Punigratane, a novel pyrrolidine alkaloid from <i>Punica granatum</i> rind with putative efflux inhibition activity

Rafiq, Zumaana; Narasimhan, Sreevidya; Vennila, Rosy; Vaidyanathan, Rama

doi:10.1080/14786419.2016.1146883

Cited by 20 publications

(6 citation statements)

References 11 publications

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“…Sedridine, 2-(2′-hydroxypropyl)-∆ 1 piperideine, 2-(2′-propenyl)-∆ 1 piperideine, norpseudopelletierine, and the pyrrolidine alkaloids (with a five-membered N -containing ring) hygrine and norhygrine, were also found in root barks at low quantities [ 34 ]. In addition to the alkaloids that accumulate in root and stem barks, N -(2′,5′-dihydroxyphenyl)pyridinium chloride was identified in pomegranate leaves [ 19 ], and a pyrrolidine-type alkaloid punigratane (2,5-diheptyl- N -methylpyrrolidine) was recently characterized in pomegranate fruit peel [ 35 ]. Besides alkaloids, low levels of indolamines (amine derivatives of indole), including tryptamine, melatonin, and serotonin, were present in the extract of pomegranate fruit [ 36 ].…”

Section: Occurrence and Structure Of Diverse Phytochemicals In Pommentioning

confidence: 99%

Diverse Phytochemicals and Bioactivities in the Ancient Fruit and Modern Functional Food Pomegranate (Punica granatum)

2017

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Having served as a symbolic fruit since ancient times, pomegranate (Punica granatum) has also gained considerable recognition as a functional food in the modern era. A large body of literature has linked pomegranate polyphenols, particularly anthocyanins (ATs) and hydrolyzable tannins (HTs), to the health-promoting activities of pomegranate juice and fruit extracts. However, it remains unclear as to how, and to what extent, the numerous phytochemicals in pomegranate may interact and exert cooperative activities in humans. In this review, we examine the structural and analytical information of the diverse phytochemicals that have been identified in different pomegranate tissues, to establish a knowledge base for characterization of metabolite profiles, discovery of novel phytochemicals, and investigation of phytochemical interactions in pomegranate. We also assess recent findings on the function and molecular mechanism of ATs as well as urolithins, the intestinal microbial derivatives of pomegranate HTs, on human nutrition and health. A better understanding of the structural diversity of pomegranate phytochemicals as well as their bioconversions and bioactivities in humans will facilitate the interrogation of their synergistic/antagonistic interactions and accelerate their applications in dietary-based cancer chemoprevention and treatment in the future.

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Section: Occurrence and Structure Of Diverse Phytochemicals In Pommentioning

confidence: 99%

Diverse Phytochemicals and Bioactivities in the Ancient Fruit and Modern Functional Food Pomegranate (Punica granatum)

2017

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“…Some alkaloids are known to have an effect in both phases of the formalin test [ 21 ]. In this context, we think that the short effect in phase 1 can be explained because pomegranate peel and pomegranate juice have some alkaloids like caffeine, peelletierine, and punigranate (a pyrrolidine type alkaloid), although they are not considered rich in these compounds [ 22 , 23 , 24 ]. Previous reports indicate that pomegranate peel of the Sefri variety has pain inhibition percentages (IPI) like ours (4 to 8.9%), but not the peel of the Amrouz variety, which achieved inhibition percentages of 37 to 75% (at doses of 25, 50, and 100 mg/kg intraperitoneal weight before injection of 20 µL of 2% formalin) [ 25 ].…”

Section: Discussionmentioning

confidence: 99%

Differential Antinociceptive Efficacy of Peel Extracts and Lyophilized Juices of Three Varieties of Mexican Pomegranate (Punica granatum L.) in the Formalin Test

Guerrero-Solano

Bautista

Espinosa-Juárez

et al. 2022

Plants

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Pharmacological treatment of pain often causes undesirable effects, so it is necessary to look for natural, safe, and effective alternatives to alleviate painful behavior. In this context, it is known that different parts of pomegranate have been widely consumed and used as preventive and therapeutic agents since ancient times. For example, it has been shown to have an antinociceptive effect, however, there are many varieties. Each part has been found to display unique and attractive pharmacological activities. The content of the active phytochemicals in pomegranate depends on the cultivar, geographical region, the maturity, and the processing method. In this context, the effects of various pomegranate varieties and other parts of the pomegranate (e.g., peel and juice) on pain behavior have not been examined. The aim was to evaluate and compare the antinociceptive effect of ethanolic extracts (PEx) and lyophilized juices (Lj) of three varieties of pomegranate in the formalin test. In addition, computer-aided analysis was performed for determining biological effects and toxicity. Peels were extracted with ethanol and evaporated by rotary evaporation, and juices were filtered and lyophilized. Wistar rats (N = 48) were randomly distributed into 8 groups (n = 6) (Vehicle, Acetylsalicylic Acid, PEx1, PEx2, PEx3, Lj1, Lj2, and Lj3). The formalin test (2%) was carried out, which consists of administering formalin in paw and counting the paw flinches for 1 h, with prior administration of treatments. All samples have an antinociceptive effect (phase 1: 2.8–10%; phase 2: 23.2–45.2%). PEx2 and Lj2 had the greatest antinociceptive effect (57.8–58.9%), and bioactive compounds such as tannins and flavonoids showed promising pharmacodynamic properties that may be involved in the antinociceptive effect, and can be considered as a natural alternative for the treatment of nociceptive and inflammatory pain.

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“…Alkaloids found in pomegranate are pelletierine, pseudopelletierine, and N-methylpelletierine, sedridine, 2-(2′-hydroxypropyl)-∆ 1 piperideine, 2-(2′propenyl)-∆ 1 piperideine, norpseudopelletierine, hygrine and norhygrine (root-bark), [3,4]. N-(2′,5′dihydroxyphenyl)pyridinium chloride (leaves) [5], and pyrrolidine-type alkaloid punigratane (2,5-diheptyl-Nmethylpyrrolidine) (fruit peel) [6]. Besides alkaloids, indolamines, tryptamine, melatonin, and serotonin, were present in the extract of pomegranate fruit [7].…”

Section: Introductionmentioning

confidence: 99%

A Collateral Approach on the 13 C NMR Analysis of Pseudopelletierine, an Alkaloid From Pomegranate

Bravo¹,

Vila²

2022

Rev. Bol. Quim.

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We reviewed a subchapter of “Natural Products, Isolation, Structure Elucidation, History” by D. Sicker et al. regarding the study of Pseudopelletierine (9-Methyl-9-azabimiccyclo[3.3.1]nonan-3-one). We boarded the NMR data in the subchapter with didactical purposes, doing an analysis of 13 C NMR chemical shifts in a spectral/structural approach. We established the structure by doing a 13 C NMR “Pure Shift” analysis if the term is worth.

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Punigratane, a novel pyrrolidine alkaloid from Punica granatum rind with putative efflux inhibition activity

Cited by 20 publications

References 11 publications

Diverse Phytochemicals and Bioactivities in the Ancient Fruit and Modern Functional Food Pomegranate (Punica granatum)

Diverse Phytochemicals and Bioactivities in the Ancient Fruit and Modern Functional Food Pomegranate (Punica granatum)

Differential Antinociceptive Efficacy of Peel Extracts and Lyophilized Juices of Three Varieties of Mexican Pomegranate (Punica granatum L.) in the Formalin Test

A Collateral Approach on the 13 C NMR Analysis of Pseudopelletierine, an Alkaloid From Pomegranate

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