5-O-β-d-galactopyranosyl-7-methoxy-3′,4′-dihydroxy-4-phenylcoumarin, an inhibitor of photophosphorylation in spinach chloroplasts
Tóm tắt
5-O-β-d-galactopyranosyl-7-methoxy-3′,4′-dihydroxy-4-phenylcoumarin isolated from Exostema caribaeum (Rubiaceae) has been found to act as an energy-transfer inhibitor in spinach chloroplasts. ATP synthesis and phosphorylating (coupled) electron flow were inhibited by 89 and 72%, respectively, at a concentration of 400 μM. H+-uptake, basal and uncoupled electron transport were not affected by the coumarin. The light-activated Mg+2-ATPase activity from bound membrane thylakoid chloroplasts was slightly inhibited by the coumarin. Also, the heat-activated Ca+2-ATPase activity of the isolated coupling factor protein was insensitive to this compound. In chloroplasts partially stripped of coupling factor 1 by an EDTA treatment, the coumarin showed a restoration of the proton uptake process. These results suggest that the 4-phenylcoumarin under investigation inhibited phosphorylation in chloroplasts by specifically blocking the transport of protons through a membrane-bound component or a carrier channel (CFO) located in a hydrophobic region at or near the functional binding site for the coupling factor 1.
Tài liệu tham khảo
Arntzen CJ, Falkenthal SV and Bobick S (1974) Inhibition of photophosphorylation by kaempferol. Plant Physiol 53: 304–306
Brown SA (1981) Coumarins. In: Conn EE (ed) The Biochemistry of Plant, Vol 7, pp 269–299. Academic Press, New York
Datta DB, Ryrie IJ and Jagendorf AT (1974) Light-dependent modification of spinach chloroplast coupling factor 1 by permanganate ion. J Biol Chem 249: 4404–4411
Demos EK, Woolwine M, Wilson RH and McMillan C (1975) The effects of ten phenolic compounds on hypocotyl growth and mitochondrial metabolism of mung bean. Am J Bot 62: 97–102
Dilley RA (1972) Ion transport (H+, K+, Mg2+ exchange phenomena). In: San Pietro A (ed) Methods in Enzymology, Vol 24, pp 68–74. Academic Press, New York
Einhellig FA (1986) Mechanisms and modes of action of allelochemicals. In: Putnam AR and Tang CS (eds) The Science of Allelopathy, pp 171–188. Wiley-Interscience, USA
Einhellig FA (1995) Mechanism of action of allelochemicals in allelopathy. In: Inderjit, Dakshini KMM and Einhellig FA (eds) Allelopathy: Organisms, Processes and Applications, Vol 582, pp 96–116. American Chemical Society, Washington, DC
Feuer G (1974) The metabolism and biological actions of coumarins. Prog Med Chem 10: 85–158
Giaquinta RT, Selman BR, Bering CH and Dilley R (1974) Inhibition of coupling factor activity of chloroplast membranes by diazonium compounds. J Biol Chem 249: 2873–2878
Good NE, Izawa S and Hind G (1981) Uncoupling and energy transfer inhibition in photophosphorylation. In: Sanadi DR (ed) Current Topics in Bioenergetics, Vol 1, pp 75–112. Academic Press, New York
Gould JM (1976) Inhibition by triphenyltin chloride of a tightly-bound membrane component involved in photophosphorylation. Eur J Biochem 62: 567–575
Gross E, Shavit N and San Pietro A (1968) Synthalin: An inhibitor of energy transfer in chloroplasts. Arch Biochem Biophys 127: 224–228
Izawa S, Winget CD and Good NE (1966) Phlorizin, a specific inhibitor of photophosphorylation and phosphorylation-coupled electron transport in chloroplasts. Biochem Biophys Res Commun 22: 223–226
Kady MM, Brimer L, Furu P, Lemmich E, Nielsen HM, Thiiborg ST, Thastrup O and Christensen SB (1992) The molluscicidal activity of coumarins from Ethulia conyzoides and of dicoumarol. Planta Med 58: 334–337
Klein-Hitpass L and Berzborn RJ (1984) Accessibility and function of CFo-subunits in chloroplast thylakoids. In: Sybesma C (ed) Advances in Photosynthesis Research, Vol II, pp 6563–6566. Martinus Nijhoff/Dr W Junk Publishers, The Hague, Netherlands
Kumar V, Bulumulla HNK, Wimalasiri WR and Reisch J (1994) Coumarins and an indole alkaloid from Pamburus missionis. Phytochemistry 36: 879–881
Lotina-Hennsen B, Roque-Reséndiz JL, Jiménez M and Aguilar M (1991) Inhibition of oxygen evolution by cacalol and its derivatives. Z Naturforsch 46c: 777–780
Mata R, Calzada F, García M del R and Reguero MT (1987) Chemical studies on mexican plants used in traditional medicine, III: New 4-phenylcoumarins from Exostema caribaeum. J Nat Prod 50: 866–871
Mata R (1993) Chemical studies and biological aspects of some mexican plants used in traditional medicine. In: Downum KR (ed) Phytochemical Potential of Tropical Plants, pp 41–64. Plenum Press, New York
McCarty RE, Guillory RJ and Racker E (1965) Dio-9, an inhibitor of coupled electron transport and phosphorylation in chloroplasts. J Biol Chem 240: PC4822-PC4823
McCarty RE and Racker E (1967) Partial resolution of the enzymes catalyzing photophosphorylation. J Biol Chem 242: 3435–3439
McCarty RE and Racker E (1968) Partial resolution of the enzymes catalyzing photophosphorylation III. Activation of adenosine triphosphate and 32Pi-labeled orthophosphate-adenosine triphosphate exchange in chloroplasts. J Biol Chem 243: 129–137
Mersie W and Singh M (1993) Phenolic acids afect photosynthesis and protein synthesis by isolated leaf cells of velvet-leaf. J Chem Ecol 19: 1293–1301
Mills JD, Mitchell P and Schurmann P (1980) Modulation of coupling ATPase activity in intact chloroplasts. FEBS Lett 112: 173–177
Moreland DE and Novitzky WP (1987) Effects of phenolic acids, coumarins, and flavonoids on isolated chloroplasts and mitochondria. In: Waller GR (ed) Allelochemicals: Role in Agriculture and Forestry, Vol 330, pp 247–261. American Chemical Society, Washington, DC
Neumann J and Jagendorf AT (1964) Light-induced pH changes related to phosphorylation by chloroplasts. Arch Biochem Biophys 107: 109–119
Noster S and Kraus L (1990) In vitro antimalarial activity of Coutarea latiflora and Exostema caribaeum extracts on Plasmodium falciparum. Planta Med 56: 63–65
Paña-Valdivia CB, Rodríguez-Flores L, Tuena de Gómez-Puyou M and Lotina-Hennsen B (1991) Inhibition of photophosphorylation and electron transport by N,N-dimethylformamide. Biophys Chem 41: 169–174
Robinson T (1991) The Organic Constituents of Higher Plants. Cordus Press, North Amherst
Rojas A, Hernández L, Pereda-Miranda R and Mata R (1992) Screening for antimicrobial activity of crude drug extracts and pure natural products from Mexican medicinal plants. J Ethnopharmacol 32: 275–283
Rosskopf F, Kraus J and Franz G (1992) Immunological and antitumor effects of coumarin and some derivatives. Pharmazie 47: 139–142
Strain HH, Coppe BT and Svec WA (1971) Analytical procedures for the isolation, identification, estimation, and investigation of the chlorophylls. In: San Pietro A (ed) Methods in Enzymology, Vol 23, pp 452–466. Academic Press, New York
Sumner JB (1944) Scientific apparatus and laboratory methods. A method for the colorimetric determination of phosphorous. Science 100: 413–415
Teng CM, Li HL, Wu TS, Huang SC and Huang TF (1992) Antiplatelet actions of some coumarin compounds isolated from plant sources. Thromb Res 66: 549–557
Tissut M, Chevallier D and Douce R (1980) Effet de différents polyphénols sur les mitochondries et les chloroplastes isoles. Phytochemistry 19: 495–500
Vambutas VK and Racker E (1965) Partial resolution of the enzymes catalyzing photophosphorylation. J Biol Chem 240: 2660–2667
Vallejos RH and Andreo CS (1974) Alkaloids as inhibitors of photophosphorylation in spinach chloroplasts. Biochim Biophys Acta 333: 141–148
Waterman PG and Mole S (1994) Analysis of Phenolic Plant Metabolites. Blackwell Scientific Publications, London
Yoshikawa M, Uchida E, Chatani N, Kobayashi H, Naitoh Y, Okuno Y, Matsuda H, Yamahara J and Murakami N (1992) Thunberginols C, D and E, new antiallergic and antimicrobial dihydroisocoumarins, and thunberginol G 3′-O-glucoside and (−)-hydrangenol 4′-O-glucoside, new dihydroisocoumarin glycosides, from Hydrangeae dulcis-folium. Chem Pharm Bull 40: 3352–3354
Zobel AM and Brown SA (1995) Coumarins in the interaction between plant and its environment. Allelopathy J 2: 9–20