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Phytochemistry Aug 2023Cembrane diterpenoids (cembranoids), characterized by a 14-membered carbon ring and wide variety of functional groups, found in marine and terrestrial organisms. Many... (Review)
Review
Cembrane diterpenoids (cembranoids), characterized by a 14-membered carbon ring and wide variety of functional groups, found in marine and terrestrial organisms. Many studies have shown that cembrane diterpenoids have cytotoxic and anti-inflammatory activities and are widely used in the development of new drugs. This review covered publications from 2011 to 2022 and classified the cembrane-type diterpenoids into isopropyl (ene) type, γ-lactone or unsaturated five-membered ring, δ-lactone or unsaturated six-membered ring, ε-lactone or unsaturated seven-membered ring, and other cembrane diterpenes. In addition, the biological activity and structure-activity relationship were summarized. This will provide guidance for new cembrane-type diterpenes as lead compounds to explore their potential application for treating cancer and inflammatory diseases.
Topics: Structure-Activity Relationship; Antineoplastic Agents; Diterpenes; Lactones; Molecular Structure
PubMed: 37164145
DOI: 10.1016/j.phytochem.2023.113703 -
Phytochemistry Sep 2022Scutellaria genus, a member of the Lamiaceae family, distributed worldwide and known as skullcaps, contains a wide range of pharmacologically active constituents... (Review)
Review
Scutellaria genus, a member of the Lamiaceae family, distributed worldwide and known as skullcaps, contains a wide range of pharmacologically active constituents including flavonoids and diterpenes. There are different classes of diterpenes in the plant kingdom, of which many have medicinal applications. Scutellaria spp. contain neo-clerodane diterpenes, a large group of naturally occurring specialized metabolites found in both plant species and in organisms from other taxonomic groups, such as fungi, bacteria, and marine sponges. Although many phytochemical studies have been established reporting interesting specialized diterpene structures from Scutellaria spp., there has not been a comprehensive study reviewing these compounds. Hence, the present review reports on natural diterpenoids from the Scutellaria genus and their pharmacological activities. For this purpose, the scientific databases including Scopus, PubMed, and Google Scholar were searched using the keywords "Scutellaria" and "Diterpenes" or "Diterpenoids". The literature review showed that up to now, more than 300 diterpenes have been isolated and reported from the Scutellaria genus, belonging to neo-clerodane scaffolds. Anticancer, antifeedant, phytotoxic, antimicrobial, and nitric oxide production inhibitory activities are the most reported properties for the diterpenoids from the Scutellaria genus. Diterpenes of Scutellaria spp. have therapeutic potentials to be used for the treatment of different diseases. Further phytochemical, pharmacological, and clinical studies are required in this regard.
Topics: Diterpenes, Clerodane; Phytochemicals; Scutellaria
PubMed: 35728674
DOI: 10.1016/j.phytochem.2022.113285 -
Angewandte Chemie (International Ed. in... Nov 2019This Minireview summarises recent developments in the biosynthesis of diterpenes by diterpene synthases in bacteria. It is structured by the class of enzyme involved in... (Review)
Review
This Minireview summarises recent developments in the biosynthesis of diterpenes by diterpene synthases in bacteria. It is structured by the class of enzyme involved in the first committed step towards diterpenes, starting with type I diterpene synthases, followed by type II enzymes and the more recently discovered UbiA-related diterpene synthases. A special emphasis lies on the reaction mechanisms of diterpene synthases that convert simple linear precursors through cationic cascades into structurally complex, usually polycyclic carbon skeletons with multiple stereogenic centres. A further main focus of this Minireview is a discussion of how these mechanisms can be unravelled. Downstream modifications to bioactive molecules are also covered.
Topics: Alkyl and Aryl Transferases; Bacteria; Diterpenes
PubMed: 31183935
DOI: 10.1002/anie.201905312 -
Zhongguo Zhong Yao Za Zhi = Zhongguo... Sep 2023Tigliane type macrocyclic diterpenoids with special structures and diverse bioactivities are mainly extracted from plants of Euphorbiaceae and Thymelaeaceae. According... (Review)
Review
Tigliane type macrocyclic diterpenoids with special structures and diverse bioactivities are mainly extracted from plants of Euphorbiaceae and Thymelaeaceae. According to the different functional groups, they can be classified into types of phorbol esters, C-4 deoxyphorbol esters, C-12 deoxyphorbol esters, C-16 or C-17 substituted phorbol esters and others. Most of them present promising antiviral activities and cytotoxic activities and are expected to be developed as candidates for anti-AIDS, anti-tuberculosis, and anti-tumor clinical trials, demonstrating great potential for the application in healthcare. This paper reviews 115 novel tigliane-type diterpenoids discovered since 2013 and summarize their chemical structures and bioactivities, aiming to lay a foundation for further development and utilization of these compounds and provide new ideas for the development of clinical drugs.
Topics: Phorbols; Molecular Structure; Diterpenes; Antiviral Agents; Phorbol Esters
PubMed: 37802801
DOI: 10.19540/j.cnki.cjcmm.20230427.201 -
Planta Medica Oct 2021Unlike those of coffee beans, the healthy properties of coffee leaves have been overlooked for a long time, even if they are consumed as a beverage by local communities... (Review)
Review
Unlike those of coffee beans, the healthy properties of coffee leaves have been overlooked for a long time, even if they are consumed as a beverage by local communities of several African countries. Due to the presence of xanthines, diterpenes, xanthones, and several other polyphenol derivatives as main secondary metabolites, coffee leaves might be useful to prevent many daily disorders. At the same time, as for all bioactive molecules, careless use of coffee leaf infusions may be unsafe due to their adverse effects, such as the excessive stimulant effects on the central nervous system or their interactions with other concomitantly administered drugs. Moreover, the presence of some toxic diterpene derivatives requires careful analytical controls on manufactured products made with coffee leaves. Accordingly, knowledge about the properties of coffee leaves needs to be increased to know if they might be considered a good source for producing new supplements. The purpose of the present review is to highlight the biosynthesis, metabolism, and distribution of the 4 main classes of secondary metabolites present in coffee leaves, their main pharmacological and toxicological aspects, and their main roles . Differences in coffee leaf chemical composition depending on the coffee species will also be carefully considered.
Topics: Coffee; Dietary Supplements; Diterpenes; Plant Leaves; Polyphenols
PubMed: 34560791
DOI: 10.1055/a-1533-0021 -
Molecules (Basel, Switzerland) Dec 2021(Lamiaceae), which-according to the latest systematic revision-includes three separate genera (, , and ), is a genus widely used in traditional medicine-mainly in the... (Meta-Analysis)
Meta-Analysis Review
(Lamiaceae), which-according to the latest systematic revision-includes three separate genera (, , and ), is a genus widely used in traditional medicine-mainly in the treatment of various ailments of the digestive tract, respiratory tract, and skin. Many species of have been shown to produce phenolic compounds and terpenes. Diterpenes, especially those of the abietane class, are the most studied group of secondary metabolites found in , which is characterized by a significant structural diversity arising from the oxygenation and further rearrangement of the basic tricyclic abietane skeleton to a complete aromatization of the ring system. This review summarizes the known information on abietane diterpenes, showing their structures, sources, and biosynthesis. A classification of these compounds into nine groups, according to the arrangement of their ring C, is used. Royleanones, spirocoleons, and hydroquinones are the largest classes of abietane diterpenes, covering more than 70% of all the compounds reviewed.
Topics: Abietanes; Diterpenes; Molecular Structure; Phytochemicals; Plant Extracts; Plectranthus; Structure-Activity Relationship
PubMed: 35011401
DOI: 10.3390/molecules27010166 -
Natural Product Reports Nov 2019Covering January to December 2017; previous review Nat. Prod. Rep., 2017, 34, 1233-1243. This review covers the isolation and chemistry of diterpenoids from terrestrial... (Review)
Review
Covering January to December 2017; previous review Nat. Prod. Rep., 2017, 34, 1233-1243. This review covers the isolation and chemistry of diterpenoids from terrestrial as opposed to marine sources and includes labdanes, clerodanes, abietanes, pimaranes, kauranes, cembranes and their cyclization products. There are 228 references.
Topics: Abietanes; Cyclization; Diterpenes; Diterpenes, Clerodane; Humans; Molecular Structure; Plants, Medicinal
PubMed: 31417997
DOI: 10.1039/c8np00079d -
Accounts of Chemical Research May 2021The taxane diterpenes are a pharmaceutically vital family of natural products, consisting of more than 550 congeners. All taxane diterpenes are isolated from slow... (Review)
Review
The taxane diterpenes are a pharmaceutically vital family of natural products, consisting of more than 550 congeners. All taxane diterpenes are isolated from slow growing evergreen shrubs (genus Taxus) commonly known as "yews" and have a history of over 50 years as potent anticancer compounds. The most prominent congener, taxol (paclitaxel = PTX), has been used in clinics for more than 25 years and is one of the top-selling anticancer drugs worldwide, with annual sales reaching 1.5 billion USD in 1999. Within the taxane diterpene family 11 different scaffolds originating from rearrangements, fragmentations, or transannular C-C bond formations of the "classical taxane core" are known. Among them, five different scaffolds alone belong to the so-called complex or cyclotaxane subfamily, their signature structural feature bearing different types and numbers of transannular C-C bonds across the classical taxane backbone. For synthetic chemists, these five scaffolds represent by far the most challenging of all and have thus evaded total synthesis as well as detailed pharmaceutical evaluation-the latter due to extremely poor sourcing from natural producers. The cousinship of complex taxanes to taxol renders them potentially interesting compounds for drug research in the fight against cancer.This Account specifically summarizes the work on nonclassical taxanes from a biosynthetic, as well as a synthetic, point and provides a synthetic perspective on complex taxanes. Special attention is given to the biosynthetic relationship of complex taxanes and their biological emergence from classical taxanes. The transannular C-C bond forming events in the biosynthesis leading to the five individual scaffolds within this subfamily are structured on the basis of the exact type and number of these specific C-C bond formations. Since functionalization of the classical taxane core in the "oxidase phase" of the biosynthesis precedes the formation of complex taxanes, and is in part prerequisite for these transannular cyclization events, a detailed discussion of these oxidations of the classical taxane backbone is provided. Synthetic efforts toward nonclassical taxanes are scarce in literature and are thus presented in a comprehensive manner for abeotaxanes and complex taxanes. The last part of this Account deals with a synthetic perspective on the synthesis of complex taxanes (cyclotaxanes) and how these most intricate scaffolds can potentially be obtained via a deconvolution strategy. This discussion involves in part unpublished results by our group and is based upon synthetic studies in the literature. The deconvolution strategy we advocate aims for selective fragmentations of the signature transannular C-C bonds of the most intricate scaffold represented by the natural product canataxpropellane, which has recently been synthesized by our group. This strategy represents the converse process of the biosynthesis of complex taxanes (e.g., transannular cyclizations) and is enabled and feasible due to our approach to the canataxpropellane scaffold. We show that, by following this deconvolution strategy, all five scaffolds of complex taxanes can thereby be accessed.
Topics: Antineoplastic Agents, Phytogenic; Biological Products; Cell Proliferation; Diterpenes; Humans; Neoplasms; Taxoids
PubMed: 33942612
DOI: 10.1021/acs.accounts.0c00873 -
Fundamental & Clinical Pharmacology Aug 2022Andrographis paniculata is an annual medicinal herb from the family Acanthaceae. Andrographolide is generally considered an essential bioactive component of plant A.... (Review)
Review
Andrographis paniculata is an annual medicinal herb from the family Acanthaceae. Andrographolide is generally considered an essential bioactive component of plant A. paniculata. Since ancient times, it has been widely recognized for its therapeutic qualities and has attracted the scientific and medical communities' attention. This review summarizes the molecular, clinical, and in vitro research of compound andrographolide and its mechanism of action. Andrographolide, when combined with other enhancing agents, offers a wide variety of health benefits. The therapeutic potential of andrographolide has been exemplified and exhibited by directly regulating genes and indirectly interacting with small molecules and different enzymes. This review compiles and consolidates the pharmacological action of andrographolide and its analogs and deciphers the gaps that have hindered its use in medicinal research.
Topics: Andrographis; Diterpenes; Plant Extracts; Plants, Medicinal
PubMed: 35001431
DOI: 10.1111/fcp.12757 -
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