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The conversion of CO2 into carbon-neutral fuels such as methane (CH4) through selective photoreduction is highly sought after yet remains challenging due to the slow multistep proton-electron transfer processes and the formation of various C1 intermediates. This research highlights the cooperative interaction between Fe3+ and Cu2+ ions transitioning to Fe2+ and Cu+ ions, enhancing the photocatalytic conversion of CO2 to methane. We introduce an S-scheme heterojunction photocatalyst, CuFe2O4/ZnIn2S4, which demonstrates significant efficiency in CO2 methanation under light irradiation. The CuFe2O4/ZnIn2S4 heterojunction forms an internal electric field that aids in the mobility and separation of exciton carriers under a wide solar spectrum for exceptional photocatalytic performance. Remarkably, the optimal CuFe2O4/ZnIn2S4 heterojunction system achieved an approximately 68-time increase in CO2 conversion compared with ZnIn2S4 and CuFe2O4 nanoparticles using only pure water, with nearly complete CO selectivity and yields of CH4 and CO reaching 172.5 and 202.4 µmol g-1 h-1, respectively, via a 2-electron oxygen reduction reaction (ORR) process. The optimally designed CuFe2O4/ZnIn2S4 heterojunctional system achieved approximately 96% conversion of BA and 98.5% selectivity toward benzaldehyde (BAD). Additionally, this photocatalytic system demonstrated excellent cyclic stability and practical applicability. The photogenerated electrons in the CuFe2O4 conduction band enhance the reduction of Fe3+/Cu2+ to Fe2+/Cu+, creating a microenvironment conducive to CO2 reduction to CO and CH4. Simultaneously, the appearance of holes in the ZnIn2S4 valence band facilitates water oxidation to O2. The synergistic function within the CuFe2O4/ZnIn2S4 heterojunction plays a pivotal role in facilitating charge transfer, accelerating water oxidation, and thereby enhancing CO2 reduction kinetics. This study offers valuable insights and a strategic framework for designing efficient S-scheme heterojunctions aimed at achieving carbon neutrality through solar fuel production.
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Six compounds were isolated from lettuce latex. They were identified as 2,5-dihydroxybenzaldehyde (1), 3ß-hydroxy-4,15-dehydrograndolide (2), annuolide D (3), lactucin (4), lactucopicrin (5), and hanphyllin (6). Bioassays showed that the inhibition rate of compound 1 (2,5-dihydroxybenzaldehyde) and 6 (hanphyllin, a sesquiterpene lactone) on the weight gain of S. litura were 52.4% and 10%, respectively, at the concentration of 100 µg/g. RNA-seq analyses showed that larval exposure to compound 1 down-regulated the genes associated with heterobiotic metabolism including drug metabolism-cytochrome P450, metabolism of xenobiotics by cytochrome P450, retinol metabolism, glutathione metabolism, and drug metabolism-other enzymes (mainly uridine diphosphate glucuronyltransferase, UGTs). RT-qPCR further confirmed that 33 genes in the family of carboxylesterase (CarE), P450s and UGTs were down-regulated by compound 1. The activities of CarE, P450s and UGTs in the larvae fed on diets containing compound 1 were significantly lower than those fed on control diets, with the inhibition for the three detoxification enzymes being 55.4%, 53.9%, and 52.9%. These findings suggest that secondary metabolites including 2,5-dihydroxybenzaldehyde in the latex play a key role in protecting lettuce from insect herbivory.
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The aim of this study was to investigate the chemical composition and antioxidant capacity of various polar fractions obtained from Dendrobium fimbriatum Hook (DH). First, a 90% ethanol-aqueous extract of DH (CF) was subjected to sequential fractionation using different organic solvents, resulting in the isolation of a methylene chloride fraction (DF), an ethyl acetate fraction (EF), an n-butanol fraction (BF), and a remaining water fraction (WF) after condensation. Additionally, the CF was also subjected to column chromatography via a D101 macroreticular resin column, eluted with ethanol-aqueous solution to yield six fractions (0%, 20%, 40%, 60%, 80%, and 100%). UPLC-Q-Exactive Orbitrap-MS/MS analysis identified a total of 47 chemical compounds from these polar fractions, including fatty acids, amino acids, phenolic acids, flavonoids, organic heterocyclic molecules, and aromatic compounds. Moreover, DF, EF, and the 60%, 80%, and 100% ethanol-aqueous fractions had higher total phenol content (TPC) and total flavonoid content (TFC) values and greater 2,2'-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS-) and 1,1-diphenyl-2-picrylhydrazyl (DPPH)-scavenging abilities. In H2O2-induced HepG2 cells, the aforementioned fractions could increase the activities of antioxidative enzymes NAD(P)H: quinone oxidoreductase 1 (NQO1), superoxide dismutase (SOD), heme oxygenase-1 (HO-1) and catalase (CAT), stimulate glutathione (GSH) synthesis by increasing the activities of glutamic acid cysteine ligase (GCL) and glutathione synthetase (GS), regulate GSH metabolism by increasing glutathione peroxidase (GSH-Px) and glutathione reductase (GR) activities, and reduce levels of reactive oxygen species (ROS) and malondialdehyde (MDA). Furthermore, the antioxidative stress effect of the DH fractions was found to be positively correlated with the activation of nuclear factor-erythroid 2-related factor 2 (Nrf2) protein and the presence of antioxidative chemical constituents. In conclusion, this study highlights the efficacy of both liquid-liquid extraction and macroporous resin purification techniques in the enrichment of bioactive compounds from natural food resources. The comprehensive analysis of chemical constituents and antioxidant effects of different polar fractions from Dendrobium fimbriatum Hook contributes to the understanding of its potential application in functional foods and nutraceuticals.
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Antioxidantes , Dendrobium , Antioxidantes/farmacología , Peróxido de Hidrógeno , Espectrometría de Masas en Tándem , GlutatiónRESUMEN
Melodinus cochinchinensis (Lour.) Merr. is a Yunnan endemic folk medicine. Our previous study showed that 11-methoxytabersonine (11-MT) isolated from M. cochinchinensis has strong cytotoxicity on human T-ALL cells, but its molecular mechanism has not been studied. In current study, the cytotoxicity and possible mechanism of 11-MT on T-cell acute lymphoblastic leukemia was explored using network pharmacology and molecular biology techniques. 11-MT significantly inhibited the cell proliferations on different four human T-ALL cells (MOLT-4, Jurkat, CCRF-CEM, and CEM/C1 cells). 11-MT triggered ROS accumulation, calcium concentration and cell apoptosis, and decreased the mitochondrial membrane potential (MMP) in human T-ALL cells, especially MOLT-4 cells. Western blot analysis showed that it can induce MOLT-4 cell apoptosis by up-regulating PI3K/Akt signaling pathway. Therefore, 11-MT induces human T-ALL cells apoptosis via up-regulation of ROS-mediated mitochondrial dysfunction and down-regulation of PI3K/Akt/mTOR signaling pathway.
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Leucemia-Linfoma Linfoblástico de Células T Precursoras , Proteínas Proto-Oncogénicas c-akt , Apoptosis , Línea Celular Tumoral , China , Humanos , Alcaloides Indólicos , Mitocondrias/metabolismo , Monoterpenos , Farmacología en Red , Fosfatidilinositol 3-Quinasas/metabolismo , Proteínas Proto-Oncogénicas c-akt/metabolismo , Especies Reactivas de Oxígeno , Transducción de SeñalRESUMEN
(±)-Involucrasin C (1), a pair of new 2,3-dihydro-1H-indene enantiomers, along with an enantiomeric analog (2), were isolated from Shuteria involucrata. Their structures were established by the basis of comprehensive spectroscopic data analysis and X-ray crystallographic diffraction. Both 1 and 2 significantly inhibited the secretion of pro-inflammatory cytokines IL-6, TNF-α, and IL-1ß, suggesting that these two natural 2,3-dihydro-1H-indene derivatives may be active components of S.â involucrata and may block inflammation in the initial stage.
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Indenos , Factor de Necrosis Tumoral alfa , Antiinflamatorios/química , Antiinflamatorios/farmacología , China , Citocinas , Indenos/química , Interleucina-6RESUMEN
(±)-Involucrasins A (1) and B (2), two pairs of flavanone enantiomers were isolated from Shuteria involucrata. Structurally, both 1 and 2 are rare representatives of 5-dehydroxy/5-demethoxy 2',3',4'-trisubstituted flavanones. Their structures were elucidated on the basis of comprehensive spectroscopic data analysis and comparison with the literature data. Involucrasin B (2) exhibited moderate anti-proliferative activity against Caco-2, MCF-7, MDA-MB-468, and HCT116 cell lines with IC50 values ranging from 7.9-22.7 µM. Involucrasin A (1) exhibited weak inhibitory activity against Caco-2 and MCF-7 cell lines with IC50 values of 25.8 and 26.5 µM, respectively.
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Flavanonas , Neoplasias , Células CACO-2 , Línea Celular Tumoral , Proliferación Celular , Flavanonas/química , Flavanonas/farmacología , Humanos , Concentración 50 Inhibidora , Estructura MolecularRESUMEN
This study comparatively investigated the influence of changes in pyrolysis temperature on the physicochemical, structural, and adsorptive properties of biochars derived from a green waste (Cynodon dactylon L.). For this purpose, the biophysically dried green wastes were pyrolyzed at 400 °C, 600 °C, and 800 °C under the same pyrolysis conditions. The results revealed that the physicochemical and structural properties were varied, depending upon the pyrolysis temperatures. With the increase of pyrolysis temperature, the surface functional groups were escaped, the structure became more porous (pore volume of 0.089 ± 0.001), the metal oxides were remained consistent, and the biochars turned into more alkaline nature (pH of 11.9 ± 0.2). Furthermore, as referring to the adsorptive performance for potentially toxic elements, with experimental adsorption capacity of up to 33.7 mg g-1 and removal rate up to 96% for a multi-metals containing solution, the biochars pyrolyzed at high temperature (800 °C) was significantly (p < 0.05) higher than those pyrolyzed at low temperature (400 °C). According to the physicochemical and structural properties, and the adsorptive performances of the biochars, the optimal pyrolysis temperature was herein recommended to be 800 °C.
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Carbón Orgánico , Pirólisis , Adsorción , Carbón Orgánico/química , TemperaturaRESUMEN
Traditional Chinese Medicine is generally used as a decoction to guard health. Many active ingredients in the decoction are chemical ingredients that are not usually paid attention to in phytochemical research, such as polysaccharides, etc. Based on research interest in Chinese herbal decoction, crude polysaccharides from G. wilfordii (GCP) were purified to obtain two relatively homogeneous polysaccharides, a neutral polysaccharide (GNP), and an acid polysaccharide (GAP) by various chromatographic separation methods, which were initially characterized by GC-MS, NMR, IR, and methylation analysis. Studies on the hepatoprotective activity of GCP in vivo showed that GCP might be a potential agent for the prevention and treatment of acute liver injury by inhibiting the secretion levels of ALT, AST, IL-6, IL-1ß, TNF-α, and MDA expression levels, increasing SOD, and the GSH-Px activity value. Further, in vitro assays, GNP and GAP, decrease the inflammatory response by inhibiting the secretion of IL-6 and TNF-α, involved in the STAT1/T-bet signaling pathway.
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Geranium , Polisacáridos , Enfermedad Hepática Inducida por Sustancias y Drogas/prevención & control , Geranium/química , Humanos , Interleucina-6/metabolismo , Hígado/metabolismo , Polisacáridos/química , Polisacáridos/farmacología , Factor de Necrosis Tumoral alfa/metabolismoRESUMEN
A general protocol has been developed for the construction of carbon-heteroatom (C-N, C-Cl, C-O, C-S, and C-Se) bonds using the bench stable, earth-abundant, and environmentally benign copper catalyst. Only oxygen is sufficient to regenerate the copper catalyst. Control experiments suggested that the proto-demetalation step is reversible. Depending on the coupling partner, the reaction follows either disproportionation or radical pathways to complete the catalytic cycle. The synthetic utility of the developed protocol has been demonstrated via various functional group transformations.
RESUMEN
A ytterbium triflate-catalyzed diastereoselective [3 + 2] cycloaddition of quinoxalinones with donor-acceptor cyclopropanes and cyclobutanes is described. A series of tetrahydropyrrolo-quinoxalinone derivatives were obtained in high yields (up to 96%) with excellent diastereoselectivities (up to 46:1). Other medicinally important heterocycles like benzoxazinone, isoquinoxalinone, and dibenzoxazepine derivatives were also suitable for the desired annulation reaction. The current method is applicable for the scale-up reaction. Further, the utility of this annulation reaction is demonstrated by the synthesis of densely functionalized proline derivatives.
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Ciclopropanos , Quinoxalinas , Catálisis , Reacción de Cicloadición , Estructura Molecular , EstereoisomerismoRESUMEN
Chemical investigation of the twigs and leaves of Rhodomyrtus tomentosa led to the isolation and structural identification of a novel polymethylated phloroglucinol meroterpenoid (PPM) featuring a 6/6/6/6 tetracyclic system, rhotomentodione F (1), five new polymethylated polycyclic phloroglucinols (PPPs) with a rare bis-furan framework, rhotomentosones A-E (2-6), and one new adduct composed of an acylphloroglucinol and two ß-triketone units, rhotomentosone F (7), as well as five known analogues (8-12). Their structures and absolute configurations were unambiguously determined by comprehensive spectroscopic data and electronic circular dichroism (ECD) calculations. All isolates were evaluated for their anti-inflammatory and acetylcholinesterase (AChE) inhibitory activities. Compound 6 displayed significant AChE inhibitory effect with an IC50 value of 8.68 µM. Further molecular docking studies of 6 revealed that the interactions with AChE residues Ser125, Glu202, and Tyr133 are crucial for AChE inhibitory activity. The current study not only enriches the chemical diversity of phloroglucinols in Myrtaceae species, but also provides potential lead compounds for the further design and development of new AChE inhibitors to treat Alzheimer's disease.
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Acetilcolinesterasa/metabolismo , Antiinflamatorios/farmacología , Inhibidores de la Colinesterasa/farmacología , Myrtaceae/química , Floroglucinol/análogos & derivados , Floroglucinol/farmacología , Animales , Antiinflamatorios/química , Antiinflamatorios/metabolismo , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/metabolismo , Humanos , Ratones , Simulación del Acoplamiento Molecular , Estructura Molecular , Floroglucinol/metabolismo , Hojas de la Planta/química , Unión Proteica , Células RAW 264.7RESUMEN
Phloridzin is an important phytochemical which was first isolated from the bark of apple trees. It is a member of the dihydrochalcones and mainly distributed in the plants of the Malus genus, therefore, the extraction method of phloridzin was similar to those of other phenolic substances. High-speed countercurrent chromatography (HSCCC), resin adsorption technology and preparative high-performance liquid chromatography (HPLC) were used to separate and purify phloridzin. Many studies showed that phloridzin had multiple pharmacological effects, such as antidiabetic, anti-inflammatory, antihyperglycaemic, anticancer and antibacterial activities. Besides, the physiological activities of phloridzin are cardioprotective, neuroprotective, hepatoprotective, immunomodulatory, antiobesity, antioxidant and so on. The present review summarizes the biosynthesis, distribution, extraction and bioavailability of the natural compound phloridzin and discusses its applications in food and medicine.
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Florizina , Animales , Disponibilidad Biológica , Productos Biológicos/aislamiento & purificación , Productos Biológicos/metabolismo , Productos Biológicos/farmacología , Productos Biológicos/uso terapéutico , Chalconas/biosíntesis , Chalconas/aislamiento & purificación , Chalconas/farmacología , Chalconas/uso terapéutico , Fraccionamiento Químico/métodos , Cromatografía Líquida de Alta Presión , Distribución en Contracorriente , Humanos , Malus/química , Florizina/biosíntesis , Florizina/aislamiento & purificación , Florizina/farmacología , Florizina/uso terapéutico , Extractos Vegetales/biosíntesis , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Extractos Vegetales/uso terapéutico , Relación Estructura-ActividadRESUMEN
Anneslea fragrans Wall., commonly known as "Pangpo Tea", is traditionally used as a folk medicine and healthy tea for the treatment of liver and intestine diseases. The aim of this study was to purify the antioxidative and cytoprotective polyphenols from A. fragrans leaves. After fractionation with polar and nonpolar organic solvents, the fractions of aqueous ethanol extract were evaluated for their total phenolic (TPC) and flavonoid contents (TFC) and antioxidant activities (DPPH, ABTS, and FRAP assays). The n-butanol fraction (BF) showed the highest TPC and TFC with the strongest antioxidant activity. The bio-guided chromatography of BF led to the purification of six flavonoids (1-6) and one benzoquinolethanoid (7). The structures of these compounds were determined by NMR and MS techniques. Compound 6 had the strongest antioxidant capacity, which was followed by 5 and 2. The protective effect of the isolated compounds on hydrogen peroxide (H2O2)-induced oxidative stress in HepG2 cells revealed that the compounds 5 and 6 exhibited better protective effects by inhibiting ROS productions, having no significant difference with vitamin C (p > 0.05), whereas 6 showed the best anti-apoptosis activity. The results suggest that A. fragrans could serve as a valuable antioxidant phytochemical source for developing functional food and health nutraceutical products.
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Ericales/química , Estrés Oxidativo/efectos de los fármacos , Fenoles/aislamiento & purificación , Antioxidantes/química , Antioxidantes/farmacología , China , Flavonoides/farmacología , Células Hep G2 , Humanos , Peróxido de Hidrógeno/farmacología , Fenoles/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Hojas de la Planta/química , Polifenoles/farmacologíaRESUMEN
Vaccinium dunalianum Wight, usually processed as a traditional folk tea beverage, is widely distributed in the southwest of China. The present study aimed to investigate the antioxidant, α-glucosidase and pancreatic lipase inhibitory activities of V.dunalianum extract and isolate the bioactive components. In this study, the crude extract (CE) from the buds of V. dunalianum was prepared by the ultrasound-assisted extraction method in 70% methanol and then purified with macroporous resin D101 to obtain the purified extract (PM). Five fractions (Fr. A-E) were further obtained by MPLC column (RP-C18). Bioactivity assays revealed that Fr. B with 40% methanol and Fr. D with 80% methanol had better antioxidant with 0.48 ± 0.03 and 0.62 ± 0.01 nM Trolox equivalent (TE)/mg extract for DPPH, 0.87 ± 0.02 and 1.58 ± 0.02 nM TE/mg extract for FRAP, 14.42 ± 0.41 and 19.25 ± 0.23 nM TE/mg extract for ABTS, and enzyme inhibitory effects with IC50 values of 95.21 ± 2.21 and 74.55 ± 3.85 for α-glucosidase, and 142.53 ± 11.45 and 128.76 ± 13.85 µg/mL for pancreatic lipase. Multivariate analysis indicated that the TPC and TFC were positively related to the antioxidant activities. Further phytochemical purification led to the isolation of ten compounds (1-10). 6-O-Caffeoylarbutin (7) showed significant inhibitory effects on α-glucosidase and pancreatic lipase enzymes with values of 38.38 ± 1.84 and 97.56 ± 7.53 µg/mL, and had the highest antioxidant capacity compared to the other compounds.
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Antioxidantes/aislamiento & purificación , Arbutina/análogos & derivados , Ácidos Cafeicos/aislamiento & purificación , Flavonoides/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Lipasa/química , Vaccinium/química , alfa-Glucosidasas/química , Antioxidantes/química , Arbutina/química , Arbutina/aislamiento & purificación , Benzotiazoles/antagonistas & inhibidores , Benzotiazoles/química , Compuestos de Bifenilo/química , Ácidos Cafeicos/química , Flavonoides/química , Inhibidores de Glicósido Hidrolasas/química , Lipasa/antagonistas & inhibidores , Lipasa/metabolismo , Extracción Líquido-Líquido/métodos , Metanol/química , Picratos/química , Extractos Vegetales/química , Hojas de la Planta/química , Solventes/química , Sonicación , Ácidos Sulfónicos/antagonistas & inhibidores , Ácidos Sulfónicos/química , alfa-Glucosidasas/metabolismoRESUMEN
Four new aromatic polyketides (1-4) were isolated from Penicillium sp. RO-11, obtained from the sediment of a hydrothermal spring in the southwestern region of Saudi Arabia. The new compounds are penipyranicins A-C (1-3), characterized by a 4-methyl-4H-pyran moiety, a structural motif unprecedented among fungal polyketides, and the naphthopyrone derivative isopyrenulin (4). The structures of the new compounds were elucidated on the basis of data from mass spectrometry, 1D and 2D NMR analysis, and comparison between experimental and time-dependent density functional theory-calculated electronic circular dichroism spectra. A plausible biosynthetic pathway connecting penipyranicins and isopyrenulin is proposed. The isolated compounds were active against Gram-positive and Gram-negative bacteria.
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Antibacterianos/aislamiento & purificación , Penicillium/aislamiento & purificación , Policétidos/aislamiento & purificación , Antibacterianos/química , Antibacterianos/farmacología , Fermentación , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Estructura Molecular , Penicillium/química , Policétidos/química , Policétidos/farmacología , Análisis Espectral/métodosRESUMEN
Two new sesquiterpenoids belonging to the guaiane, 4α,9α,10α-trihydroxyguaia-11(13)en-12,6α-olide (1), and germacrane, 9ß-hydroxyparthenolide-9-O-ß-D-glucopyranoside (2), classes have been isolated from the leaves of the Saudi medicinal plant Anvillea garcinii along with seven known compounds (3-9). The structures of the new metabolites were elucidated by spectroscopic analysis, including one-dimensional (1D) and two-dimensional (2D) Nuclear Magnetic Resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESIMS). The antimicrobial properties of 1-9 were screened against seven different pathogenic microbes, and compounds 1-3 showed a potent antifungal activity.
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Antibacterianos/química , Antibacterianos/farmacología , Antifúngicos/química , Antifúngicos/farmacología , Asteraceae/química , Componentes Aéreos de las Plantas/química , Sesquiterpenos/química , Sesquiterpenos/farmacología , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Plantas MedicinalesRESUMEN
A facile and efficient Cu-mediated protocol for the cross-dehydrogenative coupling of indoline with sulfonamides, carboxamides, and anilines is reported. The reaction takes place through Cu-mediated C7-H activation via a 6-membered metallacycle to afford the amide and amine derivatives in good yields with a wide range of functional group tolerance. The importance of the protocol has been demonstrated by synthesizing the antiproliferative agent, ER-67836.
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Unlike reported bisindoles linked by single bond directly, alstoniasidines A (1) and B (2), from Alstonia scholaris featuring unprecedented skeleton with two indole moieties bridged by a sugar, represented a novel bisindole type having strictosamide-glucopyranose-picraline scaffold. Both compounds exhibited selective cytotoxicity against human glioma stem cells (GSCs) and induced caspase-3 dependent extrinsic apoptosis by increasing the expression of interleukin 1 (IL-1), tumor necrosis factor (TNF-α), and the cleaved caspase-3, while damaged the unlimited proliferation and self-renewal capacity of GSCs. This finding might provide new type of leads for the selective killing of human glioma stem cells.
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Alstonia/química , Antineoplásicos/farmacología , Glioma/tratamiento farmacológico , Indoles/farmacología , Células Madre Neoplásicas/efectos de los fármacos , Azúcares/química , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Glioma/patología , Humanos , Indoles/química , Indoles/aislamiento & purificación , Estructura Molecular , Hojas de la Planta/química , Relación Estructura-Actividad , Células Tumorales CultivadasRESUMEN
Ten new formyl-phloroglucinol-terpene meroterpenoids, eucalypglobulusals A-J (1-10), and ten known analogues were isolated from Eucalyptus globulus fruits. The structures of 1-10 were determined by spectroscopic analysis, while their absolute configurations were established using calculated and experimental electronic circular dichroism (ECD) spectra. Eucalypglobulusal A was assigned as a new formyl-phloroglucinol-terpene meroterpenoid with a rearranged sesquiterpene skeleton, and an aldol condensation between C-3 and C-5 of the germacrene C moiety was proposed to be a key step in its putative biosynthetic pathway. Eucalypglobulusal F exhibited cytotoxicity against the human acute lymphoblastic cell line (CCRF-CEM) with an IC50 value of 3.3 µM, while eucalypglobulusal A, eucarobustol C, macrocarpal A, macrocarpal B, and macrocarpal D exhibited DNA topoisomerase I (Top1) inhibition. The compounds eucalypglobulusal A and macrocarpal A act as Top1 catalytic inhibitors and delay Top1 poison-mediated DNA double-strand damage.