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Impairment of Photorespiratory Carbon Flow into Rubber by the Inhibition of the Glycolate Pathway in Guayule (Parthenium argentatum Gray).

Cut shoots of guayule (Parthenium argentatum Gray) were treated with four inhibitors of the glycolate pathway (alpha-hydroxypyridinemethanesulfonic acid; isonicotinic acid hydrazide, glycine hydroxamate, and amino-oxyacetate, AOA) in order to evaluate the role of photorespiratory intermediates in providing precursors for the biosynthesis of rubber. Photorespiratory CO(2) evolution in guayule leaves was severely inhibited by AOA. Application of each of the four inhibitors has resulted in a significantly decreased incorporation of (14)C into rubber fractions suggesting that the glycolate pathway is involved in the biosynthesis of rubber in guayule. However, the application of each of the glycolate pathway inhibitors showed no significant effect on photosynthetic CO(2) fixation in the leaves. The inhibitors individually also reduced the incorporation of labeled glycolate, glyoxylate, and glycine into rubber, while the incorporation of serine and pyruvate was not affected. The effective inhibition of incorporation of glycolate pathway intermediates in the presence of AOA was due to an inhibition of glycine decarboxylase and serine hydroxymethyltransferase. It is concluded that serine is a putative photorespiratory intermediate in the biosynthesis of rubber via pyruvate and acetyl coenzyme A.

Journal Article↗

Photosynthetic Characteristics of the C(3)-C(4) Intermediate Parthenium hysterophorus.

The weedy species Parthenium hysterophorus (Asteraceae) possesses a Kranz-like leaf anatomy. The bundle sheath cells are thick-walled and contain numerous granal chloroplasts, prominent mitochondria, and peroxisomes, all largely arranged in a centripetal position. Both mesophyll and bundle sheath chloroplasts accumulate starch. P. hysterophorus exhibits reduced photorespiration as indicated by a moderately low CO(2) compensation concentration (20-25 microliters per liter at 30 degrees C and 21% O(2)) and by a reduced sensitivity of net photosynthesis to 21% O(2). In contrast, the related C(3) species P. incanum and P. argentatum (guayule) lack Kranz anatomy, have higher CO(2) compensation concentrations (about 55 microliters per liter), and show a greater inhibition of photosynthesis by 21% O(2). Furthermore, in P. hysterophorus the CO(2) compensation concentration is relatively less sensitive to changes in O(2) concentrations and shows a biphasic response to changing O(2), with a transition point at about 11% O(2). Based on these results, P. hysterophorus is classified as a C(3)-C(4) intermediate. The activities of diagnostic enzymes of C(4) photosynthesis in P. hysterophorus were very low, comparable to those observed in the C(3) species P. incanum (e.g. phosphoenolpyruvate carboxylase activity of 10-29 micromoles per milligram of chlorophyll per hour). Exposures of leaves of each species to (14)CO(2) (for 8 seconds) in the light resulted in 3-phosphoglycerate and sugar phosphates being the predominant initial (14)C products (77-84%), with </=4% of the (14)C-label in malate plus aspartate. These results indicate that in the C(3)-C(4) intermediate P. hysterophorus, the reduction in leaf photorespiration cannot be attributed to C(4) photosynthesis.

Journal Article↗

Stimulation of Isopentenyl Pyrophosphate Incorporation into Polyisoprene in Extracts from Guayule Plants (Parthenium argentatum Gray) by Low Temperature and 2-(3,4-Dichlorophenoxy) Triethylamine.

Rubber particles isolated from guayule (Parthenium argentatum Gray) stem homogenates contain a polyprenyl transferase which catalyzes the polymerization of isopentenyl pyrophosphate into polyisoprene. The polymerization reaction is stimulated with the addition of an allylic pyrophosphate initiator and forms a polymer of polyisoprene with a molecular weight distribution from 10(3) to 10(7). The polymerization reaction in crude stem homogenates is not affected by the addition of an initiator probably due to the high activity of isopentenyl pyrophosphate isomerase furnishing saturating levels of dimethylallyl pyrophosphate. Polyisoprene formation in stems of guayule plants exposed to cold winter temperatures increased from 15.4 milligrams per gram dry weight in October to 24.5 milligrams per gram dry weight in January and increased from 16.2 to 38.1 milligrams per gram dry weight in the same period by additionally treating the plants with 5000 ppm of 2-(3,4-dichlorophenoxy)triethylamine. The rate of polymerization of isopentenyl pyrophosphate into polyisoprene in stem homogenates of the cold treated plants increased from 12.1 nanomoles per hour per gram fresh weight in October to 144.3 nanomoles per hour per gram fresh weight in January and increased from 17.7 to 446.8 nanomoles per hour per gram fresh weight in the same period by additionally treating the plants with 5000 ppm of 2-(3,4-dichlorophenoxy)triethylamine. These results show that the increase in polyprenyl transferase activity partially accounts for the increase in polyisoprene synthesis in guayule plants exposed to low temperature and treated with 2-(3,4-dichlorophenoxy)triethylamine.

Journal Article↗

The Enzymatic Synthesis of Rubber Polymer in Parthenium argentatum Gray.

Washed rubber particles isolated from stem homogenates of Parthenium argentatum Gray by ultracentrifugation and gel filtration on columns of LKB Ultrogel AcA34 contain rubber transferase which catalyzes the polymerization of isopentenyl pyrophosphate into rubber polymer. The polymerization reaction requires Mg(2+) isopentenyl pyrophosphate, and an allylic pyrophosphate. The K(m) values for Mg(2+), isopentenyl pyrophosphate, and dimethylallyl pyrophosphate were 5.2 x 10(-4) molar, 8.3 x 10(-5) molar, and 9.6 x 10(-5) molar, respectively. The molecular characteristics of the rubber polymer synthesized from [(14)C]isopentenyl pyrophosphate were examined by gel permeation chromatography on three linear columns of 1 x 10(6) to 500 Angstroms Ultrastyragel in a Waters 150C Gel Permeation Chromatograph. The peak molecular weight of the radioactive polymer increased from 70,000 in 15 minutes to 750,000 in 3 hours. The weight average molecular weight of the polymer synthesized over a 3 hour period was 1.17 x 10(6) compared to 1.49 x 10(6) for the natural rubber polymer extracted from the rubber particles. Over 90% of the in vitro formation of the rubber polymer was de novo from dimethylallyl pyrophosphate and isopentenyl pyrophosphate. Treatment of the washed rubber particles with 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate solubilized the rubber transferase. The solubilized enzyme(s) catalyzed the polymerization of isopentenyl pyrophosphate into rubber polymer with a peak molecular weight of 1 x 10(5) after 3 hours of incubation with Mg(2+) and dimethylallyl pyrophosphate. The data support the conclusion that the soluble preparation of rubber transferase is capable of catalyzing the formation of a high molecular weight rubber polymer from an allylic pyrophosphate initiator and isopentenyl pyrophosphate monomer.

Journal Article↗

Allergenic nature of Parthenium hysterophorus.

Parthenin has been reported as the active allergen in Parthenium hysterophorus contact sensitivity. A study was carried out to test various chemical fractions of the plant for isolating and identifying the exact allergens. Two additional sesquiterpene lactones apart from parthenin have been shown to be allergenically active. Structures of these sesquiterpenoids are presented. Photopatch tests do not indicate a photosensitizing capacity for these compounds.

Allergens↗

The current status of the weed Parthenium hysterophorus L. as a cause of allergic contact dermatitis.

The dissemination of allergenic plants as horticultural introductions, or in the case of the weed Parthenium hysterophorus L. apparently by chance, can have undesirable results. This species of the Compositae family, native to the Caribbean region, has spread widely in India, causing allergic contact dermatitis from its content of sesquiterpene lactones, and has recently appeared in Australia. The clinical features consist of dermatitis of the exposed skin surfaces from direct contact with the weed, but resembling photodermatitis. In fact, contact dermatitis from the plant can coexist with light sensitivity. The plant does not show phototoxic activity but may contain an unidentified photoallergen. Since plant hairs and the pollen contain sesquiterpene lactones, they can probably cause airborne contact dermatitis. Attempts to control spread of the plant have so far not been successful.

Chemical Phenomena↗

The effect of an aqueous extract of Tanacetum parthenium L. on arachidonic acid metabolism by rat peritoneal leucocytes.

The effect of feverfew (Tanacetum parthenium L., Schultz Bip.) as a whole plant on an aqueous extract equivalent to 20 mg dried plant per ml, has been examined on both cyclo-oxygenase and lipoxygenase activity in rat leucocytes in-vitro. At 10-25 micrograms ml-1 feverfew had no effect on the formation of arachidonate metabolites while at highest concentrations (50-200 micrograms ml-1) it inhibited both cyclo-oxygenase and lipoxygenase metabolic products.

Animals↗

Potent contact allergen in the rubber plant guayule (Parthenium argentatum).

Chemical and dermatotoxicological investigations of the natural and processed resin of the Mexican rubber plant, guayule (Parthenium argentatum), has established the presence of a sesquiterpene cinnamic acid ester (guayulin A) that is a potent elicitor of allergic contact dermatitis in experimental animals. The guayule contact allergen is comparable to the poison ivy skin allergens as an elicitor of dermatitis in sensitized guinea pigs.

Allergens↗

Allergic reactivity of Parthenium hysterophorus (Santa Maria feverfew) pollen: an unrecognized allergen.

Parthenium hysterophorus (PH), a member of the Asteraceae, is a ubiquitous weed found in great profusion in the United States Gulf coast area. A plant survey carried out in Texas Gulf coast demonstrated that around Corpus Christi, PH is the most prevalent weed. We have studied known ragweed-sensitive patients living in Austin and Corpus Christi, by radioallergosorbent test (RAST) analysis for PH and Ambrosia psilostachya (AP; western ragweed). Nine of ten patients from Austin were RAST-positive to PH and AP; 8 of the 10 patients had positive scores to both pollen extracts. All of the 8 patients from Corpus Christi were positive to both PH and AP. The Austin group showed a significant correlation between AP and PH RAST scores while no correlation between RAST values was seen in the Corpus Christi group. RAST inhibition analysis in this highly selected population did reveal patients that had true sensitivity to PH pollen alone or who were sensitive to both PH and AP pollen. This suggests that in areas where it is highly prevalent PH pollen is an overlooked cause of allergic disease.

Allergens↗

Insect growth regulatory activity of some extracts and compounds from Parthenium argentatum on fall armyworm Spodoptera frugiperda.

The methanolic extract from aerial parts of Parthenium argentatum, afforded argentatin A and B. These compounds were evaluated for their effect on the fall armyworm (Spodoptera frugiperda). Toosendanin, a commercial insecticide derived from Melia azedarach was used as positive control. When tested for activity, using neonate larvae into the no-choice artificial diet bioassays, argentatin A, argentatin B and methanol extract caused significant growth inhibitory activity with GC50 of 17.8, 36.1 and 6.4 ppm at 7 days, respectively, and increased the development time of surviving larvae in a concentration-dependent manner with RGI values of 0.40, 0.60 and 0.26, at 25.0, 25.0 and 5.0 ppm, respectively. In addition, it was possible to observe in most of the treated groups a significant delay in the time of pupation, adult emergence and deformities. Acute toxicity against adults of S. frugiperda was also found, MeOH extract had the most potent activity with LD50 value of 3.10 ppm. In addition, MeOH extract and argentatin A caused acetylcholinesterase inhibition of 93.7% and 90.0%, at 5.0 and 50.0 ppm, respectively; whereas argentatin B had only slight inhibitory activity. Therefore, the MeOH extract was identified as insecticidal extract from P. argentatum with activity at concentrations above 15.0 ppm.

Acetylcholinesterase↗

Pyridine alkaloids from a Parthenium hybrid.

Two pyridine alkaloids were isolated from the derubberized resin of the hybrid Parthenium argentatum x P tomentosa. These alkaloids are (+/-)-N-[4-(1-aminoethyl) phenyl]-4-[3-methylbutenylidine]-1,4-dihydropyridine (guayulamine A) and (+/-)-N-[4-(1-aminoethyl) phenyl]-4-[4-methylpentenylidine]-1, 4-dihydropyridine (guayulamine B). The structures were established by one- and two-dimensional NMR spectroscopy and mass spectrometry.

Alkaloids↗

Evaluation of the pesticidal potential of the congress grass, Parthenium hysterophorus Linn. on the mustard aphid, Lipaphis erysimi (Kalt.).

Petroleum ether extracts of leaves, stem and inflorescence of Parthenium hysterophorus Linn. at 500, 1000, 2000 and 5000 ppm concentrations were tested in the laboratory for their toxic effects on the mean life span and progeny production of adults of the mustard aphid, Lipaphis erysimi (Kalt.). The investigations revealed a significant decrease in life span and progeny production with treatment. Among the three plant parts tested for their efficacy, the leaf extract showed the most significant effect in causing a dose dependent decline in both the life span and progeny production.

Animals↗

Parthenium weed and human health in Queensland.

Allergic reactions to the pollen and plant dust of parthenium weed are causing major health problems in central Queensland, which can be expected to increase, especially as the pasture weed is rapidly spreading south. This paper reviews published information on health aspects of this weed and calls attention to its spread into areas with much greater population.

Animals↗

Inhibition of interleukin-12 production in lipopolysaccharide-activated mouse macrophages by parthenolide, a predominant sesquiterpene lactone in Tanacetum parthenium: involvement of nuclear factor-kappaB.

Pharmacological control of interleukin-12 (IL-12) production may be a key therapeutic strategy for modulating immunological diseases dominated by type-1 cytokine responses. In this study, we investigated the effects of parthenolide, an anti-inflammatory sesquiterpene, on the production of IL-12 from mouse macrophages stimulated with lipopolysaccharide (LPS). Parthenolide potently inhibited the LPS-induced IL-12 production in a dose-dependent manner. The effect of parthenolide on IL-12 p40 promoter activation was analyzed by transfecting RAW264.7 monocytic cells with p40 promoter/luciferase constructs. The repressive effect mapped to a region in the p40 promoter containing a binding site for nuclear factor-kappaB (p40-kappaB). Furthermore, activation of macrophages by LPS resulted in markedly enhanced binding activity to the kappaB site, which significantly decreased upon addition of parthenolide. These results suggest that parthenolide-induced inhibition of IL-12 production in macrophages may explain some of the biological effects of parthenolide including its anti-inflammatory activity.

Animals↗