Agastaquinone, a New Cytotoxic Diterpenoid Quinone from Agastache rugosa

Abstract

A new diterpenoid quinone, agastaquinone [1], was isolated from the roots of Agastache rugosa. An oxime derivative [2] of agastaquinone was prepared with hydroxylamine hydrochloride. The structure of agastaquinone [1] was established as 7-hydroxy-12-methoxy-20-norabieta-1,5(10),6,8,12-pentaene-3,11,14- trione by spectroscopic techniques. Compounds 1 and 2 showed nonspecific cytotoxic activities against several human cancer cell lines in vitro (A549, SK-OV-3, SK-MEL-2, XF498, and HCT15).

Phytochemistry and bioactivity of aromatic and medicinal plants from the genus Agastache (Lamiaceae)

“…Various extraction techniques were applied: maceration at ambient or elevated temperature, reflux extraction, infusions and decoctions in hot water. The extracts were usually dried under reduced pressure or by lyophilization (Itokawa et al 1981; Ganeva et al 1994; Lee et al 1995, 2002, 2007, 2008; Kim et al 1999; Molina-Hernandez et al 2000; Suvitayavat et al 2004; Vera-Montenegro et al 2008; Xu et al 2008; Hernandez-Abreu et al 2009, 2011, 2013; Gonzalez-Trujano et al 2012). …”

“…Non-volatile analysis was usually made with reversed phase HPLC using C18 silica columns eluted with acetonitrile/water or methanol/water mixtures, with photometric detection. Individual isolated compounds were identified by routine spectroscopic methods such as 1 H and 13 C NMR, UV/VIS, infrared, and mass spectrometry (RA—Kim et al 1999; acacetin, tilianin, agastachoside, linarin—Zakharova et al 1980; thymol, myrcene, limonene, β-caryophyllene, pulegone, menthone, isomenthone, camphor, linalyl acetate, linalool, β-phellandrene—Skakovskii et al 2010; acacetin, tilianin, isoagastachoside, agastachin—Itokawa et al 1981; Hernandez-Abreu et al 2009; agastinol, agastenol—Lee et al 2002, agastaquinone—Lee et al 1995). …”

“…The compounds were mostly purified using column chromatography on silica gel eluted with various solvents, sometimes preceded by liquid–liquid extraction:Chloroform–methanol mixture, methanol–water mixture, chloroform–methanol mixture, methanol (RA—Kim et al 1999; tilianin–Hong et al 2001; agastinol, agastenol—Lee et al 2002);Petroleum ether-acetone mixture (estragole, methyleugenol—Li et al 2013);Ethyl acetate/n-hexane gradient n-hexane/chloroform/methanol (for the elution of fractions) (agastaquinone—Lee et al 1995);Hexane–ethyl acetate ( l -pulegone—Maruyama et al 2002, Estrada-Reyes et al 2004; estragole, triterpenoids, flavonoids—Estrada-Reyes et al 2004). …”

“…Ethyl acetate/n-hexane gradient n-hexane/chloroform/methanol (for the elution of fractions) (agastaquinone—Lee et al 1995);…”

Essential oil composition of Agastache anethiodora Britton (Lamiaceae) infected by cucumber mosaic virus (CMV)

“…15,16 Non-volatile diterpenoids and lignans from this species also showed various biological activities, ranging from HIV integrase and apoptosis inhibition to cytotoxic activity. 17,18 Moreover, giant hyssop is also reputed as a source of nectar for honey bees, 19 a process in which the floral scent is deeply involved.…”