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1.
Mol Biol Rep ; 51(1): 785, 2024 Jun 29.
Article in English | MEDLINE | ID: mdl-38951450

ABSTRACT

BACKGROUND: Kaempferia parviflora Wall. ex. Baker (KP) has been reported to exhibit anti-obesity effects. However, the detailed mechanism of the anti-obesity effect of KP extract (KPE) is yet to be clarified. Here, we investigated the effect of KPE and its component polymethoxyflavones (PMFs) on the adipogenic differentiation of human mesenchymal stem cells (MSCs). METHODS AND RESULTS: KPE and PMFs fraction (2.5 µg/mL) significantly inhibited lipid and triacylglyceride accumulation in MSCs; lipid accumulation in MSCs was suppressed during the early stages of differentiation (days 0-3) but not during the mid (days 3-7) or late (days 7-14) stages. Treatment with KPE and PMFs fractions significantly suppressed peroxisome proliferator-activated receptor-γ (PPARγ), CCAAT/enhancer binding protein α (C/EBPα), and various adipogenic metabolic factors. Treatment with KPE and PMFs fraction induced the activation of AMP-activated protein kinase (AMPK) signaling, and pretreatment with an AMPK signaling inhibitor significantly attenuated KPE- and PMFs fraction-induced suppression of lipid formation. CONCLUSIONS: Our findings demonstrate that KPE and PMFs fraction inhibit lipid formation by inhibiting the differentiation of undifferentiated MSCs into adipocyte lineages via AMPK signaling, and this may be the mechanism underlying the anti-obesity effects of KPE and PMFs. Our study lays the foundation for the elucidation of the anti-obesity mechanism of KPE and PMFs.


Subject(s)
AMP-Activated Protein Kinases , Adipogenesis , Cell Differentiation , Flavones , Mesenchymal Stem Cells , Plant Extracts , Signal Transduction , Zingiberaceae , Humans , Mesenchymal Stem Cells/drug effects , Mesenchymal Stem Cells/metabolism , Adipogenesis/drug effects , Plant Extracts/pharmacology , Zingiberaceae/chemistry , AMP-Activated Protein Kinases/metabolism , Flavones/pharmacology , Cell Differentiation/drug effects , Signal Transduction/drug effects , PPAR gamma/metabolism , PPAR gamma/genetics , Adipocytes/drug effects , Adipocytes/metabolism , Adipocytes/cytology , Cells, Cultured
2.
J Nat Prod ; 87(2): 340-348, 2024 02 23.
Article in English | MEDLINE | ID: mdl-38354299

ABSTRACT

Norlignans are a rare class of natural products isolated from a diverse range of plant species, many of which have interesting biological activities including antibacterial, antioxidant, phytotoxic, platelet aggregation inhibitory effects, and more. Isolated from Amomum villosum (Amomi Fructus), amovillosumins A (1) and C (3) are norlignans which were of interest to synthesize, due to their interesting bioactivities, specifically their ability to increase stimulation of glucagon-like peptide-1 (GLP-1) secretion. In this research, key intermediate 15 was used to stereoselectively synthesize (7R,8R)-amovillosumins A (1) and C (3). The developed method includes a Mitsunobu coupling, a modified rhodium-catalyzed Miyaura arylation, and an acid-catalyzed cyclization in key bond-forming steps. After synthesis, the structure of 1 was confirmed, but it was revealed that the benzodioxane-containing structure of amovillosumin C (3) that had been proposed in the literature was incorrect. Thus, with further investigation a structure correction of 3 was achieved by synthesis, the correct structure being 8-O-4'-oxynorlignan.


Subject(s)
Biological Products , Drugs, Chinese Herbal , Lignans , Zingiberaceae , Biological Products/analysis , Cyclization , Drugs, Chinese Herbal/chemistry , Fruit/chemistry , Lignans/chemistry , Molecular Structure , Zingiberaceae/chemistry
3.
Phytochem Anal ; 35(3): 579-585, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38130156

ABSTRACT

INTRODUCTION: The active compound (E)-1-(3',4'-dimethoxyphenyl)butadiene (DMPBD) isolated from the rhizomes of Zingiber cassumunar Roxb. has potent anti-inflammatory and anticancer activities. Although DMPBD is one of the promising drug candidates for phytomedicine, its limited stability impedes its widespread use. For the development of new drugs, the assessment of their chemical stability is essential, ensuring they maintain their properties within specified limits throughout the period from production until use. OBJECTIVE: In the present study, we aimed to evaluate the stability of DMPBD under various conditions, including different solvents, temperatures, and lighting conditions, to identify the factors affecting stability and optimize the storage and handling conditions. METHODOLOGY: DMPBD samples subjected to the different conditions tested were monitored by quantitative 1H NMR (qHNMR), using an internal standard for the determination of the absolute quantity of DMPBD as a function of time and the changes thereof within 1 month. RESULTS: Significant decomposition of DMPBD was observed in chloroform-d1, whereas its content remained constant in methanol-d4. The content of DMPBD was maintained upon storage at temperatures below 4°C, both as methanolic solution and in the crude extract. Exposure to light had a slight negative impact on its contents. Some degradation products could be identified as resulting from O2-induced cleavage of the diene moiety. CONCLUSIONS: For pharmacological/therapeutic applications, DMPBD should be stored in the form of the crude extract or as a purified material in methanolic solution. Ideally, the storage temperature should be below 4°C and O2 should be excluded.


Subject(s)
Plant Extracts , Zingiberaceae , Plant Extracts/chemistry , Butadienes/analysis , Butadienes/pharmacology , Rhizome/chemistry , Zingiberaceae/chemistry
4.
Molecules ; 29(6)2024 Mar 08.
Article in English | MEDLINE | ID: mdl-38542853

ABSTRACT

Zingiber purpureum Roscoe, known as plai in Thailand, is a perennial plant of the Zingiberaceae family and has traditionally been used in Southeast Asian countries to treat inflammation, pain, and asthma. In this study, we performed the characterization of the volatile constituents in ethyl acetate extracts of plai. Ethyl acetate extracts derived from the rhizomes of plai were subjected to gas chromatography-mass spectrometry, and the key peaks in the total ion current chromatograms were annotated or identified. In total, twenty-one compounds were identified using isolation procedures or standards, and nine compounds were annotated by comparing their Kovats retention index (RI) and electron ionization (EI) mass spectra with those in the literature. Most of the identifications were inconsistent with the tentative annotations found via library search and suggested that some peaks were incorrectly assigned in previous studies. Thus, to avoid further misannotations and contribute to the research on dereplication, the RI value, EI mass spectral data, and NMR spectroscopy data of the isolated compounds are reported.


Subject(s)
Zingiberaceae , Gas Chromatography-Mass Spectrometry , Zingiberaceae/chemistry , Acetates , Plant Extracts/chemistry , Thailand
5.
Inflammopharmacology ; 32(2): 1621-1631, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38319475

ABSTRACT

Aframomum melegueta K Schum (A. melegueta), an herbaceous plant renowned for its medicinal seeds, was investigated for its potential immunomodulatory effects in vitro and in vivo using ethanolic and methanolic extracts. The immunomodulatory effect was evaluated by measuring antibody titers using the agglutination technique, while anti-inflammatory activity was assessed in a carrageenan-induced mouse paw edema model. In vitro immunomodulatory activity was measured by lysozyme release from neutrophils. Additionally, white blood cell counts were analyzed post-extracts treatment. The MTT assay was employed to determine cytotoxicity, and the biochemical parameters of liver toxicity were evaluated. Remarkably, both extracts exhibited a dose-dependent reduction in paw edema (p < 0.001), with the most significant reduction observed at 1 g/kg (78.13 and 74.27% for ethanolic and methanolic extracts, respectively). Neutrophil degranulation was significantly inhibited in a dose-dependent manner (p < 0.003), reaching maximal inhibition at 100 µg/mg (60.78 and 39.7% for ethanolic and methanolic extracts, respectively). In comparison to the control group, both antibody production and white blood cell counts were reduced. Neither of the extracts showcased any cytotoxicity or toxicity. These findings suggest that A. melegueta extracts exhibit immunosuppressive and anti-inflammatory activities due to the presence of various biomolecules.


Subject(s)
Plant Extracts , Zingiberaceae , Mice , Animals , Plant Extracts/chemistry , Seeds/chemistry , Anti-Inflammatory Agents/pharmacology , Methanol , Ethanol , Zingiberaceae/chemistry , Edema
6.
Medicina (Kaunas) ; 60(8)2024 Aug 22.
Article in English | MEDLINE | ID: mdl-39202650

ABSTRACT

Cancer has become a consistent concern globally and increasingly fatal. Malignant melanoma is a rising concern, with its increased mortality. Kaempferia parviflora Wall. ex Baker (K. parviflora (KP)), commonly known as black ginger, is well known for its medicinal contributions. For the first time, in the following study we investigated the antimelanoma potential of Laos KP extracts in human cell lines. KP extracts (KPE) in methanol, DCM, and ethyl acetate showed strong cell inhibition in both melanomas, with KPE-DCM being particularly effective in inhibiting melanoma cell migration, invasion, and proliferation by inducing cell cycle arrest and apoptosis, while KPE-Hexane exhibited a low cell inhibition rate and a more limited effect. KPE affected the increased expression of caspase-3, PARP andBax and the decreased expression of the BcL-2, Mu-2-related death-inducing gene (MUDENG, MuD) protein. Furthermore, KPE enhanced apoptotic cells in the absence and presence of the pancaspase inhibitor Z-VAD-FMK. Interestingly, these apoptotic cells were significantly suppressed by the caspase inhibitor. Moreover, elevated mitochondrial membrane potential (MMP) and intracellular reactive oxygen species (ROS) levels, suggestive of KPE's mitochondrial-mediated apoptosis in melanoma cells, were also confirmed. KPE treatment increased MMP levels, and upregulated the generation of ROS in A375 cells but not in A2058 cells. However, pretreatment with an ROS scavenger (NAC) suppressed KPE-induced cell death and ROS generation. These results clearly pointed out KPE-induced mitochondrial-mediated apoptotic cell death as the mechanism behind the inhibition of the human melanoma cells. Future studies exploring the role of specific ROS sources and their interaction with mitochondrial dynamics could deepen the existing understanding on KPE-induced apoptosis.


Subject(s)
Apoptosis , Melanoma , Plant Extracts , Humans , Melanoma/drug therapy , Cell Line, Tumor , Apoptosis/drug effects , Plant Extracts/pharmacology , Plant Extracts/therapeutic use , Zingiberaceae/chemistry , Cell Proliferation/drug effects , Laos , Cell Movement/drug effects , Reactive Oxygen Species/metabolism , Membrane Potential, Mitochondrial/drug effects , Zingiber officinale/chemistry , Antineoplastic Agents/pharmacology , Antineoplastic Agents/therapeutic use
7.
Chem Biodivers ; 20(6): e202201205, 2023 Jun.
Article in English | MEDLINE | ID: mdl-37202876

ABSTRACT

Pseudomonas aeruginosa can regulate its pathogenicity via quorum sensing (QS) system. Zingiber cassumunar and Z. officinale have been used for the treatment of infectious diseases. The study aimed to evaluate and compare the chemical constituents, antibacterial, and QS inhibitor of Z. cassumunar essential oils (ZCEO) and Z. officinale essential oils (ZOEO). The chemical constituent was analysed using GC/MS. Broth microdilution and spectrophotometry analysis were used to evaluate their antibacterial and QS inhibitor activities. The main constituent of ZOEO with percent composition above 6 % (α-curcumene, α-zingiberene, ß-sesquiphellandrene, and ß-bisabolene, α-citral, and α-farnesene) were exist in a very minimal percentage less than 0.7 % in Z. cassumunar. All major components of ZCEO with percentages higher than 5 % (terpinen-4-ol, sabinene, γ-terpinene) were present in low proportion (<1.18 %) in Z. officinale. ZCEO demonstrated moderate antibacterial activity against P. aeruginosa. The combination of ZCEO and tetracycline showed a synergistic effect (FICI of 0.5). ZCEO exhibited strong activity in inhibiting biofilm formation. ZCEO at 1 / 2 ${{ 1/2 }}$ MIC (62.5 µg/mL) was able to reduce pyoverdine, pyocyanin, and proteolytic activity. This is the first report on the activity of ZCEO in the inhibition of P. aeruginosa QS system and it may be used to control the pathogenicity of P. aeruginosa.


Subject(s)
Oils, Volatile , Zingiber officinale , Zingiberaceae , Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Zingiber officinale/chemistry , Quorum Sensing , Pseudomonas aeruginosa , Zingiberaceae/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Biofilms
8.
Molecules ; 28(21)2023 Oct 31.
Article in English | MEDLINE | ID: mdl-37959789

ABSTRACT

Torch ginger, Etlingera elatior, is a Zingiberaceae plant with various red, pink, and white inflorescence. The wound healing potential and anti-aging effects of freeze-dried torch ginger inflorescence extracts (FTIEs) from three varieties were compared. The red FTIE had the highest content of phenolic, flavonoid, caffeoylquinic acid, and chlorogenic acid, followed by the white and pink FTIE. Consistent with the chemical constituents, the red FTIE demonstrated the greatest capacities for free radical scavenging, anti-tyrosinase, and anti-collagenase activity, followed by the white and pink FTIE. In cell-based studies, FTIEs displayed cytotoxicity to B16F10 melanoma cells, with the red FTIE showing the greatest activity (LC50 of 115.5 µg/mL). In contrast, the pink and the white FTIEs had less cytotoxicity impact. Nonetheless, at 1000 µg/mL, all three FTIE variants were safe on L929 fibroblasts or RAW 264.7 monocyte cells. White FTIE (500 µg/mL) exhibited the highest activity in stimulating collagen production and the greatest impact on cell migration, whereas the pink and red FTIE had a lesser effect. All FTIEs slightly suppressed the pro-inflammatory cytokines produced by lipopolysaccharide-stimulated monocytes, with no significant variation between FTIE variants. In conclusion, all FTIEs revealed promising potential for anti-aging cosmeceuticals and wound care products at specific concentrations.


Subject(s)
Plant Extracts , Zingiberaceae , Plant Extracts/pharmacology , Plant Extracts/chemistry , Inflorescence , Zingiberaceae/chemistry , Wound Healing
9.
Molecules ; 28(1)2023 Jan 03.
Article in English | MEDLINE | ID: mdl-36615610

ABSTRACT

Antimicrobial resistance (AMR) has arisen as a global concern in recent decades. Plant extracts used in combination with antibiotics are promising against AMR, synergistically. The purpose of this study was to evaluate the component of the bitter ginger (Zingiber zerumbet) extract in different solvents using high-performance liquid chromatography (HPLC), in addition to evaluate the antibacterial activity of these extracts, in combination with their antibiotic potential against four multi-drug resistant (MDR) bacterial strains (Lactobacillus acidophilus, Streptococcus mutans, Enterococcus faecalis and Staphylococcus aureus). Ethanol and the aqueous extracts of bitter ginger were prepared using a conventional solvent extraction method and were evaluated for their phytochemistry using HPLC, qualitatively and quantitatively. Moreover, the antibiotic susceptibility of the pathogenic isolates was determined. A disc diffusion assay was used to obtain the antimicrobial potential of the extracts alone and with antibiotics. Eight components were identified from the separation of the bitter ginger extract by HPLC. For AMR bacteria, the combination of the antibiotic solution with the bitter ginger crude extracts could improve its susceptibility of these antibiotics. This study indicates that the combination of an antibiotic solution with the bitter ginger crude extract exhibits potent antibacterial activities against MDR bacterial strains. Therefore, they can be used for the treatment of various diseases against the microbial pathogen and can be incorporated into medication for antibacterial therapy.


Subject(s)
Anti-Infective Agents , Zingiberaceae , Microbial Sensitivity Tests , Plant Extracts/chemistry , Zingiberaceae/chemistry , Anti-Bacterial Agents/chemistry , Solvents , Phytochemicals/pharmacology , Lactobacillus acidophilus
10.
Molecules ; 28(7)2023 Apr 06.
Article in English | MEDLINE | ID: mdl-37050042

ABSTRACT

In this review, we describe and discuss the phytoconstituents present in Hedychium species and emphasize their potential as drug candidates. Though they are widely validated in vitro and in vivo models, to date, no efforts have been made to compile in a single review all the pharmacologically active phytoconstituents from Hedychium species, and their pharmacological and toxicity profile. In this study, we present a reinvestigation of the chemical constituents present in Hedychium species obtained from the essential oil and solvent extraction of the flowers, leaves and rhizomes under consideration. Key databases such as PubMed, Science Direct, Scopus, and Google Scholar amongst others were probed for a systematic search using keywords to retrieve relevant publications on this plant. An exhaustive electronic survey of the related literature on Hedychium species resulted in around 200 articles. Articles published between the years 1975-2021 were included. The studies conducted on either crude extracts, solvent fractions or isolated pure compounds from Hedychium species reported with a varied range of biological effects such as anti-inflammatory, analgesic, antidiabetic, potentially anti-asthmatic, and cytotoxic, among other related activities of the chemical constituents present in its essential oil and solvent extract deployed in this review. Traditional and herbal medication around the world that uses different parts of Hedychium species were considered for anti-inflammatory, skincare, analgesic, anti-asthmatic, anti-diabetic, antidotal uses, among others. These uses support the idea that chemical constituents obtained from solvent extraction may also exert the same action individually or in a synergistic manner. The review concluded that there is scope for computation and biological study to find out possible new targets for strengthening the potency and selectivity of the relevant compounds, and to find a commercial method for extraction of active pharmaceutical ingredients.


Subject(s)
Oils, Volatile , Zingiberaceae , Ethnopharmacology , Phytotherapy , Zingiberaceae/chemistry , Plant Extracts/chemistry , Analgesics , Anti-Inflammatory Agents , Oils, Volatile/pharmacology , Anti-Inflammatory Agents, Non-Steroidal , Phytochemicals/chemistry
11.
Molecules ; 28(10)2023 May 11.
Article in English | MEDLINE | ID: mdl-37241765

ABSTRACT

An increase in life expectancy leads to a greater impact of chronic non-communicable diseases. This is even more remarkable in elder populations, to whom these become main determinants of health status, affecting mental and physical health, quality of life, and autonomy. Disease appearance is closely related to the levels of cellular oxidation, pointing out the importance of including foods in one's diet that can prevent oxidative stress. Previous studies and clinical data suggest that some plant-based products can slow and reduce the cellular degradation associated with aging and age-related diseases. Many plants from one family present several applications that range from the food to the pharmaceutical industry due to their characteristic flavor and scents. The Zingiberaceae family, which includes cardamom, turmeric, and ginger, has bioactive compounds with antioxidant activities. They also have anti-inflammatory, antimicrobial, anticancer, and antiemetic activities and properties that help prevent cardiovascular and neurodegenerative diseases. These products are abundant sources of chemical substances, such as alkaloids, carbohydrates, proteins, phenolic acids, flavonoids, and diarylheptanoids. The main bioactive compounds found in this family (cardamom, turmeric, and ginger) are 1,8-cineole, α-terpinyl acetate, ß-turmerone, and α-zingiberene. The present review gathers evidence surrounding the effects of dietary intake of extracts of the Zingiberaceae family and their underlying mechanisms of action. These extracts could be an adjuvant treatment for oxidative-stress-related pathologies. However, the bioavailability of these compounds needs to be optimized, and further research is needed to determine appropriate concentrations and their antioxidant effects in the body.


Subject(s)
Elettaria , Zingiber officinale , Zingiberaceae , Zingiberaceae/chemistry , Antioxidants/pharmacology , Antioxidants/metabolism , Zingiber officinale/chemistry , Curcuma/chemistry , Quality of Life , Plant Extracts/chemistry
12.
Pharm Biol ; 61(1): 590-597, 2023 Dec.
Article in English | MEDLINE | ID: mdl-36994846

ABSTRACT

CONTEXT: Attempts are ongoing to develop medications to fight against the COVID-19 pandemic. Our previous study revealed the in vitro anti-SARS-CoV-2 activity of fingerroot [Boesenbergia rotunda (L.) Mansf. (Zingiberaceae)] and its phytochemical, panduratin A. OBJECTIVE: To investigate the pharmacokinetic profiles of panduratin A as a pure compound and in a fingerroot extract formulation in beagle dogs. MATERIALS AND METHODS: A total of 12 healthy dogs were randomly divided into three groups, a single dose of 1 mg/kg panduratin A by intravenous and multiple doses of 5 and 10 mg/kg panduratin A fingerroot extract formulation by oral administration for seven consecutive days. The plasma concentration of panduratin A was determined by LCMS. RESULTS: The peak concentrations of a single dose of 5 and 10 mg/kg panduratin A fingerroot extract formulation were 12,416 ± 2,326 and 26,319 ± 8,221 µg/L, respectively. Increasing the oral dose of fingerroot extract formulation, equivalent to panduratin A 5-10 mg/kg, showed dose proportionality, with an approximately 2-fold increase in Cmax and AUC. The absolute oral bioavailability of panduratin A in the fingerroot extract formulation was approximately 7-9%. The majority of panduratin A was biotransformed into several products via oxidation and glucuronidation, and predominantly excreted via the faecal route. CONCLUSION: The oral formulation of fingerroot extract was safe in beagle dogs, and increasing dose showed dose proportionality in terms of the systemic exposure of panduratin A. This information will support the phytopharmaceutical product development of fingerroot extract against the COVID-19 pandemic.


Subject(s)
COVID-19 , Zingiberaceae , Dogs , Animals , Humans , Biological Availability , Pandemics , Zingiberaceae/chemistry , Administration, Oral , Plant Extracts , Metabolic Networks and Pathways
13.
J Nat Prod ; 85(7): 1691-1696, 2022 07 22.
Article in English | MEDLINE | ID: mdl-35790346

ABSTRACT

The labdane diterpene hedychenone, isolated from Hedychium spicatum, is an example of a furan-containing natural product. Herein, a new and efficient method for the synthesis of 19 new thio analogues of hedychenone is reported. The present methodology exhibits a broad substrate scope with good to excellent yields without metal or base under mild reaction conditions. The natural compound 1 and four semisynthetic derivatives (3a, 3b, 3i, and 3j) exhibited strong α-glucosidase inhibition activity with IC50 values of 15.93 ± 0.29, 9.70 ± 0.33, 11.82 ± 0.06, 12.23 ± 0.33, and 12.15 ± 0.14 µg/mL, respectively. In addition, compound 3e (6.0 ± 0.04 mm; zone of inhibition) displayed antibacterial activity against Staphylococcus aureus. This study increases the chemical diversity of bioactive hedychenone derivatives and provides a direction for the development of antidiabetic agents.


Subject(s)
Diterpenes , Zingiberaceae , Diterpenes/chemistry , Hypoglycemic Agents/pharmacology , Molecular Structure , Sulfur , Zingiberaceae/chemistry
14.
An Acad Bras Cienc ; 94(3): e20210932, 2022.
Article in English | MEDLINE | ID: mdl-35920490

ABSTRACT

The aim of present study was to evaluate chemical composition and different biological activities viz., pharmacological and antioxidant activities of essential oils. The chemical composition of essential oils was determined by gas chromatography/mass spectrometry while biological activities were evaluated by standard protocols. Essential oils of Hedychium spicatum Sm. from two different ecological niches viz; Nainital (Site-I) and Himachal Pradesh (Site-II) of India revealed the qualitative and quantitative chemo-diversity. Both the oils were dominated by oxygenated terpenoids. Major marker compounds identified were eucalyptol, camphor, linalool, α-eudesmol, 10-epi-γ-eudesmol, and iso-borneol. Both the oils exhibited anti-inflammatory activity suppressing 17.60 % to 33.57 % inflammation at 100mg/kg b. wt. dose levels compared to ibuprofen-treated group (40.06 %). The sub-acute inflammation in oils-treated mice groups (50 and 100 mg/kg b. wt.) increased on day 2 but showed a gradual decrease from day 3 onwards and then recovered to normal by day 10. The antinociception percentage for doses (50 and 100 mg/kg b. wt.) ranged from 33.70-40.46 % in Site-I and 30.34-42.39 % in Site-II compared to standard drug, ibuprofen (43.08 %). The oils also showed a good antipyretic effect by suppressing Brewer's yeast (Saccharomyces cerevisiae) induced pyrexia after oil dose injection. The oils also exhibited good antioxidant activity.


Subject(s)
Ibuprofen/chemistry , Oils, Volatile , Zingiberaceae , Animals , Antifungal Agents/pharmacology , Antioxidants/analysis , Camphor/analysis , Camphor/pharmacology , Eucalyptol/analysis , Ibuprofen/analysis , Ibuprofen/pharmacology , Inflammation , Mice , Oils, Volatile/chemistry , Plant Oils/chemistry , Rhizome/chemistry , Zingiberaceae/chemistry
15.
Phytochem Anal ; 33(1): 57-71, 2022 Jan.
Article in English | MEDLINE | ID: mdl-34056774

ABSTRACT

INTRODUCTION: Zingiber montanum (J.Koenig) Link ex A.Dietr. is a popular medicinal plant in Thailand. Its rhizomes have been used as an ingredient in various Thai traditional medicine formulas. While many reports have focused on the chemical constituents and biological activities of this plant, a comprehensive study on secondary metabolite profiling using tandem mass spectrometry has, to this point, never been documented. OBJECTIVE: To analyze the chemical constituents in Z. montanum rhizomes using ultra-high performance liquid chromatography coupled with ultra-high-resolution electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-HR-ESI-QTOF-MS/MS) analyses and to utilize the characteristic fragmentation patterns of these compounds to facilitate their identification. METHODOLOGY: UHPLC-HR-ESI-QTOF-MS/MS in positive ion mode was used for chemical identification of secondary metabolites from the ethanolic extract of the plant material. MS/MS data of some known reference compounds, together with detailed fragmentation pattern information of several compounds obtained from the crude extract, were used to elucidate their chemical structures. RESULTS: In this work, one benzaldehyde, ten phenylbutenoid monomers, six curcuminoids, and nine phenylbutenoid dimers were assigned based on their characteristic fragment ions. Among these compounds, 2-(3,4-dimethoxystyryl)oxirane was tentatively suggested as a potential new compound. Several characteristic fragment ions from these compounds were assigned and the relative ion abundance of these was also used to differentiate the chemical structures of compounds having the same molecular mass. CONCLUSIONS: The results will benefit future high-throughput screening of bioactive compounds and method development for the quality control of raw materials and herbal drugs derived from Z. montanum rhizome extracts.


Subject(s)
Plant Extracts/chemistry , Rhizome , Zingiberaceae/chemistry , Chromatography, High Pressure Liquid , Rhizome/chemistry , Spectrometry, Mass, Electrospray Ionization , Tandem Mass Spectrometry
16.
Phytochem Anal ; 33(5): 670-677, 2022 Jul.
Article in English | MEDLINE | ID: mdl-35303761

ABSTRACT

INTRODUCTION: Kaempferia parviflora or black ginger is abundantly cultivated because its rhizomes contain methoxyflavones that have many pharmacological properties. K. parviflora can be divided into two types, based on morphological characteristics, but differences in their chemical compositions have never been explored. OBJECTIVES: This research aims to find chemical markers that can be used to differentiate between the two types of K. parviflora, the red-leaf and green-leaf types, by quantifying the amounts of methoxyflavones. MATERIAL AND METHODS: K. parviflora samples were collected from 39 locations in Thailand. Their genetic diversity was assessed by a genotyping-by-sequencing (GBS) technique to construct the population structure. Their chemical compositions were analyzed by high performance liquid chromatography-photodiode array detection to determine the methoxyflavone contents. RESULTS: The population structure based on >3,000 single nucleotide polymorphism (SNP) markers showed that the samples can be divided into two groups, which were consistent with the classification by leaf margin color (red-leaf and green-leaf types). HPLC analysis revealed 3,5,7,3',4'-pentamethoxyflavone (PMF), 5,7-dimethoxyflavone (DMF), 5,7,4'-trimethoxyflavone (TMF), 3,5,7-trimethoxyflavone and 3,5,7,4'-tetramethoxyflavone as major methoxyflavones that can be used as chemical markers. The red-leaf type showed higher amounts of PMF, TMF and 3,5,7,4'-tetramethoxyflavone than the green-leaf type, while the green-leaf type showed higher amounts of DMF and 3,5,7-trimethoxyflavone than the red-leaf type. CONCLUSION: These results provide another approach to discriminate the two types of K. parviflora using chemical profiles alongside genetic and morphological analyses. Therefore, a specific type of K. parviflora can be selected over the other based on preferences for a certain methoxyflavone.


Subject(s)
Zingiberaceae , Chromatography, High Pressure Liquid , Plant Extracts/chemistry , Rhizome/chemistry , Zingiberaceae/chemistry , Zingiberaceae/genetics
17.
J Asian Nat Prod Res ; 24(2): 146-152, 2022 Feb.
Article in English | MEDLINE | ID: mdl-33565351

ABSTRACT

Three new compounds, i.e. stenophyllols A-C (1-3), were isolated from the rhizome of Boesenbergia stenophylla. The structures were determined by spectroscopic analysis (UV, IR, NMR and HRESIMS). In-vitro neuroblastoma cell viability assay showed stenophyllol A (1) was able to reduce the N2A cell viability to 20% within 24 h.


Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Zingiberaceae , Animals , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Cell Survival , Mice , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Extracts , Rhizome/chemistry , Zingiberaceae/chemistry
18.
Molecules ; 27(9)2022 Apr 29.
Article in English | MEDLINE | ID: mdl-35566177

ABSTRACT

Plant of the genus Zingiber (Zingiberaceae) have primarily distributed in subtropical and tropical Asia, South America and Africa. The species of this genus have been widely used as food and in folk with a long history for treating various diseases. Reports related to the phytochemistry and phytochemistry of Zingiber species are numerous, but articles on the summary of the genus Zingiber remain scarce. This review aims at presenting comprehensive information about the genus Zingiber and providing a reference for the future application by systematically reviewing the literature from 1981 to 2020. Currently, a total of 447 phytochemical constituents have been isolated and identified from this genus, in which volatile oils, diarylheptanoids, gingerols, flavonoids and terpenoids are the major components. Gingerols, which are the main functional components, are the spicy and aromatic ingredients in the Zingiber species. Extracts and single compounds from Zingiber plants have been discovered to possess numerous biological functions, such as anti-inflammatory, anticancer, antimicrobial, larvicidal, antioxidant and hypoglycemic activities. This review provides new insights into the ethnomedicine, phytochemistry and pharmacology of the genus Zingiber and brings to the forefront key findings on the functional components of this genus in food and pharmaceutical industries.


Subject(s)
Medicine, Traditional , Zingiberaceae , Ethnopharmacology , Phytochemicals/chemistry , Phytotherapy , Plant Extracts/chemistry , Plant Extracts/pharmacology , Zingiberaceae/chemistry
19.
Molecules ; 27(11)2022 May 27.
Article in English | MEDLINE | ID: mdl-35684405

ABSTRACT

Essential oils of plants have been used widely in cosmetic preparations. Being both perfuming and active ingredients, the functions of essential oils mean they are high-value ingredients. In this study, the leaf of Etlingera elatior (Jack) or Torch ginger was used. The essential oils (EO) were prepared by conventional hydrodistillation (HD) and microwave-assisted hydrodistillation (MAHD). The volatile compounds of EOs were analyzed by gas chromatography spectroscopy (GC-MS). The antioxidant activities by means of DPPH radical scavenging and ferric-reducing antioxidant power (FRAP) were determined. The inhibition of tyrosinase activity was investigated. The cytotoxicity was performed against human fibroblast cell lines (NIH/3T3) and melanoma cell lines (A375 and B16F10). The decreasing melanin content was measured in melanoma cell lines. The resulting essential oils were detected for 41 compounds from HD extraction dominants by terpenes, namely sesquiterpenes (48.499%) and monoterpenes (19.419%), while 26 compounds were detected from MAHD with the fatty alcohols as the major group. The higher antioxidant activities were found in HD EO (IC50 of 16.25 ± 0.09 mg/mL from DPPH assay and 0.91 ± 0.01 mg TEAC/g extract from FRAP assay). The survival of normal fibroblast cell lines remained at 90% at 500 µg/mL HD EO, where the EO possessed the half-maximal toxicity dose (TD50) of 214.85 ± 4.647 and 241.128 ± 2.134 µg/mL on B16F10 and A375 cell lines, respectively. This could suggest that the EO is highly selective against the melanoma cell lines. The melanin content was decreased at the half-maximum efficacy (IC50) at 252.12 ± 3.02 and 253.56 ± 3.65 in the A375 and B1610 cell lines, respectively, which were approximately 2.8-fold lower than kojic acid, the standard compound. The results of this study evidence the use of Etlingera elatior (Jack) leaf as a source of essential oil as an active agent in cosmetics.


Subject(s)
Monophenol Monooxygenase , Oils, Volatile , Zingiberaceae , Animals , Antioxidants/chemistry , Cell Line, Tumor , Humans , Melanins , Melanoma, Experimental , Mice , Monophenol Monooxygenase/antagonists & inhibitors , NIH 3T3 Cells , Oils, Volatile/chemistry , Plant Leaves/chemistry , Zingiberaceae/chemistry
20.
Molecules ; 27(13)2022 Jun 29.
Article in English | MEDLINE | ID: mdl-35807408

ABSTRACT

The major bioactive components of Kaempferia parviflora (KP) rhizomes, 3,5,7,3',4'-pentamethoxyflavone (PMF), 5,7-dimethoxyflavone (DMF), and 5,7,4'-trimethoxyflavone (TMF), were chosen as the quantitative and qualitative markers for this plant material. In order to extract bioactive components (total methoxyflavones) from KP rhizomes, ultrasound-assisted extraction (UAE) was proposed as part of this study. Plackett-Burman design (PBD) and Box-Behnken design (BBD) were utilized to optimize the effects of UAE on extraction yields and total methoxyflavone contents in KP rhizomes. First, PBD was utilized to determine the effect of five independent variables on total yields and total methoxyflavone contents. The results indicated that the concentration of the extracting solvent (ethanol), the extraction time, and the ratio of solvent to solid were significant independent terms. Subsequently, BBD with three-level factorial experiments was used to optimize the crucial variables. It was discovered that the concentration of ethanol was the most influential variable on yields and total methoxyflavone contents. Optimum conditions for extraction yield were ethanol concentration (54.24% v/v), extraction time (25.25 min), and solvent-to-solid ratio (49.63 mL/g), while optimum conditions for total methoxyflavone content were ethanol concentration (95.00% v/v), extraction time (15.99 min), and solvent-to-solid ratio (50.00 mL/g). The relationship between the experimental and theoretical values was perfect, which proved that the regression models used were correct and that PBD and BBD were used to optimize the conditions in the UAE to obtain the highest yield and total methoxyflavone content in the KP rhizomes.


Subject(s)
Flavones , Plant Extracts , Ultrasonics , Zingiberaceae , Chromatography, High Pressure Liquid/methods , Flavones/chemistry , Flavones/isolation & purification , Plant Extracts/chemistry , Rhizome/chemistry , Thailand , Ultrasonics/methods , Zingiberaceae/chemistry
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