et al 2008;Hafez Ghoran et al 2014). These compounds possess antibacterial and antiangiogenic activities, and inhibit in vitro the growth of several microorganisms (Heller & Tamm 1981;Srinivas et al 2003;Shim et al 2004).…”