A new compound, (2S)-p-hydroxyphenethyl 2-bromo-2-methyldodeconate (1) and 7,3′-dimethoxy-5,4′-dihydroxy flavone, together with lupeol and stigmasterol were isolated from the stem bark of Citharexylum fruticosum (Verbenaceae). The structures of the compounds were established on the basis of the interpretation of NMR (1H, 13C, COSY and HMBC) spectra, as well as low and high-resolution mass spectrometric data. In this paper, we report on the structure elucidation of 1.
GribleG. (1996) Naturally occurring organohalogen compounds: a comprehensive review. In: HertzW, KirbyGW, MooreRE, SteglichW, TammC. (Eds.), Progress in the Chemistry of Organic Natural Products, Vol. 63. Springer Verlag, Vienna and New York, pp. 24–36.
2.
MuHL, WesenC, SundinP. (1997) Halogenated fatty acids. Formation and occurrence in lipids. Trac-trends in Analytical Chemistry, 16, 266–274.
3.
FusetaniN, SuganoM, MatsunagaS, HashimotoK. (1987) H,K-ATPase inhibitors from the marine sponge Siphnochalina truncata Absolute configuration of siphonodiol and two related metabolites. Tetrahedron Letters, 28, 4311–4312.
4.
BrantleySE, MolinskiTF, PrestonCM, DelongEF. (1995) Brominated acetylenic fatty acids from Xestospongia sp., a marine sponge bacteria association. Tetrahedron, 51, 7667–7672.
5.
CarballeiraNM, SostreA, StefanovK, PopovS, KujumigievA, Dimitrova-KonaklievaS, TostesonCG, TostesonTR. (1997) The fatty acid composition of a Vibrio alginolyticus associated with the alga Cladophora coelothrix. Identification of the novel 9-methyl-10-hexanedecenoic acid. Lipids, 32, 1271–1275.
6.
Van SoestRWM, FusetaniN, AndersenRJ. (1998) In Sponge Sciences: Multidisciplinary Perspectives; WatanabeY, FusetaniN, (Eds), Springer-Verlag, Tokyo, pp 3–30.
7.
LerchML, HarperMK, FaulknerJD. (2003) Brominated polyacetylenes from the Philippines sponge Diplastrella sp. Journal of Natural Products, 66, 667–670.
8.
Mac MillanJB, MolinskiTF. (2005) Majusculoic acid, a brominated cyclopropyl fatty acid from a marine cyanobacterial mat assemblage. Journal of Natural Products, 68, 604–606.
9.
QuinnRJ, TuckerD. (1991) Further acetylenic acids from the marine sponge Xestospongia testudinaria. Journal of Natural Products, 54, 290–294.
CrewsP, Kho-WisemanE. (1974) Cartilagineal. An unusual monoterpene aldehyde from a marine alga. Journal of Organic Chemistry, 39, 3303–3304.
25.
MynderseJS, FaulknerDJ. (1975) Polyhalogenated monoterpenes from the red alga Plocamium cartilagineum. Tetrahedron, 31, 1963–1967.
26.
Díaz-MarreroAR, DortaE, CuetoM, RovirosaJ, San-MartinA, DariasJ. (2004) Supporting the NMR-based empirical rules to determine the stereochemistry and halogen regiochemistry of vicinal vinyl dihalides. Naturally occurring monoterpenes as chemical models. Tetrahedron, 60, 5049–5052.
27.
JetterR, RiedererM. (1996) Cuticular waxes from the leaves and fruit capsules of eight Papaveraceae species. Canadian Journal of Botany, 74, 419–430.
28.
SteinbauerMJ, SchiestlFP, DaviesNW. (2004) Monoterpenes and epicuticular waxes help female autumn gum moth differentiate between waxy and glossy Eucalyptus and leaves of different ages. Journal of Chemical Ecology, 30, 1117–1142.
29.
AnjaneyuluASR, MadhusudhanaRA., KameswaraRV, RamachandraRL, PelterA, WardRS. (1975) The isolation and structure of 6″-bromo-isoarboreol –the first bromine containing lignan. Tetrahedron Letters, 52, 4697–4700.