A novel method for the prenylation of phenols has been developed using 2-methyl-but-3-ene-2-ol as the prenylating agent in the presence of Amberlyst 15. The prenylated catechols and quinols showed better antioxidant activity than the corresponding non-prenylated compounds in the in vitro DPPH and lipid peroxidation assay. The resorcinol derivatives did not show significant antioxidant activity.
NumataA, KanbaraS, TakahashiC, FujikiR, YonedaM, UsamiY, FujitaE. (1992) A cytotoxic principle of the brown alga Sargassum tortile and structures of chromenes. Phytochemistry, 31, 1209–1213
2.
BrownPE, LewisR, WaringMA. (1990) Studies of chromenes. Part 9. Syntheses of chromenequinones. Journal of Chemical Society Perkin Transaction1, 2979–2988
3.
SrivastavaR, ProkschP. (1991) Contact toxicity and feeding inhibitory activity of chromenes from Asteraceae against Spodoptera littoralis (Lepidoptera). Entemology General, 15, 265–274
4.
BergmannR, GerickeR. (1990) Synthesis and antihypertensive activity of 4-(1,2-dihydro-2-oxo-1-pyridyl)-2H-1-benzopyrans and related compounds, new potassium channel activators. Journal of Medicinal Chemistry, 33, 492–504
MerrillGB. (1989) Eupatoriochromene and encecalin, plant growth regulators from yellow starthistle (Centaurea solstitialis L.)Journal of Chemical Ecology, 15, 2073–2087
7.
SatohY, StantonJL, HutchisonAJ, LibbyAJ, KowalskiTJ, LeeWH, WhiteDH, KimbleEF. (1993) Substituted chromenes as potent, orally active 5-lipoxygenase inhibitors. Journal of Medicinal Chemistry, 36, 3580–3590.
8.
HoarauC, PettusTRR. (2003) Strategies for the preparation of differentially protected ortho-prenylated phenols. Synlett, 127–137
9.
AhluwaliaVK, AroraKK, JollyRS. (1982) Acid-catalysed condensation of isoprene with phenols. Formation of 2,2-dimethylchromans. Journal of Chemical Society Perkin Transaction1, 335–338
10.
AhluwaliaVK, AroraKK. (1981) Nuclear isoprenylation of polyhydroxyacetophenones: Acid catalysed condensation with isoprene. Tetrahedron, 37, 1437–1439
11.
DavesGD, MooreHW, SchwabDE, OlsenRK, WilczynskiJJ, FolkersK. (1967) Synthesis of 2-multiprenylphenols and 2-multiprenyl-6-methoxyphenols, biosynthetic precursors of the ubiquinones. Journal of Organic Chemistry, 32, 1414–1417
YamadaS, OnoF, KatagiriT, TanakaJ. (1977) The reaction of phenolic compounds with isoprenoids. VIII. The o-isoprenylation of phenols in the presence of metallic sodium. Bulletin of Chemical Society of Japan, 50, 750
14.
HowardBM, ClarksonK, BernsteinRL. (1979) Simple prenylated hydroquinone derivatives from the marine urchordate Aplidium californicum. Natural anticancer and antimutagenic agents. Tetrahedron Letters, 20, 4449–4452
15.
Van De WaterRW, MagdziakDJ, ChauJN, PettusTRR. (2000) New construction of ortho ring-alkylated phenols via generation and reaction of assorted o-quinone methides. Journal of the American Chemical Society, 122, 6502–6503
16.
JonesRM, Van De WaterRW, LindseyCC, HoarauC, UngT, PettusTRR. (2001) A mild anionic method for generating o-quinone methides: Facile preparations of ortho-functionalized phenols. Journal of Organic Chemistry, 66, 3435–3441.
17.
ReynoldsG, RodriguegE. (1979) Geranylhydroquinone: A contact allergen from trichomes of Phacelia crenulata. Phytochemistry, 18, 1567–1568
18.
RudaliG, MenetrierL. (1967) Action of geranyl-hydroquinone on different spontaneous and induced cancers in the mouse. Therapie, 22, 895–905.
19.
NjamenD, MbaforJT, FomumZT, KamanyiA, MbanyaJC, RecioMC, GinerRM, ManezS, RiosJL. (2004) Anti-inflammatory activities of two flavanones, sigmoidin A and sigmoidin B, from Erythrina sigmoidea. Planta Medica, 70, 104–107
20.
Savikin-FodulovicK, AljancicI, VajsV, MenkovicN, MacuraS, GojgicG, MilosavljevicS. (2003) Hyperatomarin, an antibacterial prenylated phloroglucinol from Hypericumatomarium ssp. degenii. Journal of Natural Products, 66, 1236–1238
21.
DanelutteAP, LagoJH, YoungMC, KatoMJ. (2003) Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth. Phytochemistry, 64, 555–559
22.
GilB, SanzMJ, TerencioMC, De GiulioA, De RosaS, AlcarazMJ, PayaM. (1995) Effects of marine 2-polyprenyl-1,4-hydroquinones on phospholipase A2 activity and some inflammatory responses. European Journal of Pharmacology, 285, 281–288
23.
CidadeHM, NacimentoMS, PintoMM, KijjoaA, SilvaAM, HerzW. (2001) Artelastocarpin and carpelastofuran, two new flavones, and cytotoxicities of prenyl flavonoids from Artocarpus elasticus against three cancer cell lines. Planta Medica, 67, 867–870.
24.
KalenaGP, JainA, BanerjeeA. (1997) Amberlyst 15 catalyzed prenylation of phenols: One step synthesis of benzopyrans. Molecules, 2, 100–105.
25.
PotteratO. (1997) Antioxidants and free radical scavengers of natural origin. Current Organic Chemistry, 1, 415–440.
26.
JoshiR, AdhikariS, PatroBS, ChattopadhyayS, MukherjeeT. (2001) Pulse radiolysis study on free radical scavenging behaviour of folic acid: Evidence for possible antioxidant activity. Free Radical Biology Medicine, 30, 1390–1399
27.
SubramanianM, ChintalwarGJ, ChattopadhyayS. (2002) Antioxidant properties of a Tinospora cordifolia polysaccharide. Redox Report, 7, 137–143
28.
AdhikariS, JoshiR, PatroBS, GhantyTK, ChintalwarGJ, SharmaA, ChattopadhyayS.MukherjeeT. (2003) Antioxidant activity of bakuchiol: Experimental evidences and theoretical treatments on the possible involvement of the terpenoid chain. Chemical Research Toxicology, 16, 1062–1069
29.
SubramanianM, SadakshariU, ChattopadhyayS. (2004) A mechanistic study on the nuclease activities of some hydroxystilbenes. Bioorganic Medicinal Chemistry, 12, 1231–1237.
30.
MellorsA, TappelAL. (1966) The inhibition of mitochondrial peroxidation by ubiquinone and ubiquinol. Journal of Biological Chemistry, 241, 4353–4356
31.
RekkaE, KourounakisPN. (1991) Effect of hydroxyethyl rutosides and related compounds on lipid peroxidation and free radical scavenging activity. Some structural aspects. Journal of Pharmaceutical Pharmacology, 43, 486–491.
32.
EscamesG, GuerreroJM, ReiterRG. (1997) Melatonin and vitamin E limit nitrite-induced lipid peroxidation in rat brain homogenates. Neoroscience Letters, 230, 147–150
33.
EsterbauerH. (1996) Estimation of peroxidative damage: A critical review. Pathologie Biologie(Paris), 44, 25–28
34.
BoxHC, MaccubbinAE. (1997) Lipid peroxidation and DNA damage. Nutrition, 13, 920–921
VisioliF, BordoneR, PeruginiC, BagnatiM, CauC, BellomoG. (2000) The kinetics of copper-induced LDL oxidation depend upon its lipid composition and antioxidant content. Biochemical Biophysical Research Communication, 268, 818–822
37.
LiegeoisC, LermusieauG, CollinS. (2000) Measuring antioxidant efficiency of wort, malt, and hops against the 2,2′-azobis(2-amidinopropane) dihydrochloride-induced oxidation of an aqueous dispersion of linoleic acid. Journal of Agricultural and Food Chemistry, 48, 1129–1134.
38.
HeijnenCG, HaenenGR, OostveenRM, StplersEM, BastA. (2002) Protection of flavonoids against lipid peroxidation: the structure activity relationship revisited. Free Radical Research, 36, 575–581
39.
HeijnenCGM, HaenenGR, van AckerFA, van der VijghWJ, BastA. (2001) Flavonoids as peroxynitrite scavengers: the role of the hydroxyl groups. Toxicology in vitro, 15, 3–6
40.
LucariniM, PedulliGF. (1994) Bond dissociation enthalpy of alpha-tocopherol and other phenolic antioxidants. Journal of Organic Chemistry, 59, 5063–5070.
41.
JovanovicSV, BooneCW, SteenkenS, TrigonaM, KaskeyRB. (2001) How Curcumin Works Preferentially with Water Soluble Antioxidants. Journal of the American Chemical Society, 123, 3064–3068.
42.
KoFN, ChengZJ, LinCN, TengCM. (1998) Scavenger and antioxidant properties of prenylflavones isolated from Artocarpus heterophyllus. Free Radical Biology Medicine, 25, 160–168
43.
KoHH, WangJJ, LinHC, WangJP, LinCN. (1999) Chemistry and biological activities of constituents from Morus australis. Biochimica Biophysica Acta, 1428, 293–299
44.
ChiYS, JongHG, SonKH, ChangHW, KangSS, KinSS. (2001) Effects of naturally occurring prenylated flavonoids on enzymes metabolizing arachidonic acid: Cyclooxygenases and lipoxygenases. Biochemical Pharmacology, 62, 1185–1191
45.
KimuraY, OkudaH, NomuraT, FukaiT, ArichiS. (1986) Effects of phenolic constituents from the mulberry tree on arachidonate metabolism in rat platelets. Journal of Natural Products, 49, 639–644.
46.
PatroBS, ReleS, ChintalwarGJ, ChattopadhyayS, AdhikariS, MukherjeeT. (2002) Protective activities of some phenolic 1,3-diketones against lipid peroxidation: Possible involvement of the 1,3-diketone moiety. ChemBioChem, 3, 364–370.
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