Pellitorine, a Potential Anti-Cancer Lead Compound against HL60 and MCT-7 Cell Lines and Microbial Transformation of Piperine from Piper Nigrum

Ee, Gwendoline Cheng Lian; Lim, Chyi Meei; Rahmani, Mawardi; Shaari, Khozirah; Bong, C. F. J.

doi:10.3390/molecules15042398

Cited by 64 publications

(40 citation statements)

References 7 publications

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“…33a, 101a (Tackie et al 1975) P. hancei Maxim. 101a, 117a (Narui et al 1995) P. longum L. 1a, 11a, 13b b , 16a, 33a, 36ab, 37 b , 39b, 46a, 47ab, 50b, 51a, 53b, 84a, 101ab (Dhar and Atal 1967;Koul et al 1988;Sun et al 2007;Li et al 2013) P. nigrum L. 8b, 13abk, 14abk, 16a, 33a, 34a, 37abkp, 38abk, 41k, 51a, 62ak, 89b, 99ab, 100a, 101abk, 103b, 112a, pipercycliamide (Wei et al 2004;Siddiqui et al 2004;Ee et al 2010;Dawid et al 2012) P. novae-hollandiae Miq. 101a, 112a (Loder et al 1969) P. peepuloides Roxb.…”

Section: Phytochem Revmentioning

confidence: 96%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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Alkamides are natural products formed by connecting straight-chain, mostly unsaturated, aliphatic acids with various amines by an amide linkage. More than 300 derivatives are known from eight plant families consisting of various combinations of 200 acids with 23 amines. Apart from a few saturated derivatives alkamides with unsaturated acid parts are grouped into compounds with purely olefinic patterns and those with olefinic and acetylenic linkages. Derived from C 18 oleic acid the acid parts are modified either by chain elongations to C 28 or by oxidative shortenings to C 4 acid residues. Substrate and regiospecific desaturases and acetylenases are responsible for their characteristic patterns of unsaturation. Amine parts are derived from various amino acids by decarboxylation. Beside the widespread isobutylamines alkamides with six-and five-membered ring amines and those with phenylalanine derived amines are characteristic for the Asteraceae and Piperaceae while benzylamines are restricted to the Brassicaceae. Within the Asteraceae 2-methylbutylamine distinguishes the tribe Heliantheae from Anthemideae characterized by ring amines. Alkamides with elongated olefinic acid parts are mainly found in Piperaceae and Brassicaceae while acetylenic acid parts are typical for Asteraceae. A wide variety of biological activities ranges from the characteristic pungent/ tingling property and high insecticidal toxicity to significant antifungal, antibacterial, antiprotozoal, molluscicidal, cercaricidal, and acaricidal activity. They also act as plant growth-promoting substances. Position and stereochemistry of the double bonds are essential for the different qualities of the pungent taste. Medically alkamides possess anti-inflammatory and analgesic properties and are responsible for immunomodulatory and cannabinomimetic effects.

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Section: Phytochem Revmentioning

confidence: 96%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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“…The compound 37 showed inhibition of sICAM1/LFA1 interaction‐mediated human THP1 cell adhesion at IC 50 25.0 μg/ml after 1 hr by The enzyme‐linked immunosorbent assay (ELISA) (Matsuda et al, ). A study performed by Ee, Lim, Rahmani, Shaari, and Bong () found that 37 is extremely cytotoxic (IC 50 13.0 μg/ml) against the HL60 (human promyelocytic leukemia cells) cell line. It, however, showed a much lower potential (IC 50 1.8 μg/ml) against the MCF‐7 (breast cancer) cell line.…”

Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

“…It, however, showed a much lower potential (IC 50 1.8 μg/ml) against the MCF‐7 (breast cancer) cell line. The compound 37 after an extensive investigation has been established as a potential anticancer hit and subjected to further optimization (Ee et al, ). Likewise, the compound 37 (n‐isobutyldeca‐trans‐2‐trans‐4‐dienamide) has been approved as a flavoring agent or adjuvant by FDA (The Joint Expert Committee on Food Additives Flavor No.…”

Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

Rashid

Alamzeb²,

Ali³

et al. 2019

Phytotherapy Research

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Several reviews have been published on Artemisia's derived natural products, but it is the first attempt to review the chemistry and pharmacology of more than 80 alkaloids and allied nitrogen compounds obtained from various Artemisia species (covering the literature up to June 2018). The pharmacological potential and unique skeleton types of certain Artemisia's alkaloids provoke the importance of analyzing Artemisia species for bioactive alkaloids and allied nitrogen compounds. Among the various types of bioactive Artemisia's alkaloids, the main classes were the derivatives of rupestine (pyridine–sesquiterpene), lycoctonine (diterpene), pyrrolizidine, purines, polyamine, peptides, indole, piperidine, pyrrolidine, alkamides, and flavoalkaloids. The rupestine derivatives are Artemisia's characteristic alkaloids, whereas the rest are common alkaloids found in the family Asteraceae and chemotaxonomically links the genus Artemisia with the tribes Anthemideae. The most important biological activities of Artemisia's alkaloids are including hepatoprotective, local anesthetic, β‐galactosidase, and antiparasitic activities; treatment of angina pectoris, opening blocked arteries, as a sleep‐inducing agents and inhibition of HIV viral protease, CYP450, melanin biosynthesis, human carbonic anhydrase, [3H]‐AEA metabolism, kinases, and DNA polymerase β1. Some of the important nitrogen metabolites of Artemisia include pellitorine, zeatin, tryptophan, rupestine, and aconitine analogs, which need to be optimized and commercialized further.

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“…The amide group and the aliphatic chain could be the key domain for the insecticidal activities of the compounds, while the methylenedioxy phenyl unit might be a synergistic group. Several isobutyl-type amides weakly inhibited cell proliferation of breast cancer (MCT-7) and human leukemia (HL-60) cell lines and displayed major apoptosis-inducing effects [27,28]. Among them, the isopentyl amides possessed more biological diversities than that of amides only bearing a long chain.…”

Section: Isobutyl-typementioning

confidence: 99%

A Survey of the Chemical Compounds of Piper spp. (Piperaceae) and Their Biological Activities

Xiang

Shi

Liu

et al. 2016

Natural Product Communications

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The genus Piper is one of the largest genera in the Piperaceae, with most species widely distributed globally, covering all continents. To date, many Piper species have been scientifically investigated for their chemical diversities and interesting broad spectrum of bioactivities, including central nervous system (CNS), pesticidal, antifungal and antibacterial effects. This review systematically summarizes the scaffolds of the alkaloids reported, the major chemicals isolated from Piper spp., and their biological activities. Besides the alkaloids, some neolignans with rearranged skeletons show structural diversities, while the chalcones, flavonoids and kava-pyrones have some potential activities. Herein, the sesquiterpenes and phenolic compounds from Piper species and their bioactivities are also surveyed.

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Pellitorine, a Potential Anti-Cancer Lead Compound against HL60 and MCT-7 Cell Lines and Microbial Transformation of Piperine from Piper Nigrum

Cited by 64 publications

References 7 publications

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

A Survey of the Chemical Compounds of Piper spp. (Piperaceae) and Their Biological Activities

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