Structure-activity relationship of antioxidants for inhibitors of linoleic acid hydroperoxide-induced toxicity in cultured human umbilical vein endothelial cells
Open accessAbstract
Structure-activity relationship of antioxidants for the protective effects on linoleic acid hydroperoxide (LOOH)-induced toxicity were examined in cultured human umbilical vein endothelial cells. alpha-Tocopherol, 2,2,5,7,8-pentamethylchroman-6-ol, butylated hydroxytoluene, probucol, and fatty acid esters of ascorbic acid provided efficient protection against the cytotoxicity of LOOH in pretreatment, but phenols without alkyl groups at the ortho positions and hydrophilic antioxidants such as Trolox and ascorbic acid provided no protection. Probably, the effectiveness of the protection against cytotoxicity by these antioxidants dependsprimarily on their rate of incorporation into cells due to their lipophilicity, secondly on their antioxidant activity, and thirdly on their orientation in biomembranes. On the other hand, flavones, such as baicalein and luteolin bearing 3 to 5 hydroxyl groups, and flavonols showed a protective effect against LOOH cytotoxicity when added together with LOOH,but not by pretreatment. Among catechins, (+)-catechin and (-)-epigallocatechin gallate monoglucoside and diglucoside were effective in suppressing LOOH-induced cytotoxicity, but their effects were not so strong. The structure-activity relationship of flavonoids revealed the presence of either theortho-dihydroxy structure in the B ring of flavonoids or the 3-hydroxyl and 4-oxo groups in the C ring to be important forthe protective activities. Furthermore, coumarins such as esculetin containing the ortho catechol structure had protective effects in both pretreatment and concurrent treatment. These results suggest that ortho catechol moiety of flavonoids, catechins, and coumarins is an important structure in the protection against LOOH-induced cytotoxicity,and that the alkyl groups of monophenols are critical for protection.
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Esculetin has been reported to protect HUVEC against cytotoxicity after exposure of linoleic acid hydroperoxide, likely via its radical scavenging ability.
“Esculetin has been reported to protect HUVEC against cytotoxicity after exposure of linoleic acid hydroperoxide, which is likely via its radical scavenging ability [166].”
From AMPK, Mitochondrial Function, and Cardiovascular Disease (2020) · cites this paper as [166]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Cites
The pathogenesis of atherosclerosis: a perspective for the 1990s
Ross, R. (1993) · Nature · doi:10.1038/362801a0 · Cited by 10,618 · see citing works
[36] Flavonoids as antioxidants: Determination of radical-scavenging efficiencies
Bors, W., Heller, W. E., Michel, C., & Sarán, M. (1990) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/0076-6879(90)86128-i · Cited by 1,726 · see citing works
Flavonoids, a class of natural products of high pharmacological potency
Havsteen, B. (1983) · Biochemical Pharmacology · doi:10.1016/0006-2952(83)90262-9 · Cited by 1,616 · see citing works
Structural aspects of antioxidant activity of flavonoids
van Acker, S. A. B. E., van den Berg, D., Tromp, M. N. J. L., Veening-Griffioen, D. H., Bennekom, W. P. V., van der Vijgh, W. J. F., & Bast, A. (1996) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(95)02047-0 · Cited by 1,341 · see citing works
Jovanović, S. V., Steenken, S., Tošić, M., Marjanović, B., & Simic, M. G. (1994) · Journal of the American Chemical Society · doi:10.1021/ja00090a032 · Cited by 1,197 · see citing works
Afanas'ev, I. B., Dcrozhko, A. I., Brodskii, A. V., Kostyuk, V. A., & Potapovitch, A. I. (1989) · Biochemical Pharmacology · doi:10.1016/0006-2952(89)90410-3 · Cited by 982 · see citing works
The correlation between active oxygens scavenging and antioxidative effects of flavonoids
Hanasaki, Y., Ogawa, S., & Fukui, S. (1994) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(94)90202-x · Cited by 957 · see citing works
Burton, G. W., Joyce, A., & Ingold, K. U. (1983) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(83)90145-5 · Cited by 808 · see citing works
Morel, D. W., DiCorleto, P. E., & Chisolm, G. M. (1984) · Arteriosclerosis An Official Journal of the American Heart Association Inc · doi:10.1161/01.atv.4.4.357 · Cited by 808 · see citing works
Autoxidation of biological molecules. 4. Maximizing the antioxidant activity of phenols
Burton, G. W., Doba, T., Gabe, E., Hughes, L., Lee, F. L., Prasad, L., & Ingold, K. U. (1985) · Journal of the American Chemical Society · doi:10.1021/ja00310a049 · Cited by 779 · see citing works
Antioxidant activity of flavonoids and reactivity with peroxy radical
Torel, J., Cillard, J., & Cillard, P. (1986) · Phytochemistry · doi:10.1016/s0031-9422(00)85485-0 · Cited by 605 · see citing works
Role of hydrogen peroxide in neutrophil-mediated destruction of cultured endothelial cells.
Weiss, S. J., Young, J. K., LoBuglio, A., et al. (1981) · Journal of Clinical Investigation · doi:10.1172/jci110307 · Cited by 577 · see citing works
Terao, J., Piskuła, M. K., & Yao, Q. (1994) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1994.1039 · Cited by 567 · see citing works
The Pharmacology, Metabolism, Analysis, and Applications of Coumarin and Coumarin-Related Compounds
Egan, D. A., O’Kennedy, R. J., Moran, E., Cox, D. M., Prosser, E. S., & THORNES, R. D. (1990) · Drug Metabolism Reviews · doi:10.3109/03602539008991449 · Cited by 558 · see citing works
Intestinal absorption of luteolin and luteolin 7‐O‐β‐glucoside in rats and humans
Shimoi, K., Okada, H., Furugori, M., Goda, T., Takase, S., Suzuki, M., Hara, Y., Yamamoto, H., & Kinae, N. (1998) · FEBS Letters · doi:10.1016/s0014-5793(98)01304-0 · Cited by 418 · see citing works
Effects of flavonoids on nonenzymatic lipid peroxidation: Structure-activity relationship
Ratty, A. K., & Das, N. P. (1988) · Biochemical Medicine and Metabolic Biology · doi:10.1016/0885-4505(88)90060-6 · Cited by 415 · see citing works
ESR study on the structure–antioxidant activity relationship of tea catechins and their epimers
Guo, Q., Zhao, B., Shen, S., Hou, J., Hu, J., & Xin, W. (1999) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/s0304-4165(98)00168-8 · Cited by 411 · see citing works
Interactions of a series of coumarins with reactive oxygen species
Payá, M., Halliwell, B. B., & Hoult, J. R. S. (1992) · Biochemical Pharmacology · doi:10.1016/0006-2952(92)90002-z · Cited by 399 · see citing works
L-C, H. C.-T. V. T. L. S.-Y. T. A. H. H.-M. P. (1993) · Lung Cancer · doi:10.1016/0169-5002(93)90327-t · Cited by 347 · see citing works
Lipid Peroxidation and Mechanisms of Toxicity
Horton, A. A., Fairhurst, S., & Bus, J. S. (1987) · Critical Reviews in Toxicology · doi:10.3109/10408448709089856 · Cited by 340 · see citing works
Lobb, R. R., & Fett, J. W. (1984) · Biochemistry · doi:10.1021/bi00321a001 · Cited by 295 · see citing works
In vitro scavenger activity of some flavonoids and melanins against O2
Sichel, G., Corsaro, C., Scalia, M., Di Bilio, A. J., & Bonomo, R. P. (1991) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(91)90181-2 · Cited by 295 · see citing works
Yoshizawa, S., Horiuchi, T., Fujiki, H., Yoshida, T., Okuda, T., & Sügimura, T. (1987) · Phytotherapy Research · doi:10.1002/ptr.2650010110 · Cited by 290 · see citing works
Will antioxidant nutrients slow aging processes?
Tappel, A. L. (1968) · PubMed · Cited by 275 · see citing works
Inhibitory effects of phenolic compounds on CCl4-induced microsomal lipid peroxidation
Cholbi, M. R., Payá, M., & Alcaraz, M. J. (1991) · Cellular and Molecular Life Sciences · doi:10.1007/bf01945426 · Cited by 265 · see citing works
Flavonoids as antioxidants evaluated by in vitro and in situ liver chemiluminescence
Fraga, C. G., Martino, V. S., Ferraro, G., Coussio, J., & Boveris, A. (1987) · Biochemical Pharmacology · doi:10.1016/0006-2952(87)90724-6 · Cited by 234 · see citing works
Okuda, T., Kimura, Y., Yoshida, T., et al. (1983) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.31.1625 · Cited by 220 · see citing works
Quercetin prevents the cytotoxicity of oxidized LDL on lymphoid cell lines
Nègre‐Salvayre, A., & Salvayre, R. (1992) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(92)90002-x · Cited by 180 · see citing works
Phenolic compounds and an analog as superoxide anion scavengers and anti oxidants
Yan-Chun, Z., & Rong-Liang, Z. (1991) · Biochemical Pharmacology · doi:10.1016/0006-2952(91)90251-y · Cited by 171 · see citing works
Suppression of active oxygen-induced cytotoricity by flavonoids
Tsutomu, N., Yamada, M., Osawa, T., & Kawakishi, S. (1993) · Biochemical Pharmacology · doi:10.1016/0006-2952(93)90402-i · Cited by 166 · see citing works
Scavenger and antioxidant properties of ten synthetic flavones
Cotelle, N., Bernier, J., Hénichart, J., Catteau, J. P., Gaydou, E. M., & Wallet, J. ‐. (1992) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(92)90017-b · Cited by 164 · see citing works
Radical Chemistry of Flavonoid Antioxidants
Bors, W., Heller, W. E., Michel, C., et al. (1990) · Advances in experimental medicine and biology · doi:10.1007/978-1-4684-5730-8_25 · Cited by 117 · see citing works
Hiramoto, K., Ojima, N., Sako, K.-I., et al. (1996) · Biological and Pharmaceutical Bulletin · doi:10.1248/bpb.19.558 · Cited by 116 · see citing works
Kaneko, T., Kaji, K., & Matsuo, M. (1988) · Chemico-Biological Interactions · doi:10.1016/0009-2797(88)90065-8 · Cited by 102 · see citing works
Self-citationSuppression of hydroperoxide-induced cytotoxicity by polyphenols.
Nakayama, T. (1994) · PubMed · Cited by 91 · see citing works
Kaneko, T., Honda, S., Nakano, S., et al. (1987) · Chemico-Biological Interactions · doi:10.1016/0009-2797(87)90093-7 · Cited by 82 · see citing works
Self-citationNègre‐Salvayre, A., Alomar, Y., Troly, M., et al. (1991) · Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease · doi:10.1016/0925-4439(91)90065-h · Cited by 82 · see citing works
Protection of linoleic acid hydroperoxide-induced cytotoxicity by phenolic antioxidants
Kaneko, T., Kaji, K., & Matsuo, M. (1994) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(94)90043-4 · Cited by 68 · see citing works
Self-citationStructure of ascorbic acid and its biological function
Lohmann, W., PAGEL, D., & Penka, V. (1984) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1984.tb07941.x · Cited by 63 · see citing works
KANEKO, T., & Baba, N. (1999) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.63.323 · Cited by 58 · see citing works
Self-citationMartín‐Aragón, S., Benedı́, J., & Villar, Á. (1997) · Gerontology · doi:10.1159/000021978 · Cited by 58 · see citing works
A kinetic study of reactions of tocopherols with a substituted phenoxyl radical
Mukai, K., Fukuda, K., Tajima, K., et al. (1988) · The Journal of Organic Chemistry · doi:10.1021/jo00237a040 · Cited by 58 · see citing works
Enzymatic Syntheses of Two Stable (–)-Epigallocatechin Gallate-glucosides by Sucrose Phosphorylase
Kitao, S., Matsudo, T., Saitoh, M., et al. (1995) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.59.2167 · Cited by 58 · see citing works
Effect of various flavonoids on lysosomes subjected to an oxidative or an osmotic stress
Decharneux, T., Dubois, F., Beauloye, C., et al. (1992) · Biochemical Pharmacology · doi:10.1016/0006-2952(92)90521-j · Cited by 57 · see citing works
Synthesis of Methyl Substituted 6-Hydroxychromans, Model Compounds of Tocopherols.
Nilsson, J., Sievertsson, H., Selander, H. G., et al. (1968) · Acta chemica Scandinavica/Acta chemica Scandinavica. B, Organic chemistry and biochemistry/Acta chemica Scandinavica. A, Physical and inorganic chemistry/Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry/Acta chemica Scandinavica. Series A, Physical and inorganic chemistry · doi:10.3891/acta.chem.scand.22-3160 · Cited by 55 · see citing works
Kaneko, T., Nakano, S., & Matsuo, M. (1991) · Lipids · doi:10.1007/bf02537196 · Cited by 50 · see citing works
Self-citationAntioxidants/Antimutagens in Foods
Namiki, M., & Osawa, T. (1986) · Springer eBooks · doi:10.1007/978-1-4684-5182-5_11 · Cited by 47 · see citing works
Injury to cultured endothelial cells from human umbilical vein by linoleic acid hydroperoxide.
Sasaguri, Y., Nakashima, T., Morimatsu, M., et al. (1984) · PubMed · Cited by 37 · see citing works
Protection by multiple antioxidants against lipid peroxidation in rat liver homogenate
Chen, H. L., & Tappel, A. L. (1996) · Lipids · doi:10.1007/bf02522409 · Cited by 35 · see citing works
Kaneko, T., Kaji, K., & MATSUO, M. (1993) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1993.1336 · Cited by 34 · see citing works
Self-citationEffects of coumarin derivatives on superoxide anion generation.
Payá, M., Ferrándiz, M. L., Miralles, F., et al. (1993) · PubMed · Cited by 34 · see citing works
Chen, H., & Tappel, A. L. (1995) · Free Radical Research · doi:10.3109/10715769509147537 · Cited by 30 · see citing works
Fujiki, H., & OKUDA, T. (1992) · Drugs of the Future · doi:10.1358/dof.1992.017.06.175517 · Cited by 30 · see citing works
Kaneko, T., Baba, N., & Matsuo, M. (1996) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(96)00025-1 · Cited by 28 · see citing works
Self-citationTakahashi, M., Niki, E., Kawakami, A., et al. (1986) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.59.3179 · Cited by 26 · see citing works
Kaneko, T., Matsuo, M., & Baba, N. (1998) · Chemico-Biological Interactions · doi:10.1016/s0009-2797(98)00055-6 · Cited by 19 · see citing works
Self-citationKaneko, T., Baba, N., & Matsuo, M. (1994) · Life Sciences · doi:10.1016/0024-3205(94)00684-9 · Cited by 18 · see citing works
Self-citationIsomerization of linoleic acid hydroperoxides under argon and under degassed conditions.
Kaneko, T., & Matsuo, M. (1984) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.32.332 · Cited by 18 · see citing works
Self-citationEsterbauer, H., & Cheeseman, K. H. (1987) · Chemistry and Physics of Lipids · doi:10.1016/0009-3084(87)90061-2 · Cited by 18 · see citing works
Lipid peroxidation: Part II. Pathological implications.
(1988) · PubMed · Cited by 3 · see citing works
Jl, N., Sievertsson, H., & Selander, H. G. (1968) · PubMed · Cited by 1 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
AMPK, Mitochondrial Function, and Cardiovascular Disease
Wu, S., & Zou, M.-H. (2020) · International Journal of Molecular Sciences · doi:10.3390/ijms21144987 · Cited by 286 · see citing works
Karnewar, S., Vasamsetti, S. B., Gopoju, R., Kanugula, A. K., Ganji, S. K., Prabhakar, S., Rangaraj, N., Tupperwar, N., Kumar, J. M., & Kotamraju, S. (2016) · Scientific Reports · doi:10.1038/srep24108 · Cited by 62 · see citing works
- Authors
- Kaneko, T., Baba, N., & Matsuo, M.
- Affiliations
- Tokyo Metropolitan Institute of Gerontology (JP)
- Okayama University (JP)
- Konan University (JP)
- Corresponding author
- Kaneko, Takao
- Venue
- Cytotechnology
- Published
- 2001-01
- Volume
- 35
- Issue
- 1
- Pages
- 43-55
- ISSN
- 0920-9069 (ISSN-L)
- 1573-0778
- PMC
- PMC3466616
- OpenAlex
- W1607828670
- Cited by
- 28
- References
- 61
- Citations by year
- 2024: 1 · 2023: 1 · 2022: 1 · 2021: 1 · 2020: 1 · 2019: 1 · 2018: 1 · 2016: 2 · 2015: 3 · 2014: 1
- FWCI
- 0.90
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Licence
- Locations
- Cytotechnology (publishedVersion)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Health Sciences › Medicine › Biochemistry › Phytochemicals and Antioxidant Activities
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Keywords
- structure-activity relationship, antioxidants, linoleic acid hydroperoxide, lipid peroxidation, endothelial cell cytotoxicity, human umbilical vein endothelial cells, alpha-tocopherol, butylated hydroxytoluene, probucol, ascorbic acid esters, flavonoids, catechins, coumarins, lipophilicity, membrane incorporation, epigallocatechin gallate
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
