Ming-Hua Qiu

Chinese Academy of Sciences | CAS · State Key Laboratory of Phytochemistry

Artemisinin is a natural sesquiterpene lactone obtained from the traditional Chinese medicinal herb Artemisia annua L. (qinghao). Artemisinin and its derivatives share an unusual endoper-oxide bridge and are extensively used for malaria treatment worldwide. In addition to antimalarial activities, artemisinin and its derivatives have been reported t...

This study attempted to improve commercial Arabica coffee quality by integrating flavor precursors with anaerobic germination. Using raw coffee beans as materials, anaerobic germination was conducted with 5 g/100 g of flavor precursors (sucrose, glucose, fructose). The chemical composition and sensory quality of roasted coffee beans were analyzed....

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...

Ten structurally diverse Ganoderma triterpenoids, including one unprecedently highly degraded A-seco-nortriterpenoids, ganolearin A (1) with a 6/6/5-tricyclo structure containing an unique benzene ring, three new rearranged nortriterpenoids, ganolearin B (2)...

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 suga...

Six new (1, 2, 3, 5, 6, and 8) and seven known (4, 7, 9, 10, 11, 12, and 13) diterpenoids have been identified in the pulp of Coffea arabica. The structures of new diterpenoids were elucidated by extensive spectroscopic analysis, including 1D, 2D NMR (HSQC, HMBC, 1H–1H COSY, and ROESY), HRESIMS, IR, DP4+, electronic circular dichroism, and X-ray cr...

Objective: To investigate the feasibility and safety of extracorporeal membrane oxygenation (ECMO)-supported percutaneous coronary intervention (PCI) in chronic coronary total occlusion (CTO) patients with reduced left ventricular ejection fraction (LVEF). Methods: The CTO patients with LVEF≤35% and undergoing CTO-PCI assisted by ECMO in the Genera...

Covering: up to March 2023Machine learning (ML) has emerged as a popular tool for analyzing the structures of natural products (NPs). This review presents a summary of the recent advancements in ML-assisted mass spectrometry (MS) and nuclear magnetic resonance (NMR) data analysis to establish the chemical structures of NPs. First, ML-based MS/MS an...

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 ( ¹ H and ¹³ C NMR, ¹ H- ¹ H COSY, HSQC, HMBC and ROESY), among which the stereostructure of compound 4 was determined by calculate...

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 polysac...

Previous studies have shown that coffee has a role in regulating lipid metabolism. However, the active compounds and pharmacological mechanism(s) are still unclear. Here, four new coffee diterpenoids (1-4) were identified from roasted arabica coffee (Coffea arabica L.) beans, and together with 31 known coffee diterpenoids (5-35), their bioactivitie...

In this study, medium roasted coffee with four different fermented coffee fruits post-treatments (dry, wet, semi-dry and hot air dry) was used as the material. Chemical profile and sensorial analysis were used to comprehensively analyze the effects of post-treatments on coffee flavor characteristics from multiple dimensions. A total of 31 water-sol...

Covering: 2018 to 2022Meroterpenoids found in fungal species of the genus Ganoderma and known as Ganoderma meroterpenoids (GMs) are substances composed of a 1,2,4-trisubstituted benzene and a polyunsaturated side chain. These substances have attracted the attention of chemists and pharmacologists due to their diverse structures and significant bioa...

Twelve undescribed 15,16-seco-cycloartane triterpenoids, 15,16-seco-cimiterpenes C-N, as well as five previously reported analogs were isolated by NMR-tracking methods from the rhizomes of Cimicifuga acerina (Sieb. et Zucc.) Tanaka. Among them, 15,16-seco-cimiterpenes C-N were the first 15,16-seco-cycloartane triterpenoids featuring acetal or hemia...

Actein is a natural triterpenoid glycoside, isolated from the rhizomes of Cimicifuga foetida, which have been demonstrated to be potential in the treatment of breast cancer previously. Herein, we described the design and synthesis of a series of actein derivatives as anti-triple negative breast cancer (TNBC) inhibitors. Of which, the most promising...

Ganoapplins A and B (1 and 2) with a 6/6/6/5/6-fused pentacyclic skeleton containing an aromatic E ring, were obtained from Ganoderma applanatum. Their structures were established through extensive spectroscopic analyses, quantum chemical calculations, including calculated chemical shifts with DP4 + analysis and electronic circular dichroism (ECD)....

This study aimed to improve the brewing quality of commercial Arabica coffee through anaerobic germination. Changes in important compounds and cupping scores of germination roasting coffee with different germination degrees were investigated by 1H NMR, HS-SPME-GC-MS and sensory analysis. Statistical analysis of multivariate analysis results indicat...

Two new degrade cycloartane triterpenoids, named buboditones A, B (1, 2), together with ten known alkaloids, cyclobuxoviridine (3), N-dimethylcycloxobuxovircine (4), cyclovirobuxine C (5), cyclovirobuxine A (6), cycloprotobuxine C (7), cycloprotobuxine A (8), cyclobuxoxazine (9), cyclobuxoxazine A (10), buxruguline B (11), irehine (12), were isolat...

Green coffee oil can be used as a biologically active emulsifier. In this study, corn starch-based composite films with different concentrations of Arabica coffee oil (ACO) and Robusta coffee oil (RCO) were prepared using the solution-casting method. The film-forming properties and physicochemical characteristics of the composite films were investi...

Three new meroterpenoids, cochlearins J-L (1-3) and three known meroterpenoids (4-6) were isolated from the fruiting bodies of Ganoderma cochlear. NMR (1H and 13C NMR, 1H - 1H COSY, HSQC, HMBC and ROESY), and HRESIMS were employed for the structure elucidation of new compounds. The stereostructures of 1-3 were confirmed by calculated ECD and optica...

ATP citrate lyase (ACLY) is a key enzyme in glucolipid metabolism with therapeutic prospect for treating hyperlipidemia and various cancers. Much effort has been put into discovering ACLY inhibitors. However, current screening approaches have limitations in sensitivity, portability and high-throughput. To develop a general screening assay, we inves...

Comprehensive Summary Ganoderma triterpenoids (GTs), a class of major active constituents of Ganoderma fungi, possess diverse structures and remarkable activities. In the present study, nine new GTs, namely applanoids A—I (1—9), were isolated from the medicinal fungus of Ganoderma applanatum. Their structures including absolute configurations were...

A new limonoid, 3-acetoxy-7-(2′-methylpropenoyl)-vilasinin lactone (1), together with a known analogue, 3-acetoxy-7-tigloylvilasinin lactone (2), was isolated from the leaves and stems of Azadirachta indica. Their structures were elucidated based on spectral methods and by comparison with the literature.

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 fo...

A pair of meroterpenoid dimers, (±)-spiroganoapplanain A (1) represents a new subtype of Ganoderma meroterpenoid dimers with a 6/5/5/6/5/6 hexacyclic system were isolated from Ganoderma applanatum. Their structures were determined...

Seven new (1-4, 6-8) diterpenoids with rare skeletons and seven known ones (9, 12, 17, 18 and 23-25) were isolated from roasted beans of Coffea arabica L. Together with previously obtained diterpenoids, a total of 26 molecules (1-25, 4a) were evaluated their activities on Cav3.1 low voltage-gated Ca²⁺ channel. Compounds 1, 3, 6, 7, 12, 13, 17, 19 a...

The objective of this review is to evaluate the influence of six factors on coffee volatiles. At present, the poor aroma from robusta or low‐quality arabica coffee can be significantly improved by advanced technology, and this subject will continue to be further studied. On the other hand, inoculating various starter cultures in green coffee beans...

Objective: To develop a set of data elements and standardized definitions of Coronary Artery Disease and Creative Antithrombotic Clinical Research Collaboration (CardiaCare), aiming to facilitate the exchange of disparate data sources, enhance the abilities to support multicenter researches, and subsequently ensure the databases use under standardi...

Objective: To compare the efficacy and safety of ticagrelor and clopidogrel in elderly Chinese patients with acute coronary syndrome (ACS) underwent percutaneous coronary intervention (PCI) in the real world. Methods: This study is a post-hoc analysis of a single center, retrospective cohort study. Between March 2016 and March 2018, elderly (age≥65...

Bitter melon (Momordica charantia) has traditionally been used in the management of diabetes in many countries and territories. However, standardized information on the use of this vegetable as an antidiabetic drug is still very limited. Many animal studies and clinical trials have showed the remarkable effect of bitter melon on diabetes. The resea...

Four pairs of novel meroterpenoid dimers, (±)-applandimeric acids A-D (1-4) with an unprecedented spiro[furo[3], [2], [3], [4], [5], [6], [7], [8], [9], [10], [11], [12], [13], [14], [15], [16], [17], [18], [19], [20], [21], [22], [23], [24], [25], [26], [27], [28], [29], [30], [31], [32], [33], [34], [35], [36], [37], [38], [39], [40]benzofuran-3,...

Five new thiohydantoin derivatives (1–5) were isolated from the rhizomes of Lepidium meyenii Walp. NMR (1H and 13C NMR, 1H−1H COSY, HSQC, and HMBC), HRESIMS, and ECD were employed for the structure elucidation of new compounds. Significantly, the structure of compound 1 was the first example of thiohydantoins with thioxohexahydroimidazo [1,5-a] pyr...

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 pres...

Background Coffee is one of the most commonly consumed drink around the world. During the coffee roasting process, sugars and amines undergo a violent Maillard reaction, resulting in a large number of volatile and non-volatile components . These ingredients have a huge impact on the formation of coffee flavor. In addition, many maillard products in...

This work aimed to study the composition differences of roasted beans between 12 coffee cultivars (Catimor 7963, HIBRIDO DE TIMOR, Ruiru 11, Castillo, DTARI 296, DTARI 366, DTARI 392, DTARI 585, SL28, SL34, Catuai-Amarelo and Catuai-Vermelho) from Bourbon-Typica group and Introgressed group under subtropical humid monsoon climate. The water-soluble...

Main observation and conclusion A HPLC-UV-guided separation was performed and four pairs of unprecedented macathiohydantoin dimers, lepithiohydimerins A–D (1–4) bearing a rare disulfide bond were isolated from the tubers of Maca. Their structures were unambiguously confirmed by NMR spectroscopic, X-ray crystallographic and electronic circular dichr...

Previously, we have demonstrated the antiadipogenic benefits of Ganoderma triterpenoids (GTs), which indicated GTs have potential therapeutic implications for obesity. In this study, the EtOAc extract of Ganoderma applanatum was further phytochemically investigated for searching new antiadipogenic agents, which led to the isolation of a total of 15...

Nine new pyrrole alkaloids, including two undescribed dimeric pyrrole 2‑carbaldehyde alkaloids, lepipyrrolins A-B (1-2), seven pyrrole-alkaloid derivatives, macapyrrolins D–J (3–9), along with three known ones (10-12) were isolated from the rhizomes of Lepidium meyenii. Their structures and absolute configurations were demonstrated by extensive spe...

Macamides are considered bioactive markers of maca, and they have been used as food and medicine for centuries. In the present study, a ¹H qNMR method was developed, and the analyses of the specificity, linearity, sensitivity, accuracy, and precision further indicate the validity of this method. Furthermore, the ¹H qNMR method was applied for the q...

Objective: To explore the medication compliance for secondary prevention drugs and long-term prognosis of patients with acute coronary syndrome (ACS) undergoing percutaneous coronary intervention (PCI) between hospitals in different regions of China. Methods: The Optimal Antiplatelet Therapy for Chinese Patients with Coronary Artery Disease (OPT-CA...

The seed oil of Prinsepia utilis is extensively used as an edible oil by the nationalities of Naxi, Tibetan, and Mosuo in China, which is particularly good for beauty care and has a health protection function. A large amount of industrial waste is thrown away during the production process of seed oil. Therefore, to recover bioactive compounds from...

Ethnopharmacological relevance Mu opioid receptor (MOR) is mainly a drug target for analgesia. Opioid-like agonists such as morphine have been clinically used for analgesia but have potential adverse effects. MOR antagonists have been demonstrated to alleviate these side effects. Plants (Carthamus tinctorius L, Cynanchum otophyllum C. K. Schneid.,...

Two unprecedented Ganoderma meroterpenoid dimers, applanmerotic acids A and B (1 and 2), were isolated from the fruiting bodies of Ganoderma applanatum. Their structures including stereostructures were established by spectroscopic...

Ten new (1–10) and five known (11–15) ent-kaurane diterpene derivatives were identified from the roasted beans of coffea arabica. Their structures were established by extensive spectroscopic analysis including 1D, 2D NMR (HSQC, HMBC, COSY, and ROESY), HRESIMS, and X-ray diffraction analysis. Compounds 1–3 were three types of rearranged ent-kaurane...

The nectar of Camellia reticulata Lindl. contains sugar, amino acids and other nutritional components, suggesting that it could be developed for food and food additives. To understand the effects of the nectar on human health, we investigated its chemical constituents. Two new flavonoid glycosides, cameretiins A and B (1 and 2), and two known flavo...

Ganoderma triterpenoids (GTs), a class of major active constituents in Ganoderma species, play an important role in the anti-obesity effect of Ganoderma fungi. In the study, seventeen new highly oxygenated lanostane triterpenoids, ganoapplanoids A-Q (1-17), together with five previously reported compounds (18-22), were isolated from the fruiting bo...

Two new triterpenoid-chromone hybrids, cimitriteromones H (1) and I (2), along with two known analogues (3, 4) were isolated from the phytochemical research on the n-butyl alcohol extracts of Actaea cimicifuga rhizomes. The new compounds were elucidated by spectroscopic experiments and chemical method. The cytotoxic activities of the isolated compo...

Background : The ethanolic extract of Actaea racemosa L. (Cimicifuga racemosa (L.) Nutt.) has recently been reported to ameliorate obesity-related insulin resistance, hyperlipidemia, and fatty liver in rodents. However, it remains unclear which A. racemosa components are responsible for these beneficial effects. Purpose : We aimed to examine the a...

As the most consumed beverage in the world, the material basis of the sensory quality for roasted coffee beans has always received much attention. The objective of the present study was to clarify the physical morphology changes, main chemical ingredients and cupping scores of arabica coffee beans of different roasting degrees, by scanning electron...

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 mec...

Meroapplanins A‒E (1‒5) with a 2,3,4,5-tetrahydropyridine fragment were isolated from the fruiting bodies of Ganoderma applanatum. Their structures were elucidated by comprehensive spectroscopic analyses. Absolute configurations were established based on the X-ray diffraction, electronic circular dichroism (ECD) and calculated nuclear magnetic reso...

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 a...

As the major biologically active constituents in Ganoderma species, Ganoderma triterpenoids (GTs) also showed potential anti-obesity effect in recent reports. To further elucidate the anti-obesity effect of GTs, four new compounds Ganoderenses H–K (1–4) and four known compounds (5–8) from Ganoderma resinaceum were determined by extensive spectrosco...

Six previously undescribed cycloartane triterpenes glycosides, cimimanols A–F (1–6), together with thirteen known analogues (7–19) were isolated from the rhizomes of Cimicifuga foetida. Among them, cimimanol A (1) was the first example of cycloartane triterpene glycoside featuring a unique cyclic carbonate, and cimimanol B (2) was a rare trinortrit...

Seven new lactam ent-kaurane diterpenoids, cafemide A-G (1-7), were isolated form roasted beans of Coffea arabica. Their structures were elucidated by extensive spectroscopic analysis including 1D, 2D NMR (HSQC, HMBC, 1H-1H COSY, and ROESY), HRESIMS and IR spectra. They were divided into subtype I-III according to the structure. Further, LC-MS/MS b...

Ganoderma resinaceum is a multi-purpose herbal medicine that is homologous to functional food that has long been used for enhancing health and treating chronic hepatopathy in Traditional Chinese Medicine. In a search program to discover the key bioactive composition of G. resinaceum, sixteen new lanostane-type triterpenoids (1−16), and twenty known...

Two new pyrrolizidine alkaloids, sclerwalins A and B (1 and 2), and one known 9-O-E-hydroxysenecioylretronecine (3) were first isolated from the seeds of Scleropyrum wallichianum. Their chemical structures were elucidated by extensive 1 D NMR and 2 D NMR (HSQC, HMBC, COSY, and ROESY), MS and IR spectra. Cytotoxicities of all isolates were evaluated...

Formyl peptide receptors (FPRs) are G protein-coupled receptors (GPCRs) widely expressed in neutrophils and other phagocytes. FPRs play important roles in host defense, inflammation, and the pathogenesis of infectious and inflammatory diseases. Because of these functions, FPRs are potential targets for anti-inflammatory therapies. In order to searc...

Cynanchum otophyllum was traditionally used for treating muscle and skeletal pain, epilepsy, abdominal pain, and tightness. Four known C21 steroidal glycosides, namely caudatin 3-O-β-cymaropyranoside (1), caudatin 3-O-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside (2), otophylloside B (3), and otophylloside A (4) were isolated from the roots of t...

Objective: To evaluate the long-term prognosis of coronary artery disease (CAD) patients undergoing percutaneous coronary intervention (PCI) by risk stratification with American College of Cardiology (ACC)/American Heart Association (AHA) classification of coronary lesions. Methods: Data used in this study derived from the I-LOVE-IT 2 trial. I-LOVE...

Ganoderma lucidum is one of the most famous medicinal fungi and is traditional Chinese medicine with various biological activities in Asian countries. To clarify its pharmacodynamic material basis, 15 lanostane triterpenoidswere obtained from the fruiting bodies of G. lucidum, including 8 previously undescribed lanostanoids. Their structures, inclu...

Ganoderma mushrooms have been widely used as functional food in China, Japan, and Korea. Ganoderma triterpenoids are deemed to be the main functional constituents. The structures of Ganoderma triterpenoids are complex but quite similar, which made their analyses markedly limited. In this study, we developed a general 2D NMR method to differentiate...

Background: P53 is the most frequently mutated gene in most tumour types, and the mutant p53 protein accumulates at high levels in tumours to promote tumour development and progression. Thus, targeting mutant p53 for degradation is one of the therapeutic strategies used to manage tumours that depend on mutant p53 for survival. Buxus alkaloids are...

H NMR detection combined with partial least squares discriminant analysis (PLS-DA) was used to establish models for distinguishing between Arabica coffee immature beans and mature beans. By screening Variable importance in projection (VIP) values of the discriminant model, sugars, caffeoylquinic acids (CQAs), caffeine, trigonelline and quinic acid...

Large-scale conversions from monoculture arabica coffee systems to agroforestry systems started in 2012 in southern Yunnan Province. This study analyses the impact of young shade trees (Cinnamomum camphora, Bishofia javanica and Jacaranda mimosifolia) on microclimate, coffee fruit development cycle, coffee yield, and coffee quality only 4 years aft...

Despite the ecological and economic significance of Ganoderma, the taxonomy of this group of mushrooms remains largely unresolved. In line with an attempt to further our understanding of Ganoderma, we describe a new species collected from Yunnan Province, China. Ganoderma weixiensis is described here based on the morphological characteristics and p...

Objective: To explore the value of SYNTAX revascularization index (SRI) on evaluating the long-term prognosis of coronary artery disease (CAD) patients implanted with biodegradable polymer drug-eluting stents (BP-DES) and define the best threshold of SRI for predicting all-cause mortality in these patients. Methods: Data used in this study derived...

Eight new limonoids, toononoids A-H (1-8), eight new B-seco-29-norlimonoids, toonanoronoids A-H (9-16), and seven known analogues were obtained from the EtOAc extract of the twigs and leaves of Toona ciliata. Compounds 2, 4, 8, and 16 are rare lactam-bearing limonoids. Compounds 1, 14, and 15 possess an unusual γ-methoxybutenolide moiety at C-17, w...

Eight undescribed ergostane-type steroids, (22E,24R)-ergosta-7,22-dien-3β,5α-diol- 6,5-olide, (22E,24R)-ergosta-7,9(11),22-trien-3β,5β,6β-triol, (22E,24R)-6β-methoxy ergosta-7,9(11),22-trien-3β,5α,14β-triol, (22E,24R)-9α,15α-dihydroxyergosta-4,6,8 (14),22-tetraen-3-one, (22E,24R)-ergosta-5,8,22-trien-3β,11α-dihydroxyl-7-one, (22E,24R)-ergosta-4,7,2...