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Artemisinin is a natural sesquiterpene lactone obtained from the traditional Chinese medicinal herb Artemisia annua L. (qinghao). Artemisinin and its derivatives share an unusual endoperoxide bridge and are extensively used for malaria treatment worldwide. In addition to antimalarial activities, artemisinin and its derivatives have been reported to exhibit promising anticancer effects in recent decades. In this review, we focused on the research progress of artemisinin and its derivatives with potential anticancer activities. The pharmacological effects, potential mechanisms, and clinical trials in cancer therapy of artemisinin and its derivatives were discussed. This review may facilitate the future exploration of artemisinin and its derivatives as effective anticancer agents.

Abstract Four undescribed pyrethrins C-F (1–4) as well as four known pyrethrins (5–8) were isolated from seeds of Pyrethrum cinerariifolium Trev. The structures of compounds 1–4 were elucidated by UV, HRESIMS, and NMR (1H and 13C NMR, 1H-1H COSY, HSQC, HMBC and ROESY), among which the stereostructure of compound 4 was determined by calculated ECD. Furthermore, compounds 1–4 were evaluated for their aphidicidal activities. The insecticidal assay results showed that 1–4 exhibited moderate aphidicidal activities at the concentration of 0.1 mg/mL with the 24 h mortality rates ranging from 10.58 to 52.98%. Among them, pyrethrin D (2) showed the highest aphidicidal activity, with the 24 h mortality rate of 52.98%, which was slightly lower than the positive control (pyrethrin II, 83.52%). Graphical Abstract

Abstract Four polysaccharides (MCPa, MCPb, MCPc, MCPd) were obtained from Lepidium meyenii Walp. Their structures were characterized by chemical and instrumental methods including total sugar, uronic acid and protein content determination, UV, IR and NMR spectroscopy, as well as monosaccharide composition determination and methylation analyses. Four polysaccharides were a group of glucans with different molecular weights ranging from 3.12 to 14.4 kDa, and shared a similar backbone chain consisting of (1→4)-glucose linkages with branches attached to C-3 and C-6. Furthermore, bioactivity assay showed that MCPs had concentration-dependent inhibitory activity on α-glucosidase. MCPb (Mw = 10.1 kDa) and MCPc (Mw = 5.62 kDa) with moderate molecular weights exhibited higher inhibitory activity compared with MCPa and MCPd. Graphical Abstract

Obesity, a major public health problem, causes numerous complications that threaten human health and increase the socioeconomic burden. The pathophysiology of obesity is primarily attributed to lipid metabolism disorders. Conventional anti-obesity medications have a high abuse potential and frequently deliver insufficient efficacy and have negative side-effects. Hence, functional foods are regarded as effective alternatives to address obesity. Coffee, tea, and cocoa, three widely consumed beverages, have long been considered to have the potential to prevent obesity, and several studies have focused on their intrinsic molecular mechanisms in past few years. Therefore, in this review, we discuss the mechanisms by which the bioactive ingredients in these three beverages counteract obesity from the aspects of adipogenesis, lipolysis, and energy expenditure (thermogenesis). The future prospects and challenges for coffee, tea, and cocoa as functional products for the treatment of obesity are also discussed, which can be pursued for future drug development and prevention strategies against obesity.

Defective coffee beans (DCB) are one of the main reasons for poor coffee quality. In the current research, chemical difference of three common DCB including sour beans (SCB), black beans (BCB), and mold beans (MCB) were clarified using 1H qNMR method and compared with that of non-defective beans (NDCB). The results indicated that DCB has lower sugar and lipid content compared to NDCB, yet it boasts a higher acetate concentration. The 1H NMR from water-soluble content was shown to be more effective than that of oil fraction for qualitative of DCB blends, regardless of whether partial least squares discriminant analysis (PLS-DA) or machine learning (ML) algorithms were used. Support vector machine (SVM) was proved to be excellent for distinguishing DCB blends. Finally, a partial least squares regression (PLS) model was built for quantitative analysis of DCB blends. In summary, current research will not only help to reveal the material basis of DCB and their impact on coffee flavor, but also provide feasible strategies for the identification of DCB.

Abstract Ten cucurbitane-type triterpene glycosides, including five new compounds named charantosides H (1), J (2), K (3), momorcharacoside A (4), goyaglycoside-l (5), and five known compounds (6–10), were isolated from the EtOAc extract of Momordica charantia fruits. The chemical structures of these compounds were identified by 1D and 2D NMR and HRESIMS spectroscopic analyses. Configurations of new compounds were determined by ROESY correlations and comparison of their 13C NMR data with literature reported values. All compounds were evaluated for their inhibition against α-glucosidase, in which compounds 2, 5, 7, 8, 9 showed moderate inhibitory activities with IC50 values ranging from 28.40 to 63.26 μM comparing with the positive control (acarbose, IC50 87.65 ± 6.51 μM). Graphic Abstract

Abstract To enrich the bioactive cycloartane triterpenoid glycoside named actein and find out more cytotoxic cycloartane triterpenes, a phytochemical study of Cimicifuga foetida was conducted. 113 g (0.17%) actein was purified by recrystallization while eight cycloartane-type triterpenes (1–8) were isolated from the mother liquid. The chemical structures of new compounds (1–4) were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses. Moreover, new compounds showed moderate and broad-spectrum cytotoxicity against 5 human cancer cell lines with IC50 values ranging from 4.02 to 15.80 μM. Graphic Abstract

HER2-positive breast cancer accounts for 15–20% in breast cancer and 50% of the metastatic HER2-positive breast cancer patients died of central nervous system progression. The present study investigated the effects of actein (a natural cycloartane triterpene) on cells adhesion, migration, proliferation and matrix degradation, and its underlying mechanism in HER2-positive breast cancer cells. The in vivo effect of actein on tumor growth and metastasis in MDA-MB-361 tumor-bearing mice as well as the anti-brain metastasis in tail vein injection mice model were also investigated. Our results showed that actein inhibited HER2-positive breast cancer cells viability, proliferation and migration. Actein also induced MDA-MB-361 cells G1 phase arrest and inhibited the expressions of cyclins and cyclin-dependent kinases. For intracellular mechanisms, actein inhibited the expressions of molecules in AKT/mTOR and Ras/Raf/MAPK signaling pathways. Furthermore, actein (15 mg/kg) was shown to exhibit anti-tumor and anti-metastatic activities in MDA-MB-361 breast tumor-bearing mice, and reduced brain metastasis in tail vein injection mice model. All these findings strongly suggested that actein is a potential anti-metastatic agent for HER2-positive breast cancer.

Our previous research has shown that lanostane triterpenoids from Ganoderma applanatum exhibit significant anti-adipogenesis effects. In order to obtain more structurally diverse lanostane triterpenoids to establish a structure–activity relationship, we continued the study of lanostane triterpenoids from the fruiting bodies of G. applanatum, and forty highly oxygenated lanostane-type triterpenoinds (1–40), including sixteen new compounds (1–16), were isolated. Their structures were elucidated using NMR spectra, X-ray crystallographic analysis, and Mosher’s method. In addition, some of their parts were evaluated to determine their anti-adipogenesis activities in the 3T3-L1 cell model. The results showed that compounds 16, 22, 28, and 32 exhibited stronger anti-adipogenesis effects than the positive control (LiCl, 20 mM) at the concentration of 20 μM. Compounds 15 and 20 could significantly reduce the lipid accumulation during the differentiation process of 3T3-L1 cells, comparable to the untreated group. Their IC50 values were 6.42 and 5.39 μM, respectively. The combined results of our previous and present studies allow us to establish a structure-activity relationship of lanostane triterpenoids, indicating that the A-seco-23→26 lactone skeleton could play a key role in anti-adipogenesis activity.

Abstract In present study, four new dammarane-type triterpenoids, namely caffruones A–D (1–4), were isolated from the cherries of Coffea arabica. Their structures were elucidated by extensive spectroscopic analysis including 1D, 2D NMR (HSQC, HMBC, 1H–1H COSY, and ROESY), HRMS and IR spectra. This is the first time that tetracyclic triterpenes have been reported in genus Coffea. Graphical Abstract

Abstract Maca (Lepidium meyenii Walp.), a famous food supplement, has drawn an unprecedented international interest over the last two decades. It was assumed that glucosinolates, macamides, macaenes, and alkaloids are the main bioactive components of Maca before. Recently, a series of novel thiohydantoins which generally exhibit a variety of activities have been isolated from Maca. This review focuses on the progress on the main bioactive components of Maca and their biosynthetic pathway, which indicates that macamides, thiohydantoins, and some alkaloids may originate from glucosinolates. Interestingly, thiohydantoins from Maca are the first type of thiohydantoin derivatives to be found from a natural source and may contribute to some significant effects of Maca. Graphical Abstract

Nuclear magnetic resonance (NMR) spectroscopy was used for the qualitative and quantitative analysis of aqueous extracts of unroasted and roasted coffee silverskin (CS). Twenty compounds were identified from 1D and 2D NMR spectra, including caffeine, chlorogenic acid (CGA), trigonelline, fructose, glucose, sucrose, etc. For the first time, the presence of trigonelline was detected in CS. Results of the quantitative analysis showed that the total amount of the main components after roasting was reduced by 45.6% compared with values before roasting. Sugars in the water extracts were the main components in CS, and fructose was the most abundant sugar, its relative content accounting for 38.7% and 38.4% in unroasted and roasted CS, respectively. Moreover, 1D NMR combined with 2D NMR technology shows application prospects in the rapid, non-destructive detection of CS. In addition, it was observed by optical microscopy and scanning electron microscopy (SEM) that the morphology of CS changed obviously before and after roasting.

Abstract Three new limonoid-type triterpenoids, namely toonasins A–C (1–3) with a rare lactam E ring, along with six known compounds (4–9) were isolated from the barks of Toona sinensis. The structures of new compounds were elucidated by interpretation of spectroscopic data, and the relative configuration of compound 1 was further characterized by X-ray crystallographic analyses. The isolated compounds were evaluated for their cytotoxic activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480), and compounds 3 and 5 showed weak cytotoxicities.

Background and purpose: Metastasis is an important cause of death in breast cancer patients. Anti-metastatic agents are urgently needed since standard chemotherapeutics cannot diminish the metastatic rate. Actein, a cycloartane triterpenoid, has been demonstrated to exhibit anti-angiogenic and anti-cancer activities. Its anti-metastatic activity and underlying mechanisms were evaluated in the present study.Methods: The effects of actein on the proliferation, cell cycle phase distribution, migration, motility and adhesion were evaluated using two human breast cancer cell lines, MDA-MB-231 (estrogen receptor-negative) and MCF-7 cells (estrogen receptor-positive) in vitro. Western blots and real-time PCR were employed to examine the protein and mRNA expression of relevant signaling pathways. A human metastatic breast cancer cell xenograft model was established in transparent zebrafish embryos to examine the anti-migration effect of actein in vivo.Results:In vitro results showed that actein treatment significantly decreased cell proliferation, migration and motility. Furthermore, actein significantly caused G1 phase cell cycle arrest and suppressed the protein expression of matrix metalloproteinases of MDA-MB-231 cells. In addition, actein inhibited breast cancer cell adhesion to collagen, also reduced the expression of integrins. Actein treatment down-regulated the protein expression of epidermal growth factor receptor (EGFR), AKT and NF-κB signaling proteins. In vivo results demonstrated that actein (60 μM) significantly decreased the number of zebrafish embryos with migrated cells by 74% and reduced the number of migrated cells in embryos.Conclusion: Actein exhibited anti-proliferative, anti-adhesion and anti-migration activities, with the underlying mechanisms involved the EGFR/AKT and NF-kappaB signalings. These findings shed light for the development of actein as novel anti-migration natural compound for advanced breast cancer.

Acerola cherry is a world famous fruit which contains abundant antioxidants such as vitamin C, anthocyanins, flavonoids, and phenolics. However, studies concerning bioactivity components from aerial parts of acerola (Malpighia emarginata) are scarce. In view of this, we have examined the constituents of aerial parts of acerola, and three new tetranorditerpenes acerolanins A–C (1–3) with a rare 2H-benz[e]inden-2-one substructure were isolated. Their structures were determined on the basis of spectral studies and acerolanin C was confirmed by X-ray crystallographic analysis. Furthermore, three new compounds have been studied for their cytotoxic activity.

Deregulation of the Wnt signaling pathway leads to colorectal cancer progression. Natural dietary compounds serve as promising candidates for development as chemopreventive agents by suppressing the Wnt/β-catenin signaling pathway. Physalis peruviana-derived 4βHWE showed a significant inhibitory activity with a calculated IC50 of 0.09 μΜ in a screening of novel inhibitors of Wnt signaling with the dual-luciferase reporter assay. This study investigated the anti-tumor effect of 4βHWE and the potential Wnt signaling inhibitory mechanism. Both the western blot analysis and immunofluorescence assay showed that 4βHWE promoted the phosphorylation and degradation of β-catenin and the subsequent inhibition of its nuclear translocation to attenuate the endogenous Wnt target gene expression in colorectal cancer (CRC) cells. The cell viability assay indicated that 4βHWE preferentially inhibited the proliferation of CRC compared with CCD-841-CoN, a normal human colonic epithelial cell line. 4βHWE-mediated G0/G1 cell cycle arrest and apoptosis induction contributed to the suppression of the proliferation of CRC in the cell cycle and Annexin V-FITC/Propidium Iodide apoptosis analysis. Moreover, in vivo, 4βHWE dramatically inhibited tumor growth in HCT116 xenografts by attenuating the Wnt/β-catenin signaling pathway. In conclusion, our study suggested that 4βHWE could be of potential use in anti-tumor agent development as a novel Wnt signaling inhibitor.

Two new 9,19-cycloartane triterpene glycosides 1-2, together with four known compounds—26-deoxyactein (3), actein (4), 7,8-didehydro-26-deoxyactein (5) and cimiaceroside B (6)—were isolated from the rhizome of Cimicifuga foetida. The new triterpene glycosides were identified as 23-O-methyl-24-deoxy-2'-O-(3''-methylmalonyl)-cimiaceroside B (1) and 2'-O-(3''-methylmalonyl)actein (2) based on analysis of their spectral data and chemical reactions.

Three new cucurbitane triterpenoids 1–3 and one new steroidal glycoside 4, were isolated together with ten known compounds from Momordica charantia. The structures of new compounds were determined to be 19(R)-n-butanoxy-5β,19-epoxycucurbita-6,23-diene-3β,25-diol 3-O-β-glucopyranoside (1), 23-O-β-allopyranosylecucurbita-5,24-dien-7α,3β,22(R),23(S)-tetraol 3-O-β-allopyranoside. (2), 23(R),24(S),25-trihydroxycucurbit-5-ene 3-O-{[β-glucopyranosyl(1→6)]-O-β-glucopyranosyl}-25-O-β-glucopyranoside (3), and 24(R)-stigmastan-3β,5α,6β-triol-25-ene 3-O-β-glucopyranoside (4), respectively. Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments and chemical reactions.

Two novel lanostane-type triterpenes, Ganolactone B and Ganoderiol A triacetate, were isolated from the fruiting bodies of G. sinense, together with six known compounds. The structures of the two new triterpenes were determined as 3β,7β- dihydroxy-11,15-dioxo-lanosta-8-en-24→20 lactone (1) and 3β,24,26-triacetoxy-5α-lanosta-7,9(11)-dien-25-ol (2), respectively, by chemical and spectroscopic means.

Triple negative breast cancer (TNBC) is a highly aggressive form of breast cancer resistant to many common treatments. In this study, we compared the effects of 12 phytochemical drugs on four cancer cell lines, and noticed that Cucurbitacin E (CuE) significantly inhibited TNBC cell growth by inducing cell cycle G2/M phase arrest and apoptosis. CuE reduced expression of Cyclin D1, Survivin, XIAP, Bcl2, and Mcl-1 in MDA-MB-468 and SW527, and within MDA-MB-468, CuE significantly increased activation of JNK and inhibited activation of AKT and ERK. Collectively, these results suggest that CuE may be a viable compound for developing novel TNBC therapeutics.

Three new triterpenoid alkaloids, namely buxmicrophyllines P–R (1–3), were isolated from the twigs and leaves of Buxus microphylla. Their structures were elucidated on the basis of NMR and MS spectroscopic analyses. Structurally, compounds 1–3 belong to the 9,10-cycloartane type alkaloids. In addition, compound 3 exhibited moderate cytotoxic activities in vitro against HL-60, SMMC-7221, A-549, MCF-7, and SW480 cell lines (with IC50 values ranging from 4.51 to 15.58 μM).

Two new cycloartane-type triterpene glycosides, namely cimicifoetisides A (1) and B (2), along with seven known compounds cimigenol, 25-O-acetylcimigenol, cimigenol 3-O-β-D-xylopyranoside, 12β-hydroxycimigenol 3-O-β-D-xylopyranoside, cimigenol 3-O-α-L-arabinopyranoside, 25-deoxyshengmanol 3-O-β-D-xylopyranoside and cimilactone A, were isolated from the rhizomes of Cimicifuga foetida. Their structures were elucidated as cimigenol 3-O-(2'-O-acetyl)-α-L-arabinopyranoside (1) and 25-O-acetylcimigenol 3-O-(2'-O-acetyl)-α-L-arabinopyranoside (2). Both compounds 1 and 2 exhibited potent cytotoxicity against rat EAC (Ehrlich ascites carcinoma) and MDA-MB-A231 (human breast cancer) cells with IC50 values of 0.52 and 6.74 μM for 1, and 0.19 and 10.21 μM for 2, suggesting their potential for further investigation as anti-cancer agents.