A re-investigation of the methanolic extract of the aerial parts of Tanacetum santolinoides has resulted in the isolation of a new sesquiterpene, tanacetonic acid (1), along with three known methoxylated flavonoids. The structure of the isolated compounds was secured based on their IR, UV, 1D and 2D (1H-1H COSY, HSQC and HMBC) NMR spectroscopic and FAB mass spectral characteristics. The new sesquiterpene showed a significant cytotoxic activity when tested using the brine shrimp bioassay, while the three flavonoids demonstrated anti-inflammatory effects in the rat paw oedema test.
(a) GuerraJA, MolinaMF, AbadMJ, VillarAM, PaulinaB. (2006) Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids isolated from Tanacetum microphyllum.International Immunopharmacology, 6, 1723–1728
2.
(b) JainNK, KulkarniSK (1999) Antinociceptive and anti-inflammatory effects of Tanacetum parthenium L. extract in mice and rats. Journal of Ethnopharmacology, 68, 251–259
3.
(c) GorenN, WoerdenbagHJ, Bozok-JohanssonC. (1996) Cytotoxic and antibacterial activities of sesquiterpene lactones isolated from Tanacetum praeteritum subsp. praeteritum. Planta Medica, 62, 419–422
(e) BukhariIA, KhanRA, GilaniAU, ShahAJ, HussainJ, AhmedVU. (2007) The analgesic, anti-inflammatory and calcium antagonist potential of Tanacetum artemisioides.Archives of Pharmacal Research, 30, 303–312
6.
(f) TiumanTS, Ueda-NakamuraT, Garcia CortezDA, Dias FilhoBP, Morgado-DiazJA, de SouzaW, NakamuraCV. (2005) Antileishmanial activity of parthenolide, a sesquiterpene lactone isolated from Tanacetum parthenium.Antimicrobial Agents and Chemotherapy, 49, 176–182
7.
(g) LahlouS, TahraouiA, IsrailiZ, LyoussiB. (2007) Diuretic activity of the aqueous extracts of Carum carvi and Tanacetum vulgare in normal rats. Journal of Ethnopharmacology, 110, 458–463
8.
(h) TepeB, SokmenA. (2007) Screening of the antioxidant properties and total phenolic contents of three endemic Tanacetum subspecies from Turkish flora. Bioresource Technology, 98, 3076–3079
9.
(i) SusurlukH, CaliskanZ, GuerkanO, KirmiziguelS, GoerenN. (2007) Antifeedant activity of some Tanacetum species and bioassay guided isolation of the secondary metabolites of Tanacetum cadmeum ssp. cadmeum (Compositae). Industrial Crops and Products, 26, 220–228
10.
(j) PetrovicSD, DobricS, BokonjicD, NiketicM, MerfortI, Garca-PineresA. (2003) Evaluation of Tanacetum larvatum for anti-inflammatory activity and for the protection against indomethacin-induced ulcerogenesis in rats. Journal of Ethnopharmacology, 87, 109–113
11.
(k) ShrivastavaR, PechadreJC, JohnGW. (2006) Tanacetum parthenium and Salix alba (Mig-RL) combination in migraine prophylaxis: a prospective, open-label study. Clinical Drug Investigation, 26, 287–296.
12.
TackholmV. (1974) Students, Flora of Egypt. Anglo-Egyptian Book Shop, Cairo. pp. 579–580.
MarcoJA, Sanz-CerveraJF. (1990) New sesquiterpene lactones and acetylenes from Chrythanthemum lavandulifolium.Tetrahedron, 46, 6931–6938.
18.
TalzhanovNA, MukanovRM, RalduginVA, ShakirovMM, AtazhanovaGA, AdekenovSM. (2005) Dihydroridentin from Artemisia ponica and its stereochemistry. Chemistry of Natural Compounds, 423–425.
19.
MeyerBN, FerrigniNR, PutnamJE, JacobsenLB, NicholsDE, McLaughlinJL. (1982) Brine shrimp: A convenient general bioassay for active plant constituents. Planta Medica, 45, 31–34.
20.
GonzalezAG, HerreraJR, LuisJG, RaveloAG, FerroEA. (1988) Terpenes and flavones of Salvia cardiophylla.Phytochemistry, 27, 1540–1541.
HongYC, SuJC, BeomSH, HoJH, HyeGK, MiJK, DongHS. (2004) Low-molecular weight flavonoids extracted from Artemisia absinthium inhibiting acetylcholinesterase activity and protecting neural cells and extracting process thereof. Republic of Korean Kongkae Taeho Kongbo, No page numbers given. CODEN: KRXXA7 KR 2004094081 A 20041109 patent written in Korean.
23.
DellaLR, SosaS, TubaroA, MorazzoniP, BombardelliE, GriffiniA. (1996) Oxo-anti-inflammatory activity of Ginkgo biloba constituents and of their phospholipid complexes. Fitoterapia, 67, 257–264
