Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds

Assay for and enzymatic formation of an ethylene precursor, 1-aminocyclopropane-1-carboxylic acid

Böller, T., Herner, R. C., & Kende, H. (1979) · Planta · doi:10.1007/bf00454455 · Cited by 456

Xylem Transport of 1-Aminocyclopropane-1-carboxylic Acid, an Ethylene Precursor, in Waterlogged Tomato Plants

Bradford, K. J., & Yang, S. F. (1980) · Plant Physiology · doi:10.1104/pp.65.2.322 · Cited by 374

1-アミノシクロプロパン-1-カルボキシル酸の代謝

Honma, M., & Shimomura, T. (1978) · Cited by 308

CC-1065 (NSC-298223), a new antitumor antibiotic. Production, in vitro biological activity, microbiological assays and taxonomy of the producing microorganism.

HANKA, L. J., DIETZ, A., GERPHEIDE, S. A., KUENTZEL, S. L., & MARTIN, D. G. (1978) · The Journal of Antibiotics · doi:10.7164/antibiotics.31.1211 · Cited by 272

CC-1065 and the Duocarmycins: Synthetic Studies

Boger, D. L., Boyce, C. W., Garbaccio, R. M., & Goldberg, J. A. (1997) · Chemical Reviews · doi:10.1021/cr960095g · Cited by 269

Bindungseigenschaften des Cyclopropans und chemische Konsequenzen

De Meijere, A. (1979) · Angewandte Chemie · doi:10.1002/ange.19790911104 · Cited by 227

Structural Dynamics of Green Fluorescent Protein Alone and Fused with a Single Chain Fv Protein

Hink, M. A., Griep, R. A., Borst, J. W., van Hoek, A., Eppink, M. H. M., Schots, A., & Visser, A. J. W. G. (2000) · Journal of Biological Chemistry · doi:10.1074/jbc.m001348200 · Cited by 216

Volatile compounds from marine algae

Moore, R. E. (1977) · Accounts of Chemical Research · doi:10.1021/ar50110a002 · Cited by 204

Carcinogenic Activity of Bracken

EVANS, I. A., & MASON, J. (1965) · Nature · doi:10.1038/208913a0 · Cited by 194

Metabolism and environmental degradation of pyrethroid insecticides produce compounds with endocrine activities

Tyler, C. R., Beresford, N., van der Woning, M., Sumpter, J. P., & Tchorpe, K. (2000) · Environmental Toxicology and Chemistry · doi:10.1002/etc.5620190404 · Cited by 189

Some factors affecting cyclopropane acid formation in Escherichia coli

Knivett, V. A., & Cullen, J. (1965) · Biochemical Journal · doi:10.1042/bj0960771 · Cited by 151

Mechanism of cytochrome P-450 inhibition by cyclopropylamines

Macdonald, T. L., Zirvi, K. A., Burka, L. T., et al. (1982) · Journal of the American Chemical Society · doi:10.1021/ja00371a056 · Cited by 140

Hypoglycin A and B, two biologically active polypeptides from Blighia sapida

Hassall, C. H., & Reyle, K. (1955) · Biochemical Journal · doi:10.1042/bj0600334 · Cited by 133

New observations on the secondary chemistry of world Ephedra (Ephedraceae)

Caveney, S., Charlet, D. A., Freitag, H., Maier-Stolte, M., & Starratt, A. N. (2001) · American Journal of Botany · doi:10.2307/3558330 · Cited by 123

Ptaquiloside, a novel norsesquiterpene glucoside from bracken, var.

Niwa, H., Ojika, M., Wakamatsu, K., Yamada, K., Hirono, I., & Matsushita, K. (1983) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)88276-3 · Cited by 121

Biosynthetic studies on marine natural products

Garson, M. J. (1989) · Natural Product Reports · doi:10.1039/np9890600143 · Cited by 114

A novel antifungal antibiotic, FR-900848. I. Production, isolation, physico-chemical and biological properties.

Yoshida, M., Ezaki, M., Hashimoto, M., Yamashita, M., Shigematsu, N., OKUHARA, M., KOHSAKA, M., & Horikoshi, K. (1990) · The Journal of Antibiotics · doi:10.7164/antibiotics.43.748 · Cited by 112

Bracken (Pteridium aquilinum)—toxic effects and toxic constituents

Fenwick, G. R. (1989) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.2740460204 · Cited by 108

Mechanistic studies on the pyridoxal phosphate enzyme 1-aminocyclopropane-1-carboxylate deaminase from Pseudomonas sp

Walsh, C. T., Pascal, R. A., Johnston, M., Raines, R. T., Dikshit, D. K., Krantz, A., & Honma, M. (1981) · Biochemistry · doi:10.1021/bi00529a028 · Cited by 92

Recent progress in the marine sterol field

Djerassi, C., Theobald, N., KOKKE, W. C. M. C., Pak, C. S., & Carlson, R. M. K. (1979) · Pure and Applied Chemistry · doi:10.1351/pac197951091815 · Cited by 90

Ptaquiloside, a potent carcinogen isolated from bracken fern var. : structure elucidation based on chemical and spectral evidence, and reactions with amino acids, nucleosides, and nucleotides

Ojika, M., Wakamatsu, K., Niwa, H., & Yamada, K. (1987) · Tetrahedron · doi:10.1016/s0040-4020(01)87702-4 · Cited by 89

Potent Pyrethroid Insecticides from Modified Cyclopropane Acids

Elliott, M. L., Farnham, A. W., Janes, N. F., NEEDHAM, P. H., & Pulman, D. A. (1973) · Nature · doi:10.1038/244456a0 · Cited by 89

Biosynthesis of non-head-to-tail terpenes. Formation of 1'-1 and 1'-3 linkages

Poulter, C. (1990) · Accounts of Chemical Research · doi:10.1021/ar00171a003 · Cited by 87

Plant Sterol Metabolism

Heintz, R., & Benveniste, P. (1974) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)42512-x · Cited by 81

CC-1065 (NSC 298223), a most potent antitumor agent: kinetics of inhibition of growth, DNA synthesis, and cell survival.

Bhuyan, B. K., Newell, K. A., Crampton, S. L., et al. (1982) · PubMed · Cited by 81

Solandelactones A-I, lactonized cyclopropyl oxylipins isolated from the hydroid Solanderia secunda

Seo, Y., Cho, K. W., Rho, J., et al. (1996) · Tetrahedron · doi:10.1016/0040-4020(96)00606-0 · Cited by 79

Isolation and structure of a new antibiotic, indolizomycin, produced by a strain SK2-52 obtained by interspecies fusion treatment.

Gomi, S., Ikeda, D., Nakamura, H., et al. (1984) · The Journal of Antibiotics · doi:10.7164/antibiotics.37.1491 · Cited by 78

Yeast Squalene Synthase: Expression, Purification, and Characterization of Soluble Recombinant Enzyme

Zhang, D. L., Jennings, S. M., Robinson, G. W., & Poulter, C. D. (1993) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1993.1331 · Cited by 77

Potent NMDA‐like actions and potentiation of glutamate responses by conformational variants of a glutamate analogue in the rat spinal cord

Shinozaki, H., Ishida, M., Shimamoto, K., & Ohfune, Y. (1989) · British Journal of Pharmacology · doi:10.1111/j.1476-5381.1989.tb12667.x · Cited by 77

Suicide inactivation of monoamine oxidase by trans-phenylcyclopropylamine.

Paech, C., Salach, J. I., & Singer, T. P. (1980) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)85793-9 · Cited by 72

Curacin D, aN antimitotic agent from the marine Cyanobacterium Lyngbya majuscula

Márquez, B. L., Gerwick, W. H., Verdier‐Pinard, P., & Hamel, E. (1998) · Phytochemistry · doi:10.1016/s0031-9422(98)00365-3 · Cited by 72

Sterol compositions in some green algae and brown algae

Ikekawa, N., Morisaki, N., Tsuda, K., & Yoshida, T. (1968) · Steroids · doi:10.1016/s0039-128x(68)80078-9 · Cited by 72

Structure and stereochemistry of constanolactones A-G, lactonized cyclopropyl oxylipins from the red marine alga Constantinea simplex

Nagle, D. G., & Gerwick, W. H. (1994) · The Journal of Organic Chemistry · doi:10.1021/jo00103a012 · Cited by 69

Biosynthesis of the Diterpene Phytoalexin Casbene

Dueber, M. T., Adolf, W., & West, C. A. (1978) · PLANT PHYSIOLOGY · doi:10.1104/pp.62.4.598 · Cited by 69

Isolation and structure of constanolactones A and B, new cyclopropyl hydroxy-eicosanoids from the temperate red alga constantinea simplex

Nagle, D. G., & Gerwick, W. H. (1990) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)89007-3 · Cited by 66

The partial purification and properties of a phytoene synthesizing enzyme system

Maudinas, B., Bucholtz, M. L., Papastephanou, C., Katiyar, S. S., Briedis, A. V., & Porter, J. W. (1977) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(77)90049-2 · Cited by 63

Prephytoene pyrophosphate. New intermediate in the biosynthesis of carotenoids

Altman, L. J., Ash, L., Kowerski, R. C., et al. (1972) · Journal of the American Chemical Society · doi:10.1021/ja00764a073 · Cited by 63

H-rasActivation Is an Early Event in the Ptaquiloside-Induced Carcinogenesis: Comparison of Acute and Chronic Toxicity in Rats

Shahin, M., Moore, M. R., Worrall, S., Smith, B. L., Seawright, A. A., & Prakash, A. S. (1998) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.1998.9341 · Cited by 63

Squalene Synthetase

Beytía, E., Qureshi, A. A., & Porter, J. W. (1973) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)44269-5 · Cited by 59

Involvement of cytochrome P-450 in Δ22-desaturation in ergosterol biosynthesis of yeast

Hata, S., Nishino, T., Komori, M., & Katsuki, H. (1981) · Biochemical and Biophysical Research Communications · doi:10.1016/0006-291x(81)91689-2 · Cited by 59

Isolation of two new c30 sterols, (24e)-24-n-propylidenecholesterol and 24ξ-n-propylcholesterol, from a cultured marine chrysophyte

Rohmer, M., KOKKE, W. C. M. C., Fenical, W., & Djerassi, C. (1980) · Steroids · doi:10.1016/0039-128x(80)90104-x · Cited by 55

Biosynthesis of the algal pheromone hormosirene by the fresh-water diatom Gomphonema parvulum (Bacillariophyceae)

Pohnert, G., & Boland, W. (1996) · Tetrahedron · doi:10.1016/0040-4020(96)00548-0 · Cited by 55

Cultivation of Bacteria-Free Hydra viridis : Missing Budding Factor in Nonsymbiotic Hydra

Rahat, M., & Dimentman, C. (1982) · Science · doi:10.1126/science.7063873 · Cited by 54

2-(carboxycyclopropyl)glycines: binding, neurotoxicity and induction of intracellular free Ca2+ increase

Kawai, M., Horikawa, Y., Ishihara, T., Shimamoto, K., & Ohfune, Y. (1992) · European Journal of Pharmacology · doi:10.1016/0014-2999(92)90529-d · Cited by 51

Biosynthesis of algal pheromones. A model study with the composite Senecio isatideus.

Boland, W., & Mertes, K. (1985) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1985.tb08722.x · Cited by 46

Mechanism of inactivation of mitochondrial monoamine oxidase by N-cyclopropyl-N-arylalkyl amines

Silverman, R. B., & Hoffman, S. J. (1980) · Journal of the American Chemical Society · doi:10.1021/ja00522a093 · Cited by 44

Properties and biosynthesis of cyclopropane fatty acids in Escherichia coli

Cronan, J. E., Reed, R. R., Taylor, F. R., & Jackson, M. B. (1979) · Journal of Bacteriology · doi:10.1128/jb.138.1.118-121.1979 · Cited by 43

Bracken Fern Carcinogenesis: Multiple Intravenous Doses of Activated Ptaquiloside Induce DNA Adducts, Monocytosis, Increased TNFα Levels, and Mammary Gland Carcinoma in Rats

Shahin, M., Smith, B. L., Worral, S., Moore, M. R., Seawright, A. A., & Prakash, A. S. (1998) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.1998.8240 · Cited by 41

Biosynthesis of the Diterpene Verrucosan-2β-ol in the Phototrophic Eubacterium Chloroflexus aurantiacus

Rieder, C., Strauß, G., Fuchs, G., Arigoni, D., Bacher, A., & Eisenreich, W. (1998) · Journal of Biological Chemistry · doi:10.1074/jbc.273.29.18099 · Cited by 38

Conversion of 14c-labeled geranylgeranyl pyrophosphate to phytoene by a soluble tomato plastid enzyme system

Shah, D. V., Feldbruegge, D. H., Houser, A. R., et al. (1968) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(68)90208-7 · Cited by 38

Mechanism of the enzymatic cleavage of the 9β,19-cyclopropane ring of cycloeucalenol

Rahier, A., Cattel, L., & Benveniste, P. (1977) · Phytochemistry · doi:10.1016/s0031-9422(00)94357-7 · Cited by 37

Isolation and synthesis of 23-methyl-22-dehydrocholesterol -a marine sterol of biosynthetic significance

KOKKE, W. C. M. C., Withers, N. W., Massey, I. J., Fenical, W., & Djerassi, C. (1979) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)95474-7 · Cited by 37

Biosynthetic studies of marine lipids. 31. Evidence for a protonated cyclopropyl intermediate in the biosynthesis of 24-propylidenecholesterol

Giner, J. L., & Djerassi, C. (1991) · Journal of the American Chemical Society · doi:10.1021/ja00004a047 · Cited by 37

Biosynthesis of head-to-head terpenes. Carbonium ion rearrangements which lead to head-to-head terpenes

Poulter, C. D., MUSCIO, O. J. J., & Goodfellow, R. J. (1974) · Biochemistry · doi:10.1021/bi00704a032 · Cited by 33

Stereochemical studies of botryococcene biosynthesis: analogies between 1'-1 and 1'-3 condensations in the isoprenoid pathway

Huang, Z., & Poulter, C. D. (1989) · Journal of the American Chemical Society · doi:10.1021/ja00189a056 · Cited by 31

Structure of cyclizidine (antibiotic M146791) : X-ray crystal structure of an indolizidinediol metabolite bearing a unique cyclopropyl side-chain

Freer, A. A., Gardner, D. E., Greatbanks, D., Poyser, J. P., & SIM, G. A. (1982) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39820001160 · Cited by 31

Biosynthesis of (+)-car-3-ene in Pinus species

BANTHORPE, D. V., & Ekundayo, O. (1976) · Phytochemistry · doi:10.1016/s0031-9422(00)89063-9 · Cited by 29

Myrocin C, a new diterpene antitumor antibiotic from Myrothecium verrucaria. I. Taxonomy of the producing strain, fermentation, isolation and biological properties.

Nakagawa, M., Hsu, Y.-H., Hirota, A., Shima, S., & Nakayama, M. (1989) · The Journal of Antibiotics · doi:10.7164/antibiotics.42.218 · Cited by 28

On the mode of action of myrocin C: Evidence for a CC-1065 connection

Chu‐Moyer, M. Y., & Danishefsky, S. J. (1993) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)93369-0 · Cited by 27

Biosynthesis of dictyopterene A: stereoselectivity of a lipoxygenase/hydroperoxide lyase from Gomphonema parvulum (Bacillariophyceae)

Hombeck, M., Pohnert, G., & Boland, W. (1999) · Chemical Communications · doi:10.1039/a808409b · Cited by 26

Biosynthesis of the antitumor antibiotic CC-1065 by Streptomyces zelensis.

Hurley, L. H., & Rokem, J. S. (1983) · The Journal of Antibiotics · doi:10.7164/antibiotics.36.383 · Cited by 24

Properties of a 2,3‐oxidosqualene‐cycloartenol cyclase from Ochromonas malhamensis

Beastall, G. H., Rees, H. H., & Goodwin, T. W. (1971) · FEBS Letters · doi:10.1016/0014-5793(71)80438-6 · Cited by 20

Nitrogenous constituents of Billia hippocastanum and Acer pseudoplatanus

Fowden, L., Pratt, H. M., & Smith, A. (1972) · Phytochemistry · doi:10.1016/s0031-9422(00)89850-7 · Cited by 19

Olefin Cyclopropanation via Carbene Transfer Catalyzed by Engineered Cytochrome P450 Enzymes

Coelho, P. S., Brustad, E. M., Kannan, A., & Arnold, F. H. (2013) · Science · doi:10.1126/science.1231434 · Cited by 832

Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis

Thibodeaux, C. J., Chang, W.-C., & Liu, H.-W. (2012) · Chemical Reviews · doi:10.1021/cr200073d · Cited by 275

The colibactin warhead crosslinks DNA

Vizcaino, M. I., & Crawford, J. M. (2015) · Nature Chemistry · doi:10.1038/nchem.2221 · Cited by 247