Friedelane triterpenes from celastrus vulcanicola as photosynthetic inhibitors

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 20, 2010, Pages 10847-10854

  Torres Romero, David ^a,b   King Díaz, Beatriz ^c   Strasser, Reto J ^d   Jiménez, Ignacio A ^a   Lotina Hennsen, Blas ^c   Bazzocchi, Isabel L ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b Universidad de El Salvador   (Brazil)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^d UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Canophyllol; Celastrus vulcanicola; Epifriedelinol; Friedelane triterpenes; Herbicide; Photophosphorylationchlorophyll a fluorescence

Indexed keywords

CANOPHYLLOL; CELASTRUS VULCANICOLA; EPIFRIEDELINOL; PHOTOPHOSPHORYLATIONCHLOROPHYLL A FLUORESCENCE; TRITERPENES;

DETOXIFICATION; ENERGY TRANSFER; FLUORESCENCE; PHOTOSYNTHESIS; SPECTROSCOPIC ANALYSIS; WEED CONTROL;

HERBICIDES;

CELASTRACEAE; CELASTRUS; LOLIUM PERENNE; PHYSALIS; PHYSALIS PHILADELPHICA IMMACULATA;

FRIEDELANE; HERBICIDE; PLANT EXTRACT; TRITERPENE;

CELASTRUS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; LOLIUM; METABOLISM; PHOTOSYNTHESIS; WEED;

CELASTRUS; HERBICIDES; LOLIUM; MOLECULAR STRUCTURE; PHOTOSYNTHESIS; PLANT EXTRACTS; PLANT WEEDS; TRITERPENES;

EID: 78049255028     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1022115     Document Type: Article

References (29)

1. Dzubak, P.; Hajduch, M.; Vydra, D.; Hustova, A.; Kvasnica, M.; Biedermann, D.; Markova, L.; Urbanc, M.; Sarek, J. Pharmacological activities of natural triterpenoids and their therapeutic implications. Nat. Prod. Rep. 2006, 23, 394-411.
2. Kuo-Hsiung, L. Discovery and Development of Natural Product- Derived Chemotherapeutic Agents Based on a Medicinal Chemistry Approach. J. Nat. Prod. 2010, 73, 500-516.
3. Macías, F. A.; Simonet, A. M.; Esteban, M. D. Potential allelopathic lupane triterpenes from bioactive fractions of Melilotus messanensis. Phytochemistry 1994, 36, 1369-1379.
4. Silva, S. R. S.; Silva, G. D. F.; Barbosa, L. C. A.; Duarte, L. P.; King-Díaz, B.; Archundia-Camacho, F.; Lotina-Hennsen, B. Uncoupling and inhibition properties of 3,4-seco-friedelan-3-oic acid isolated from Maytenus imbricata. Pestic. Biochem. Physiol. 2007, 87, 109-114.
5. Torres-Romero, D.; King-Díaz, B.; Jiménez, I. A.; Lotina-Hennsen, B.; Bazzocchi, I. L. Sesquiterpenes from Celastrus vulcanicola as Photosynthetic inhibitors. J. Nat. Prod. 2008, 71, 1331-1335.
6. Bruun, T.; Jefferies, P. R. Triterpenoids in lichens. I. The Occurrence of Friedelin and epiFriedelinol. Acta Chem. Scand. 1954, 8, 71-75.
7. Betancor, C.; Freire, R.; González, A. G.; Salazar, J. A.; Pascard, C.; Prange, T. Three triterpenes and other terpenoids from Catha cassinoides. Phytochemistry 1980, 19, 1989-1993.
8. Ramiah, P. A.; Devi, P. U.; Frolow, F.; Lavie, D. 3-Oxo-friedelan- 20a-oic acid from Gymnosporia emarginata. Phytochemistry 1984, 23, 2251-2255.
9. Strasser, R. J.; Tsimilli-Michael, M.; Srivastava, A. Analysis of the chlorophyll a fluorescence transient. In Chlorophyll fluorescence: A signature of photosynthesis; Papageorgion, G. C., Govindjee, Eds.; Kluwer Academic Publishers: Netherlands, 2004; Chapter 12, pp 321-362.
10. Morales-Flores, F.; Aguilar, M. I.; King-Díaz, B.; Santiago-Gómez, J.-R. De; Lotina-Hennsen, B. Natural diterpenes from Croton ciliatoglanduliferus as photosystem II and photosystem I inhibitors in spinach chloroplasts. Photosynth. Res. 2007, 91, 71-88.
11. Mills, J. D.; Mitchell, P.; Schurrmann, P. Modulation of coupling ATPase activity in intact chloroplasts. FEBS Lett. 1980, 191, 144-148.
12. Strain, H. H.; Cope, B. T.; Svec, W. A. Analytical procedures for the isolation, identification, estimation and investigation of the chlorophylls. Methods Enzymol. 1971, 23, 452-1266
13. 2+exchange phenomena). Methods Enzymol. 1972, 24, 68-74.
14. Aguilar, M. I.; Romero, M. G.; Chávez, M. I.; King-Díaz, B.; Lotina-Hennsen, B. Biflavonoids isolated from Selaginella lepidophylla inhibit photosynthesis in spinach chloroplasts. J. Agric. Food Chem. 2008, 56, 6994-7000.
15. Saha, S.; Ouitrakul, R.; Izawa, S.; Good, N. Electron transport and photophosphorylation in chloroplasts as a function of the electron acceptor. J. Biol. Chem. 1971, 246, 3204-3209.
16. Yruela, I.; Montoya, G.; Alonso, P. J.; Picorel, R. Identification of the pheophytin-QA-Fe domain of the reducing side of the photosystem II as the Cu(II)-inhibitory binding site. J. Biol. Chem. 1991, 266, 22847-22850.
17. Guiaquinta, R. T.; Dilley, R. A.Apartial reaction in photosystem II: reduction of silicomolybdate prior to the site of dichlorophenyldimethyl- urea inhibition. Biochim. Biophys. Acta 1975, 387, 288-305.
18. Allen, J. F.; Holmes, N. G. Electron transport partial reactions. In Photosynthesis, energy transduction. A practical approach; Hipkinns, M. F., Baker, N. R., Eds.; IRL Press: Oxford, U.K., 1986; Chapter 5, pp 103-141.
19. Sumner, J. B. Scientific apparatus and laboratory methods. A method for the colorimetric determination of phosphorus. Science 1944, 100, 413-418.
20. Strasser, R. J.; Srivastava, A.; Govindjee Polyphasic chlorophyll a fluorescence transients in plants and cyanobacteria. Photochem. Photobiol. 1995, 61, 32-42.
21. Panda, D.; Rao, D. N.; Sharma, S. G.; Strasser, R. J.; Sarkar, R. K. Subemergence effects on rice genotypes during seedling stage: Probing of subemergence driven changes of photosystem II by chlorophyll a fluorescence induction O-J-I-P transients. Photosynthetica 2006, 44, 69-75.
22. Huan-Xin, J.; Li-Song, C.; Jin-gui, Z.; Shuang, H.; Ning, T.; Brandon, R. S. Aluminum-induced effects on photosystem II photochemistry in Citrus leaves assessed by the chlorophyll a fluorescence transient. Tree Physiol. 2008, 28, 1863-1871.
23. González-Ibarra, M.; Farfán, N.; Trejo, C.; Uribe, S.; Lotina- Hennsen, B. Selective herbicide activity of 2,5-di(benzylamine)- p-benzoquinone against the monocot weed Echinochloa crusgalli. An in vivo analysis of photosynthesis and growth. J. Agric. Food Chem. 2005, 53, 3415-3420.
24. Joan Saary, M. Radar plots: a useful way for presenting multivariate health care data. J. Clin. Epidem. 2008, 60, 311-317.
25. Schansker, G.; Tóth, S. Z.; Strasser, R. J. Methylviologen and dibromothymoquinone treatments of pea leaves reveal the role of photosystem I in the Chl a fluorescence rise OJIP. Biochim. Biophys. Acta 2005, 1706, 250-261.
26. González-Vázquez, R.; King-Díaz, B.; Aguilar, M. I.; Diego, N.; Lotina-Hennsen, B. Pachypodol from Croton ciliatoglanduliferus Ort. as water-splitting enzyme inhibitor on thylakoids. J. Agric. Food Chem. 2006, 54, 1217-1221.
27. Morales-Flores, F.; Aguilar, M. I.; King-Díaz, B.; de Santiago- Gómez, J. R.; Lotina- Hennsen, B. Natural diterpenes from Croton ciliatoglanduliferus as photosystem II and photosystem I inhibitors in spinach chloroplasts. Photosynth. Res. 2007, 91, 71-80.
28. González-Bernardo, E.; Aguilar, M. I.; Delgado, G.; King-Díaz, B.; Lotina-Hennsen, B. Photosynthetic electron transport interaction of xanthorrhizol isolated from Iostephane heterophylla and its derivatives. Physiol. Plant. 2003, 119, 598-604.
29. Bussotti, F.; Strasser, R. J.; Schaub, M. Photosynthetic behavior of woody species under high ozone exposure probed with the JIP-test: A review. Environ. Pollut. 2007, 147, 430-437.