Isolation and Identification of Antiplatelet Aggregatory Principles from the Leaves of Piper lolot

Tsai, Wei‐Jern; Damu, Amooru G.; Lee, E-Jian; Wu, Tzi Yi; Dũng, Nguyên Xuân; Thăng, Trân Đình; Thanh, Le Thi Ha

doi:10.1021/jf071963l

Cited by 38 publications

(24 citation statements)

References 37 publications

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“…Pipernonaline (124) showed excellent larvicidal activity against Aedes aegypti, comparable to pirimiphos-methyl, the insecticide commonly used; 201 retrofractamide A (126) offered satisfactory adipogenic activity, can be considered a promising candidate for the development of antidiabetic agents, 28 and the N-[trans-cinnamoyl] pyrrolidine (36) inhibitor of platelet aggregation with IC 50 of 7.3 mg/mL, comparable with aspirin (IC 50 5.5 mg/mL), an anti-clotting agent used clinically to combat the formation of thrombi. 131 Data demonstrated the biological and medicinal importance of piplartine isolated from the roots of P. chaba, and indicated that E-piplartine may be a promising candidate for use in combinatorial treatments to combat cancer. 275 To date, the presence of 277 amides from Piper has been reported while data from chemical shifts in 13 C NMR is available for 182 compounds.…”

Section: Concluding Remarks and Future Perspectivesmentioning

confidence: 97%

Occurrence, biological activities and 13C NMR data of amides from Piper (Piperaceae)

Nascimento¹,

Paula²,

David³

et al. 2012

Quím. Nova

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Recebido em 30/3/12; aceito em 24/7/12; publicado na web em 26/10/12 This manuscript describes an update review with up to 285 references concerning the occurrence of amides from a variety of species of the genus Piper (Piperaceae). Besides addressing occurrence, this review also describes the biological activities attributed to extracts and pure compounds, a compiled 13 C NMR data set, the main correlations between structural and NMR spectroscopic data of these compounds, and employment of hyphened techniques such as LC-MS, GC-MS and NMR for analysis of amides from biological samples and crude Piper extracts. Keywords: Piper;13 C NMR compilation; amides. INTRODUCTIONPiperaceae is one of the largest families among the basal Angiosperms, with approximately 3,000 species described to date. 1The family is currently divided into five genera: Macropiper, Zippelia, Piper, Peperomia and Manekia, 2 consisting of a wide variety of species found commonly around the world. Piper, Peperomia and Manekia occur in Brazil, mainly in the Amazonian and Atlantic forests. 3 Piper is the largest genus of this family, including more than 1,000 species, and can also be considered the largest genus of the basal angiosperms. 4 Amides are the major constituents of several species of Piper. Currently, they can be considered alkaloids in accordance with the modern definition by Pelletier.5 Natural amides can be classified as open-chain alkamides, aristolactams, 4,5-dioxoaporphines, ceramides, amides with pyrrolidine, piperidone and piperidine groups, cyclobutanamides and cyclohexanamides. The term piperamide is restricted to describe all compounds carrying an aromatic group and an amide group.In 1997, a review of this genus was published 6 dealing with chemical distribution and biological activities of amides. In the present review, an update with new chemical constituents of this genus is described and a compilation of 13 C NMR data and biological activities of these compounds are provided. Piper SPECIES, TRADITIONAL USES AND BIOLOGICAL ACTIVITIESDespite the large number of species of Piper, the use of these plants in folk medicine remains limited. One of the most well-known Piper Brazilian medicinal plants is P. corcovadensis, commonly found in North and Northeast regions, and popularly known as "João-brandinho". The leaves of this plant are used for the treatment of rheumatism in the form of poultice and infusions as well for flu and cough. In the Southeast region, the roots and branches of this specie are chewed to relieve toothache due to its anesthetic action on the mucous membrane. 7 In China, the use of leaves of P. futokasura is recommended in the treatment of cardiac arrhythmias and asthma. In Jamaica, stomach pains are treated with an infusion of leaves from P. aduncum and P. hispidum. Leaves from P. amalago are also employed in Mexico and Brazil for stomach pains and for the treatment of various infections. 8 Leaves and stems of P. marginatum and P. tuberculatum are used in Brazil, especially in Paraíba State (Brazil) agains...

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Section: Concluding Remarks and Future Perspectivesmentioning

confidence: 97%

Occurrence, biological activities and 13C NMR data of amides from Piper (Piperaceae)

Nascimento¹,

Paula²,

David³

et al. 2012

Quím. Nova

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“…Mục đích của bài báo này tập trung nghiên cứu ảnh hưởng của một số dịch chiết thực vật của Việt Nam, có hoạt tính sinh học, đã được dùng đề chữa bệnh trong dân gian (Abdullah et al, 2014;Abrahim et al, 2012;Behera et al, 2013;Dosoky et al, 2015;Li et al, 2007;Mahabusarakam et al, 2005;Saraiva et al, 2012;Padmapriya & Poonguzhali, 2015;Wu et al, 2015;Đỗ Tất Lợi, 1991). Tuy nhiên, những dịch chiết này chưa được nghiên cứu đầy đủ về hoạt tính gây độc tính tế bào và khả năng loại bỏ gốc tự do in vitro trên tế bào HaCaT để trả lời cho một số câu hỏi như: Các dịch chiết thực vật này có tác dụng gây độc tế bào keratinocyte HaCaT hay không và có hay không sự khác nhau về độc tính giữa dịch chiết methanol và hexane?…”

Section: Mở đầUunclassified

Cytotoxicity and antioxidant activity of plant extracts from Vietnam

Phương

Boger

Lindequist³

2020

V J Bio

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Traditional medicine plays an important role in treatment of human diseases. Extracts from medicinal plants exhibit many valuable biological activities. However, the exploitation and application of the extracts requires knowlege on the mechanism of action. In this study, cytotoxic and antioxidant activites of the methanol and hexane extracts of 09 Vietnamese plants have been studied in vitro on keratinocyte HaCaT cell line. The results showed that all plant extracts had a cytotoxyc effect on HaCaT cells. The hexane extracts showed more potent than the methanol extract. Garcinia mangostana exhibited the best cytotoxicity with IC50 values of 14.42 mg/ml (for hexane extract) và 14.27 mg/ml (for MeOH extract). All tested extracts resulted in the generation of intracellular reactive oxygen radicals in HaCaT cells. Mangifera indica, Cleistocalyx operculatus and Terminalia catappa had the best DPPH radical scavenging activity with EC50 values of 23.0 mg/ml, 27.4 mg/ml and 23.73 mg/ml, respectively. Besides, G. mangostana and T.catappa exhibited capacity of eliminating active oxygen radicals (iROS). The test extracts significantly reduced the number of cells in phase G1 and increased the number of cells in S and G2/M phases. The data obtained in this study are the preliminary results for further studies on the mechanisms of action and therapeutic applications of these plants.

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“…Sarmentine, 1-(1-pyrrolidinyl)-(2 E ,4 E )-2,4-decadien-1-one, is a Piper amide with several biological properties, including antiplasmodial, antimycobacterial, and antituberculosis activity (Rukachaisirikul et al, 2004 ; Tuntiwachwuttikul et al, 2006 ), as well as antiplatelet aggregation (Li et al, 2007 ). Interest in sarmentine as a biopesticide renewed when its herbicidal activity was discovered through a bioactivity-guided isolation of the active components of the fruits of Piper sarmentosum and Piper nigrum (Huang et al, 2010 ).…”

Section: Introductionmentioning

confidence: 99%

Sarmentine, a natural herbicide from Piper species with multiple herbicide mechanisms of action

et al. 2015

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Sarmentine, 1-(1-pyrrolidinyl)-(2E,4E)-2,4-decadien-1-one, is a natural amide isolated from the fruits of Piper species. The compound has a number of interesting biological properties, including its broad-spectrum activity on weeds as a contact herbicide. Initial studies highlighted a similarity in response between plants treated with sarmentine and herbicidal soaps such as pelargonic acid (nonanoic acid). However, little was known about the mechanism of action leading to the rapid desiccation of foliage treated by sarmentine. In cucumber cotyledon disc-assays, sarmentine induced rapid light-independent loss of membrane integrity at 100 μM or higher concentration, whereas 3 mM pelargonic acid was required for a similar effect. Sarmentine was between 10 and 30 times more active than pelargonic acid on wild mustard, velvetleaf, redroot pigweed and crabgrass. Additionally, the potency of 30 μM sarmentine was greatly stimulated by light, suggesting that this natural product may also interfere with photosynthetic processes. This was confirmed by observing a complete inhibition of photosynthetic electron transport at that concentration. Sarmentine also acted as an inhibitor of photosystem II (PSII) on isolated thylakoid membranes by competing for the binding site of plastoquinone. This can be attributed in part to structural similarities between herbicides like sarmentine and diuron. While this mechanism of action accounts for the light stimulation of the activity of sarmentine, it does not account for its ability to destabilize membranes in darkness. In this respect, sarmentine has some structural similarity to crotonoyl-CoA, the substrate of enoyl-ACP reductase, a key enzyme in the early steps of fatty acid synthesis. Inhibitors of this enzyme, such as triclosan, cause rapid loss of membrane integrity in the dark. Sarmentine inhibited the activity of enoyl-ACP reductase, with an I50app of 18.3 μM. Therefore, the herbicidal activity of sarmentine appears to be a complex process associated with multiple mechanisms of action.

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Isolation and Identification of Antiplatelet Aggregatory Principles from the Leaves of Piper lolot

Cited by 38 publications

References 37 publications

Occurrence, biological activities and 13C NMR data of amides from Piper (Piperaceae)

Occurrence, biological activities and 13C NMR data of amides from Piper (Piperaceae)

Cytotoxicity and antioxidant activity of plant extracts from Vietnam

Sarmentine, a natural herbicide from Piper species with multiple herbicide mechanisms of action

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