Antimycobacterial activity of chemically defined natural substances from the Caribbean flora in Guadeloupe

Rastogi, Nalin

doi:10.1016/s0928-8244(98)00021-2

Cited by 10 publications

(11 citation statements)

References 14 publications

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“…The aryl substituent at the 2-position is either phenyl (compound 1 ) or 3-pyridyl (compound 2 ). Compounds 1 and 2 are also similar to the diaryloxazoles texalin (Figure 2), previously isolated from Amyris elemifera , 13 and balsoxin (Figure 2), isolated from Amyris balsamifera . 14,15 Additionally, Cheplogoi and colleagues reported the isolation of uguenenazole (Figure 2) from Vepris uguenensis , 16 suggesting similar compounds may be present in multiple plant genera.…”

Section: Resultssupporting

confidence: 65%

Structure–Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells

Robles

McCowen

Cai³

et al. 2017

J. Med. Chem.

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Targeted therapies for ER+/PR+ and HER2-amplified breast cancers have improved patient survival, but there are no therapies for triple negative breast cancers (TNBC) that lack expression of estrogen and progesterone receptors (ER/PR), or amplification or overexpression of HER2. Gene expression profiling of TNBC has identified molecular subtypes and representative cell lines. An extract of the Texas native plant Amyris texana was found to have selective activity against MDA-MB-453 cells, a model of the luminal androgen receptor (LAR) subtype of TNBC. Bioassay-guided fractionation identified two oxazole natural products with selective activity against this cell line. Analog synthesis and structure-activity relationship studies conducted provided analogs with more potent and selective activity against two LAR subtype cell line models, culminating in the discovery of compound 30 (CIDD-0067106). Lead compounds discovered have potent and selective antiproliferative activities, and mechanisms of action studies show they inhibit the activity of the mTORC1 pathway.

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Section: Resultssupporting

confidence: 65%

Structure–Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells

Robles

McCowen

Cai³

et al. 2017

J. Med. Chem.

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“…With more than 50,000 compounds, terpenes are the most diverse family of plant defences described to date (Conolly & Hill, ). Their protective effects include antimicrobial properties (Lunde & Kubo, ; Rastogi et al., ) as well as feeding deterrence and toxicity against insects, and thus might be involved in conifer resistance against herbivores. Although the exact mode of terpene action is unknown in most cases (Gershenzon & Dudareva, ), they seem to derive some of their toxic properties from the disruption of gut membranes due to their lipophilic nature or by causing neural damage through compromised ion channels (Keeling & Bohlmann, ).…”

Section: Introductionmentioning

confidence: 99%

Gut microbiota of the pine weevil degrades conifer diterpenes and increases insect fitness

et al. 2017

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The pine weevil (Hylobius abietis), a major pest of conifer forests throughout Europe, feeds on the bark and cambium, tissues rich in terpenoid resins that are toxic to many insect herbivores. Here, we report the ability of the pine weevil gut microbiota to degrade the diterpene acids of Norway spruce. The diterpene acid levels present in ingested bark were substantially reduced on passage through the pine weevil gut. This reduction was significantly less upon antibiotic treatment, and supplementing the diet with gut suspensions from untreated insects restored the ability to degrade diterpenes. In addition, cultured bacteria isolated from pine weevil guts were shown to degrade a Norway spruce diterpene acid. In a metagenomic survey of the insect's bacterial community, we were able to annotate several genes of a previously described diterpene degradation (dit) gene cluster. Antibiotic treatment disrupted the core bacterial community of H. abietis guts and eliminated nearly all dit genes concordant with its reduction in diterpene degradation. Pine weevils reared on an artificial diet spiked with diterpenes, but without antibiotics, were found to lay more eggs with a higher hatching rate than weevils raised on diets with antibiotics or without diterpenes. These results suggest that gut symbionts contribute towards host fitness, but not by detoxification of diterpenes, as these compounds do not show toxic effects with or without antibiotics. Rather the ability to thrive in a terpene-rich environment appears to allow gut microbes to benefit the weevil in other ways, such as increasing the nutritional properties of their diet.

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“…The in vitro antimycobacterial activity of 1 was equivalent to those of INH and EMB, except for M. smegmatis which showed a higher susceptibility to EMB (MIC: EMB 0.6 mM; 1 6.7 mM; INH 14.6 mM). In previous investigations, a number of crude plant extracts which are active against Mycobacteria have been found [7], [8], [9] but only in a few cases have the single active compounds been evaluated [7], [10], [11], and in the case of terpenoids, some structure-activity relationships have been established [12].…”

mentioning

confidence: 99%

Ostruthin: An Antimycobacterial Coumarin from the Roots ofPeucedanum ostruthium

Schinkovitz

Gibbons²,

Stavri³

et al. 2003

Planta med

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Following a bioassay-guided fractionation, ostruthin (6-geranyl-7-hydroxycoumarin) was isolated from the roots of Peucedanum ostruthium Koch (Apiaceae) as a compound with pronounced in vitro activity against several species of rapidly growing Mycobacteria, namely Mycobacterium abscesus, M. aurum, M. fortuitum, M. phlei and M. smegmatis. Minimum inhibitory concentrations (MIC) ranged between 3.4 to 107.4 microM and were comparable to those of ethambutol and isoniazid. Imperatorin (8-isopent-2-enyloxy-6,7-furanocoumarin) showed no activity at concentrations up to 1.9 mM. Umbelliferone (7-hydroxycoumarin) was only weakly active (MIC = 0.79 mM).

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Antimycobacterial activity of chemically defined natural substances from the Caribbean flora in Guadeloupe

Cited by 10 publications

References 14 publications

Structure–Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells

Structure–Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells

Gut microbiota of the pine weevil degrades conifer diterpenes and increases insect fitness

Ostruthin: An Antimycobacterial Coumarin from the Roots ofPeucedanum ostruthium

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