Protoanemonine

Lactones. Physiologically active lactones such as parasorbic acid, coumarin, scopoletin, and protoanemonin occur in many plant families (Figure 2). The lactones may perform a regulatory function in the plant, and have been shown to inhibit germination and to repress root growth [reviewed in detail by Hemberg 61), Evenari 36,37), and Borner 12)]. 

Protoanemonin, which has been isolated from Anemone pulsatilla and Ranunculus spp., was reported to inhibit root growth by slowing down metabolism and blocking mitosis 35). Erickson and Rosen 35) observed cytological effects in corn root tips at concentrations of 10M and lower. Cells undergoing division appeared to accumulate in the interphase or prophase stages. Metaphase, anaphase, and telophase stages were not observed. Cytoplasmic and vacuolar structures were disturbed and the presence of mitochondria could not be demonstrated in treated tissue. Thimann and Bonner 141) reported that protoanemonin was 10 to 30 times more inhibitory than coumarin in coleoptile and split pea stem tests, and that BAL prevented the inhibitory action. 

In addition to effects on biochemical reactions, the inhibitors may influence the permeability of the various cellular membranes and through physical and chemical effects may alter the structure of other subcellular structures such as proteins, nucleic acid, and spindle fibers. Unfortunately, few definite examples can be listed. The action of colchicine and podophyllin in interfering with cell division is well known. The effect of various lactones (coumarin, parasorbic acid, and protoanemonin) on mitotic activity was discussed above. Disturbances to cytoplasmic and vacuolar structure, and the morphology of mitochondria imposed by protoanemonin, were also mentioned. Interference with protein configuration and loss of biological activity was attributed to incorporation of azetidine-2-carboxylic acid into mung bean protein in place of proline. 

Blasco R, M Mallavarapu, R-M Wittich, KN Timmis, DH Pieper (1997) Evidence that formation of protoanemonin from metabolites of 4-chlorobiphenyl degradation negatively affects the survival of 4-chlorobiphenyl-cometabolizing microorganisms. Appl Environ Microbiol 63 434. 

Blasco R, R-M Wittich, M Mallavarapu, KN Timmis, DH Pieper (1995) From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway. J Biol Chem 270 29229-29235. 

Briickmann M, R Blasco, KH Timmis, DH Pieper (1998) Detoxification of protoanemonin by dienelactone hydrolase. Appl Environ Microbiol 64 400-402. 

Additional limitations. Other limitations have been enconntered (a) the formation of the inhibitory protoanemonin from 4-chlorocatechols (Blasco et al. 1995) and (b) the ineffectiveness of cycloisomerases reqnired for effective degradation of 2-chlorotoluene (Polhnann et al. 2005). An example of this limitation is given later, and in the degradation of 3-flnorobenzoate in Part 3 of this chapter. 

Protoanemonin Several Ranunculacea sp. Inhibits seed germination... 

The possibility of a biradical mechanism was suggested using the MNDO and AMI semiempirical methods, for the addition of protoanemonin (5-methylene-2(5Z/)-furanone) to butadiene105 and to several substituted dienes106. Experimental evidence for this kind of mechanism has recently been published133. A biradical mechanism has also been considered for the dimerization of butadiene96. For this reaction, CASSCF calculations... 

Grigg et al. (84) also used protoanemonin-based compounds as C(5) synthetic precursors in intramolecular cycloadditions. The 4-substimted protoanemonin 278 was synthesized in seven steps and was primed for intramolecular reactions. 

Anemone cemua Thunb. A. pulsatilla A. pulsatilla var. chinensis Bunge. Bai Tu Own (Pulsatila) (root) Saponins, protoanemonin.49 A cardiac and nervous system sedative, antispasmodic, anodyne in asthma and pulmonary infections, antidiarrheic. 

Caltha palustris L. var. membranacea Turcz. C. palustris L. var. sibirica Regel Luo Ti Cao (Marsh marigold) (whole plant) Anemonin, protoanemonin, choline, hellebrin, cevadine, berberine, scopoletin, saponin, umbelliferone, isorhamnetin, xanthophyllepoxyl.48 50 Antirheumatic, antitumor. 

Ranunculus chinensis Bunge. Hui Hui Suan (whole plant) Protoanemonin, anemonin, ranunculin.48 Relieve swelling, asthma, liver disorders, toothache, night blindness. 

Ranunculus japonicus Thunb. R. sarmentosa Adams Mao Liang (Japanese radish) (whole plant) Anemonin, protoanemonin.50 Antitumor, sedative, bactericidal against bacillae of diphtheria, staphylococcus. 

Ranunculus sceleratus L. Shi Long Nei (Ground mulberry) (whole plant) Ranunculin, anemonin, 5-hydroxytryptamine, seratonin, protoanemonin, pyrogallol tannins.48 50 This herb is toxic. Relieve swelling, pain, antitoxin, treat lymphatic gland disorders, antirheumatic. 

Pulsatilla chinensis (Bunge.) Regel China Protoanemonin, anemonin, okinalin, okinalein, ranuneulin, saponins.33 Antiamebial, antibacterial, treat amebic dysentery. 

N.A. Lactone, protoanemonin, anemonin, pulsatoside, anemonol." Antibacterial, as an irritant. 

N.A. Anemone hepatica (DC.) Ker-Gawl. A. patens L. A. pulsutilla L. Lactone protoanemonin (anemonin), triterpenoid saponins, tannins, volatile oil." For cramps, menstrual problems, distress, spasmodic pain of the reproductive system. 

N.A. Clematis vitalba L. C. virginiana L. Protoanemonin, saponins.99 This herb is toxic. Analgesic, relieve pain to arthritic joints, diuretic, counter urinary problems. 

Protein (TAP29) Proteinase Proto-isoerubosides Protoanemonin... 

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