Chemical investigation of the stems of Seseli praecox (Gamisans) Gamisans, an endemic Apiaceae from Sardinia, afforded an isopropenylated chromone (5-hydroxy-6-(2-Z-butenyl-3-hydroxymethyl)-7-methoxy-2-methylchromone), along with four known linear furocoumarins and their natural precursor. For biological characterization the new compound was screened against four cancer cell lines in vitro and showed differential μM antiproliferative effects between suspension and adherent cells.
LeontiM, CasuL, SannaF, BonsignoreL. (2009) A comparison of medicinal plant use in Sardinia and Sicily – De Materia Medica revisited?Journal of Ethnopharmacology, 121, 255–267.
2.
LeontiM, NebelS, RiveraD, HeinrichM. (2006) Wild gathered food plants in the European Mediterranean: A comparative analysis. Economic Botany, 60, 130–142.
3.
BerendesJ. (1902) Des Pedanios Dioskurides aus Anazarbos Arzneimittellehre in Fünf Büchern. Book 3, Chap. 53. EnkeF., Stuttgart.
4.
MatthioliA. (1967) I Discorsi di M. Pietro Andrea Mattiholi. Sanese, Medico Cesareo, et del Serenissimo Principe Ferdinando Archiduca d'Austria & c. Nelli Sei Libri Di Pedacio Dioscoride Anazarbeo della Materia Medicale. Vincenzo Valgrisi, Venezia. Book 3, Chap. 55. Anastatic reproduction of the edition from 1568 in 6 volumes, Rome.
5.
AustinPW, SeshadriTR, SoodMS, VishwaP. (1968) Components of Seseli sibiricum. Constitution and synthesis of sibiricin, a new coumarin. Tetrahedron, 24, 3247–3253.
BergendorffO, DekermendjianK, NielsenM, ShanR, WittR, AiJ, SternerO. (1997) Furanocumarins with affinity for brain benzodiazepine receptors in vitro. Phytochemistry, 44, 1121–1124.
11.
ElgamalMHA, ElewaNH, ElkhrisyEAM, DuddeckH. (1979) 13C NMR chemical shifts and carbon-proton coupling constants of some furocoumarins and furochromones. Phytochemistry, 18, 139–143.
12.
KusterRM, BernardoRR, Da SilvaAJR, ParenteJP, MorsWB. (1994) Furocoumarins from the rhizomes of Dorstenia brasiliensis. Phytochemistry, 36, 221–223.
13.
IshiiH, SekiguchiF, IshikawaT. (1981) Studies on the chemical constituents of Rutaceous plants – XLI. Absolute configuration of rutaretin methyl ether. Tetrahedron, 37, 285–290.
14.
SavinaAA, Perel'sonME, Ban'kovskiiAI, NikonovGK. (1970) The structure of seselirin: A new chromone from the roots of Seseli sessilifolium. Chemistry of Natural Compounds, 6, 419–422.
15.
CzepaA, HofmannT. (2003) Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree. Journal of Agricultural and Food Chemistry, 51, 3865–3873.
16.
CisowskiW, GrimshawJ. (1988) Glucoside of chromone from Angelica archangelica L. and Archangelica litoralis Fries. herbs. Polish Journal of Chemistry, 62, 135–140.
17.
HarkarS, RazdanTK, WaightES. (1984) Steroids, chromone and coumarins from Angelica officinalis. Phytochemistry, 23, 419–426.
18.
RazdanTK, QadriB, HarkarS, WaightES. (1987) Chromones and coumarins from Skimmia laureola. Phytochemistry, 26, 2063–2069.
19.
HuCQ, ChangJJ, LeeKH. (1990) Antitumor agents, 115. Seselidiol, a new cytotoxic polyacetylene from Seseli mairei. Journal of Natural Products, 53, 932–935.
20.
ZidornC, JoehrerK, GanzeraM, SchubertB, SigmundEM, MaderJ, GreilR, EllmererEP, StuppnerH. (2005) Polyacetylenes from Apiaceae vegetables carrot, celery, fennel, parsley and parsnip and their cytotoxic activities. Journal of Agricultural and Food Chemistry, 53, 2518–2523.
21.
LeontiM, CasuL, RadunerS, CottigliaF, FlorisC, AltmannKH, GertschJ. (2010) Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin. Biochemical Pharmacology, doi: 10.1016/j.bcp.2010.02.015, in press.
22.
HilmiF, GertschJ, BremnerP, ValovicS, HeinrichM, SticherO, HeilmannJ. (2003) Cytotoxic versus anti-inflammatory effects in HeLa, Jurkat T and human peripheral blood cells caused by guaianolide-type sesquiterpene lactones. Bioorganic & Medicinal Chemistry, 11, 3659–3663.
23.
FeyenF, GertschJ, WartmannM, AltmannKH. (2006) Design and synthesis of 12-aza-epothilones (azathilones) - “non-natural” natural products with potent anticancer activity. Angewandte Chemie International Edition, 45, 5880–5885.