Chemical Constituents of Malagasy Liverworts, Part V: Prenyl Bibenzyls and Clerodane Diterpenoids with Nitric Oxide Inhibitory Activity from Radula appressa and Thysananthus spathulistipus

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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“…[170], liverworts [171], [172], and fungi [173]–[175]. Falcarinol is a skin irritant found in several plants that causes contact dermatitis.…”

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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“…, 357 from Scapania parvitexta , 139 359 from Croton eluteria , 142 364 from Thysanathus spathulistipus 143 ) or a 4,18-spiro-oxirane ( e.g. , 369 from Teucrium oliverianum , 146 375 from T. fruticans 123 ).…”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

“…457,502 3β,4β:15,16-Diepoxy-13(16),14-clerodadiene ( 1294 ) and thysaspathone ( 365 ) inhibited NO production in LPS-stimulated RAW 264.7 cells with IC 50 values of 20.1 and 11.6 μM, respectively. 143,438 …”

Section: Biological Activitiesmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

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“…Radula species are known to produce fl avonoids, [5,6] several linear and cyclic prenyl bibenzyls, [7][8][9][10][11][12][13][14][15][16] cyclopropanochroman derivatives, [17] sesquiterpenoids [8,9] and clerodane diterpenoids. [15,16] Based on these studies, detailed on Table 1, Radula is chemically characterized by the presence of particular fl avone glycosides, [5] prenylated bibenzyls and very low levels or an almost total lack of terpenoids. [10,[18][19][20][21][22] To the best of our knowledge, only two studies have addressed the volatile fraction, obtained by either hydrodistillation or distillation-extraction, of Radula species.…”

Section: Introductionmentioning

confidence: 99%

Liverwort Radula species from Portugal: chemotaxonomical evaluation of volatiles composition

Figueiredo

Sim‐Sim

Barroso

et al. 2009

Flavour & Fragrance J

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The volatiles isolated by distillation-extraction from 48 samples of seven liverwort Radula species collected on Azores and Madeira archipelagos and mainland Portugal, as well as one from Switzerland, were analysed by GC and GC-MS. Cluster analysis of the volatiles composition resulted in two major clusters. The chemically very diverse cluster I included the oil samples of Radula aquilegia from Madeira, R. jonesii, R. holtii, R. nudicaulis, R. lindenbergiana as well as R. complanata from Switzerland. Cluster II was characterized by high relative amounts of several sesquiterpenes and included the oil samples of R. aquilegia from the Azores as well as R. carringtonii and R. wichurae. 3-Methoxy bibenzyl was the major oil component from R. complanata and R. lindenbergiana. Except for R. aquilegia and the closely related species R. complanata and R. lindenbergiana, the cluster analysis allows distinction of all studied species, indicating the chemotaxonomical value of the volatile oil characters.

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Chemical Constituents of Malagasy Liverworts, Part V: Prenyl Bibenzyls and Clerodane Diterpenoids with Nitric Oxide Inhibitory Activity from Radula appressa and Thysananthus spathulistipus

Cited by 39 publications

References 16 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

Clerodane diterpenes: sources, structures, and biological activities

Liverwort Radula species from Portugal: chemotaxonomical evaluation of volatiles composition

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