Antimalarial (+)-<i>trans</i>-Hexahydrodibenzopyran Derivatives from <i>Machaerium multiflorum</i>

Muhammad, Ilias; Li, X C; Dunbar, D. Chuck; ElSohly, M. A.; Khan, Ikhlas A.

doi:10.1021/np0102861

Cited by 66 publications

(70 citation statements)

References 25 publications

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“…Compounds with phytocannabinoid-like moieties have been extracted from legumes [167], [168], Helichrysum [169], Rhododendron sp. [170], liverworts [171], [172], and fungi [173]–[175].…”

Section: Resultsmentioning

confidence: 99%

Care and Feeding of the Endocannabinoid System: A Systematic Review of Potential Clinical Interventions that Upregulate the Endocannabinoid System

2014

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BackgroundThe “classic” endocannabinoid (eCB) system includes the cannabinoid receptors CB1 and CB2, the eCB ligands anandamide (AEA) and 2-arachidonoylglycerol (2-AG), and their metabolic enzymes. An emerging literature documents the “eCB deficiency syndrome” as an etiology in migraine, fibromyalgia, irritable bowel syndrome, psychological disorders, and other conditions. We performed a systematic review of clinical interventions that enhance the eCB system—ways to upregulate cannabinoid receptors, increase ligand synthesis, or inhibit ligand degradation.Methodology/Principal FindingsWe searched PubMed for clinical trials, observational studies, and preclinical research. Data synthesis was qualitative. Exclusion criteria limited the results to 184 in vitro studies, 102 in vivo animal studies, and 36 human studies. Evidence indicates that several classes of pharmaceuticals upregulate the eCB system, including analgesics (acetaminophen, non-steroidal anti-inflammatory drugs, opioids, glucocorticoids), antidepressants, antipsychotics, anxiolytics, and anticonvulsants. Clinical interventions characterized as “complementary and alternative medicine” also upregulate the eCB system: massage and manipulation, acupuncture, dietary supplements, and herbal medicines. Lifestyle modification (diet, weight control, exercise, and the use of psychoactive substances—alcohol, tobacco, coffee, cannabis) also modulate the eCB system.Conclusions/SignificanceFew clinical trials have assessed interventions that upregulate the eCB system. Many preclinical studies point to other potential approaches; human trials are needed to explore these promising interventions.

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“…Compounds with phytocannabinoid-like moieties have been extracted from legumes [167], [168], Helichrysum [169], Rhododendron sp. [170], liverworts [171], [172], and fungi [173]–[175].…”

Section: Resultsmentioning

confidence: 99%

Care and Feeding of the Endocannabinoid System: A Systematic Review of Potential Clinical Interventions that Upregulate the Endocannabinoid System

2014

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“…Several members of the Fabaceae family exhibit antiplasmodial activity, both in vitro and in animal models, and some compounds with antiplasmodial activity have been isolated from them [4,6,13-21]. Here, we sought a scientific rationale for traditional use of two Fabaceae species ( Copaifera religiosa and Tetrapleura tetraptera , voucher numbers D. N. 584 and J.J. WIE 6388 respectively from the Gabonese national herbarium) traditionally used to treat malarial symptoms.…”

Section: Resultsmentioning

confidence: 99%

In vitro antiplasmodial activity of crude extracts of Tetrapleura tetraptera and Copaifera religiosa

et al. 2011

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BackgroundMalaria remains a major public health problem, especially in tropical and subtropical regions because of the emergence and widespread of antimalarial drug resistance. Traditional medicine represents one potential source of new treatments. Here, we investigated the in vitro antiplasmodial activity of bark extracts from two Fabaceae species (Tetrapleura tertaptera and Copaifera religiosa) traditionally used to treat malaria symptoms in Haut-Ogooué province, Gabon.FindingsThe antiplasmodial activity of dichloromethane and methanolic extracts was tested on P. falciparum strains FCB (chloroquine-resistant) and 3D7 (chloroquine-sensitive) and on fresh clinical isolates, using the DELI method. Host cell toxicity was analyzed on MRC-5 human diploid embryonic lung cells using the MTT test.The dichloromethane extracts of the two plants had interesting activity (IC50 between 8.5 ± 4.7 and 13.4 ± 3.6 μg/ml). The methanolic extract of Tetrapleura tetraptera was less active (IC50 around 30 μg/ml) and the methanolic extract of Copaifera religiosa was inactive. The selectivity index (toxicity/antiplasmodial activity) of the dichloromethane extract of Tetrapleura tetraptera was high (around 7), while the dichloromethane extract of Copaifera religiosa had the lowest selectivity (0.6). The mean IC50 values for field isolates were less than 1.5 μg/ml for dichloromethane extracts of both plants, while methanolic extracts of Tetrapleura tetraptera showed interesting activity (IC50 = 13.1 μg/ml). The methanolic extract of Copaifera religiosa was also inactive on field isolates.ConclusionsDichloromethane extracts of Tetrapleura tetraptera and Copaifera religiosa, two plants used to treat malaria in Gabon, had interesting antiplasmodial activity in vitro. These data provide a scientific rationale for the traditional use of these plants against malaria symptoms. Bioactivity-guided phytochemical analyses are underway to identify the active compounds.

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“…19,20 No activities were observed at the highest test concentrations, which were 20 µg/mL for antimicrobial activity or 40 µg/mL for antimalarial activity.…”

Section: Resultsmentioning

confidence: 97%

Cycloartane Glycosides from Sutherlandia frutescens

Xiang

Smillie

et al. 2008

J. Nat. Prod.

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Four new cycloartane glycosides, sutherlandiosides A–D (1–4), were isolated from the South African folk medicine Sutherlandia frutescens and their structures established by spectroscopic methods and X-ray crystallography as 1S,3R,24S,25-tetrahydroxy-7S,10S-epoxy-9,10-seco-9,19-cyclolanost-9(11)-ene 25-O-β-d-glucopyranoside (1), 3R,7S,24S,25-tetrahydroxycycloartan-1-one 25-O-β-d-glucopyranoside (2), 3R,24S,25-trihydroxycycloartane-1,11-dione 25-O-β-d-glucopyranoside (3), and 7S,24S,25-trihydroxycycloart-2-en-1-one 25-O-β-d-glucoyranoside (4). Compound 1 represents the first secocycloartane skeleton possessing a 7,10-oxygen bridge. Compounds 2–4 are also the first examples of naturally occurring cycloartanes with a C-1 ketone functionality. Biosynthetic considerations and chemical evidence suggest that the presence of the C-1 ketone in 2 may facilitate the ring opening of the strained cyclopropane system.

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Antimalarial (+)-trans-Hexahydrodibenzopyran Derivatives from Machaerium multiflorum

Cited by 66 publications

References 25 publications

Care and Feeding of the Endocannabinoid System: A Systematic Review of Potential Clinical Interventions that Upregulate the Endocannabinoid System

Care and Feeding of the Endocannabinoid System: A Systematic Review of Potential Clinical Interventions that Upregulate the Endocannabinoid System

In vitro antiplasmodial activity of crude extracts of Tetrapleura tetraptera and Copaifera religiosa

Cycloartane Glycosides from Sutherlandia frutescens

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