Chemical examination of Heracleum candicans—I

Sharma, Y.N.; Zaman, Asif; Kidwai, A.R.

doi:10.1016/s0040-4020(01)98400-5

Cited by 31 publications

(14 citation statements)

References 6 publications

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“…Recently DiGiovanni and coworkers exhaustively studied imperatorin both as inhibitor of human cytochrome P450 and as blocker of DNA adduct formation with benzo [41][42] Ammi majus, [43] Angelica spp., [44] Atalantia ceylanica, [45] Citrus spp., [46] Cnidium monnieri, [47][48] Decatropis bicolor, [49] Ferula sumbul, [50] Foeniculum vulgare, [51] Glehnia littoralis, [52] Heracleum spp., [53][54] Leptothyrsa sprucei, [55] Murraya koenigii, [56] Niphogeton ternata, [57] Opopanax chironium, [58] Peucedanum spp., [59] Phebalium spp., [19,60] Poncirus trifoliata, [61] Prangos spp., [62][63] Ptelia baldwanii, [61] Ruta spp., [64] Stauranthus perforatus, [65] Thamnosma texana [66] Heraclenin (40) H…”

Section: Isopentenyloxy-furocoumarinsmentioning

confidence: 99%

“…Angelica spp., [44] Citrus spp., [46] Cymopterus watsonii, [67] Decatropis bicolor, [49] Heracleum spp., [53][54] Magydaris pastinacea, [68] Metrodorea flavida, [69] Murraya koenigii, [56] Opopanax chironium, [58] Petroselinum crispum, [70] Phebalium spp., [19,60] Ruta spp., [64] Selinum tenuifolium, [71] Skimmia spp., [72][73] [44] Citrus spp., [46] Cymopterus watsonii, [67] Decatropis bicolor, [49] Heracleum spp., [53][54] Magydaris pastinacea, [68] Metrodorea flavida, [69] Murraya koenigii, [56] Opopanax chironium, [58] Petroselinum crispum, [70] Phebalium spp., [19,60] Ruta spp., [64] Selinum tenuifolium, [71] Skimmia spp., [72][73] [44] Heracleum spp., [53][54] Metrodorea nigra, [75] Murraya koenigii, [56] Pleurospermum rivulorum , [76] Prangos spp., [62][63] Skimmia spp., [72][73] [53]…”

Section: O Omentioning

confidence: 99%

“…[87][88] ( [44] Citrus spp., [46] Heracleum spp., [53][54] Murraya koenigii, [56] Stauranthus perforatus, [65] Byakangelicin (47) OMe OH OH O Amyris lineata, [89] Angelica spp., [44] Citrus spp., [46] Cymopterus watsonii, [67] Dorstenia gigas, [90] Magydaris pastinacea, [68] Murraya koenigii, [56] Peucedanum spp., [59] Ptelea trifoliata, [91] Ruta spp., [64] Thamnosma montana, [92] Thapsia villosa, [86] Triphasia trifolia, [24,74] Zanthoxylum pistacifolium [93] Neobyakangelicol (48) OMe OH O Angelica spp., [44] Citrus spp., [46] Murraya koenigii, [56] Peucedanum ostruthium [94] Japoangelone Angelica spp., [44] Citrus spp., [46] Dorstenia gigas, [90] Glehnia littoralis, [52] Niphogeton ternata [57] Notopterygium spp., [97][98] Petroselinum crispum, [99] Prangos spp., [62][63] Ruta spp., [64] Tordylium apulum [37] Cnidilin (53) O OMe Petroselinum crispum [99] Cnidicin (54)…”

Section: O Omentioning

confidence: 99%

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Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

274

170

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Prenyloxycoumarins and prenyloxyfuranocoumarins (isopentenyloxy-, geranyloxy-, linear and cyclic sesquiterpenyloxy compounds and their biosynthetic derivatives) represent a family of secondary metabolites that have been considered for years just as intermediates of other coumarin-based compounds. Only in the last two decades these secondary metabolites have been recognized as interesting and valuable biologically active natural products. Up to now more than 160 compounds have been isolated from plants mainly belonging to the families of Rutaceae and Umbelliferae, comprising common edible vegetables and fruits like lemons, oranges and grapefruits. In view of the biological activity of some natural prenyloxycoumarins, very recently syntheses of structurally related analogs aimed to establish detailed structure-activity relationships have also been carried out. Many of the isolated prenyloxy- and prenyloxy-furanocoumarins and their semisynthetic derivatives were shown to exert in vitro and in vivo remarkable anti-tumoral, anti-inflammatory and anti-viral effects. The object of this review is to examine in detail the different types of prenyloxycoumarins and prenyloxyfuranocoumarins from the chemical, phytochemical and biological point of view.

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Section: Isopentenyloxy-furocoumarinsmentioning

confidence: 99%

Section: O Omentioning

confidence: 99%

Section: O Omentioning

confidence: 99%

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Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

274

170

View full text Add to dashboard Cite

show abstract

“…Numerous chemical constituents in the classes of flavonoids, piperidinic alkaloids and elagic acid glycosides have been isolated from P. juliflora , notably from its roots, stems and leaf [18–27]. Extracts (Table 1) and piperidinic alkaloids (Table 2) from P. juliflora leaves were shown to exhibit antimicrobial activity against several Gram-positive bacteria and fungi [24,25,28–32].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity of the Alkaloid-Enriched Extract from Prosopis juliflora Pods and Its Influence on in Vitro Ruminal Digestion

Santos

Pereira

Silva

et al. 2013

IJMS

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The purpose of this study was to assess the in vitro antimicrobial activity of alkaloid-enriched extracts from Prosopis juliflora (Fabaceae) pods in order to evaluate them as feed additives for ruminants. As only the basic chloroformic extract (BCE), whose main constituents were juliprosopine (juliflorine), prosoflorine and juliprosine, showed Gram-positive antibacterial activity against Micrococcus luteus (MIC = 25 μg/mL), Staphylococcus aureus (MIC = 50 μg/mL) and Streptococcus mutans (MIC = 50 μg/mL), its influence on ruminal digestion was evaluated using a semi-automated in vitro gas production technique, with monensin as the positive control. Results showed that BCE has decreased gas production as efficiently as monensin after 36 h of fermentation, revealing its positive influence on gas production during ruminal digestion. Since P. juliflora is a very affordable plant, this study points out this alkaloid enriched extract from the pods of Prosopis juliflora as a potential feed additive to decrease gas production during ruminal digestion.

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“…To generate the furanocoumarin reactive intermediate, a P450 oxidizes the furan alkene to an epoxide, followed by subsequent nucleophilic attack to form the dihydrofuranocoumarin product (Figure 2C). The synthesis of probe 9 (Scheme 1H) commenced with nucleophilic substitution of methylbromoacetate by 8-hydroxypsoralen ( 31 ) yielding 32 47. The methyl ester was saponified with aqueous LiOH to give 33 ,48 followed by HOBt/EDCI coupling of the click chemistry linker yielding probe 9 .…”

Section: Resultsmentioning

confidence: 99%

A Suite of Activity-Based Probes for Human Cytochrome P450 Enzymes

2009

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Cytochrome P450 (P450) enzymes regulate a variety of endogenous signaling molecules and play central roles in the metabolism of xenobiotics and drugs. We recently showed that an aryl alkyne serves as an effective activity-based probe for profiling mouse liver microsomal P450s in vitro and in vivo. However, individual P450s display distinct substrate and inhibitor specificities, indicating that multiple probe structures may be required to achieve comprehensive coverage of this large and diverse enzyme family. Here, we have synthesized a suite of P450-directed, activity-based protein profiling (ABPP) probes that contain: 1) varied chemical architectures validated as mechanism-based inhibitors of the P450 enzyme family, and 2) terminal alkyne groups for click chemistry conjugation of reporter tags. This set of probes was screened against a wide cross-section of human P450s, leading to the discovery of an optimal set of probes that provide broad coverage of this enzyme family. We used these probes to profile the effects on P450 activity of aromatase inhibitors in current clinical use for the treatment of breast cancer. We describe the surprising discovery that one of these aromatase inhibitors, anastrozole, significantly increases probe-labeling of P450 1A2, indicative of a heterotypic cooperativity effect on a central P450 isozyme involved in metabolizing numerous drugs and xenobiotics. The results presented herein greatly expand the suite of ABPP probes for profiling P450s and illuminate new applications for these tools to understand P450-drug interactions.

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Chemical examination of Heracleum candicans—I

Cited by 31 publications

References 6 publications

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Antibacterial Activity of the Alkaloid-Enriched Extract from Prosopis juliflora Pods and Its Influence on in Vitro Ruminal Digestion

A Suite of Activity-Based Probes for Human Cytochrome P450 Enzymes

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