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Natural Product Reports Mar 2021Covering: up to 2020 ent-Atisane diterpenoids are a class of over 150 members with diverse structures and valuable bioactivities. These compounds share a curious history... (Review)
Review
Covering: up to 2020 ent-Atisane diterpenoids are a class of over 150 members with diverse structures and valuable bioactivities. These compounds share a curious history in which the synthesis of the archetypal member preceded its isolation from natural sources. In this review, we provide a comprehensive summary of the isolation, structure, and bioactivity of ent-atisane diterpenoids from their discovery in 1965 to the present day.
Topics: Animals; Anti-Bacterial Agents; Antineoplastic Agents; Antiviral Agents; Diterpenes; Humans; Molecular Structure; Oxidation-Reduction
PubMed: 32716458
DOI: 10.1039/d0np00039f -
Molecules (Basel, Switzerland) Oct 2022Kahweol and cafestol are two diterpenes extracted from beans that have distinct biological activities. Recent research describes their potential activities, which... (Review)
Review
Kahweol and cafestol are two diterpenes extracted from beans that have distinct biological activities. Recent research describes their potential activities, which include anti-inflammatory, anti-diabetic, and anti-cancer properties, among others. The two diterpenes have been shown to have anticancer effects in various in vitro and in vivo cancer models. This review aims to shed light on the recent developments regarding the potential effects of kahweol and cafestol on various cancers. A systematic literature search through Google Scholar and PubMed was performed between February and May 2022 to collect updates about the potential effects of cafestol and kahweol on different cancers in in vitro and in vivo models. The search terms "Kahweol and Cancer" and "Cafestol and Cancer" were used in this literature review as keywords; the findings demonstrated that kahweol and cafestol exhibit diverse effects on different cancers in in vitro and in vivo models, showing pro-apoptotic, cytotoxic, anti-proliferative, and anti-migratory properties. In conclusion, the diterpenes kahweol and cafestol display significant anticancer effects, while remarkably unaffecting normal cells. Our results show that both kahweol and cafestol exert their actions on various cancers via inducing apoptosis and inhibiting cell growth. Additionally, kahweol acts by inhibiting cell migration.
Topics: Humans; Diterpenes; Coffea; Apoptosis; Neoplasms; Coffee
PubMed: 36364160
DOI: 10.3390/molecules27217332 -
Molecules (Basel, Switzerland) Nov 2022Marine-derived fungi are important sources of novel compounds and pharmacologically active metabolites. As an important class of natural products, diterpenes show... (Review)
Review
Marine-derived fungi are important sources of novel compounds and pharmacologically active metabolites. As an important class of natural products, diterpenes show various biological activities, such as antiviral, antibacterial, anti-inflammatory, antimalarial, and cytotoxic activities. Developments of equipment for the deep-sea sample collection allow discoveries of more marine-derived fungi with increasing diversity, and much progress has been made in the identification of diterpenes with novel structures and bioactivities from marine fungi in the past decade. The present review article summarized the chemical structures, producing organisms and biological activities of 237 diterpenes which were isolated from various marine-derived fungi over the period from 2009 to 2021. This review is beneficial for the exploration of marine-derived fungi as promising sources of bioactive diterpenes.
Topics: Fungi; Biological Products; Diterpenes; Antimalarials; Anti-Bacterial Agents; Aquatic Organisms
PubMed: 36500394
DOI: 10.3390/molecules27238303 -
Journal of Chromatographic Science Jan 2021Bicyclic diterpenoid lactone andrographolide is regarded as a "natural antibiotic" as it is known to exhibit a range of bioactivities including anti-inflammatory,... (Review)
Review
Bicyclic diterpenoid lactone andrographolide is regarded as a "natural antibiotic" as it is known to exhibit a range of bioactivities including anti-inflammatory, antibacterial, antipyretic, antineoplastic, cardioprotective, hepatoprotective and hypoglycaemic, and is present in Andrographis paniculata. The aim of this article is to review the information on analytical methods for andrographolide in biological samples, pharmaceutical formulations and plant materials. This article includes various techniques such as Spectrophotometry, Chemiluminescence method, Electroanalytical method, Chromatography and various hyphenated techniques.
Topics: Andrographis; Chemistry Techniques, Analytical; Diterpenes; Plant Extracts
PubMed: 33221827
DOI: 10.1093/chromsci/bmaa091 -
Fitoterapia Mar 2023Five unusual kaurane diterpenes, designated as bezerraditerpenes A-E (1-5), along with six known ones (6-11), were isolated from the hexane extract of the stems of...
Five unusual kaurane diterpenes, designated as bezerraditerpenes A-E (1-5), along with six known ones (6-11), were isolated from the hexane extract of the stems of Erythroxylum bezerrae. Their structures were elucidated based on the interpretation of the NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis. The anti-inflammatory potential of the diterpenes 1-11 was screened through cellular viability and lipopolysaccharide (LPS)-induced nitric oxide (NO) production on murine macrophage-like cells RAW 264.7. Diterpene 6 (cauren-6β-ol) showed potent cytotoxicity and increased ability to inhibit NO production. Diterpenes 1 (bezerraditerpene A), 2 (bezerraditerpene B), and 8 (ent-kaur-16-ene-3β,15β-diol) exhibited the same significant anti-inflammatory activity with NO CI inhibition (3.21-3.76 μM) without cytotoxicity, in addition to decreasing the levels of pro-inflammatory cytokines TNF-α and IL-6 in LPS-induced RAW264.7 cells.
Topics: Animals; Mice; Anti-Inflammatory Agents; Diterpenes; Diterpenes, Kaurane; Lipopolysaccharides; Molecular Structure; Nitric Oxide; Erythroxylaceae
PubMed: 36603699
DOI: 10.1016/j.fitote.2022.105424 -
Journal of Industrial Microbiology &... Apr 2021Forskolin, a class of labdane-type diterpenoid, has significant medicinal value in anticancer, antiasthmatic, antihypertensive, and heart-strengthening treatments. The... (Review)
Review
Forskolin, a class of labdane-type diterpenoid, has significant medicinal value in anticancer, antiasthmatic, antihypertensive, and heart-strengthening treatments. The main source of natural forskolin is its extraction from the cork tissue of the root of Coleus forskohlii. However, conventional modes of extraction pose several challenges. In recent years, the construction of microbial cell factories to produce medicinal natural products via synthetic biological methods has effectively solved the current problems and is a research hotspot in this field. This review summarizes the recent progress in the heterologous synthesis of forskolin via synthetic biological technology, analyzes the current challenges, and proposes corresponding strategies.
Topics: Colforsin; Diterpenes
PubMed: 33928347
DOI: 10.1093/jimb/kuab009 -
Organic & Biomolecular Chemistry Oct 2019Diterpene pyrones (DTPs) are a group of well-known, mainly fungal, natural products, first isolated in 1966. As the name indicates, they are composed of two main... (Review)
Review
Diterpene pyrones (DTPs) are a group of well-known, mainly fungal, natural products, first isolated in 1966. As the name indicates, they are composed of two main structural features: a diterpenyl moiety and a pyrone ring. Various names have been given to this class of metabolites; however, biogenetic evidence indicates that they originate through the same metabolic pathway. Based on their biosynthesis, which leads to differences in their structural architecture, the DTPs can be classified into three main types. In addition to their intriguing chemistry, these compounds demonstrate a wide range of biological activities rendering them a desirable target for total synthesis. To date, sixty-seven DTPs have been isolated from various fungal species, with one example originating from the plant kingdom. This review aims at unifying the classification of these compounds, in addition to presenting a detailed description of their isolation, bioactivities, biosynthesis, and total synthesis.
Topics: Biological Products; Diterpenes; Molecular Structure; Pyrones
PubMed: 31482157
DOI: 10.1039/c9ob01501a -
Food Research International (Ottawa,... Aug 2020The coffee oil is rich in diterpenes, mainly cafestol and kahweol, which are predominantly present in the esterified form with different fatty acids. Despite their... (Review)
Review
The coffee oil is rich in diterpenes, mainly cafestol and kahweol, which are predominantly present in the esterified form with different fatty acids. Despite their beneficial effects including anti-angiogenic and anti-carcinogenic properties, they have been also associated with negative consequences such as elevation of blood cholesterol. Considering the coffee, it is an important human beverage with biological effects, including potentially health benefits or risks. Therefore, it may have important public health implications due to its widespread massive consumption, with major incidence in the varieties Arabica and Robusta. According to literatures, cafestol (182-1308 mg/100 g), kahweol (0-1265 mg/100 g) and 16-O-methycafestol (0-223 mg/100 g) are the main diterpenes in green and roasted coffee beans. Nevertheless, the coffee species, genetic background, and technological parameters like roasting and brewing have a clear effect on coffee diterpene content. Besides that, bibliographic data indicated that limited studies have specifically addressed the recent analytical techniques used for determination of this class of compounds, being HPLC and GC the most common approaches. For these reasons, this review aimed to actualize the occurrence and the profile of diterpenes in coffee matrices, focusing on the effect of species, roasting and brewing and on the other hand, introduce the current state on knowledge regarding coffee diterpenes determination which are nowadays highly regarded and widely used. In general, since diterpenes exhibit different health effects depending on their consumption dosage, several parameters needs to be carefully analyzed and considered when comparing the results.
Topics: Animals; Coffea; Diterpenes; Food Technology; Humans; Plant Oils
PubMed: 32517949
DOI: 10.1016/j.foodres.2020.109207 -
Chinese Journal of Natural Medicines Oct 2022Plant diterpenoids are widely distributed and abundant natural products with diverse structures and functions in nature, which have been commonly used in pharmaceutical,... (Review)
Review
Plant diterpenoids are widely distributed and abundant natural products with diverse structures and functions in nature, which have been commonly used in pharmaceutical, agricultural and industrial production. In recent years, plant diterpenoids have attracted increasing attention, including their biosynthetic pathways, transcriptional regulatory networks, and biological functions. Herein, the biosynthetic pathways of diterpenoids are summarized in a modular fashion. Further, the regulatory network between diterpene biosynthesis and environmental factors is reviewed. Insights into diterpene metabolism may drive elucidation of complex active diterpene pathways and serve as a knowledge repository for metabolic engineering and cell factory construction.
Topics: Plants, Medicinal; Diterpenes; Metabolic Engineering; Biosynthetic Pathways; Biological Products
PubMed: 36307198
DOI: 10.1016/S1875-5364(22)60214-0 -
Journal of the American Chemical Society Sep 2022From both structural and functional perspectives, the large family of daphnane diterpene orthoesters (DDOs) represent a truly remarkable class of natural products. As...
From both structural and functional perspectives, the large family of daphnane diterpene orthoesters (DDOs) represent a truly remarkable class of natural products. As potent lead compounds for the treatment of pain, neurodegeneration, HIV/AIDS, and cancer, their medicinal potential continues to be heavily investigated, yet synthetic routes to DDO natural products remain rare. Herein we report a distinct approach to this class of complex diterpenes, highlighted by a 15-step total synthesis of the flagship DDO, resiniferatoxin.
Topics: Biological Products; Diterpenes
PubMed: 36043948
DOI: 10.1021/jacs.2c08200