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Journal of Natural Products Jul 2022Sixteen diterpenes (-), along with 10 previously described compounds, including four flavonoids and six diterpenes, were isolated from the aerial parts of growing in... (Review)
Review
Sixteen diterpenes (-), along with 10 previously described compounds, including four flavonoids and six diterpenes, were isolated from the aerial parts of growing in Saudi Arabia. The diterpene structures were elucidated using NMR spectroscopy and mass spectrometry data. Furthermore, a DFT/NMR procedure was used to suggest the relative configuration of several compounds. The labdane-derived skeletons, namely, -atisane, -beyerene, -trachylobane, and -kaurene, were identified. The extracts, fractions, and pure compounds were then tested against , , , and . One diterpenoid, namely, psiadin, showed an additive effect with the antiseptic chlorhexidine, with a fractional inhibitory concentration index of less than 1. Additionally, psiadin showed a prospective inhibition activity for bacterial efflux pumps.
Topics: Anti-Infective Agents; Asteraceae; Diterpenes; Molecular Structure; Prospective Studies
PubMed: 35748331
DOI: 10.1021/acs.jnatprod.1c01093 -
Journal of Natural Medicines Jan 2023Ginger (Zingiber officinale Roscoe) is a perennial plant widely distributed in tropical and subtropical regions, and its rhizomes are sometimes processed for use in...
Ginger (Zingiber officinale Roscoe) is a perennial plant widely distributed in tropical and subtropical regions, and its rhizomes are sometimes processed for use in traditional medicine. In Japan, "ginger" (Shokyo in Japanese) and "processed ginger" (Kankyo in Japanese) are defined as crude drugs derived from ginger rhizomes, which have different medicinal properties due to complex changes in their chemical composition during processing. The effects of processing on gingerols and shogaols are well known, but for other phytochemicals remain unclear. Therefore, the present study prepared dried ginger and processed ginger derived from three ginger cultivars (Kintoki, Kogane, and Tosa ginger) and examined the effects of drying and processing on multiple secondary metabolites. Drying showed only a limited effect on ginger chemical constituents and significantly reduced [6]-gingerol content in Tosa ginger. In contrast, processing altered content of numerous metabolites, such as terpenes and gingerol-related compounds, in addition to those gingerols and shogaols. Notably, processing reduced labdane diterpene content, including labdadienedial, aframodial, and galanolactone in all ginger cultivars. Our results show galanolactone with anti-emetic activity was abundant in dried ginger and decreased following processing, highlighting different uses between "ginger" and "processed ginger" in traditional medicine. Overall, we comprehensively clarified the impact of drying and processing on terpenes and gingerol-related compounds. These findings help reveal the varying medicinal properties among crude drugs prepared from Z. officinale.
Topics: Zingiber officinale; Catechols; Fatty Alcohols; Diterpenes; Plant Extracts; Terpenes
PubMed: 36209453
DOI: 10.1007/s11418-022-01652-z -
Pharmacological Research May 2022Diterpenes are a diverse group of structurally complex natural products with a wide spectrum of biological activities, including antidiabetic potential. In the last 25... (Review)
Review
Diterpenes are a diverse group of structurally complex natural products with a wide spectrum of biological activities, including antidiabetic potential. In the last 25 years, numerous diterpenes have been investigated for antidiabetic activity, with some of them reaching the stage of clinical trials. However, these studies have not been comprehensively reviewed in any previous publication. Herein, we critically discussed the literature on the potential of diterpenes as antidiabetic agents, published from 1995 to September, 2021. In the period under review, 427 diterpenes were reported to have varying degrees of antidiabetic activity. Steviol glycosides, stevioside (1) and rebaudioside A (2), were the most investigated diterpenes with promising antidiabetic property using in vitro and in vivo models, as well as human subjects. All the tested pimaranes consistently showed good activity in preclinical evaluations against diabetes. Inhibitions of α-glucosidase and protein tyrosine phosphatase 1B (PTP 1B) activities and peroxisome proliferator-activated receptors gamma (PPAR-γ) agonistic property, were the most frequently used models for studying the antidiabetic activity of diterpenes. The molecular mechanisms of action of the diterpenes include increased GLUT4 translocation, and activation of phosphoinositide 3-kinase (PI3K) and AMP-activated protein kinase (AMPK)-dependent signaling pathways. This review revealed that diterpenes hold promising antidiabetic potential while stevioside (1) and rebaudioside A (2) are the only diterpenes that were advanced to the clinical trial stage of the drug discovery pipeline. Diterpenes belonging to the abietane, labdane, pimarane and kaurane classes have shown promising activity in in vitro and in vivo models of diabetes and should be further investigated.
Topics: AMP-Activated Protein Kinases; Diabetes Mellitus; Diterpenes; Diterpenes, Kaurane; Humans; Hypoglycemic Agents; Phosphatidylinositol 3-Kinases
PubMed: 35272043
DOI: 10.1016/j.phrs.2022.106158 -
Fitoterapia Nov 2019One new pseudoguaianolide (1), one new megastigmane (6), and one new ent-abietane diterpene (9), together with seven known compounds (2-5, 7, 8, and 10) were isolated...
One new pseudoguaianolide (1), one new megastigmane (6), and one new ent-abietane diterpene (9), together with seven known compounds (2-5, 7, 8, and 10) were isolated from the aerial parts of Euphorbia thymifolia. The structures of the new compounds and their relative configurations were determined by spectroscopic data analysis. The absolute configurations of compounds 1, 6, and 9 were determined by single-crystal X-ray crystallographic analysis, modified Mosher's method and calculated ECD experiment, respectively. All compounds were tested for their inhibitory effects against LPS-induced NO production in BV-2 microglial cells, and pseudoguaianolides (1-5) showed significant activity with IC values of 0.41-15.32 μM.
Topics: Abietanes; Animals; Cell Line, Tumor; China; Cyclohexanones; Diterpenes; Euphorbia; Glucosides; Mice; Microglia; Molecular Structure; Neuroprotective Agents; Nitric Oxide; Norisoprenoids; Phytochemicals; Plant Components, Aerial; Sesquiterpenes
PubMed: 31698058
DOI: 10.1016/j.fitote.2019.104408 -
Biomolecules Jan 2022The dried flower buds of the plant Sieb. et Zucc. have been largely used in traditional Chinese medicine for the treatment of inflammatory diseases. Numerous... (Review)
Review
The dried flower buds of the plant Sieb. et Zucc. have been largely used in traditional Chinese medicine for the treatment of inflammatory diseases. Numerous diterpenoids have been isolated from the Genkwa Flos (yuanhua in Chinese), including a series of daphnane-type diterpene designated as yuanhuacin (YC, often improperly designated as yuanhuacine) and analogues with a patronymic name. The series includes ten daphnane-type diterpenes: yuanhuacin, yuanhuadin (YD), yuanhuafin (YF), yuanhuagin (YG), yuanhuahin (YH), yuanhuajin (YJ), yuanhualin (YL), yuanhuamin (YM), yuanhuapin (YP), and yuanhuatin (YT). They are distinct from the rare flavonoid yuanhuanin. The series comprises several anticancer agents, such as the lead compound YC, which has revealed potent activity in vitro and in vivo against models of lung and breast cancers. The main signaling pathways implicated in the antitumor effects have been delineated. Protein kinase C is a key factor of activity for YC, but in general the molecular targets at the origin of the activity of these compounds remain little defined. Promising anticancer effects have been reported with analogues YD and YT, whereas compounds YF and YP are considered more toxic. The pharmacological activity of each compound is presented, as well as the properties of Genkwa Flos extracts. The potential toxic effects associated with the use of these compounds are also underlined.
Topics: Anti-Inflammatory Agents; Diterpenes; Flowers
PubMed: 35204693
DOI: 10.3390/biom12020192 -
Journal of Natural Products Jun 2022Thirteen new dolabrane-type diterpenoids, koilodenoids A-M (-), including a chlorinated congener (), along with six known analogues, were isolated from . The structures... (Review)
Review
Thirteen new dolabrane-type diterpenoids, koilodenoids A-M (-), including a chlorinated congener (), along with six known analogues, were isolated from . The structures were determined by analysis of spectroscopic data, ECD spectra, and X-ray crystallographic studies. The absolute configuration of C-15 in the 15,16-diol unit of compounds and was established by using the dimolybdenum tetraacetate [Mo(AcO)]-induced ECD method. Compounds , , , , and showed moderate to significant immunosuppressive activities against the proliferation of T and B lymphocytes , with compound being the most potent (IC 0.86 and 0.29 μM, respectively).
Topics: Crystallography, X-Ray; Diterpenes; Euphorbiaceae; Immunosuppressive Agents; Molecular Structure
PubMed: 35678710
DOI: 10.1021/acs.jnatprod.2c00204 -
Toxins Sep 2022Dehydroabietic acid is a tricyclic diterpenoid resin acid isolated from rosin. Dehydroabietic acid and its derivatives showed lots of medical and agricultural... (Review)
Review
Dehydroabietic acid is a tricyclic diterpenoid resin acid isolated from rosin. Dehydroabietic acid and its derivatives showed lots of medical and agricultural bioactivities, such as anticancer, antibacterial, antiviral, antiulcer, insecticidal, and herbicidal activities. This review summarized the research advances on the structural modification and total synthesis of dehydroabietic acid and its derivatives from 2015 to 2021, and analyzed the biotransformation and structure-activity relationships in order to provide a reference for the development and utilization of dehydroabietic acid and its derivatives as drugs and pesticides.
Topics: Abietanes; Anti-Bacterial Agents; Antiviral Agents; Diterpenes; Pesticides; Structure-Activity Relationship
PubMed: 36136570
DOI: 10.3390/toxins14090632 -
Molecules (Basel, Switzerland) Oct 2022Indole diterpenes are a large class of secondary metabolites produced by fungi, possessing a cyclic diterpenoid backbone and an indole moiety. Novel structures and... (Review)
Review
Indole diterpenes are a large class of secondary metabolites produced by fungi, possessing a cyclic diterpenoid backbone and an indole moiety. Novel structures and important biological activity have made indole diterpenes one of the focuses of synthetic chemists. Although the discovery, identification, structural diversity, biological activity and especially structure-activity relationship of indole diterpenes have been reported in some papers in recent years, they are absent of a systematic and comprehensive analysis, and there is no elucidation of enzymes related to this kind of natural product. Therefore, it is necessary to summarize the relevant reports to provide new perspectives for the following research. In this review, for the first time, the function of related synthases and the structure-activity relationship of indole diterpenes are expounded, and the recent research advances of them are emphasized.
Topics: Diterpenes; Fungi; Indoles; Biological Products
PubMed: 36296463
DOI: 10.3390/molecules27206870 -
Molecules (Basel, Switzerland) May 2022Dictyotaceae, the large family of brown algae with the genus as the richest one among them, produce a significant number of secondary metabolites, like diterpenes. The...
Dictyotaceae, the large family of brown algae with the genus as the richest one among them, produce a significant number of secondary metabolites, like diterpenes. The aim of this study was to investigate the variations in the composition of the volatile organic compounds (VOCs) of the brown alga collected from the Adriatic Sea. For the first time, both seasonal changes and the impact of air drying were examined. Headspace solid-phase microextraction (HS-SPME) on two fibres with different polarities and hydrodistillation (HD), followed by gas chromatography and mass spectrometry (GC-MS) analysis, was performed on both fresh (FrDd) and air-dried (DrDd) . The major compounds of HS-FrDd were pentadecane and oct-1-en-3-ol. The percentage of pentadecane in HS-DrDd was increased up to 7.8 times in comparison with HS-FrDd. Principal component analysis (PCA) identified differences between the variability of data among fresh and dried samples over months and clearly dissociated the fresh May samples from the others in the HS-SPME results. The most abundant group of VOCs in HD were terpenes, with diterpenes isopachydictyol A and cembra-4,7,11,15-tetraen-3-ol as the major compounds. Diterpene pachydictyol A was also found and among sesquiterpenes and gleenol was the most abundant. Based on the dominant compound analyses, the PCA showed distinct separation of the fresh and dried samples, indicating similarities between the samples and allowing the establishment of typical VOCs significant for the chemotaxonomy of .
Topics: Diterpenes; Gas Chromatography-Mass Spectrometry; Phaeophyceae; Seasons; Solid Phase Microextraction; Volatile Organic Compounds
PubMed: 35566357
DOI: 10.3390/molecules27093012 -
Chemistry & Biodiversity Feb 2022Vibsane-type diterpenoids isolated from the genus Viburnum, are rare 6-11 membered ring polysubstituted macrocyclic diterpenoids. Since the first report of vibsane-type... (Review)
Review
Vibsane-type diterpenoids isolated from the genus Viburnum, are rare 6-11 membered ring polysubstituted macrocyclic diterpenoids. Since the first report of vibsane-type diterpenoids from V. odoratissimum in 1980, they have attracted the attention of scientists due to their complex structures, excellent biological activities, and great synthetic challenges. Recently, there are some notable research achievements on the discovery, synthesis, structural modification, and pharmacological mechanism of vibsane-type diterpenoids. Therefore, we will focus on these aspects to review important achievements of vibsane diterpenoids between 1980-2021.
Topics: Diterpenes; Molecular Structure; Viburnum
PubMed: 34860463
DOI: 10.1002/cbdv.202100861