Acetylenes and Psoralens

Christensen, Lars Porskjær; Brandt, Kirsten

doi:10.1002/9780470988558.ch5

Cited by 15 publications

(11 citation statements)

References 163 publications

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“…This assumption is supported by a pharmacokinetic study of (3S,8S)-falcarindiol (10) and oplopandiol (18) in rats after oral administration of a polyacetylene extract of Oplopanax elatus Nakai demonstrating that these polyacetylenes were rapidly absorbed in vivo [54]. This is also in accordance with a human trial demonstrating that (3R)-falcarinol and (3R,8S)-falcarindiol is rapidly absorbed in humans after oral administration of carrot juice containing these polyacetylenes [9,55,56]. The preliminary bioavailability studies clearly show that C 17 and C 18 acetylenic oxylipins are bioavailable.…”

Section: Introductionsupporting

confidence: 73%

“…The IC 50 values of the tested polyacetylenes are presented in Table 2. Although most of the tested polyacetylenes did not show significant cytotoxicity against the tested cell lines, it is interesting to note that the synthetic enantiomer of notopolyenol A (56) showed high cytotoxicity from 0.6 µM to 1.6 µM in a dose around 24-fold lower than that of the naturally occurring (3R)-isomer (55). The latter clearly indicate the importance of (3S)-configuration for the cytotoxic effect, which is in accordance with the results from the structure-activity analysis for the cytotoxicity of C 17 polyacetylenes isolated from P. quinquefolius and their synthetic enantiomers as described in Section 2.1.1.…”

Section: Cytotoxic C 17 and C 18 Acetylenic Oxylipins From Apiaceae Mmentioning

confidence: 97%

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Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Christensen

2020

Molecules

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Bioactive C17 and C18 acetylenic oxylipins have shown to contribute to the cytotoxic, anti-inflammatory, and potential anticancer properties of terrestrial plants. These acetylenic oxylipins are widely distributed in plants belonging to the families Apiaceae, Araliaceae, and Asteraceae, and have shown to induce cell cycle arrest and/or apoptosis of cancer cells in vitro and to exert a chemopreventive effect on cancer development in vivo. The triple bond functionality of these oxylipins transform them into highly alkylating compounds being reactive to proteins and other biomolecules. This enables them to induce the formation of anti-inflammatory and cytoprotective phase 2 enzymes via activation of the Keap1–Nrf2 signaling pathway, inhibition of proinflammatory peptides and proteins, and/or induction of endoplasmic reticulum stress, which, to some extent, may explain their chemopreventive effects. In addition, these acetylenic oxylipins have shown to act as ligands for the nuclear receptor PPARγ, which play a central role in growth, differentiation, and apoptosis of cancer cells. Bioactive C17 and C18 acetylenic oxylipins appear, therefore, to constitute a group of promising lead compounds for the development of anticancer drugs. In this review, the cytotoxic, anti-inflammatory and anticancer effects of C17 and C18 acetylenic oxylipins from terrestrial plants are presented and their possible mechanisms of action and structural requirements for optimal cytotoxicity are discussed.

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Section: Introductionsupporting

confidence: 73%

Section: Cytotoxic C 17 and C 18 Acetylenic Oxylipins From Apiaceae Mmentioning

confidence: 97%

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Christensen

2020

Molecules

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“…They have been shown to inhibit metastasis and tumorigenesis [5,6], and many are known to have anti-inflammatory, antibacterial and antifungal capabilities [7]. These effects are mainly attributed to their antioxidant activity.…”

Section: Introductionmentioning

confidence: 99%

Involvement of Nitrogen on Flavonoids, Glutathione, Anthocyanin, Ascorbic Acid and Antioxidant Activities of Malaysian Medicinal Plant Labisia pumila Blume (Kacip Fatimah)

Ibrahim

Jaafar

Rahmat

et al. 2011

IJMS

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A split plot 3 by 4 experiment was designed to characterize the relationship between production of gluthatione (GSH), oxidized gluthatione (GSSG), total flavonoid, anthocyanin, ascorbic acid and antioxidant activities (FRAP and DPPH) in three varieties of Labisia pumila Blume, namely the varieties alata, pumila and lanceolata, under four levels of nitrogen fertilization (0, 90, 180 and 270 kg N/ha) for 15 weeks. The treatment effects were solely contributed by nitrogen application; there was neither varietal nor interaction effects observed. As the nitrogen levels decreased from 270 to 0 kg N/ha, the production of GSH and GSSG, anthocyanin, total flavonoid and ascorbic acid increased steadily. At the highest nitrogen treatment level, L. pumila exhibited significantly lower antioxidant activities (DPPH and FRAP) than those exposed to limited nitrogen growing conditions. Significant positive correlation was obtained between antioxidant activities (DPPH and FRAP), total flavonoid, GSH, GSSG, anthocyanin and ascorbic acid suggesting that an increase in the antioxidative activities in L. pumila under low nitrogen fertilization could be attributed to higher contents of these compounds. From this observation, it could be concluded that in order to avoid negative effects on the quality of L. pumila, it is advisable to avoid excessive application of nitrogen fertilizer when cultivating the herb for its medicinal use.

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“…However, the given mechanistic functions of SPMEs demonstrate that these metabolites are essential for plant protection from environmental stress, therefore they are important for plants in spite of the wide variety of synthesized compounds among plants [ 44 ]. Accordingly, here we consider SPMEs as products distinct from primary metabolism belonging to the following groups based on structure: (i) phenolic compounds including flavonoids; (ii) terpenoids and steroids; and (iii) compounds containing nitrogen or sulfur, such as alkaloids, glucosinolates, and non-ribosomal peptides and proteins [ 45 , 46 , 47 , 48 , 49 , 50 ]. It should be noted that the role of primary and secondary metabolites can overlap, as is demonstrated in defense against biotic stress, which can be in Arabidopsis thaliana mediated by glutathione [ 51 ] as well as by various SPMEs derived from indole-like camalexin or glucosinolates [ 52 ].…”

Section: Root Exudates and Their Effects On Present Microfloramentioning

confidence: 99%

Effects of Secondary Plant Metabolites on Microbial Populations: Changes in Community Structure and Metabolic Activity in Contaminated Environments

Musilová

Rídl

Polívková

et al. 2016

IJMS

115

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Secondary plant metabolites (SPMEs) play an important role in plant survival in the environment and serve to establish ecological relationships between plants and other organisms. Communication between plants and microorganisms via SPMEs contained in root exudates or derived from litter decomposition is an example of this phenomenon. In this review, the general aspects of rhizodeposition together with the significance of terpenes and phenolic compounds are discussed in detail. We focus specifically on the effect of SPMEs on microbial community structure and metabolic activity in environments contaminated by polychlorinated biphenyls (PCBs) and polyaromatic hydrocarbons (PAHs). Furthermore, a section is devoted to a complex effect of plants and/or their metabolites contained in litter on bioremediation of contaminated sites. New insights are introduced from a study evaluating the effects of SPMEs derived during decomposition of grapefruit peel, lemon peel, and pears on bacterial communities and their ability to degrade PCBs in a long-term contaminated soil. The presented review supports the “secondary compound hypothesis” and demonstrates the potential of SPMEs for increasing the effectiveness of bioremediation processes.

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Acetylenes and Psoralens

Cited by 15 publications

References 163 publications

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Involvement of Nitrogen on Flavonoids, Glutathione, Anthocyanin, Ascorbic Acid and Antioxidant Activities of Malaysian Medicinal Plant Labisia pumila Blume (Kacip Fatimah)

Effects of Secondary Plant Metabolites on Microbial Populations: Changes in Community Structure and Metabolic Activity in Contaminated Environments

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