Search Results (53)

As the global population grows, food security and agricultural productivity face challenges, and insect pests cause significant losses to crops. The effectiveness of traditional chemical pesticides is declining, and eco-friendly pesticides need to be developed. Diterpenoid alkaloids (DAs), natural products of plant origin, have attracted attention due to their low environmental risks. Here we review the classification, structure, insecticidal and anti-feeding activities of diterpenoid alkaloids, as well as the current state of research on these chemicals. Studies have shown that C₁₉- and C₂₀-diterpenoid alkaloids show significant activity against a variety of insects, but there are still limited studies on C₁₈-diterpenoid alkaloids. Therefore, through in-depth research on diterpenoid alkaloids, we have discovered that there are various compounds with high efficiency and specificity in insecticidal and antifeedant activities among C₁₉- and C₂₀-diterpenoid alkaloids, which exhibit high selectivity and efficiency towards target pests. This paper emphasizes the potential of diterpenoid alkaloids as novel biopesticides and highlights the need to combine new technologies to conduct further systematic evaluation and screening of these compounds. This work provides new ideas for the development of environmentally friendly pesticides and contributes to sustainable agricultural practices. Full article

Callicarpa giraldii Hesse ex Rehd. is an endemic plant in China and has long been used as a traditional medicine in several provinces. Although the plant has been reported to contain flavonoids, triterpenes, and alkaloids, this study represents the first report of the isolation of phyllocladane-type diterpenoids, a relatively rare class of compounds. In this study, 18 new phyllocladane-type diterpenoids (7–24) were isolated and structurally elucidated, including eight uncommon 3,4-seco phyllocladane-type diterpenoids (15–22) and two unusual phyllocladane-type diterpene dimers (23–24), along with six known analogues (1–6). Their structures were elucidated by a comprehensive analysis of 1D and 2D NMR, IR, and HRESIMS data. The absolute configurations were determined by single crystal X-ray diffraction experiments, DFT NMR calculations, and TDDFT ECD calculations. Based on the obtained and reported spectroscopic data, we refined a rule to distinguish phyllocladane-type diterpenoids from their diastereomeric ent-kaurane-type compounds. Additionally, the isolated compounds were evaluated for their in vitro anti-neuroinflammatory activity against lipopolysaccharide (LPS)-induced inflammation in BV-2 microglial cells. Compounds 5, 10, 13, 18, 19, and 20 showed moderate inhibitory activity at the concentration of 20 μM, with compounds 5 and 13 markedly reducing the mRNA levels of the pro-inflammatory cytokines IL-1β, IL-6, and TNF-α at this concentration. Full article

Mesaconitine (MA), a predominant diterpenoid alkaloid isolated from Aconitum species, exhibits notable pharmacological properties but is simultaneously associated with significant toxicological concerns, with its hepatotoxic mechanisms remaining largely unelucidated. In this study, zebrafish embryos were systematically exposed to MA to investigate its effects on hepatic development and function. Comprehensive analyses of liver morphology, inflammatory response, oxidative stress, and apoptotic pathways were conducted. MA induced dose-dependent hepatotoxicity, manifesting in a significant reduction in liver size and a marked downregulation of liver-specific genes, including tfa, cp, hhex, and fabp10a. The presence of oxidative stress was substantiated by elevated reactive oxygen species (ROS) levels, while hepatic inflammation was characterized by enhanced neutrophil infiltration and the upregulation of proinflammatory mediators, particularly il1b and tnfa. A global transcriptome analysis revealed the substantial upregulation of unfolded protein response (UPR)-associated genes, notably hsp90b1, hspa5, and hspb9, indicating that MA-induced oxidative stress triggered endoplasmic reticulum (ER) stress and subsequent UPR activation. Prolonged ER stress ultimately resulted in hepatocyte apoptosis, as demonstrated by the increased expression of the pro-apoptotic genes casp3a, casp3b, and baxa. These findings elucidate the molecular mechanisms underlying MA-induced hepatotoxicity and identify potential therapeutic targets for preventing and treating liver injury associated with Aconitum alkaloid exposure. Full article

Daldinia carpinicola is a newly identified species of wood-rotting fungi, with substantial aspects of its biology and ecological function yet to be clarified. A Nanopore third-generation sequencer was employed for de novo genome assembly to examine the genetic characteristics. The genome consisted of 35.93 Mb in 46 contigs with a scaffold N50 of 4.384 Mb. Glycoside hydrolases and activities enzymes accounted for a large proportion of the 522 identified carbohydrate-active enzymes (CAZymes), suggesting a strong wood degradation ability. Phylogenetic and comparative analysis revealed a close evolutionary relationship between D. carpinicola and D. bambusicola. D. carpinicola and Hypoxylon fragiforme exhibited significant collinear inter-species genome alignment. Based on transcriptome and metabolomic analyses, D. carpinicola showed a greater ability to utilize sucrose over sawdust as a carbon source, enhancing its growth by activating glycolysis/gluconeogenesis and the citrate cycle. However, compared with sucrose, sawdust as a carbon source activated D. carpinicola amino acid biosynthesis and the production of various secondary metabolites, including diterpenoid, indole alkaloid, folate, porphyrin, and biotin metabolism. The study establishes a theoretical basis for research and applications in biological processes, demonstrating a strategy to modulate the production of secondary metabolites by altering its carbon sources in D. carpinicola. Full article

Processed Fu-Zi (the lateral roots of Aconitum carmichaeli) is beneficial for the cardiac system, but, because it contains toxins, raw Fu-Zi produces arrhythmia and breathing difficulties. C₁₉ diester diterpenoid alkaloids (DDAs), including aconitine, mesaconitine, and hypaconitine, are toxic Aconitum alkaloids found in Fu-Zi and can be hydrolyzed to nontoxic monoester diterpenoid alkaloids (MDAs), including benzoylaconine, benzoylmesaconine, and benzoylhypaconine. In this study, six processed Fu-Zi decoction pieces and herbal medicines were analyzed. The highest DDA contents were found in Shengfupian, the raw Fu-Zi samples. A processing quality index (Grades A to D) was established to evaluate the processing quality of Fu-Zi. The data demonstrated that few Fu-Zi decoction pieces did not conform to the government regulation. The results of testing the inorganic elements showed that the calcium content increased by approximately 5 to 30 fold compared to raw Fu-Zi due to substances assisting with processing. Raw Fu-Zi processed by boiling, without additional substances, may have a decreased DDA content. This study provides a method of determining the quality status of pieces of Fu-Zi decoction and establishes a processing quality index for pieces of Fu-Zi decoction and herbal medicine. Furthermore, our results suggest that it is not necessary to use additional substance to assist with the processing of Fu-Zi. Through the established processing quality index, Fu-Zi may be used more safely and may demonstrate a greater consistency in quality. Full article

Aconitum vilmorinianum (A. vilmorinianum) is an important medicinal plant in the Aconitum genus that is known for its diterpenoid alkaloids, which exhibit significant pharmacological activity and toxicity, thus making it valuable for both medicinal use and as a biopesticide. Although the biosynthesis of terpenoids is well characterized, the potential gene regulatory role of microRNAs (miRNAs) in terpenoid biosynthesis in A. vilmorinianum remains unclear, and further research is needed to explore this aspect in this species. In this study, miRNA sequencing was conducted to analyze the miRNA population and its targets in A. vilmorinianum. A total of 22,435 small RNAs were identified across the nine samples. Through miRNA target gene association analysis, 356 target genes from 54 known miRNAs and 977 target genes from 151 novel miRNAs were identified. Target identification revealed that miR6300 targets the hydroxymethylglutaryl-CoA reductase (HMGR) gene, which is involved in the formation of the terpenoid backbone and regulates the synthesis of diterpenoid alkaloids. Additionally, preliminary findings suggest that miR4995 and miR5021 may be involved in the regulation of terpenoid biosynthesis, although further biochemical analysis is needed to confirm these potential roles. This study provides a foundational understanding of the molecular mechanisms by which miRNAs regulate terpenoid biosynthesis in A. vilmorinianum and offers scientific evidence for further research on the biosynthesis of diterpenoid alkaloids in this medicinal plant. Full article

Aconitum stands out among the Ranunculaceae family for its notable use as an ornamental and medicinal plant. Diterpenoid alkaloids (DAs), the characteristic compounds of Aconitum, have been found to have effective analgesic and anti-inflammatory effects. Despite their medicinal potential, the toxicity of most DAs restricts the direct use of Aconitum in traditional medicine, necessitating complex processing before use. The use of high-throughput omics allows for the investigation of Aconitum plant genetics, gene regulation, metabolic pathways, and growth and development. We have collected comprehensive information on the omics studies of Aconitum medicinal plants, encompassing genomics, transcriptomics, metabolomics, proteomics, and microbiomics, from internationally recognized electronic scientific databases such as Web of Science, PubMed, and CNKI. In light of this, we identified research gaps and proposed potential areas and key objectives for Aconitum omics research, aiming to establish a framework for quality improvement, molecular breeding, and a deeper understanding of specialized metabolite production in Aconitum plants. Full article

Aconitine is a highly poisonous C₁₉-diterpenoid alkaloid identified and isolated from the species of the genus Aconitum. Aconitine is indicated in the treatment of cardiovascular diseases (CVDs) and, due to its neurotoxic effects, is a very effective drug in pain release. A total of 101 relevant scientific papers were manually searched on the Web of Science, Scopus, Science Direct, Google Scholar, PubMed and Dovepress databases and in the books available in the library of the Department of Natural Sciences, the National University of Science and Technology POLITEHNICA Bucharest, Pitesti University Centre, Romania. In combination treatments, aconitine shows antiarrhythmic and anti-inflammatory activity, a synergistic antiproliferative effect and decreased reactive oxygen species (ROS) generation, an improved biodistribution and bioavailability. Additionally, the entrapment of aconitine in engineered nanoparticles represents a promising method for reducing the toxicity of this alkaloid. This review provides, for the first time, a comprehensive picture of the knowledge and research on the synergistic, additive and antagonistic effects of aconitine in combination treatments applied in vivo or in vitro. The summarized studies represent important clues in addressing the multitude of knowledge, which can find their utility in practical and clinical applications. Full article

Sponges are a vital source of pharmaceutically active secondary metabolites, of which the main structural types are alkaloids and terpenoids. Many of these compounds exhibit biological activities. Focusing specifically on diterpenoids, this article reviews the structures and biological activities of 228 diterpenes isolated from more than 33 genera of sponges from 2009 to 2022. The Spongia sponges produce the most diterpenoid molecules among all genera, accounting for 27%. Of the 228 molecules, 110 exhibit cytotoxic, antibacterial, antifungal, antiparasitic, anti-inflammatory, and antifouling activities, among others. The most prevalent activity is cytotoxicity, present in 54 molecules, which represent 24% of the diterpenes reported. These structurally and biologically diverse diterpenoids highlight the vast, yet largely untapped, potential of marine sponges in the discovery of new bioactive molecules for medicinal use. Full article

The perennial herb Aconitum sinomontanum Nakai (Ranunculaceae) has been utilized as a traditional oriental medicine in China for numerous years. The principal pharmacological constituent of A. sinomontanum, lappaconitine (LA), exhibits analgesic, anti-inflammatory, anti-tumor, anti-arrhythmic, and anti-epileptic activities. Due to its potent efficacy and non-addictive nature, LA is widely utilized in the management of cancer pain and postoperative analgesia. This review encompasses the research advancements pertaining to LA including extraction methods, separation techniques, pharmacological properties, chemical modifications, and clinical applications. Additionally, it offers insights into the potential applications and current challenges associated with LA to facilitate future research endeavors. Full article

Eupatorium lindleyanum DC. (EL) is a traditional Chinese herb known for its phlegm-reducing, cough-relieving and asthma-calming properties. It is widely used for treating cough and bronchitis. However, preliminary experiments have revealed wide variations in the composition of its different medicinal parts (flowers, leaves and stems), and the composition and efficacy of its different medicinal parts remain largely underexplored at present. In this study, non-targeted rapid resolution liquid chromatography coupled with a quadruple time-of-flight mass spectrometry (RRLC-Q-TOF-MS)-based metabolomics approach was developed to investigate the differences in the chemical composition of different medicinal parts of EL. We identified or tentatively identified 9 alkaloids, 11 flavonoids, 14 sesquiterpene lactones, 3 diterpenoids and 24 phenolic acids. In addition, heatmap visualization, quantitative analysis by high-performance liquid chromatography (HPLC-PDA) and ultra-high-performance liquid chromatography–triple quadrupole tandem mass spectrometry (UPLC-MS/MS) showed particularly high levels of sesquiterpene lactones, flavonoids and phenolic acids in the flowers, such as eupalinolide A and B and chlorogenic acid, among others. The leaves also contained some flavonoid sesquiterpene lactones and phenolic acids, while the stems were almost absent. The findings of in vitro activity studies indicated that the flowers exhibited a notable inhibitory effect on the release of the inflammatory factors TNF-α and IL-6, surpassing the anti-inflammatory efficacy observed in the leaves. Conversely, the stems demonstrated negligible anti-inflammatory activity. The variations in anti-inflammatory activity among the flowers, leaves and stems of EL can primarily be attributed to the presence of flavonoids, phenolic acids and sesquiterpene lactones in both the flowers and leaves. Additionally, the flowers contain a higher concentration of these active components compared to the leaves. These compounds mediate their anti-inflammatory effects through distinct biochemical pathways. The results of this study are anticipated to provide a scientific basis for the rational and effective utilization of EL resources. Full article

The white berry bush, officially Flueggea virosa (Roxb. ex Willd.) Royle is a medicinal plant distributed throughout tropical areas and traditionally used in Africa, India and China. Root decoctions are used to treat abdominal pain, whereas extracts from the aerial parts serve to treat liver and urinary diseases, inflammatory pathologies and diabetes, among other pathologies. Plant extracts have revealed antiparasitic, antimicrobial, antiepilepsy, antidiabetic, anticancer and analgesic effects. Three main categories of phytochemicals were isolated from F. virosa: polyphenols, with the lead product bergenin; terpenoids, such as the flueggenoids and related podocarpane-type diterpenoids; and many alkaloids derived from securinine and norsecurinine. A remarkable feature of S. virosa is the production of norsecurinine oligomers, including macromolecular tetramers and pentamers, such as fluevirosinines. The most potent anticancer alkaloid in the family is the dimeric indolizidine flueggine B, which was identified as a potential binder to α/β-tubulin dimer, which is a known target for securinine. This review highlights the diversity of phytochemicals identified from S. virosa and the potential therapeutic benefits of dimeric alkaloids. Studies are encouraged to further investigate the therapeutic properties of the lead compounds but also define and finesse the nutritional profile of the edible fruit. Full article

Rice (Oryza sativa L.) is thought to have been domesticated many times independently in China and India, and many modern cultivars are available. All rice tissues are rich in specialized metabolites (SPMs). To date, a total of 181 terpenoids, 199 phenolics, 41 alkaloids, and 26 other types of compounds have been detected in rice. Some volatile sesquiterpenoids released by rice are known to attract the natural enemies of rice herbivores, and play an indirect role in defense. Momilactone, phytocassane, and oryzalic acid are the most common diterpenoids found in rice, and are found at all growth stages. Indolamides, including serotonin, tryptamine, and N-benzoylserotonin, are the main rice alkaloids. The SPMs mainly exhibit defense functions with direct roles in resisting herbivory and pathogenic infections. In addition, phenolics are also important in indirect defense, and enhance wax deposition in leaves and promote the lignification of stems. Meanwhile, rice SPMs also have allelopathic effects and are crucial in the regulation of the relationships between different plants or between plants and microorganisms. In this study, we reviewed the various structures and functions of rice SPMs. This paper will provide useful information and methodological resources to inform the improvement of rice resistance and the promotion of the rice industry. Full article

Diterpenoid alkaloids (DAs) are major pharmacologically active ingredients of Aconitum vilmorinianum, an important medicinal plant. Cytochrome P450 monooxygenases (P450s) are involved in the DA biosynthetic pathway, and the electron transfer reaction of NADPH-cytochrome P450 reductase (CPR) with P450 is the rate-limiting step of the P450 redox reaction. Here, we identified and characterized two homologs of CPR from Aconitum vilmorinianum. The open reading frames of AvCPR1 and AvCPR2 were found to be 2103 and 2100 bp, encoding 700 and 699 amino acid residues, respectively. Phylogenetic analysis characterized both AvCPR1 and AvCPR2 as class II CPRs. Cytochrome c and ferricyanide could be reduced with the recombinant proteins of AvCPR1 and AvCPR2. Both AvCPR1 and AvCPR2 were expressed in the roots, stems, leaves, and flowers of A. vilmorinianum. The expression levels of AvCPR1 and AvCPR2 were significantly increased in response to methyl jasmonate (MeJA) treatment. The yeasts co-expressing AvCPR1/AvCPR2/SmCPR1 and CYP76AH1 all produced ferruginol, indicating that AvCPR1 and AvCPR2 can transfer electrons to CYP76AH1 in the same manner as SmCPR1. Docking analysis confirmed the experimentally deduced functional activities of AvCPR1 and AvCPR2 for FMN, FAD, and NADPH. The functional characterization of AvCPRs will be helpful in disclosing molecular mechanisms relating to the biosynthesis of diterpene alkaloids in A. vilmorinianum. Full article

Natural products with curative properties are gaining immense popularity in scientific and food research, possessing no side effects in contrast to other drugs. Guduchi, or Tinospora cordifolia, belongs to the menispermaceae family of universal drugs used to treat various diseases in traditional Indian literature. It has received attention in recent decades because of its utilization in folklore medicine for treating several disorders. Lately, the findings of active phytoconstituents present in herbal plants and their pharmacological function in disease treatment and control have stimulated interest in plants around the world. Guduchi is ethnobotanically used for jaundice, diabetes, urinary problems, stomachaches, prolonged diarrhea, skin ailments, and dysentery. The treatment with Guduchi extracts was accredited to phytochemical constituents, which include glycosides, alkaloids, steroids, and diterpenoid lactones. This review places emphasis on providing in-depth information on the budding applications of herbal medicine in the advancement of functional foods and nutraceuticals to natural product researchers. Full article