scholarly journals Novel Piperidine and 3,4-dihydro-2H-pyrrole Alkaloids from Tilia platyphyllos and Tilia cordata Flowers

Planta Medica ◽  
2021 ◽  
Author(s):  
Nico Symma ◽  
Marek Bütergerds ◽  
Jandirk Sendker ◽  
Frank Petereit ◽  
Alexander Hake ◽  
...  

AbstractLime flowers, traditionally used for medical purposes for the treatment of symptoms of the common cold and mental stress, consist of the dried inflorescences including the floral bracts of Tilia cordata, Tilia platyphyllos, Tilia × vulgaris, or mixtures thereof. During phytochemical investigations, 6 different alkaloids – not described until now – were detected in T. cordata and T. platyphyllos flowers. They have been isolated and characterized as alkaloids with a dihydro-pyrrole and a piperidine substructure, respectively. Compounds 1a and 1b (tiliines A and B) are characterized as 2 diastereomers containing a 2-methyl-3,4-dihydro-2H-pyrrol-3-ol, connected via a C-10 alkyl chain to a O-glucosylated hydroquinone moiety. Compounds 2a and 2b (tiliamines A and B) are diastereomers of a 2-methyl-substituted piperidin-3-ol, coupled via a C-9 alkyl chain again to an O-glucosylated hydroquinone moiety. Compounds 3a and 3b (tilacetines A and B) are 3-O-acetylated derivatives of tiliamines. Quantification of the 6 alkaloids by HPLC-ESI-qTOF analysis indicated the presence of all alkaloids in T. cordata flowers and T. platyphyllos flowers, bracts, and leaves, with tiliines A and B and tilacetines A and B being the major compounds. Acetone/water turned out be the best extraction solvent for the alkaloids, but ethanol and ethanol/water mixtures also can be used for effective extraction. Furthermore, the alkaloids are found in hot water extracts, which are typically used in the traditional medicine.

Proceedings ◽  
2020 ◽  
Vol 70 (1) ◽  
pp. 100
Author(s):  
Minerva C. García-Vargas ◽  
María del Mar Contreras ◽  
Irene Gómez-Cruz ◽  
Juan Miguel Romero-García ◽  
Eulogio Castro

Avocado has become fashionable due to its great organoleptic and nutritional properties. It is consumed as a fresh product and it is also processed to obtain salad oil and guacamole. In all cases, the only usable portion is the pulp. Therefore, to be a more sustainable and profitable agribusiness, it is important to recognize which compounds from the peel and the stone waste can be converted into valuable bio-products. Therefore, their chemical composition was determined according to the National Renewable Energy Laboratory, the total phenolic content by the Folin-Ciocalteu method and the antioxidant properties by the FRAP and TEAC assays. The main components of the peel and stone were acid-insoluble lignin (35.0% and 15.3%, respectively), polymeric sugars (23.6% and 43.9%, respectively), and the aqueous extractives (15.5% and 16.9%, respectively). Both biomasses contain lipids and protein, but a minor proportion (<6%). The valorization of lignin and sugars is of interest given the high content; stones are a rich source of glucose (93.2% of the polymeric fraction), which could be used to obtain biofuels or derivatives of interest. The extractive fraction of the peel contained the highest number of phenolic compounds (4.7 g/100 g biomass), mainly concentrated in the aqueous fraction (i.e., 87%) compared to the ethanol one, which was subsequently extracted. It correlated with major antioxidant activity and, therefore, the peel can be applied to obtain antioxidants and water can be used as an environmentally friendly extraction solvent.


Antibiotics ◽  
2018 ◽  
Vol 7 (4) ◽  
pp. 98 ◽  
Author(s):  
Eunice Mgbeahuruike ◽  
Pia Fyhrquist ◽  
Heikki Vuorela ◽  
Riitta Julkunen-Tiitto ◽  
Yvonne Holm

Piper guineense is a food and medicinal plant commonly used to treat infectious diseases in West-African traditional medicine. In a bid to identify new antibacterial compounds due to bacterial resistance to antibiotics, twelve extracts of P. guineense fruits and leaves, obtained by sequential extraction, as well as the piperine and piperlongumine commercial compounds were evaluated for antibacterial activity against human pathogenic bacteria. HPLC-DAD and UHPLC/Q-TOF MS analysis were conducted to characterize and identify the compounds present in the extracts with promising antibacterial activity. The extracts, with the exception of the hot water decoctions and macerations, contained piperamide alkaloids as their main constituents. Piperine, dihydropiperine, piperylin, dihydropiperylin or piperlonguminine, dihydropiperlonguminine, wisanine, dihydrowisanine and derivatives of piperine and piperidine were identified in a hexane extract of the leaf. In addition, some new piperamide alkaloids were identified, such as a piperine and a piperidine alkaloid derivative and two unknown piperamide alkaloids. To the best of our knowledge, there are no piperamides reported in the literature with similar UVλ absorption maxima and masses. A piperamide alkaloid-rich hexane leaf extract recorded the lowest MIC of 19 µg/mL against Sarcina sp. and gave promising growth inhibitory effects against S. aureus and E. aerogenes as well, inhibiting the growth of both bacteria with a MIC of 78 µg/mL. Moreover, this is the first report of the antibacterial activity of P. guineense extracts against Sarcina sp. and E. aerogenes. Marked growth inhibition was also obtained for chloroform extracts of the leaves and fruits against P. aeruginosa with a MIC value of 78 µg/mL. Piperine and piperlongumine were active against E. aerogenes, S. aureus, E. coli, S. enterica, P. mirabilis and B. cereus with MIC values ranging from 39–1250 µg/mL. Notably, the water extracts, which were almost devoid of piperamide alkaloids, were not active against the bacterial strains. Our results demonstrate that P. guineense contains antibacterial alkaloids that could be relevant for the discovery of new natural antibiotics.


2012 ◽  
Vol 21 (26) ◽  
pp. 200-207
Author(s):  
Jūratė Čirūnaitė

The most popular names among Jewish women in 16th century Lithuania were Simcha, Marjam, Anna, Debora. The names were most frequently recorded as diminutives (63.3%), with only 36.4% appearing in canonical forms. The smallest group comprises names formed using only anthroponyms that were derived from those of (male) family members (29.6%). 35.2% of the namings are recorded as mixed type. The same number of women are recorded using only names in the documents.Personal names are included in 70.4% of recorded women’s namings. Andronyms (anthroponyms formed from the spouse’s name) were found in 64.8% of all the records. 9.3% of women’s namings include anthroponyms formed using the spouse’s patronymic. Only 1.9% of namings had a female patronymic (the derivative of the suffix -owna/-ewna).One-member female namings prevail (59.3%). Two-member namings comprise 33.3%. Three members are found in 5.6% of the namings, while four-membered ones comprise 1.9%. The average length of the namings is 1.5 times that of the anthroponyms.Common words explaining anthroponyms were found in 68.5% of the namings. Common words related to religion prevail (51.4%). 29.7% of the common words characterize relationships or family status, and only 10.8% describe occupation, post or trade (vocation). Common words describing descent (social origin) comprise only 8.1% of all the women’s namings.Namings consisting only of anthroponyms of family members can be subdivided into the following subgroups: 1) derivatives of the suffix -owaja/-ewaja; 2) derivatives of the suffix ‑owaja/-ewaja; 3) derivatives of the suffix -owaja/-ewaja + the genitive of a male patronymic; 4) derivatives of the suffix -owaja/-ewaja + a male patronymic + the genitive of a male patronymic. Namings without anthroponyms consisting of family members included names and names with common words. Mixed namings consisted of: 1) a name + a derivative of the suffix -owaja/-ewaja; 2) a derivative of the suffix -owaja/-ewaja + the genitive of a male patronymic + a name; 3) a derivative of the suffix -owaja/-ewaja + the genitive of a male patronymic + a name + a female patronymic.The most popular type of naming is a recorded name.


2019 ◽  
pp. 195-202
Author(s):  
Serhii Razanov ◽  
Volodymyr Nedashkivskyi

The intensity of damaging the nectar and pollen trees of forest lands, parks and woods in the conditions of Vinnytsia region has been studied. It has been found that in the zones of the highest local overspreading of Viscum album L. on the nectar and pollen trees, the following sequence of their damage is observed, in particular, in the conditions of forest lands: Tilia cordata L.-Tilia platyphyllos L. -Acer platanoides L.- Acer tataricum L.; in the parks: Acer platanoides L.- Acer tataricum L.- Tilia cordata L.- Acer campestre L.- Tilia platyphyllos L. - Robinia pseudoacacia L.; in the woods: Robinia pseudoacacia L. - Tilia platyphyllos L. - Acer tataricum L. It depended both on the composition of the nectar and pollen trees and their number in the area of distribution of the parasite. It was found that the level of damage to the nectar-dust-bearing trees of forest lands, parks and forest strips was respectively within 11.7% - 34.6%, 28.5% - 85.5% and 38.4% - 84.8%. Characterizing the intensity of distribution of white mistletoe within the forest lands, it should be noted that damage to the Tilia cordata L. – 34,6%, Tilia platyphyllos L. – 23,5%, Acer platanoides L. and Acer tataricum L.– 25,0% and 11,7% . In the conditions of park plantations, damage to Viscum album L.: Tilia cordta– 51,6%, Tilia platyphyllos L. – 52,9%, Viscum album L. – 28,5%, Acer platanoides L. – 85,5%, Acer campestre L. – 71,4% and Acer tataricum L.– 63,6%. Analysis of the intensity of Viscum album L. distribution on the nectar-pollen-bearing trees of the forest area under the highways showed that this parasite was damaged: Tilia platyphyllos L. – 38,4%, Viscum album L. – 84%, Acer campestre L. – 42,8%. The intensity of damage to nectar-pollen was found to depend on the dominant tree species in the area of local Viscum album L. In the woodland, a greater proportion of the nectar-bearing trees were Tilia, in the park zones – Acer platanoides L. and in the forest strips -– Viscum album L., at the same time, and a larger percentage were observed of damaged trees in these species. The distribution of Viscum album L. depended not only on the breed of nectar-pollen-bearing trees, but also on the number of trees of a particular variety in the area of their local damage by this parasite.


1984 ◽  
Vol 246 (6) ◽  
pp. R979-R984 ◽  
Author(s):  
M. F. Roberts ◽  
A. C. Zygmunt

We measured thermal conductance (K) of the ears of 12 New Zealand White rabbits during periods of core heating in which mean skin temperature and ear temperatures (Te) were controlled. Right Te was always held at 28 degrees C; left Te was 15, 20, 24, 28, 31, 33 degrees C in separate core heating periods. Core heating was obtained by perfusing a previously implanted intravascular heat exchanger with hot water. Blood temperature (Tbl) was measured with a thermocouple that had been previously placed in contact with the common carotid artery. During heating, K rose with rising Tbl, but the relation between K and Tbl depended on Te. At high Te, K rose rapidly in the initial stages of core heating and soon reached its maximal value. At cool Te, K rose slowly with rising Tbl until high Tbl was reached; then K rose rapidly to maximal values. The maximal value of K reached at high Tbl was independent of Te. The results suggest that local temperature affects ear blood flow by affecting the way that ear blood vessels react to sympathetic reflex signals.


1985 ◽  
Vol 68 (4) ◽  
pp. 759-762
Author(s):  
Jonathan W Devries ◽  
Paul A Larson ◽  
Raymond H Bowers ◽  
Joyce A Keating ◽  
James M Broge ◽  
...  

Abstract A method is described for the determination of the common fumigants carbon tetrachloride (CC14), ethylene dichloride (EDC), and ethylene dibromide (EDB) in grain and grain-based products. A properly prepared sample is mixed with water and hexane, an internal standard mixture of 1,2-dichloropropane (DCP) and 1,2-dibromopropane (DBP) is added, and the fumigants are codistilled with the hexane into an appropriate receiver. After the hexane solution is dried over sodium sulfate, the quantities of fumigants present are quantitated on a gas chromatograph (GC) equipped with an electron capture detector (ECD). For the matrices investigated, the relative standard deviation of the method was 6.0,9.7, and 23.1% for CC14, EDC, and EDB, respectively. Recoveries of added fumigants were 107, 95, and 101%, respectively. Comparison with an acetone-water soak extraction method gave a correlation of 0.967 between methods for EDB with odds of a difference between methods of 35%.


2000 ◽  
Vol 92 (3) ◽  
pp. 786-794 ◽  
Author(s):  
Dennis Christensen ◽  
Gisèle Guilbaud ◽  
Valérie Kayser

Background Tolerance to the analgesic effect of morphine complicates the management of chronic pain states. The authors studied the ability of the glycine/N-methyl-D-aspartate receptor antagonist (+)-HA966 to modify morphine tolerance in a rat model of neuropathic pain. Methods Mononeuropathy was induced by placing four ligatures around the common sciatic nerve. The 4-day pretreatment regimens with two daily subcutaneous injections of saline and saline, saline and morphine (10 mg/kg), (+)-HA966 (2.5 mg/kg) and morphine, or (+)-HA966 and saline were begun on post-operative day 12 to test the ability of (+)-HA966 to prevent the development of tolerance. Behavioral experiments were performed on postoperative day 16, when the pain-related behavior reached a stable maximum. The effect of an acute dose of morphine (1 mg/kg intravenously) was tested against both mechanical (vocalization threshold to paw pressure) and thermal (struggle latency to hind paw immersion into a 46 degrees C hot-water bath) stimuli. In addition, to test the ability of a single injection of (+)-HA966 to reverse established morphine tolerance, groups of morphine-pretreated rats received injections of either (+)-HA966 (2.5 mg/kg subcutaneously) and morphine (1 mg/kg intravenously), saline and morphine, or (+)-HA966 and saline. Results Baseline vocalization thresholds and struggle latencies did not differ in the various pretreatment groups, indicating that the pretreatments had no effect on pain-related behavior. Coadministration of (+)-HA966 prevented the reduction of the effect observed with morphine alone in both the mechanical test and the thermal test. (+)-HA966 reversed morphine tolerance in the thermal but not in the mechanical test. Conclusion (+)-HA966 prevented morphine tolerance in both mechanical and thermal tests but reversed established morphine tolerance in the thermal test only.


2020 ◽  
Vol 15 (2) ◽  
pp. 1934578X1990070 ◽  
Author(s):  
Weida Zhang ◽  
Shaobo Cheng ◽  
Xiaona Zhai ◽  
Junshe Sun ◽  
Xuefang Hu ◽  
...  

Deep eutectic solvents (DESs) were proposed for the extraction of polysaccharides from Poria cocos (PCPs). Six types of DESs were prepared, and the DES composed of choline chloride and oxalic acid was proved to be suitable. Based on the results of single-factor test, the Box-Behnken experimental design with response surface methodology was carried out, giving the optimal extraction conditions including mole ratio of 1:2 (choline chloride:oxalic acid) and extraction 15 minutes at 100°C. Under the optimal extraction conditions, the extraction yield (46.24% ± 0.13%) was 8.6 times higher than that of hot water. The reusability of DES was demonstrated by a 6-run test, and an extraction yield of PCP was 38.40% ± 0.23% after reusing for 6 times without adding any additional chemicals. Moreover, molecular weight distributions of the resulting PCP were analyzed, and then mainly distributed in the range of 753 to 3578 g/mol. Therefore, DESs were proved to be an excellent extraction solvent alternative to the extraction of PCP.


1993 ◽  
Vol 48 (3-4) ◽  
pp. 326-333 ◽  
Author(s):  
Beate Nicolaus ◽  
Gerhard Sandmann ◽  
Peter Böger

Abstract Protoporphyrinogen oxidase, the last enzyme of the common tetrapyrrole biosynthetic pathway, is inhibited by several peroxidizing compounds resulting in accumulation of photodynamic tetrapyrroles, mainly protoporphyrin IX. The inhibition characteristics of two chemi­cally unrelated compounds were studied using membrane bound protoporphyrinogen oxidase from corn etioplasts. As shown by Lineweaver-Burk-analysis, the inhibition of enzyme activity by the diphenyl ether oxyfluorfen and the cyclic imide MCI 15 are competitive with respect to the substrate. The competitive interaction of protoporphyrinogen and the two chemically un­related inhibitors indicate a relative specificity of the binding site. The reversibility of oxyfluorfen inhibition was evaluated by dilution experiments and was shown to be independent of the presence of DTT. The analysis of structure-activity-relationship on protoporphyrinogen oxidase inhibition was investigated with para-substituted derivatives of phenyl-3,4,5,6-tetrahydro-phthalimides. The results obtained by QSAR -calculation yielded a good correlation of the inhibitory activity determined by the lipophilicity of the para-substituent. These data point to one binding region of the inhibitors within a lipophilic environment associated with the active center of the enzyme.


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