Two New Alkylated Piperidine Alkaloids from Western Honey Mesquite:Prosopis glandulosaTorr. var.torreyana
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Abstract:
Prosopis glandulosa Torr. var. torreyana (L. Benson) M. C. Johnston root bark, collected in Texas, yielded two new alkylated piperidine alkaloids, namely 3-isocassine (1) and N-methyl-3-isocassine (2), together with the previously reported N-methylcassine (3). In addition, the alkylated piperidinyl indolizidine alkaloid juliprosopine (4) was isolated from the leaves of the same plant. The structures and stereochemistry of compounds 1–4 were determined from 1D and 2D NMR data, including COSY, HMQC, HMBC and NOESY experiments, and ESI-HRMS. Juliprosopine (4) demonstrated antimicrobial activities against a panel of microorganisms, including potent antifungal activities against Aspergillus fumigatus.Keywords:
Prosopis glandulosa
Piperidine
Indolizidine
Prosopis
Cold tolerance and biomass estimation of Prosopis species were examined under field conditions. Prosopis africana and P. pallida tolerated several minus 1.5/sup 0/C freezes but none survived a minus 5/sup 0/C freeze. P. alba, P. articulata, P. chilensis, P. nigra, and P. tamarugo tolerated several minus 5/sup 0/C freezes but not a 12-hour below 0/sup 0/C freeze. Most North American native species P. glandulosa var. glandulosa, P. glandulosa var. torreyana, and P. velutina tolerated the 12 hour freeze with only moderate damage. In general trees with greater productivity belonged to the most cold sensitive accessions but sufficient variability exists to substantially improve Prosopis biomass production on the coldest areas where it now naturally occurs.
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The synthesis of 2-substituted and 2,4-disubstituted piperidine alkaloids such as (±)-coniine, (±)-hydroxypipecolic acid, (±)-pipecolic acid, (±)-coniceine, and (±)-4-hydroxy-2-hydroxymethyl piperidine have been accomplished in a highly diastereoselective manner by employing aza-Prins cyclization as a key step to construct the piperidine core of these alkaloids.
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Indolizidine
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Prosopis
Prosopis glandulosa
Cycling
Nitrogen Cycle
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Prosopis glandulosa
Prosopis
Understory
Tussock
Herbaceous plant
Larrea
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Prosopis
Prosopis glandulosa
Prosopis juliflora
Larrea
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Abstract. Prosopis glandulosa var. glandulosa has played a central role in the encroachment of woody plants in southern Texas, grasslands and savannas by acting as a nurse plant for various shrubs that establish in its understory. To test for continued facilitation of established understory shrubs by Prosopis and to determine if established shrubs compete with the Prosopis nucleus, selective removal experiments were conducted and monitored over a 2–5 yr period. Short‐term (1–3 days) and long‐term (2 yr) growth and physiological activities (midday net photosynthesis and leaf/shoot water potential) of two common understory shrubs, Zanthoxylum fagara and Berberis trifoliolata , growing with Prosopis , were generally comparable to those of individuals occurring in clusters where Prosopis was removed. Shrubs growing with an intact Prosopis occasionally showed significantly higher leaf‐[N] and pre‐dawn water potentials than those in clusters lacking a live Prosopis , especially under drought conditions; however, these differences did not translate into greater midday leaf gas exchange or shoot growth. By comparison, removal of understory shrubs elicited large increases in Prosopis net photosynthesis, annual trunk growth in each of the 5 yr monitored, and seed pod production in three of the four years monitored. Seven of 26 Prosopis plants in experimental clusters with an intact understory died over a 5‐yr period, compared to only two of the 26 plants in clusters with the cleared understory. Results indicate that (1) the founding overstory Prosopis plant may continue to facilitate understory shrubs following their establishment, but these beneficial effects appear to be small and transitory, and (2) the understory shrubs have a pronounced negative effect on Prosopis , such that competition between overstory and understory woody plants is strongly asymmetrical. These findings suggest that understory shrubs will likely persist despite changes in microclimate and soils (potentially) that occur after the Prosopis plant, which facilitated their ingress or establishment, has died. Soil resource depletion by shallow‐rooted understory shrubs appears to be a primary factor contributing to the demise of the deeply rooted, overstory Prosopis plants, especially on upland sites with duplex soils where below‐ground competition is accentuated.
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Prosopis glandulosa
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Prosopis glandulosa var. torreyana accounts for nearly 90% of the total plant cover in a mesquite woodland community near Harper's Well along the southern margin of the Salton Sea in the Sonoran Desert of California. Total above‐ground biomass in ten individuals studied in detail ranged from 43–760 kg per plant and 1.9–8.5 kg m ‐2 canopy area. Stand biomass ranged locally from a high of 23,000 kg ha ‐1 near the wash to 3,500 kg ha ‐1 in the fringe of this mesquite stand. Net above‐ground primary production for 1980 had a mean of 2.2 kg m ‐2 canopy for shrub forms and 5.3 kg m ‐2 canopy for tree forms. Mean Prosopis stand production for 1980 was 3,650 kg ha ‐1 , an extremely high value for desert communities. This level of production is particularly high in relation to the low mean annual precipitation of approximately 70 mm. New woody tissues in trunk and branches accounted for 51.5% of the allocation of productivity in Prosopis , a remarkably high woody allocation for a desert plant. Only 33.6% of net primary production was allocated to leaves.
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Prosopis
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Standing crop
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Prosopis glandulosa
Prosopis juliflora
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At savanna woodland sites in southern Texas, discrete clusters of woody plants form in herbaceous clearings following the invasion of mesquite (Prosopis glandulosa var. glandulosa), an arborescent legume. The growth rate of these clusters has been shown to vary with precipitation and size. Based on field data and a knowledge of mechanisms of woody-plant successional processes, a simulation model was developed to estimate the rates of growth and development of these woody-plant assemblages on sandy-loam uplands under different precipitation regimes. In the simulation, the establishment of other woody species beneath invading Prosopis occurred within 10-15 yr. As a cluster developed around the Prosopis nucleus, species richness increased rapidly for 35-45 yr and became asymptotic at 10 species per cluster. The estimated age of the oldest Prosopis plant found in clusters was 172-217 yr. However, model-derived size-age relationships predicted that most (90%) clusters and mesquite plants at the site are less than 100 yr old. A lack of field evidence of mortality among large clusters and Prosopis plants suggests that populations are young and expanding geometrically. There was no evidence of density-dependent restrictions on recruitment or expansion. Thus, as new clusters are initiated and existing clusters expand, coalescence to continuous canopy woodlands may eventually occur. Predicted long-term mean radial trunk growth of Prosopis (0.8-1.9 mm/yr) was reasonable in comparison with short-term field measurements on Prosopis in other, more-mesic systems (2-4 mm/yr). Model output was also consistent with historical observations suggesting that the conversion of savannas to woodlands in the Rio Grande Plains has been recent and coincident with both heavy grazing by livestock and seasonal shifts in precipitation that began in the late 1800s. This is in agreement with woody-plant invasions documented in other North American arid and semiarid systems by the direct aging of woody plants.
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Herbaceous plant
Old field
Understory
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The western honey mesquite, Prosopis glandulosa var torreyana, is one of the primary natural resources of the Seri of western Sonora, Mexico. Different parts of the mesquite are variously employed for basketry dye, face paint, hunting and fishing, firewood, games, medicine, lumber, wooden artifacts, and rope or twine. Until recently the fruit was utilized extensively for food. Relatively large quantities of flour were obtained from the mesocarp. The Seri also prepared flour from the true seed which was separated from the stony endocarp by pounding in bedrock mortars. Prepared mesquite flour products were stored for times of need. A relatively extensive vocabulary is associated with the mesquite—the Seri recognize eight growth stages of the mesquite pod. The Seri moon approximating the month of July derives from the time of mesquite harvest, a time when the monsoon begins and initiates maximum renewal of life in the desert. This moon is for the Seri the beginning of the new year.
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