Croton stipulaceus Kunth, a native Mexican medicinal plant with antioxidant and anti-inflammatory activities / Croton stipulaceus Kunth, planta medicinal mexicana con actividad antioxidante y antiinflamatoria

Leaves of Croton stipulaceuswere extracted (EHex, ECHCl3and EEtOH extracts) to assesstheir antioxidant potential, anti-inflammatory activity in murine models and acute toxicity. EEtOH showed the highest effect in DPPH (37.80% inhibition), FRAP (1065.00 ± 55.30 µmolFe2+) and total polyphenols (231.24 ± 9.05 meq AG/gM). EHex was the most active, ~ 50% inhibition of TPA-induced ear edema; while EEtOH (dose of 2 mg/ear) showed the highest inhibition in the chronic model (97% inhibition), and inhibited MPO activity (48%). In carrageenan-induced edema, ECHCl3(dose 500 mg/kg) was the most active. None of the extracts showed acute toxicity (LD50) at 2 g/kg (p.o.). This work is the first report that supports the traditional use of C. stipulaceusas an anti-inflammatory.

De las hojas de Croton stipulaceusse obtuvieron diferentes extractos (EHex, ECHCl3y EEtOH) evaluando el potencial antioxidante y la actividad antiinflamatoria en modelos murinos y la toxicidad aguda. El EEtOH mostró mayor efecto en DPPH (37.80% inhibición), FRAP (1065.00 ± 55.30 µmolFe2+) y polifenolestotales (231.24 ± 9.05 meq AG/gM). El EHex fue el más activo, cercano al 50% de inhibición del edema auricular inducido con TPA; mientras que el EEtOH (dosis de 2 mg/oreja) mostró la mayor inhibición en el modelo crónico (97% inhibición), e inhibió la actividad de la MPO (48%). En el edema inducido con carragenina, el ECHCl3(dosis 500 mg/kg) fue el más activo. Ninguno de los extractos mostró una toxicidad aguda (DL50) mayor a 2 g/kg (p.o). Este trabajo es el primer reporte que sustenta el uso tradicional de C. stipulaceuscomo antiinflamatorio.

Cytotoxic, acute oral toxicity, genotoxic and mutagenic assessment of the essential oil from fresh leaves of Croton argyrophyllus (Kunth.).

ETHNOPHARMACOLOGICAL RELEVANCE: Croton argyrophyllus Kunth., commonly known as "marmeleiro" or "cassetinga," is widely distributed in the Brazilian Northeast region. Its leaves and flowers are used in traditional medicine as tranquilizers to treat flu and headaches. AIM OF THE STUDY: This study was conducted to determine the chemical composition and toxicological safety of essential oil from C. argyrophyllus leaves using in vitro and in vivo models. MATERIALS AND METHODS: The chemical composition of the essential oil was determined using a gas chromatograph coupled to a mass spectrometer. Cytotoxicity was tested in the HeLa, HT-29, and MCF-7 cell lines derived from human cells (Homo sapiens) and Vero cell lines derived from monkeys (Cercopithecus aethiops) using the MTT method. Acute toxicity, genotoxicity. Mutagenicity tests were performed in Swiss mice (Mus musculus), which were administered essential oil orally in a single dose of 2000 mg/kg by gavage. RESULTS: The main components of the essential oil were p-mentha-2-en-1-ol, α-terpineol, ß-caryophyllene, and ß-elemene. The essential oil exhibited more than 90% cytotoxicity in all cell lines tested. No deaths or behavioral, hematological, or biochemical changes were observed in mice, revealing no acute toxicity. In genotoxic and mutagenic analyses, there was no increase in micronuclei in polychromatic erythrocytes or in the damage and index in the comet assay. CONCLUSIONS: The essential oil was cytotoxic towards the tested cell lines but did not exert toxic effects or promote DNA damage when administered orally at a single dose of 2000 mg/kg in mice.

Discovery of potential components characteristic by conjugated enone from the branches and leaves of Croton lauioides with anti-neuroinflammatory activity via regulating the NF-κB pathway.

In this study, the chemical composition and pharmacological activity of Croton lauioides were investigated for the first time. The bioactive and HPLC-UV guided isolation led to the discovery of twenty-three conjugated enone-type components (1-23), including nine previously unknown sesquiterpenoid derivatives (1-4, 9-10, 12-14). Notably, compounds 1 and 12 are epoxides containing an endoperoxide bridge (1) or a unique dioxaspiro core (12), respectively. Compounds 2-7 are non-benzenoid aromatics featuring a tropone function, while 9-11 possess a rare rearranged scaffold with tropone shift into benzene. Extensive characterization was performed using NMR spectra, HRESIMS data, and electronic circular dichroism (ECD) calculations. Furthermore, we evaluated the bioactivities of all isolated compounds against neuroinflammation in LPS-stimulated BV-2 microglial cells. Remarkably, most sesquiterpenoid derivatives exhibited significant NO inhibit activities, and compound 5 showed the most potent effect with an IC50 value of 0.14 ± 0.04 µM. Structure-activity relationship (SAR) analysis revealed that sesquiterpenoids modified with endocyclic enone conjugation may serve as a key pharmacophore for NO inhibition, particularly involving aromatic tropone moiety. The qPCR and Western blot results demonstrated that 5 exerted an inhibitory effect on the mRNA levels of iNOS, TNF-α and COX-2 in a time-dependent manner, as well as suppressed the protein expression of iNOS, TNF-α, COX-2. In mechanism, 5 could prevented activation of NF-κB pathway by suppressing phosphorylation of p65 and IκB-α. These findings revealed C. lauioides might be a promising resource for drug candidate development targeting neuroinflammation.

The molecular mechanism of action for the potent antitumor component extracted using supercritical fluid extraction from Croton crassifolius root.

ETHNOPHARMACOLOGICAL RELEVANCE: The root of Croton crassifolius has been used as a traditional Chinese medicine (TCM), called Radix Croton Crassifolius, and commonly known as "Ji Gu Xiang" in Chinese. Its medicinal value has been recorded in several medical books or handbooks, such as "Sheng Cao Yao Xing Bei Yao", "Ben Cao Qiu Yuan" and "Zhong Hua Ben Cao". It has been traditional employed for treating sore throat, stomach-ache, rheumatism and cancer. AIM OF THE STUDY: At present, there are limited studies on the evaluation of low-polarity extracts of roots in C. crassifolius. Consequently, the aim of this study was to evaluate the antitumor effect of the low-polarity extract of C. crassifolius root. MATERIALS AND METHODS: Extracts were obtained by supercritical fluid extraction. The extracts were tested for antitumor effects in vitro on several cancer cell lines. A CCK-8 kit was used for further analysis of cell viability. A flow cytometer and propidium iodide staining were used to evaluate the cell cycle and apoptosis. Hoechst staining, JC-1 staining and the fluorescence probe DCFH-DA were used to evaluate apoptotic cells. Molecular mechanisms of action were analyzed by quantitative RT‒PCR and Western blotting. Immunohistochemistry was used for the evaluation of xenograft tumors in male BALB/c mice. Finally, molecular docking was employed to predict the bond between the desired bioactive compound and molecular targets. RESULTS: Eleven diterpenoids were isolated from low-polarity C. crassifolius root extracts. Among the compounds, chettaphanin II showed the strongest activity (IC50 = 8.58 µM) against A549 cells. Evaluation of cell viability and the cell cycle showed that Chettaphanin II reduced A549 cell proliferation and induced G2/M-phase arrest. Chttaphanin II significantly induced apoptosis in A549 cells, which was related to the level of apoptosis-related proteins. The growth of tumor tissue was significantly inhibited by chettaphanin II in experiments performed on naked mice. The antitumor mechanism of chettaphanin II is that it can obstruct the mTOR/PI3K/Akt signaling pathway in A549 cells. Molecular docking established that chettaphanin II could bind to the active sites of Bcl-2 and Bax. CONCLUSIONS: Taken together, the natural diterpenoid chettaphanin II was identified as the major antitumor active component, and its potential for developing anticancer therapies was demonstrated for the first time by antiproliferation evaluation in vitro and in vivo.

The multiple roles of trichomes in two Croton species.

Trichomes are common in plants from dry environments, and despite their recognized role in protection and defense, little is known about their role as absorptive structures and in other aspects of leaf ecophysiology. We combine anatomical and ecophysiological data to evaluate how trichomes affect leaf gas exchange and water balance during drought. We studied two congeneric species with pubescent leaves which co-occur in Brazilian Caatinga: Croton blanchetianus (dense trichomes) and Croton adenocalyx (sparse trichomes). We found a novel foliar water uptake (FWU) pathway in C. blanchetianus composed of stellate trichomes and underlying epidermal cells and sclereids that interconnect the trichomes from both leaf surfaces. The water absorbed by these trichomes is redistributed laterally by pectin protuberances on mesophyll cell walls. This mechanism enables C. blanchetianus leaves to absorb water more efficiently than C. adenocalyx. Consequently, the exposure of C. blanchetianus to dew during drought improved its leaf gas exchange and water status more than C. adenocalyx. C. blanchetianus trichomes also increase their leaf capacity to reflect light and maintain lower temperatures during drought. Our results emphasize the multiple roles that trichomes might have on plant functioning and the importance of FWU for the ecophysiology of Caatinga plants during drought.

Diterpenoids with Schistosomula-Killing and Anti-Fibrosis Activities In Vitro from the Leaves of Croton tiglium.

The leaves of C. tiglium have been comprehensively researched for their structurally novel bioactive natural compounds, especially those with anti-schistosomiasis liver fibrosis activity, because ethyl acetate extract, which can be extracted from the leaves of C. tiglium, has good anti-schistosomiasis liver fibrosis effects. One new tigliane-type diterpene, 20-acetyl-13-O-(2-metyl)butyryl-phorbol (1), and nine known (2-10) analogues were isolated from the leaves of C. tiglium. Their structures were elucidated on the basis of spectroscopic analysis and ECD analysis. All diterpenoids had a stronger insecticidal effect on schistosomula, and compounds 2, 4, and 10 had good anti-liver-fibrosis effects. Furthermore, compared with the model group, compound 2 significantly downregulated the protein and mRNA expression of COL-I, COL-III, α-SMA, and TGF-ß1 on TGF-ß1-induced liver fibrosis in LX-2 cells. Meanwhile, compound 2 also regulated the expression of TGF-ß/Smad-pathway-related proteins. The results suggest that diterpenoids from C. tiglium may serve as potential schistosomula-killing and anti-liver-fibrosis agents in the future.

In vitro evaluation of cytotoxic potential of essential oil extracted from leaves of Croton heliotropiifolius Kunth in human tumor cells.

Croton heliotropiifolius Kunth, popularly known as "velame," is a shrub that resides in northeastern Brazil. The essential oil of C. heliotropiifolius contains high concentrations of volatile compounds in the leaves and is widely used in folk medicine for many purposes as an antiseptic, analgesic, sedative, and anti-inflammatory agent. Due to the apparent limited amount of information, the aim of this study was to determine the cytotoxic potential of essential oil extracted from leaves of C. heliotropiifolius, utilizing different human cancer cell lines (HL-60, leukemia; HCT-116, colon; MDA-MB435, melanoma; SF295, glioblastoma) and comparison to murine fibroblast L929 cell line. The chemical characterization of the essential oil revealed the presence of large amounts of monoterpenes and sesquiterpenes, the majority of which were aristolene (22.43%), germacrene D (11.38%), ɣ-terpinene (10.85%), and limonene (10.21%). The essential oil exerted significant cytotoxicity on all cancer cells, with low activity on murine L929 fibroblasts, independent of disruption of cell membranes evidenced by absence of hemolytic activity. The cytotoxicity identified was associated with oxidative stress, which culminated in mitochondrial respiration dysfunction and direct or indirect DNA damage (strand breaks and oxidative damage), triggering cell death via apoptosis. Our findings suggest that extracts of essential oil of C. Heliotropiifolius may be considered as agents to be used therapeutically in treatment of certain cancers.

A New Clerodane from the Leaves of Croton krabas and Its Cholinesterase Inhibitory Activities.

Chromatographic separation of the leaves of Croton krabas resulted in the isolation of one new clerodane, crotoeurin D (1), along with two known compounds, 6S-crotoeurin C (2) and blumenol A (3). Their structures were determined based on extensive nuclear magnetic resonance spectroscopic data analysis and mass spectrometry. The absolute configuration of the new clerodane was assigned by nuclear overhauser effect spectroscopy correlations and electronic circular dichroism calculations. Compound 1 exhibited significant acetylcholinesterase and butyrylcholinesterase inhibitory activities. Moreover, the binding modes of 1 revealed that its structure formed strong hydrogen bonds and hydrophobic interactions with the active sites of both enzymes.

Investigating the phytoavailability of metals in roots of Croton macrostachyus and Phytolacca dodecandra: induced rhizosphere processes.

Medicinal plants are key component of complementary and alternative medicine, and constitute the first therapeutic strategy for majority of the global population, particularly in developing nations. Croton macrostachyus and Phytolacca dodecandra are among such plants, widely used to treat various diseases. The present study aimed at investigating the elemental composition of both plant root samples collected from four districts in the Central Gondar Zone, Northwest Ethiopia. An optimized wet-digestion procedure was applied with 0.5 g of root sample using HNO3: HCl: H2O2 (v/v) in the ratio of 8:2:1 at 240 °C for 3:00 h (for P. dodecandra), and 5:2:2 at 300 °C for 3:00 h (for C. macrostachyus). Then, concentrations of metals in the digested samples were determined using a flame atomic absorption spectrophotometer; and the validity of the optimized procedure was evaluated by spiking experiments. Results showed good accuracy and repeatability of the methods with percent of recoveries ranging from 85 to 103%. The mean concentrations of metals in C. macrostachyus root samples were higher than their P. dodecandra counterparts, and the distribution of metals showed the following decreasing order: Mg > Ca ≈ Fe > Mn > Zn > Cu > Cr. One-way ANOVA revealed no significant differences (p > 0.05) between the mean concentrations of the same metals in both plant root samples, except for Mg and Cr. Correlation matrix, principal component and cluster analyses suggested that accumulation of metals in the root samples originated from both natural and anthropogenic sources. In conclusion, the roots of both medicinal plants contained substantial amounts of metals, thereby serving as valuable sources of essential elements.

Unreported ent-rosane diterpenes from Croton niveus Jacq. (Euphorbiaceae). Cytotoxic activity and docking studies.

From the bioactive extract of the euphorbiaceous Croton niveus Jacq., three previously unreported ent-rosane diterpenes have been isolated and characterized by conventional methods, in addition to the known compounds lupeol, cajucarinolide and some phytosterols. Two of the ent-rosane diterpenes displayed activity against HCT-15 and PC-3 cancer cell lines, and the results of docking calculations of these compounds with NF-κB and STAT3 receptors agreed with the proposed mode of action of diterpenes against PC-3 cells.

C-type natriuretic peptide (CNP) inhibits 7,12-Dimethylbenz[a]anthracene (DMBA)/Croton oil-induced skin tumor growth by modulating inflammation in Swiss albino mice.

C-type natriuretic peptide (CNP) exhibits anti-inflammatory activity besides its natriuretic and diuretic functions. The present study aimed to determine the anticancer and synergistic therapeutic activity of CNP against a 7,12-Dimethylbenz[a]anthracene (DMBA)/Croton oil-induced skin tumor mouse model. CNP (2.5 µg/kg body weight) was injected either alone and/or in combination with Cisplatin (CDDP) (2 mg/kg body weight) for 4 weeks. The dorsal skin tumor incidences/growth and mortality rate were recorded during the experimental period of 16 weeks. The serum C-reactive protein (CRP), and lactate dehydrogenase (LDH) levels, infiltrating mast cells, and AgNORs proliferating cells count were analyzed in control and experimental mice. Further, the expression profile of marker genes of proliferation, inflammation, and progression molecules were analyzed using Reverse transcriptase-polymerase chain reaction (RT-PCR)/quantitative PCR (qPCR), western blot, and immunohistochemistry. The DMBA/Croton oil-induced mice exhibited 100% tumor incidence. Whereas, CNP alone, CDDP alone, and CNP+CDDP combination-treated mice exhibited 58%, 46%, and 24% tumor incidence, respectively. Also, a marked reduction in the levels of serum CRP and LDH, the number of infiltrating mast cells count and AgNORs proliferating cells count were noticed in the mice skin sections. Further, a significant reduction in both mRNA and protein expression levels of proliferation, inflammation, and progression markers were noticed in CNP (p < 0.01), CDDP (p < 0.01), and CNP+CDDP combination (p < 0.001) treated mice, respectively. The results of the present study suggest that CNP has anticancer activity. Further, the CNP+CDDP treatment has more promising anticancer activity as compared with CNP or CDDP alone treatment, probably due to the synergistic antiproliferative and anti-inflammatory activities of CNP and CDDP.

Laeviganoids A-T, ent-Clerodane-Type Diterpenoids from Croton laevigatus.

Laeviganoids A-T (1-20), 20 new ent-clerodane-type diterpenoids featuring a 2-furanone (1-3) or a furan (4-20) ring, as well as six analogues (21-26), were isolated from the roots of Croton laevigatus. Their structures were determined by spectroscopic data analysis, experimental electronic circular dichroism measurements, and X-ray crystallographic studies. Compounds 4-6, 16, 21-24, and 26 could influence the anti-inflammatory protumoral phenotype of macrophages. Among these compounds, 21 and 26 are the most potent, as evidenced by consistently downregulating the classic anti-inflammatory cytokine IL-10 and upregulating the classic pro-inflammatory cytokine TNF-α on the secretion level in RAW 264.7 cells.

Pharmacokinetic and toxicological prediction of the chemical constituents of the essential oil of the leaves of Croton heliotropiifolius Kunth.

The development of new drugs through studies of candidate molecules is a complex undertaking; however, computational or in silico approaches aimed at optimizing molecules with greater development potential are being utilized for predictions of pharmacokinetic properties such as absorption, distribution, metabolism and excretion (ADME) as well as toxicological parameters. The objective of this study was to examine in silico and in vivo pharmacokinetic and toxicological properties of the chemical constituents present in the essential oil of Croton heliotropiifolius Kunth leaves. The following Pubchem platform as well as Software SwissADME and PreADMET software were employed for in silico studies while micronucleus (MN) testing for in vivo determination of mutagenicity, using Swiss adult male Mus musculus mice. In silico findings demonstrated that all chemical constituents presented (1) high oral absorption (2) medium cellular permeability and (3) high blood brain permeability. As for toxicity, these chemical constituents exhibited low to medium risk of occurrence of cytotoxicity. Regarding in vivo evaluation, peripheral blood samples obtained from animals tested with the oil showed no significant differences in number of MN compared to negative controls. Data indicate that further investigations are necessary to corroborate the findings of this study. Our data suggest that essential oil extracted from Croton heliotropiifolius Kunth leaves may serve as a candidate for new drug development.

Chemical characterization and antimicrobial activity of essential oils from Croton grewioides Baill. accessions on the phytopathogen Xanthomonas campestris pv. campestris.

Croton grewioides Baill. is an aromatic species with proven bioactive properties. Considering the potential of the species, the aim of this study was to chemically characterize and evaluate the in vitro antibacterial activity of the essential oils of C. grewioides on Xanthomonas campestris pv. campestris. The essential oils of the accessions of C. grewioides were extracted by the hydrodistillation method and analyzed by gas chromatography - mass spectrometry. For determination of the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of the essential oils and of the compound eugenol, the microdilution method was used at concentrations that ranged from 125 to 4000 µg.mL-1. Streptomycin sulfate was used as a positive control (12.5 to 100 µg.mL-1). Growth kinetics and the membrane permeability trial were evaluated for the concentrations 2×, 1×, 1/2×, 1/4×, and 1/8× MIC of the essential oil CGR-108. The major compounds identified in the essential oils were eugenol, methyl eugenol, and methyl chavicol. The essential oil of the accession CGR-108 had a lower MIC (> 500 and < 1000 µg.mL-1) and MBC equal to <2000 µg.mL-1. For eugenol, MIC was obtained with contractions >250 and < 500 µg.mL-1 and MBC with >500 µg.mL-1 and < 1000 µg.mL-1. A loss of cell viability of the bacteria was observed after 30 min of exposure to the essential oil of the accession CGR-108 at the concentrations of 2× and 1× MIC, which was proven by the fluorescence intensity with propidium iodide. The essential oils of Croton grewioides Baill. and the compound eugenol show antibacterial potential on Xanthomonas campestris pv. campestris.

Crotofolanes, rearranged crotofolanes, and a novel diterpene: isocrotofolane from Croton cascarilloides, collected in Okinawa.

To this day, since about 50% of all medicines are derived from natural sources, natural product chemistry, especially the search for biologically active natural components, remains extremely important (Newman and Cragg in J Nat Prod 83:770-803, 2020). In this review, we deal with our continuing research work for promising constituents from plants collected in the Ryukyu Archipelago. The isolation of islands in the archipelago by the sea or by straits gives rise to endemic plant species that are unique to the islands. The structural diversity of the constituents produced by this unique flora is of great scientific interest in various aspects, including chemical structures, biosynthesis, and biological activities. The components from this structural diversity have great potential as new pharmaceutical seeds. In our continuing studies, we have successfully investigated new but extremely unusual diterpenoids: crotofolanes and their rearranged varieties (nor-crotofolane, trinor-crotofolane, neocrotofolane) and a glycoside with a new skeletal diterpenoid (isocrotofolane glucoside) from Croton cascarilloides. This review summarizes our reports on the investigation of crotofolanes as well as those on crotofolanes by other research groups.

Phytochemical profile analysis by LC-ESI-MSn and LC-HR-ESI-MS and validated HPLC method for quantification of rutin in herbal drug and products from leaves of Croton blanchetianus.

Phytochemical analysis of Croton blanchetianus leaves was performed by. After that, a high performance liquid chromatography method was developed and validated for the determination of rutin in herbal drug and products of C. blanchetianus. The separation was achieved on a C18 column, and the mobile phase was composed of ultrapure water and methanol (acidified with trifluoroacetic acid) with a gradient of 0.8 ml/min. The method was validated following international guidelines. The chemical analysis revealed the presence of flavonoids. Among them rutin was used as the standard for validation. In the HPLC the presence of rutin was observed at 24.7 min. The method was robust, with no significant variations, and linear in the range evaluated with R2 > 0.99. Regarding the matrix effect, it was possible to prove the absence of interference of the constituents in the herbal drug. The precision was determined with a relative standard deviation of <1.34%. The recovery results were achieved between 89.29 and 101.21%. Furthermore, with partial validation, the method was proved to be suitable for the liquid extract, dry extract and effervescent granules. Therefore, this study demonstrated that the method is effective for the quality control analysis of C. blanchetianus leaves and products.

Chemistry and Bioactivity of Croton Essential Oils: Literature Survey and Croton hirtus from Vietnam.

Using essential oils to control vectors, intermediate hosts, and disease-causing microorganisms is a promising approach. The genus Croton in the family Euphorbiaceae is a large genus, with many species containing large amounts of essential oils, however, essential oil studies are limited in terms of the number of Croton species investigated. In this work, the aerial parts of C. hirtus growing wild in Vietnam were collected and analyzed by gas chromatography/mass spectrometry (GC/MS). A total of 141 compounds were identified in C. hirtus essential oil, in which sesquiterpenoids dominated, comprising 95.4%, including the main components ß-caryophyllene (32.8%), germacrene D (11.6%), ß-elemene (9.1%), α-humulene (8.5%), and caryophyllene oxide (5.0%). The essential oil of C. hirtus showed very strong biological activities against the larvae of four mosquito species with 24 h LC50 values in the range of 15.38-78.27 µg/mL, against Physella acuta adults with a 48 h LC50 value of 10.09 µg/mL, and against ATCC microorganisms with MIC values in the range of 8-16 µg/mL. In order to provide a comparison with previous works, a literature survey on the chemical composition, mosquito larvicidal, molluscicidal, antiparasitic, and antimicrobial activities of essential oils of Croton species was conducted. Seventy-two references (seventy articles and one book) out of a total of two hundred and forty-four references related to the chemical composition and bioactivity of essential oils of Croton species were used for this paper. The essential oils of some Croton species were characterized by their phenylpropanoid compounds. The experimental results of this research and the survey of the literature showed that Croton essential oils have the potential to be used to control mosquito-borne and mollusk-borne diseases, as well as microbial infections. Research on unstudied Croton species is needed to search for species with high essential oil contents and excellent biological activities.

Deciphering the fluorescence quenching potential of Croton bonplandianum leaves and detection of bioactive molecules using liquid chromatography and mass spectrometry.

In this study, liquid chromatography and mass spectrometry were used to screen the active phytochemicals and analyze antioxidant activity of Croton bonplandianum. In addition, cadmium telluride quantum dots were used to analyze the fluorescence quenching capabilities of Croton bonplandianum plants. UPLC-ESI-MS was used to screen polyphenols in the mass range of 100-2000, with both positive and negative ionizations. Based on molecular weight, 7-Spirostanoldihexoside isomer, Rutin, Quercetin hexoside, Kaempferol-3-O-(p-coumaroyl)-glucoside, Kaempferol, Quercetin, and (E) Catechin-(E) Gallocatechin were tentatively identified. In total, 63.34 mg of polyphenols and 20.36 mg of flavonoids were detected. Lipid peroxidation IC50 values were 212, 38, 56, and 365 g/mL for DPPH, ABTS, and superoxide radicals. Reducing power of the plant material showed the maximum absorbance of 0.56 in 500 µg/mL concentration. Furthermore, the plant extract quenched cadmium telluride quantum dots fluorescence in a dose dependent manner. The results from quenching concluded that Croton bonplandianum with QDs might be used as a drug targeting and delivery nanomaterial.

Biscroyunoid A, an Anti-Hepatic Fibrotic 19-nor-Clerodane Diterpenoid Dimer with a C-16-C-12' Linkage from Croton yunnanensis.

Biscroyunoid A (1), a 19-nor-clerodane diterpenoid dimer featuring a unique C-16-C-12' linkage and containing an unusual 4,7-dihydro-5H-spiro[benzofuran-6,1'-cyclohexane] motif, together with its biosynthetic precursor, croyunoid A (2), were isolated from Croton yunnanensis. Their structures were determined by spectroscopic, computational, and single-crystal X-ray diffraction methods. Compound 1 exerted an antihepatic fibrosis effect in LX-2 cells via inhibition of TGFß-Smad2/3 signaling.

Crotofoligandrin, a new endoperoxide crotofolane-type diterpenoid from the twigs of Croton oligandrus Pierre ex. Hutch (Euphorbiaceae).

Crotofoligandrin (1), a new endoperoxide crotofolane-type diterpenoid was isolated from the dichloromethane/methanol (1:1) extract of the twigs of Croton oligandrus Pierre Ex Hutch along with thirteen known secondary metabolites including 1-nonacosanol (2), lupenone (3), friedelin (4), ß-sitosterol (5), taraxerol (6), (-)-hardwickiic acid (7), apigenin (8), acetyl aleuritolic acid (9), betulinic acid (10), fokihodgin C 3-acetate (11), D-mannitol (12), scopoletin (13) and quercetin (14). The structures of the isolated compounds were determined based on their spectroscopic data. The crude extract and the isolated compounds were assessed in vitro for their antioxidant, lipoxygenase, butyrylcholinesterase (BChE), urease and glucosidase inhibitory potentials. Compounds 1-3, and 10 displayed activities on all the performed bioassays. All the tested samples showed strong to significant antioxidant activity with compound 1 being the most potent (IC50 39.4 µM).