The photodynamic properties of two quinones, 4-methoxydalbergione (DS1) and sissoidenone (DS2), and a coumarin, dalbergin {6-hydroxy-7-methoxy-4-phenylcoumarin, (DS3)}, have been studied. Photogeneration of singlet oxygen (1O2) was monitored by both optical and EPR methods. Based on RNO bleaching, relative to Rose Bengal (RB), the singlet oxygen generating efficiencies of DS1, DS2, and DS3 were determined as 0.10, 0.051 and 0.041, respectively. Using the SOD inhibitable cytochrome c reduction assay, the photogeneration of superoxide anion (O2-•) was monitored. The formation of O2-• was enhanced in the presence of electron donors such as EDTA, DETAPAC and NADH. Photolysis of DS1 and DS3 in DMSO in the presence of 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) generated a twelve line EPR spectrum characteristic of an O2-• adduct. In the photosensitization of the DS series, both Type I and Type II paths were involved. The quantum mechanically calculated lowest unoccupied molecular orbital (LUMO) energies of DS1 and DS2 were correlated with the experimental redox potential. Photoinduced DNA scission by DS1, DS2, and DS3 confirms the generation of O2-• from these metabolites.
BruceJM. (1974) Benzoquinones and related compounds. In Rodd's Chemistry of Carbon Compounds, Vol. III, part 4, 2nd ed., CoffeyS. (Ed). Elsevier, Amsterdam. 1–306.
2.
DichancaiteE, CenasN, KalvelyteA, SerapinieneN. (1999) Toxicity of daunorubicin and naphthaquinones to HL-60 cells: an involvement of oxidative stress. Biochemistry and Molecular Biology International, 41, 987–994.
3.
RaviP, NarayananV, RamanPV. (1989) A novel quinone from Dalbergia sissoides Grah. Indian Journal of Chemistry, 28B, 778–779.
4.
AhluwaliaVK, SeshadriTR. (1963) Dalbergenone from the heartwood of Dalbergia sissoo. Current Science, 32, 455.
5.
HookerJD. (1951) Flora of British India, L. Reeve and Co. Ltd., Kent, England, Vol. 2, p.235.
6.
The Useful Plants of India (1986) Council of Scientific and Industrial Research, New Delhi, p.161.
7.
BeldjoudiN, MambuL, LabaiedM, GrellierP, RamanitrahasimbolaD, RasoanaivoP, MartinMT, FrappierF. (2003) Flavonoids from Dalbergia louvellii and their antiplasmodial activity. Journal of Natural Products, 66, 1447–1450.
8.
WangS, ZhengZ, WengY, YuY, ZhangD, FanW, DaiR, HuA. (2004) Angiogenesis and anti-angiogenesis and activity of Chinese medicinal herbal extracts. Life Sciences, 74, 2467–2478.
CotaRH, Grassi-KassisseDM, Spadari-BratfischRC, Souza BritoAR. (1999) Anti-ulcerogenic mechanisms of a lyophilized aqueous extract of Dalbergia monetaria L. in rats, mice and guinea pigs. Journal of Pharmacy and Pharmacology, 51, 735–740.
11.
GundidzaM, GazaN. (1993) Antimicrobial activity of Dalbergia melanoxylon extracts. Journal of Ethnopharmacology, 40, 127–130.
12.
Hye HumayunKM, GafurMA. (1975) Anti-inflammatory activity of Dalbergia sissoo leaves. The Indian Journal of Medicinal Research, 63, 93–100.
13.
TakahashiM, FuchinoH, SatakeM, AgatsumaY, SekitaS. (2004) In vitro screening of leishmanicidal activity in Myanmar timber extracts. Biological and Pharmaceutical Bulletin, 27, 921–925.
14.
ItoC, ItoigawaM, KanematsuT, RuangrungsiN, HigashiharaH, TokudaH, NishinoH, FurukawaH. (2003) New cinnamylphenols from Dalbergia species with cancer chemopreventive activity. Journal of Natural Products, 66, 1574–1577.
15.
GambleJS. (1979) Flora of the Presidency of Madras, SinghBishen, Pal SinghMahendran, Dehradun, India, Vol. 1. p. 387.
16.
RajendranM, RamasamyS, RajamanickamC, GandhidasanR, MurugesanR. (2003) Photodynamic effects of two hydroxyanthraquinones. Biochemica et Biophysica Acta, 1622, 65–72.
17.
ChanSC, ChangYS, WangJP, ChenSC, KuoSC. (1998) Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera. Planta Medica, 64, 153–158.
18.
DiwuZJ, LownJW. (1995) Photosensitization with anticancer agents. 20-EPR studies on the photodynamic action of phleichrome: formation of semiquinone radical and activated oxygen species on illumination with visible light. Free Radical Biology and Medicine, 18, 357–363.
19.
DiwuZJ, LownJW. (1993) Photosensitization with anticancer agents: 15. Perylenequinonoid pigments as potential photodynamic therapeutic agents: formation of semiquinone radicals and reactive oxygen species on illumination. Journal of Photochemistry and Photobiology, B: Biology, 18, 131–143.
20.
LeeM, RoldanMC, HaskellMK, McAdamSR, HartleyJA. (1994) In vitro photoinduced cytotoxicity and DNA binding properties of psoralen and coumarin conjugates of netrospin analogues: DNA sequence directed alkylation and cross-link formation. Jounal of Medicinal Chemistry, 37, 1208–1213.
21.
BeckerRS, ChakravortiS, GarterCA. (1993) Photosensitizers: comprehensive photophysics/photochemistry and theory of coumarins, chromones, their homologues and thione analogues. Journal of the Chemical Society, Faraday Transactions, 89, 1007–1019.
22.
(a) PotapenkoAJ. (1991) Mechanisms of photodynamic effects of furocoumarins. Journal of Photochemistry and Photobiology, B: Biology, 9, 1–33;
23.
BruceJM. (1974) Benzoquinones and related compounds. In Rodd's Chemistry of Carbon Compounds, Vol. III, part 4, 2nd ed., CoffeyS. (Ed). Elsevier, Amsterdam. 1–306.
24.
De MolNJ, BeijersbergenGM.J, HenegoumenV, WeedaB, KnoxCW, TruscottTG. (1986) Photobinding of psoralens to bacterial macromolecules in situ and induction of genetic effects in a bacterial test system. Effects of singlet diagnostic aids D2O and DABCO. Photochemistry and Photobiology, 44, 747–755.
25.
KraljicI, El MohsniS. (1978) A new method for the detection of singlet oxygen in aqueous solution. Photochemistry and Photobiology, 28, 577–581.
26.
GandinE, LionY, Van de VorstAJ. (1983) Quantum yield of singlet oxygen production by xanthene derivatives. Photochemistry and Photobiology, 37, 271–278.
27.
ELionY. (1982) Mechanisms of photobleaching investigated by fluorescence spectroscopy. Photochemistry and Photobiology, 20, 77–81.
28.
WilkinsonE, BrummerJG. (1981) Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen solution. Journal of Physical Chemistry Reference Data, 10, 809–999.
29.
KrishnaCM, UppuluriS, RieszP, ZiglerSJJr, BalasubramanianDA. (1991) A study of the photodynamic efficiencies of some eye lens constituents. Photochemistry and Photobiology, 54, 51–58
30.
GandinE, LionY, Van de VorstA. (1979) Production of radicals by singlet oxygen reaction: an E.S.R. study [proceedings]. Archives of International Physiology and Biochemistry, 89, 1046–1047.
31.
KrishnaMC, De GraffW, TamuraS, GonazalezFJ, SamuniA, RussoA, MitchellJB. (1991) Mechanisms of hypoxic and aerobic cytotoxicity of mitomycin C in Chinese hamster V79 cells. Cancer Research, 51, 6622–6628.
McCordJM, FridovichI. (1969) Superoxide dismutase. An enzymatic function for erythrocuprein (hemocuprein). Journal of Biological Chemistry, 244, 6049–6055.
34.
KoppenolWH, ButlerJ. (1981) The radiation chemistry of cytochrome C. Israel Journal of Chemistry, 24, 11–16.
35.
DiwuZJ, LownJW. (1993) Photosensitization with anticancer agents: 15 Perylenequinonoid pigments as potential photodynamic therapeutic agent: formation of semiquinone radicals and reactive oxygen species on illumination. Journal of Photochemistry and Photobiology, B: Biology, 18, 131–143.
36.
WuT, ShenJ, SongA, ChenS, ZhangM, ShenT. (2000) Photodynamic action of amino substituted hypocrellins: EPR studies on the photogeneration of active oxygen and free radical species. Journal of Photochemistry and Photobiology B: Biology, 57, 14–21.
37.
BeuttnerGR, OberleyLW. (1978) Considerations in the spin trapping of superoxide and hydroxyl radical in the aqueous systems using 5,5-dimethyl-1-pyrroline-1-oxide. Biochemical and Biophysical Research Communications, 83, 69–74.
38.
FinkelsteinF, RosenGM, RquckmanEJ. (1982) Production of hydroxyl radical by decomposition of superoxide spin trapped adducts. Molecular Pharmacology, 21, 262–265.
39.
Ben-HurE, CarmichaelA, RieszP, RosenthalI. (1985) Photochemical generation of superoxide anion radical and the cytotoxicity of phthalocyanines. International Journal of Radiation Biology, 48, 837–846.
40.
BuettnerGR. (1987) Spin trapping: ESR parameters of spin adducts. Free Radical Biology and Medicine, 3, 259–303.
41.
DiscrollJS, HazardGF, WoodHB, GoldinA. (1974) Structure antitumor activity relationships among quinone derivatives. Cancer Chemotherapy Reports. Part 2 (April) 1–362.
42.
HanschC, LeoA, VngerSH, KimKH, NikaitainiD, LienEJ. (1973) Aromatic substituent constants for structure-activity relationship. Journal of Medicinal Chemistry, 16, 1207–1216.
43.
MothilalKK, KarunakaranC, RajendranA, MurugesanR. (2004) Synthesis, X-ray crystal structure, antimicrobial activity and photodynamic effects of some thiabendazole complexes. Journal of Inorganic Biochemistry, 98, 322–332.
ZernerMC, LoewG, KirchnerR, Mueller-WesterhoffV. (1980) An intermediate neglect of differential overlap technique for spectroscopy of transition metal complexes. Ferrocene. Journal of the American Chemical Society, 102, 589–599.
46.
KalyanaramanB, MorehouseKM, MasonRP. (1991) An electron paramagnetic resonance study of the interactions between the adriamycin semiquinone, hydrogen peroxide, iron-chelators and radical scavengers. Archives of Biochemistry and Biophysics, 286, 164–170.
47.
SchreiberJ, MottleyC, SinhaBK, KalyanaramanB, MasonRP. (1987) One electron reduction of daunomycin, daunomycinone and 7-deoxydaunomycin by the xanthine/xanthine oxidase system: Detection of semiquinone free radical by electron spin resonance spectroscopy. Journal of American Chemical Society, 109, 348–351.
48.
ZagottoG, MoroS, UriarteE, FerrzziE, PaluG, PalumboM. (1997) Amido analogs of mixatosantrone: physicochemical properties, molecular modeling, cellular effects and antineoplastic potential. Anticancer Drug Designing, 12, 99–112.
49.
KuzykMG, KirkCW. (1990) Effects of centrosymmetry on the nonresonant electronic third-order nonlinear optical susceptibility. Physical Review A, 41, 5098–5109.
50.
SinhaBK, MimnaughEG. (1990) Free radicals and anticancer drug resistance: oxygen free radicals in the mechanism of drug cytotoxicity and resistance by certain tumors. Free Radical Biology and Medicine, 8, 561–581.
51.
KalyanaramanB, SealyRC, SinhaBK. (1984) An electron spin resonance study of the reduction of peroxides by anthracycline semiquinones. Biochimica et Biophysica Acta, 799, 271–278.
52.
StoutDL, BeckerFF. (1986) Xenobiotic metabolizing enzymes in genetically and chemically initiated mouse liver tumors. Cancer Research, 46, 2693–2696.
53.
CrawfordPW, GrossJ, LawsonK, ChengCC, DongQ, LiuDF, LuoYL, SzczepankiewiczBG, HeathcockCH. (1997) Electrochemical properties of some biologically active quinine derivatives: Furanquinones, pyridoquinones and diplamine, a cytotoxic pyridoacridine alkaloid. Journal of the Electrochemical Society, 144, 3710–3715.
54.
ConstantinescuA, HanD, PackerL. (1993) Vitamin E recycling in human erythrocyte membranes. Journal of Biological Chemistry, 268, 10906–10913.
55.
ChatterjeeSR, ShettySJ, DevasagayamTPA, SrivastavaTS. (1997) Photocleavage of plasmid DNA by the prophyrin meso-tetrakis[4-(carboxymethyleneoxy)phenyl]prophyrin. Journal of Photochemistry and Photobiology, B: Biology, 41, 128–135.
56.
StubbeJ, KozarichJW. (1987) Mechnisms of bleomycin-induced DNA-degradation. Chemical Reviews, 87, 1107–1136.
57.
KalyanaramanB, FelixRC, SealyRC. (1982) Photoionisation of melanin precursors: an electron spin resonance investigation using the spin trap 5,5-dimethyl-1-pyrroline-1-oxide (DMPO). Photochemistry and Photobiology, 36, 5–12.
