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Antimicrobial resistance has been posing an alarming threat to the treatment of infectious diseases over the years. Ineffectiveness of the currently available synthetic and semisynthetic antibiotics has led the researchers to discover new molecules with potent antimicrobial activities. To overcome the emerging antimicrobial resistance, new antimicrobial compounds from natural sources might be appropriate. Secondary metabolites from natural sources could be prospective candidates in the development of new antimicrobial agents with high efficacy and less side effects. Among the natural secondary metabolites, diterpenoids are of crucial importance because of their broad spectrum of antimicrobial activity, which has put it in the center of research interest in recent years. The present work is aimed at reviewing recent literature regarding different classes of natural diterpenes and diterpenoids with significant antibacterial, antifungal, antiviral, and antiprotozoal activities along with their reported structure—activity relationships. A total of diterpenoids from various sources like plants, marine species, and fungi are summarized in this systematic review, including their chemical structures, classification, and significant antimicrobial activities together with their reported mechanism of action and structure—activity relationships. The outcomes herein would provide researchers with new insights to find new credible leads and to work on their synthetic and semisynthetic derivatives to develop new antimicrobial agents. Over the past few decades, the world population has witnessed an alarming surge of antimicrobial resistance AMR —the tip of the iceberg being witnessed during the ongoing coronavirus pandemic. Continued emergence of antibiotic resistance has posed a big risk for health, which increases the mortality and economic burden worldwide Ciorba et al. Innovative targeted therapeutic strategies involving newer technology are being considered to deal with these multi-drug-resistant pathogenic bacteria Yang et al. New strategies are being developed for sustainable discovery of antibiotics in order to keep up with the ever-increasing demand of novel antimicrobials and reduce the lack of investment in their development Miethke et al. Particularly, antimicrobial agents derived from natural sources could be a great tool to deal with these multi-drug-resistant pathogens. Natural products are a rich source of bioactive compounds and are continuously being investigated to discover new compounds with therapeutic potential to act as lead compounds for drug development Porras et al. Several natural products have been adopted as conventional drugs or have been valuable lead compounds for new drug discovery Newman and Cragg, ; Rodrigues et al. Several important drugs such as morphine, tubocurarine, reserpine, cocaine, vincristine, vinblastine, lovastatin, and paclitaxel originated from natural sources. Natural products also possess potential antimicrobial activity via various mechanisms Khameneh et al. Among natural products, diterpenes and diterpenoids are widely prevalent secondary metabolites, with various significant pharmacological effects, which include antitumor, anti-inflammatory, immune modulation, and so on Mantaj et al. Diterpenes and diterpenoids are isoprene C5 -derived chemical compounds consisting of four isoprene units joined head to tail, with the basic molecular formula C 20 H 32 , and have diverse possibilities of structure subtypes Eksi et al. They are mainly classified based on the number of rings present on their chemical structure. Major classes include acyclic diterpenes phytane , monocyclic diterpenes retinol—vitamin A , bicyclic diterpenes clerodane, halimane, and labdane , tricyclic diterpenes abietane, rosane, pimarane, podocarpane, cassane, vouacapane, and chinane , tetracyclic diterpenes kaurene, gibberellane, trachylobane, scopadulane, aphidicolane, atisane, stemodane, beyerene, stemarane , macrocyclic diterpenes polycyclic—cembrane, jatrophane, taxane, ingenane, daphnane, and tigliane , and miscellaneous structures Eksi et al. Although the terms diterpenes and diterpenoids are often used interchangeably in scientific literature, diterpenes are strictly hydrocarbons and have no heteroatoms in their structure, whereas functionalized structures produced by oxidation, substitution, and a wide range of skeletal rearrangements are termed as diterpenoids. They are produced via the mevalonic acid biosynthetic pathway, by condensation reaction of isopentenyl pyrophosphate IPP with farnesyl pyrophosphate FPP , which yields geranylgeranyl pyrophosphate GGPP in a few consecutive reactions Singh and Sharma, As secondary metabolites, diterpenes and diterpenoids are biosynthesized in various plant, marine, sponge, insect, and fungal species in response to biotic and abiotic stresses Zi et al. Several diterpenes have been synthetically produced as well, which possess various potent biological activities Rahman et al. Medicinal plants that have been widely used in traditional medicines for the treatment of various types of infections are rich in terpenoids—monoterpenes, diterpenes, triterpenes, and tetraterpenes. Diterpene- and diterpenoid-rich herbal plants are traditionally used for the treatment of various diseases. Andrographis paniculata Burm. Nees, a medicinal herb with the labdane diterpenoid andrographolide as its major constituent, is widely used in Ayurveda and traditional Chinese medicine TCM for the treatment of cold, fever, sore throat, swollen and painful gums, and inflammation caused by virus-related diseases Jiang et al. Plectranthus madagascariensis Pers. Isodon herbs, which are native to Japan and used traditionally as bitter stomachic, contains ent -kaurane diterpenoids as their major phytoconstituent Tanaka and Ito, Plants from the Daphne genus contain an abundance of natural diterpenoids and have a long history of traditional use as treatments for acne, rheumatism, and inflammation Nie et al. There are numerous similar examples of medicinal plants which contain diterpenes and diterpenoids and are being traditionally used as ailments for various diseases throughout the world. Remarkable biological activities have been reported by natural diterpenes and diterpenoids, making them potential candidates for lead development Mafu and Zerbe, Many existing drugs and herbal medicines, such as paclitaxel Bernabeu et al. However, due to their vast biodiversity, and even newer ones being discovered each year, few papers have reviewed diterpenes in general, focusing on their antimicrobial potency. Instead, most literature have focused on structure identification and bioactive evaluation of diterpenes or diterpenoids belonging to individual classes. In this present work, we aimed to extensively cover diterpenes and diterpenoids possessing antibacterial, antiviral, antifungal, and antiprotozoal activities, by screening recent studies that have reported isolation of such potent antimicrobials from natural sources. We have systematically summarized these activities, with an emphasis on recent studies that have been reported since , with more than references cited. These insights into the antimicrobial potency of diterpene and diterpenoids will help to identify potential candidates for lead development that would contribute towards the development of more effective clinical antimicrobial drugs in the future. The study was designed as a systematic review of recent literature for investigation into diterpenes and diterpenoids with potent antimicrobial activity isolated from natural sources. Chemical structures used in this manuscript have been drawn using ChemDraw The extensive literature search for relevant articles, papers, and books was conducted systematically using three databases: PubMed, Scopus, and Google Scholar. Literature search included publications from the last 5 years, from to , to ensure systematic analysis and presentation of recently isolated antimicrobial diterpenes and diterpenoids. Articles pooled from the databases were manually checked, and duplicates were removed. Database-specific filters such as full text, English language, and publication year were applied to specify the search pool. Articles that did not align with the selection criteria were excluded. All relevant articles were downloaded, and the full text was assessed according to the inclusion and exclusion criteria. Certain inclusion and exclusion criteria were predetermined in order to determine eligibility of relevant literatures for this present review. Inclusion criteria for article selection included journal articles, conference papers, and book chapters that have been published between January and August , articles published in English language and available as full text, studies which isolated diterpenes and diterpenoids from natural sources plant, marine species, fungi, etc. Exclusion criteria for primarily screened articles included reviews or systematic reviews, articles preceding , papers written in languages other than English or with no full text available, studies where diterpenoids were synthetically produced, and articles where none of the isolated diterpenoids exhibited any sort of antimicrobial characteristics. Based on the selection criteria and search strategy implemented, a total of articles were identified and accumulated from PubMed, Scopus, and Google Scholar. After data cleaning for duplicates, articles were pooled for screening. The total number of articles that met the eligibility criteria was 95, and they were critically analyzed to give a comprehensive overview of the isolated diterpenoids, their chemical structures, and the reported antimicrobial activity against different microorganisms. Natural diterpenoids can be potential candidates for designing new antibiotics against the emerging bacterial resistance. A number of classes of natural diterpenoids have been found to have broad-spectrum antibacterial activity Table 1. TABLE 1. Different classes of diterpenoids isolated from natural sources with significant antibacterial activity. Abdissa et al. Compounds 3 , 8 , and 9 exhibited a significant ZOI in the range of 13—23 mm against M. Structures of abietane diterpenoids with significant antibacterial activity. Boonsombat et al. The compounds were tested for antibacterial activity against several Gram-positive and Gram-negative organisms along with fungal and malarial species. No activity was reported against any of the Gram-negative, fungal, and malarial strains Boonsombat et al. Wang et al. Among all the compounds, ent- abietane-type diterpenoids exhibited overall more potent antitubercular activity than the tigliane-type diterpenoids, and compound 11 exhibited the most potent antitubercular activity with an MIC value of 1. Nzogong et al. Paton \[Lamiaceae\] and examined their antibacterial activity against Gram-positive bacteria B. Three diterpenoids were isolated from Plectranthus barbatus Andrews \[Lamiaceae\] by Mothana et al. Among all the abietanes, compound 14 was found to be the most potent antibacterial agent with an MIC of Tsujimaru and coworkers isolated four abietane diterpenoids from the wood drying product of Cryptomeria japonica Thunb. Don \[Cupressaceae\] sugi and investigated their antibacterial activities against anaerobic Gram-positive bacteria Cutibacterium acnes. Among all the diterpenoids, 15 and 16 showed the most potent antibacterial activity with MIC values ranging from 3. Li et. All these diterpenoids were subjected to antituberculosis bioassay by co-incubation with Mycobacterium tuberculosis H37Ra by alamarBlue cell viability assay Thermo Fisher Scientific Inc. Among the isolated diterpenoids, compounds 17—19 showed moderate inhibition of the proliferation of M. Three new ent- abietane diterpenoids isolated from Euphorbia wallichii Hook. Ndjoudi et al. Benth \[Lamiaceae\] and tested for their antitubercular activity against the M. The results implied that the activity of the compounds could be affected by the protein binding capacity of the compounds, and a structure—activity relationship SAR could be inferred from the activity pattern of the diterpenoids. Bozov et al. Arcang \[Lamiaceae\]. The novel compound scordidesin 23 Figure 3 and previously identified compound teucrin A 24 were tested for both antibacterial and antifungal activities against several bacterial and fungal species. Structures of clerodane, copaiba, dolabellane, ent -beyerene, and furano diterpenoids with significant antibacterial activity. Fozia et al. Benth \[Lamiaceae\]. The compounds were tested for antibacterial activity against a number of bacterial species. Two major copaiba diterpenoids, 27 and 28 , were isolated from the oleoresin of Copaifera reticulata Ducke \[Fabaceae\]. The natural compounds seemed to be effective only against Enterococcus faecium and methicillin-resistant S. Further testing revealed that 27 and 28 were much more potent than their semisynthetic derivatives with IC 50 values of 8. Yu and coworkers isolated two new and two known dolabellane diterpenes from marine sponge Dactylospongia elegans Thiele \[Thorectidae\] and evaluated their antibacterial effects using the broth microdilution assay method against E. Yang et al. Only compound 30 was found to be active against A. Quaglio et al. Among the isolated diterpenes, compounds 32 — 34 were found to be active against the tested microorganisms. Compound 32 showed significant activity against Gram-positive bacterial strains, especially against Bacillus spp. The inactivity of the dimeric diterpenes towards any of the tested microorganisms could indicate that the acidic group at C 18 of the tetracyclic ent -beyerene scaffold for the antibacterial effects and the length and flexibility of the alkyl chain between the two carbonyl groups are important factors for the antibacterial activity of the molecule Quaglio et al. Four ent- beyerene diterpenoids from F. Among them, compound 34 was recently patented for its novel colistin adjuvant activity by inhibiting the undecaprenyl phosphate-alphaaminodeoxy-L-arabinose arabinosyl transferase ArnT enzyme, which is responsible for resistance. The ent -beyerene skeleton was found to be a privileged scaffold for further development of colistin resistance inhibitors Quaglio et al. Bisio et al. The compounds were tested for antimicrobial activity on 26 clinical strains, which included several multidrug-resistant strains. Although the compounds did not show any growth inhibition of the Gram-negative species, compounds 35—41 inhibited the growth of several E. Wu et al. Maire \[Psathyrellaceae\], and the compounds were subjected to antibacterial assay against E. Structures of guanacastane, harziane, and indole diterpenoids with significant antibacterial activity. Four harziane-type diterpenoids isolated from the endophytic fungus Trichoderma atroviride from the healthy flower of a Lamiaceae plant Colquhounia coccinea var. Among all the harzianes, only compound 45 exhibited significant antibacterial activity against S. The probable reason behind the inactivity of other harziane diterpenoids may be the functionality at C-2 or C-3 of the compounds, which might be responsible for diminishing their antibacterial activities Li WY. Hu et al. AS, a fungal strain isolated from the fresh tissue of the sea anemone Haliplanella luciae. The isolated compounds were tested against several human, aqua, and plant pathogenic microbes. Compound 46 was also isolated from Penicillium javanicum HK obtained from mangrove rhizosphere soil, and it exhibited selectivity towards S. Compound 49 was bioactive against E. Zhao and coworkers isolated seven new and four known diterpenoids from Drechmeria sp. For getting insight into the mechanism of antimicrobial activity of the diterpenoids, molecular docking was performed, targeting peptide deformylase PDF , which plays an important role in bacterial protein maturation, growth, and survival, and so it has become a pivotal target for designing antimicrobial drugs. Compounds 52 — 55 along with drechmerin B showed significant accessibility to the ligand-binding domain of the PDF protein binding energy ranging from —3. Two new indole diterpenoids, 56 and 57 , as well as two other previously identified diterpenoids were isolated from the Bohai Sea fungus Penicillium janthinellum in an effort to discover anti- Vibrio natural products. Conventional broth dilution assay was utilized to measure their antimicrobial activity. Compound 56 demonstrated strong anti- Vibrio activity against Vibrio anguillarum , V. Liang et al. SYPF strain isolated from the root of P. Chen ex C. Feng \[Araliaceae\] and assayed for antimicrobial effects against Candida albicans , S. The compound showed an inhibitory effect against B. For predicting the probable mechanism of antimicrobial activity, PDF was used for molecular docking target because of its important role in bacterial protein maturation, growth, and survival by N -formyl group degradation for the polypeptide. Xu with coworkers reported two new and one known prenylated indole diterpenoids from a mine soil-derived fungus Tolypocladium sp. XL and investigated their antibacterial activity against eight human pathological bacterial strains, including Micrococcus lysodeikticus , M. Among all three diterpenoids, only compound 59 exhibited remarkable antibacterial activity against M. Compound 60 , a new sterically congested indole diterpenoid alkaloid, was isolated from the fungi Cladosporium sp. Its antimicrobial activity was evaluated against S. Strong antibacterial activity was reported against S. Isca et al. The compounds were tested for antibacterial activity against several clinical strains of S. Among all the diterpenes, compounds 61 — 63 were found to be bioactive against the tested strains. Compound 61 Figure 5 showed the most potent activity, with an MIC value ranging between 6. Compound 62 was bioactive only against two strains of S. The diterpene 63 also exhibited potent antibacterial activity with MIC values ranging between The other diterpenes did not show any antimicrobial potency Isca et al. Structures of isopimarane, kaurene, labdane, lactone, pimarane, and quinone diterpenoids with significant antibacterial activity. Two novel kaurane-type diterpenoids along with 10 other known ones were isolated from the whole plant Wedelia chinensis Osbeck. Merr \[Compositae\]. Some of these compounds were evaluated for their antibacterial activities, and only compounds 64 and 65 exhibited moderate inhibitory activity against S. A total of 19 diterpenoids were isolated from the rhizomes of Kaempferia elegans Wall. Baker and Kaempferia pulchra Ridl \[Zingiberaceae\]. The compounds were tested for antimicrobial activities against several Gram-positive and Gram-negative bacterial strains as well as antifungal activity against several yeast and fungal strains. Compound 67 exhibited activity only against B. Langat et al. Regel \[Pinaceae\] , more commonly known as Siberian dwarf pine or Japanese stone pine , along with nine other previously identified labdane- and abietane-type diterpenoids. Qiao et al. These compounds were subjected to an antibacterial test by a microdilution assay in sterile well microtiter plates using standard penicillin G and ceftazidime against E. Mothana et al. Among the compounds, 71 and 72 were found to exhibit the most potent antimicrobial activity with MIC values between The lipophilic nature of the diterpenoids could be an attributing factor for easy transport through the cell membrane and accumulation inside the cell to affect the cells Mothana et al. Satari et al. Perry \[Rubiaceae\] and tested it against S. The diterpene 73 was found to possess significant antibacterial activity against the tested strain with ZOIs of Yu et al. Hook \[Taxodiaceae\] and evaluated their antibacterial activity against B. Among these compounds, four labdane derivatives, 74—77 , showed significant antibacterial activity IC 50 values ranging from 5. Only 78 showed significant growth inhibition against the E. Andrographolide 79 , a diterpenoid lactone found in traditional medicinal herb A. Among the Gram-positive strains, methicillin-susceptible S. Further investigation to determine the mechanism of action of the lactone diterpenoid revealed that it interferes with RNA and protein synthesis of microbes by impairing their DNA synthesis. This results in the inhibition of the downstream biosynthetic pathway. The compound is also thought to prevent biofilm formation as it efficiently inhibited biofilm formation of S. Two new and five known pimarane diterpenoids were isolated from an arctic fungus Eutypella sp. D-1, and their antibacterial potential was checked against E. Only compound 80 was found to show weak antibacterial activity against E. Three new and one known diterpenoids were isolated from Eutypella sp. D-1 and tested against S. Among the compounds, only 81 showed antibacterial activity against S. Among the isolated pimarane-type diterpenoids from the wood drying product of C. Don \[Cupressaceae\] sugi , 82 showed significant activity against C. Xu et al. Drug interactions between the compound and antibiotics like metronidazole and clarithromycin were tested by the checker-board assay method, which exhibited an additive effect in combination with both metronidazole and clarithromycin, each against G27 strains. The most effective additive action was found in combination with metronidazole or amoxicillin against the clinical strain HP with a fractional inhibitory concentration index FICI value of 0. Cryptotanshinone 84 , a potential diterpenoid quinone with antimicrobial properties, is found in the root of Salvia miltiorrhiza Bunge \[Lamiaceae\]. It is used as the major active ingredient in several Chinese patent medicines used for the treatment of acne vulgaris and other skin infections. Chen et al. The diterpenoid was tested against several clinical strains of S. It also rapidly dissipates bacterial membrane potential Chen et al. The compounds were also tested for their N -acetylglucosaminephosphate uridyltransferase GlmU inhibitory activity by a GlmU acetyltransferase assay, and 85 inhibited GlmU activity moderately IC 50 value In consideration of the inhibitory effect of 85 on both M. Structures of rosane, spongian, vakognavine, and miscellaneous diterpenoids with significant antibacterial activity. Four diterpenoids were isolated from crude extracts of the marine sponge Chelonaplysilla sp. Compound 88 also inhibited the growth of M. The compounds were tested for antibacterial activity against B. Wang \[Ranunculaceae\], a traditional Chinese herb. The diterpenoids were tested against Gram-positive S. Two new and one known C 19 diterpenoid alkaloids were isolated from the roots of Aconitum heterophyllum Wall. Three new diterpenes were reported by Chen and coworkers from the endophytic fungus Trichoderma koningiopsis A and tested for their antibacterial activity against S. Compounds 95 and 96 exhibited the most potent antibacterial activities against B. Five diterpenes were reported from Leptosphaeria sp. XL isolated from P. Chen \[Araliaceae\] and investigated against 10 bacterial strains, namely, M. Among the isolated diterpenoids, compounds 97 — 99 showed moderate antibacterial activity against the selected strains with MIC values ranging from Liu et al. The novel diterpenoid showed significant antibacterial activity against S. Two skeletally novel tetracyclic diterpenoids were characterized by Liu et al. They were screened for antibacterial activities using the MHB dilution method against S. Compounds and exhibited weak activities against S. Zhao et al. Antibacterial activity of these compounds was tested against S. A considerable number of diterpenoids isolated from natural sources have been identified with their significant antiviral activity against several viruses Table 2. TABLE 2. Different classes of diterpenoids isolated from natural sources with significant antiviral activity. Among them, compounds — Figure 7 displayed significant antiviral activities against human rhinovirus 3, with IC 50 values of Structures of atisane, biarane, and clerodane diterpenoids with significant antiviral activity. Fifteen diterpenoids including three new ones were isolated from E. Among all these diterpenes, only and showed potential anti-HIV-1 activities with EC 50 values of 6. Twelve biarane diterpenoids including eight new congeners isolated from Ellisella sp. These outcomes suggest that acts as a transcription inhibitor of cccDNA and is a promising lead for new anti-HBV agent development Wu et al. A total of six clerodane diterpenoids were isolated from marine sponge Raspailia bouryesnaultae , and their anti-herpes activity was tested against herpes simplex virus type 1 HSV Fifteen clerodanes including ten new diterpenoids were isolated from Polyalthia lauii Merr \[Annonaceae\] and tested against HIV Three new and eight known daphnane diterpenes isolated from Wikstroemia chuii Merr \[Thymelaeaceae\] showed potent anti-HIV reverse transcriptase RT effects with EC 50 values ranging from 0. Structures of daphane, dolabellane, and flexibilene diterpenoids with significant antiviral activity. Eighteen dolabellane diterpenoids including five new dolabellanes were isolated from Nigella damascena L \[Ranunculaceae\] and tested against HSV The results indicated that the diacylated diterpenes and diterpenes with a nicotinoyl group displayed better antiviral activity Ogawa et al. The compounds were tested for antiviral activity against the Zika virus PE strain where only exhibited significant inhibition of Zika virus replication by reducing viral titer by approximately 1. Huang et al. All of the aliphatic diterpenoids with aliphatic side chains — displayed potent activity against HIV-1, with IC 50 values of 0. These results imply that aliphatic side chain substituents are crucial factors for the antiviral activity of the ingenane diterpenoids Huang et al. Five diterpenoids isolated from Euphorbia helioscopia L \[Euphorbiaceae\] were tested for their antiviral potential against HSV-1, and among them, compound showed moderate activity against HSV-1 with an IC 50 value of 6. The SAR study of the diterpenes revealed that seco-jatrophane skeleton exhibited more potent antiviral activity against HSV-1 than the jatrophane skeleton Mai et al. Three new and nine known ent- kauranoid diterpenoids isolated from Rabdosia japonica Burm. Ban et al. Among the compounds, and exhibited potent antiviral activity against CBV3 infection with IC 50 values of 0. Compound also showed antiviral activity against the EV71 virus, indicating broad-spectrum antiviral activity of the compound Ban et al. Tan et al. The labdane diterpenoids showed more potent antiviral activity than the pimarane ones. Compound showed broad-spectrum antiviral activity against the tested viruses with IC 50 values of 1. The mechanism of broad-spectrum antiviral activity of can be suggested as its capability of blocking viral RNA replication either through direct or indirect means. It could act on the cellular pathways broadly utilized by the enveloped viruses or could activate innate antiviral responses. Alternatively, 79 can act in different mechanisms as it showed narrow-spectrum antiviral activity Tan et al. One new and nine previously reported labdane diterpenoids isolated from Globba sherwoodiana W. Kress and V. This suggests that the lactone ring and carbonyl group could be important functionalities to increase the anti-Vpr activity of labdane diterpenoids Prema et al. Eight labdane-type diterpenoids isolated from Forsythia suspensa Thunb. All of the isolated labdane diterpenoids — ; Figure 9 displayed moderate antiviral activities against H1N1 virus and RSV, with IC 50 values ranging from Structures of ingenane, jatrophane, kauranoid, labdane, oxazole-containing, spongian, tigilane, and miscellaneous diterpenoids with significant antiviral activity. Zhang et al. The time-of-addition TOA assay and long terminal repeat LTR luciferase reporter assay results suggested that compound might inhibit the wild-type HIV-1 transcription, leading to the blocking of HIV-1 replication at the submicromolar level Zhang et al. Ahmadi et al. Among the diterpenoids, and showed significant antiviral activity with IC 50 values of Abreu et al. Pax \[Euphorbiaceae\]. The compounds were significant inhibitors of Zika virus replication. Compound significantly reduced Zika virus replication. Compared to the titer of 6. It was also reported that the presence of a hydroxyl group in the C 20 position was necessary for activity while the presence of a formyl group seemed to decrease activity. These compounds are definitely potential antiviral candidates against the Zika virus and require further testing in animal models Abreu et al. Esposito et al. Among the isolated compounds, was the most active one, with an EC 50 value of 4. Li et al. Several classes of natural diterpenoids have been recognized for their potential antifungal activity against a number of human and plant pathogens Table 3. TABLE 3. Different classes of diterpenoids isolated from natural sources with significant antifungal activity. A novel abietane diterpenoid Figure 10 was isolated from the hulls of rice Oryza sativa L \[Poaceae\]. The compound was tested for antifungal activity against four crop pathogenic fungal strains. It exhibited potent antifungal properties with MIC values ranging from Structures of abietane, cembrane, diterpenoid alkaloids, epi-neoverrucosane, indole, isopimarane, kaurene, labdane, phenolic, pimarane, tetraquinane, and miscellaneous diterpenoids with significant antifungal activity. Tsujimaru et al. Don \[Cupressaceae\] sugi and investigated their antifungal activities against two fungal strains Trichophyton mentagrophytes and Trichophyton rubrum. Compounds and 16 showed the maximum fungal growth inhibition against the selected fungal strains ranging from A new abietane diterpenoid was isolated from Isodon interruptus C. Wu and H. Hara \[Lamiaceae\], and its potential against the growth inhibition of C. Tani et al. Among all the compounds, and exhibited significant antifungal activity against L. Compounds 25 and 26 extracted from the roots of B. Benth \[Lamiaceae\] exhibited strong antifungal property. Copaiba-type diterpenoids 27 and 28 Figure 2 demonstrated strong antifungal properties. Compound 27 was active against T. Compound 28 was active against T. Alhilal et al. Six new dolabellane-type diterpenoids were isolated from a fungal strain Stachybotrys chartarum and evaluated for their antifungal activity against C. Among them, compound 31 significantly inhibited the growth of C. Transmission electron microscopy TEM was employed for visualizing the morphological changes of C. At a higher dose, i. Kamada et al. The compounds were tested against six fungal strains isolated from the Bornean ocean. The newly identified compound showed the strongest activity, with MIC values of Among all the indole diterpenoids, only showed a significant inhibitory effect against C. It also showed significant binding affinity in the ligand-binding site of the PDF enzyme, implying a probable mechanism of its antifungal activity Zhao et al. Three prenylated indole diterpenoids from a mine soil-derived fungus Tolypocladium sp. XL were investigated against seven agricultural pathological fungal strains, Sclerotinia sclerotiorum , Helminthosporium maydis , Verticillium dahliae Kleb, Phytophthora parasitica , Gibberella saubinetii , Botrytis cinerea Pers. Compound displayed moderate antifungal activity against S. Seven indole diterpenes were isolated from the fungus P. Han et al. Potent antifungal activity was observed against C. The diterpenoids were tested for antimicrobial activity against 11 human and aqua-pathogenic bacterial strains and also for antifungal activity against seven plant pathogenic fungi. Only exhibited antifungal activity against four fungal species— P. A kaurene-type diterpenoid was isolated from the hulls of rice O. Two labdane diterpenoids, including the novel 7, E -labdadien,dioic-acidmethyl ester , were isolated from the resinous exudate of Haplopappus velutinus J. Remy \[Asteraceae\], an herbaceous shrub. The compounds were tested against the phytopathogen B. Two diterpenoids 71 and 72 isolated by Mothana et al. Ramirez et al. Epling \[Lamiaceae\], which was testes against M. Only compound showed significant antifungal activity against M. Among the pimarane diterpenoids isolated from Eutypella sp. D-1, 81 showed broad-spectrum antifungal activity against Candida parapsilosis , C. Four pimaranes, including two new ones, were isolated from the hulls of rice O. The diterpenes — ; Figure 10 were tested for antifungal activity against four crop pathogenic fungal species where all of them exhibited potent antifungal properties with MIC values ranging from 6. The result indicates that rice can produce secondary metabolites that are capable of preventing fungal growth and can also be used as potential natural leads for development of future fungicidal drugs Gu et al. The pimarane diterpenoids isolated from C. Don \[Cupressaceae\] sugi were tested against two fungal strains, namely, T. Two diterpenoids, crinipellin A and crinipellin I , were isolated from the culture filtrate of the basidiomycete fungus Crinipellis rhizomaticola. The compounds were tested for antifungal activity against seven plant pathogenic fungi and antibacterial activity against nine plant pathogenic bacteria. Compound also exclusively inhibited the growth of leaf blight-causing bacteria Acidovorax avenae ssp. Compounds 92 and 93 were tested against Trichophyton longifusus clinical isolate , C. Compound 94 showed moderate antifungal activity against T. Compounds 97 — 99 were tested against 10 fungal strains, namely, B. Among the diterpenes, 97 and 99 showed moderate antifungal activity against R. Among the seven diterpenoids isolated from A. A number of diterpenoids from natural sources have been found to be active against several parasites responsible for causing different parasitic diseases like malaria, leishmaniasis, giardiasis, Chagas disease, and trichomoniasis Table 4. TABLE 4. Different classes of diterpenoids isolated from natural sources with significant antiprotozoal activity. Ten diterpenoids, including abietanes, labdanes, and halimane, were isolated from Plectranthus spp. The compounds were tested for their antiparasitic effect against Trypanosoma cruzi , a protozoal parasite responsible for the fatal Chagas disease, which affects the heart and gastrointestinal system. Several of the isolated abietanes completely inhibited the growth of epimastigote forms of T. Structures of abietane, beyerene, cassane, kaurene, labdane, pimarane, and miscellaneous diterpenoids with significant antiprotozoal activity. Four abietane diterpenoids were isolated from Salvia austriaca Jacq \[Lamiaceae\], and their antiprotozoal activity was tested against several parasites including Trypanosoma brucei rhodesiense , T. Among them, compound was found to be the most active antiprotozoal agent against T. Farimani et al. Among all the diterpenoids, compound displayed antimalarial activity with an IC 50 value of 0. Seventeen diterpenoids isolated from Perovskia abrotanoides Kar \[Lamiaceae\] were evaluated against T. Among the diterpenoids, , , and 16 showed antiprotozoal activity against the tested microorganisms. Compound with an IC 50 of 0. None of the compounds showed any selective activity against T. Four new diterpenoids including three new abietanes and one new icetexane were reported from the aerial parts of Salvia clinopodioides Kunth \[Lamiaceae\] and tested against Entamoeba histolytica and Giardia lamblia. Compounds and showed better effects in the inhibition of lipid peroxidation with IC 50 values of 5. Eight abietane diterpenoids were isolated from the roots of Zhumeria majdae Rech. Among all diterpenoids, showed significant inhibition against P. The presence of a keto group at C-7 and OH group at C and C could be a crucial factor of the reported antiprotozoal activity of Zadali et al. Two natural ent- beyerene-type diterpenoids isolated from Baccharis tola Phil \[Compositae\] were tested for their antileishmanial potential against Leishmania braziliensis intracellular amastigotes, and was found to be most potent against the pathogen with an EC 50 of 4. Twelve new and three known furanocassane-type diterpenoids were isolated from the seeds of Bowdichia virgilioides Kunth \[Fabaceae\] and investigated for their antiplasmodic activity against P. Among the diterpenoids, and exhibited weak antimalarial activity with IC 50 values of Erharuyi et al. Sw \[Fabaceae\], and their leishmanicidal potential was evaluated against the promastigotes of Leishmania major. Compounds — showed significant activity against promastigotes of L. Compounds and were also found to exhibit moderate antimalarial activity by inhibiting two strains of P. Two diterpenoids including one new cassane-type diterpenoid were isolated from Caesalpinia sappan L \[Fabaceae\] and tested for their antimalarial activity against P. Compound exhibited relatively good antiplasmodial activity in vitro with an IC 50 value of 3. It indicates that the presence of the N-bridge in cassane-type diterpenoids can be responsible for increasing activity against the chloroquine-resistant K1 strain of P. Three new kaurane diterpenoids were isolated from Baccharis retusa DC \[Asteraceae\] and their antitrypanosomal activity was evaluated against T. Among them, compound showed enhanced activity against trypomastigotes of T. The results implied an expressive interference with the plasma membrane permeability in the parasites which were treated with the diterpenes Ueno et al. Four new and five known labdane diterpenoids were isolated from Psiadia arguta Pers. Voigt \[Asteraceae\], and their antimalarial property was evaluated against P. The known labdanes — showed significant antimalarial activity with IC 50 values of A lactone or an endoperoxide group in their structure might lead to their interference with parasite development Mahadeo et al. Seven natural pimaranes were isolated from Aeollanthus rydingianus van Jaarsv. The compounds were tested for their antiparasitic effect against T. Du et al. Greene \[Asteraceae\] and investigated against P. Among the diterpenes, showed moderate antiplasmodial activity, with an IC 50 value of 7. Three new and five known diterpenoids were isolated from Vitex rotundifolia L. Among the isolated diterpenoids, — showed significant antimalarial activity with IC 50 values of 1. The natural diterpenoids could be potential compounds to confront the continuous outbreaks of new viruses and viral strains. In the current review work, a total of natural diterpenoids of different chemical classes have been summarized along with their sources plants, fungi, marine species, etc. Among them, there have been some promising molecules like andrographolide, koninginol A and B, and psathyrins A and B with significant MIC, which could be further investigated for discovering new antimicrobial agents. For example, some daphane diterpenoids, wikstroechuins A—C — , were found to exhibit potent anti-HIV activity with very low EC 50 values Table 2. Abietane- and cassane-type diterpenoids were found to be most active against parasites causing trypanosomal disease and malaria Table 4. Several diterpenoids were found to have a synergistic antibacterial action which could improve the activity of available antibiotics. For example, ent -beyeren O -oxalate has been patented as an adjuvant therapy with the available antibiotic colistin because of its ability to block the ArnT enzyme responsible for causing resistance. Moreover, in several cases, a combination of diterpenoids with standard antibiotics and combination of different diterpenoids reduced the MIC values for the tested strains. Therefore, the role of diterpenoids as synergists and adjuvant therapies should be explored extensively to potentiate the available antibiotics. In numerous in vitro studies in recent years, it has been demonstrated that the diterpenoid compounds are capable of inhibiting the growth of different strains of resistant bacteria emerging from irrational use of antibiotics. However, clinical trials of diterpenoids as antimicrobial agents are yet to be explored because of lack of sufficient in vivo data, unclear mode of action, lack of selectivity, etc. Most of the diterpenoids consist of diverse lipophilic compounds, which poses a new challenge in developing drug delivery systems to improve bioavailability of the compounds. Another challenge in the path of new drug development from natural diterpenoids is toxicity and lack of selectivity. Most of the diterpenoids in their pure form have the capacity to be absorbed in the epithelial cells before reaching the site of infection because of their highly lipophilic nature. So an exquisite delivery system is necessary for in vivo studies, leading to clinical trials of these compounds which will help to identify the mode of action of these compounds. Several in silico studies have been conducted targeting some bacterial proteins and enzymes like PDF, GlmU, and NADH-2 to evaluate the binding pattern of diterpenoids in the active sites of these proteins, which have shed some light on their mechanisms of actions. More extensive research on their SAR is required by synthesizing new synthetic and semisynthetic derivatives from the natural diterpenoids to develop new antimicrobial agents to combat the upcoming pre-antibiotic era. AMR has created a global challenge for effective treatment of infectious diseases. Although most of the commonly used antimicrobial drugs have gradually become ineffective or less effective, inclusion of new drugs to overcome the situation is not satisfactory. Natural sources, especially plants and microorganisms, contain several secondary metabolites that have potential antimicrobial properties. In this review, we have concentrated on searching for natural diterpenoids possessing potential antimicrobial properties. This review summarizes prospective diterpenoids for the last 5 years with their promising antimicrobial properties such as antibacterial, antiviral, antifungal, and antiprotozoal properties. Additionally, SAR data have been presented in different sections where the SAR studies were accomplished by the authors. This review will enable the potential researchers identifying credible lead compounds for antimicrobial drug development to combat AMR. Chemical synthesis of the potential leads along with their derivatization followed by further SAR studies might be useful for effective drug discovery for infectious diseases. All authors reviewed and approved the final manuscript. The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest. All claims expressed in this article are solely those of the authors and do not necessarily represent those of their affiliated organizations, or those of the publisher, the editors and the reviewers. Any product that may be evaluated in this article, or claim that may be made by its manufacturer, is not guaranteed or endorsed by the publisher. Abdissa, N. Antimicrobial Abietane-type Diterpenoids from Plectranthus Punctatus. Molecules 22, Abreu, L. Ahmadi, P. Spongian Diterpenes from the Sponge Hyattella Aff. Tokyo 65, — Antiparasitic Activity of Diterpenoids against Trypanosoma Cruzi. Planta Med. Alhilal, M. Eriocarpum Boiss. Molecules 26, Ban, N. Banerjee, A. The Chemistry of Bioactive Diterpenes. Coc 12, — Banerjee, M. Folia Microbiol. Praha 62, — Bernabeu, E. Bisio, A. Antibacterial and Hypoglycemic Diterpenoids from Salvia Chamaedryoides. Boonsombat, J. Phytochemistry , 36— Bozov, P. Diterpenoid Constituents of Teucrium Scordium L. Scordioides Shreb. Maire Et Petitmengin. Bustos-Brito, C. Cai, C. Chassagne, F. Chawengrum, P. Phytochemistry Lett. Chen, B. Chen, H. Fitoterapia , Chen, S. Chen, X. Phytochemistry , 1—9. Ciorba, V. Inhibit Mycobacterium tuberculosis Growth. Tokyo 73, — Ding, Y. Du, Y. Antiplasmodial Diterpenoids and a Benzotropolone from Petradoria Pumila. Eksi, G. Editors S. Nabavi, M. Saeedi, S. Nabavi, and A. Amsterdam: Elsevier , — Endo, Y. Erharuyi, O. Esposito, M. Farimani, M. Fozia, A. Pharmaceutics 13, Gu, C. Guo, X. Han, J. Molecules 23, Han, X. Hayashi, K. Hu, X. Drugs 15, Huang, Y. Isca, V. Molecules 25, Jiang, M. Andrographis Paniculata Burm. Kamada, T. Bioprospect 10, 51— Khameneh, B. Review on Plant Antimicrobials: a Mechanistic Viewpoint. Kim, Y. Kishore, V. Koehn, F. Drug Discov. Lambrechts, I. Langat, M. Lhullier, C. Drugs 17, Li, D. Phytochemistry , Li, H. Asian Nat. Li, J. Li, Q. Li, S. Phytochemistry , 17— Li, W. Li, X. RSC Adv. Liang, J. And its Antimicrobial Activity. Liang, X. Wang with Their Antitumor and Antibacterial Activities. Liang, Z. Lin, L. Liu, H. Fitoterapia , 94— Liu, Y. Psathyrins: Antibacterial Diterpenoids from Psathyrella Candolleana. Mafu, S. Mahadeo, K. Antiplasmodial Diterpenoids from Psiadia Arguta. Mai, Z. Mantaj, J. Miethke, M. Mothana, R. Saudi Pharm. Murillo, J. Nabavi, S. Ndjoubi, K. Plants 10, Newman, D. Natural Products as Sources of New Drugs from to Nie, Y. Nzogong, R. Obaidullah, M. Drug Des. Google Scholar. Ogawa, K. Ogbeide, O. Tjnpr 2, — Review on Antimicrobial Resistance. Porras, G. Prema, , Kodama, T. Qiao, Y. Tetrahedron 74, — Quaglio, D. ACS Med. Rahman, S. Tetrahedron 57, — Pharmaceuticals Basel 11, Remy, S. Structurally Diverse Diterpenoids from Sandwithia Guyanensis. Rodrigues, T. Counting on Natural Products for Drug Design. Satari, M. Valensi 5, — Sichaem, J. Singh, B. Tabefam, M. Antiprotozoal Diterpenes from Perovskia Abrotanoides. Tan, Y. Tanaka, S. Tanaka, T. Tani, K. With Antifungal Activity against Lagenidium Thermophilum. Tsujimura, M. Wood Sci. Ueno, A. Fitoterapia , 55— Wang, B. Wang, C. Wang, X. Wu, H. Wu, J. Xu, L. And Their Antimicrobial Activities. Xu, M. Yan, S. Phytochemistry , 40— Yang, B. Yu, H. New Diterpenoids from the marine Sponge Dactylospongia Elegans. Tetrahedron 73, — Drugs 16, Yu, J. Yu, Z. Zadali, R. Daru 28, — Zhang, D. Zhao, B. Zhao, J. As Natural Antimicrobial Agents. Phytochemistry , 21— Zhao, L. Zhu, N. Zi, J. To Gibberellins and beyond! Surveying the Evolution of Di Terpenoid Metabolism. Plant Biol. Keywords: diterpenes, diterpenoids, antimicrobial resistance, antibacterial activity, antifungal activity, antiviral activity, antiprotozoal activity. The use, distribution or reproduction in other forums is permitted, provided the original author s and the copyright owner s are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. Abdur Rahman, smarahman du. Mukhlesur Rahman, m. Disclaimer: All claims expressed in this article are solely those of the authors and do not necessarily represent those of their affiliated organizations, or those of the publisher, the editors and the reviewers. Any product that may be evaluated in this article or claim that may be made by its manufacturer is not guaranteed or endorsed by the publisher. Top bar navigation. About us About us. Sections Sections. About journal About journal. Article types Author guidelines Editor guidelines Publishing fees Submission checklist Contact editorial office.

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