1.Systematic identification of chemical forms of key terpene synthase in Cinnamomum camphora.
Qing MA ; Rui MA ; Ping SU ; Ye SHEN ; Mei-Lan CHEN ; Bao-Long JIN ; Shao-Lin OUYANG ; Juan GUO ; Guang-Hong CUI ; Lu-Qi HUANG
China Journal of Chinese Materia Medica 2023;48(9):2307-2315
Cinnamomum camphora is an important economic tree species in China. According to the type and content of main components in the volatile oil of leaf, C. camphora were divided into five chemotypes, including borneol-type, camphor-type, linalool-type, cineole-type, and nerolidol-type. Terpene synthase(TPS) is the key enzyme for the formation of these compounds. Although several key enzyme genes have been identified, the biosynthetic pathway of(+)-borneol, which has the most economic value, has not been reported. In this study, nine terpenoid synthase genes CcTPS1-CcTPS9 were cloned through transcriptome analysis of four chemical-type leaves. After the recombinant protein was induced by Escherichia coli, geranyl pyrophosphate(GPP) and farnesyl pyrophosphate(FPP) were used as substrates for enzymatic reaction, respectively. Both CcTPS1 and CcTPS9 could catalyze GPP to produce bornyl pyrophosphate, which could be hydrolyzed by phosphohydrolase to obtain(+)-borneol, and the product of(+)-borneol accounted for 0.4% and 89.3%, respectively. Both CcTPS3 and CcTPS6 could catalyze GPP to generate a single product linalool, and CcTPS6 could also react with FPP to generate nerolidol. CcTPS8 reacted with GPP to produce 1,8-cineol(30.71%). Nine terpene synthases produced 9 monoterpene and 6 sesquiterpenes. The study has identified the key enzyme genes responsible for borneol biosynthesis in C. camphora for the first time, laying a foundation for further elucidating the molecular mechanism of chemical type formation and cultivating new varieties of borneol with high yield by using bioengineering technology.
Cinnamomum camphora/enzymology*
;
Alkyl and Aryl Transferases/chemistry*
2.Chemical constituents of Lindera aggregata and their bioactivities: a review.
Fang-You CHEN ; Yang LIU ; Dan XIE ; Yong-Ming LUO
China Journal of Chinese Materia Medica 2023;48(21):5719-5726
The medicinal Lindera aggregata(Lindera, Lauraceae) boasts abundant resources, which is widely used in clinical settings. It has been found that the main chemical constituents of this medicinal species are sesquiterpenoids, alkaloids, sesquiterpenoid dimers, flavonoids, and phenolic acids. Some unreported novel structures, including lindenane-type sesquiterpene dimers and trimers, have been discovered from L. aggregata in recent years. The extracts and active components of L. aggregata have anti-tumor, anti-inflammatory, antalgic, liver-protecting, antioxidant, lipid-lowering, and glucose-lowering activities, and their mechanisms of action have been comprehensively investigated. This study summarizes the research on the chemical constituents and bioactivities of L. aggregata over the past decade, which is expected to serve as a reference for the future research and utilization of L. aggregata.
Lindera/chemistry*
;
Alkaloids
;
Flavonoids
;
Antioxidants
;
Sesquiterpenes/chemistry*
3.Mechanism of Linderae Radix against gastric cancer based on network pharmacology and in vitro experimental validation.
Xiao LIANG ; Jun-Hao ZHANG ; Hao-Tian BAI ; Ya-Lan LI ; Shu-Hui SUN ; Qian-Qian ZHANG ; Jing YANG ; Rui WANG
China Journal of Chinese Materia Medica 2022;47(18):5008-5021
The present study explored the main active ingredients and the underlying mechanism of Linderae Radix the treatment of gastric cancer by network pharmacology, molecular docking, and in vitro cell experiments. TCMSP, OMIM and GeneCards database were used to obtain the active ingredients of Linderae Radix to predict the related targets of both Linderae Radix and gastric cancer. After screening the common potential action targets, the STRING database was used to construct the PPI network for protein interaction of the two common targets. Enrichment analysis of GO and KEGG by DAVID database. Based on STRING and DAVID platform data, Cytoscape software was used to construct an "active ingredient-target" network and an "active ingredient-target-pathway" network. Molecular docking was performed using the AutoDock Vina to predict the binding of the active components to the key action targets, and finally the key targets and pathways were verified in vitro. According to the prediction results, there were 9 active components, 179 related targets of Radix Linderae, 107 common targets of Linderae Radix and gastric cancer, 693 biological processes, 57 cell compositions, and 129 molecular functions involved in the targets, and 161 signaling pathways involved in tumor antigen p53, hypoxia-indu-cible factor 1, etc. Molecular docking results showed that the core component, jimadone, had high binding activity with TP53. Finally, in an in vitro experiment, the screened radix linderae active ingredient gemmadone is used for preliminarily verifying the core targets and pathways of the human gastric cancer cell SGC-7901, The results showed that germacrone could significantly inhibit the proliferation of gastric cancer cells and induce the apoptosis of SGC-7901 by regulating the expression of p53, Bax, Bcl-2 and other key proteins. In summary, Radix Linderae can control the occurrence and development of gastric cancer through multi-components, multi-targets and multi-pathways, which will provide theoretical basis for further clinical discussion on the mechanism of Radix Linderae in treating gastric cancer.
Antigens, Neoplasm
;
Drugs, Chinese Herbal/therapeutic use*
;
Humans
;
Lindera/chemistry*
;
Medicine, Chinese Traditional
;
Molecular Docking Simulation
;
Network Pharmacology
;
Stomach Neoplasms/drug therapy*
;
Tumor Suppressor Protein p53
;
bcl-2-Associated X Protein
4.Diverse sesquiterpenoids from Litsea lancilimba Merr. with potential neuroprotective effects against H2O2-induced SH-SY5Y cell injury.
Yi-Jie ZHANG ; Ming BAI ; Jia-Yi LI ; Shu-Yan QIN ; Yu-Yang LIU ; Xiao-Xiao HUANG ; Jiang ZHENG ; Shao-Jiang SONG
Chinese Journal of Natural Medicines (English Ed.) 2022;20(9):701-711
Five undescribed sesquiterpenoids (1-5), and nine known sesquiterpenoids (6-14) were obtained from the fruits of Litsea lancilimba Merr. by LC-MS/MS molecular networking strategies. Litsemene A (1) possessed a unique 8-member ring through unexpected cyclization of the methyl group on C-10 of guaiane. Their structures were elucidated by spectroscopic techniques including IR, UV, NMR, HR-ESI-MS, and their absolute configurations were assigned by ECD calculations. All isolated sesquiterpenoids were analyzed by bioinformatics and evaluated for their neuroprotective effects against H2O2-induced injury in human neuroblastoma SH-SY5Y cells.
Chromatography, Liquid
;
Humans
;
Hydrogen Peroxide/toxicity*
;
Litsea
;
Molecular Structure
;
Neuroblastoma/drug therapy*
;
Neuroprotective Agents/pharmacology*
;
Sesquiterpenes/chemistry*
;
Tandem Mass Spectrometry
5.Improvement in compatibility of hot melt pressure-sensitive adhesive with cinnamon volatile oil and in vitro transdermal property by physical blending.
Shuo YIN ; Tan WU ; Jian-Ying LU ; Zhen-da LIU ; Teng GUO ; Nian-Ping FENG
China Journal of Chinese Materia Medica 2021;46(21):5650-5657
Hot melt pressure-sensitive adhesive(HMPSA) has broad application potential in the field of traditional Chinese medicine(TCM) plasters due to its high drug loading, weak skin irritation, satisfactory adhesion, etc. compared with rubber plasters.However, the structure of HMPSA is prone to suffer from the damage caused by volatile oils in TCM plasters. In view of this, a kind of HMPSA with a stable structure was prepared by physical blending of DINCH, polypropylene wax and liquid rubber(LIR) in the present study, which is denoted as DPL. The dosage of cinnamon volatile oil(CVO), the model drug, was selected with viscosity, softening point and cohesion as evaluation indexes. The interaction between DPL and HMPSA was investigated by Fourier transform infrared spectroscopy(FT-IR) and differential scanning calorimetry(DSC). The compatibility of HMPSA with CVO and its transdermal ability were studied by in vitro transdermal test, adhesion, scanning electron microscopy( SEM) and rheological evaluation. The results showed that 5% CVO began to damage the structure of HMPSA. The initial adhesion and holding adhesion of DPL-modified HMPSA(DPL-HMPSA) were not significantly changed compared with those of HMPSA, whereas the 180° peel strength was decreased. FI-IR unraveled that DPL formed the n-π conjugated system with styrene-isoprene-styrene block copolymer(SIS), and there was no significant difference in the glass transition temperature according to DSC results, which indicated the good compatibility of DPL with HMPSA. With 5% CVO loaded, the drug content of DPL-HMPSA was 1. 14 times higher than that of HMPSA, and the decrease rate of drug content in DPL-HMPSA was 16% lower than that in HMPSA after 3 months. SEM demonstrated that CVO did not cause obvious structural damage to DPL-HMPSA. Rheological evaluation revealed that the storage modulus and loss factor of DPL-HMPSA were higher than those of HMPSA, and the cohesion was also stronger. The percutaneous penetration rate of cinnamaldehyde in DPL-HMPSA was 2. 25 times that of HMPSA. In conclusion, DPL-HMPSA had more stable structure, better compatibility with CVO, and higher in vitro transdermal efficiency of cinnamaldehyde than before the modification. This study can provide reference for the mitigation of the matrix structure damage caused by volatile oil components in TCM plasters and the enhancement of the content and in vitro transdermal rate of drug.
Adhesives
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Administration, Cutaneous
;
Cinnamomum zeylanicum
;
Oils, Volatile
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Spectroscopy, Fourier Transform Infrared
6.Chemical constituents from the leaves of Cinnamomum camphora var. linaloolifera and their anti-inflammatory activities.
Mei-Ting WU ; Shi-Yao LIU ; Da-Long HUANG ; Li-Na HE ; Mao GUO ; Lin NI ; Shuang-Quan ZOU
China Journal of Chinese Materia Medica 2021;46(14):3592-3598
Thirteen compounds were isolated and purified from the leaves of Cinnamomum camphora by the macroporous resin,silica gel,and Sephadex LH-20 column chromatographies. Those compounds were further identified by IR,UV,MS,and NMR techniques:( 2 S)-1-( 3″,4″-methylenedioxy phenyl)-3-( 2',6'-dimethoxy-4'-hydroxyphenyl)-propan-2-ol( 1),( 2 R,3 R)-5,7-dimethoxy-3',4'-methylenedioxy flavanol( 2),9-hydroxysesamin( 3),sesamin( 4),piperitol( 5),kobusin( 6),(-)-aptosimon( 7),acuminatolide( 8),1β,11-dihydroxy-5-eudesmene( 9),lasiodiplodin( 10),vanillin( 11),p-hydroxybenzaldehyde( 12),and p-hydroxybenzoic acid ethyl ester( 13). Compound 1 was a novel compound,and compounds 2,6,7,9 and 10 were isolated from Cinnamomum plants for the first time. Compounds 4,7 and 10 were found to possess good inhibitory effect on IL-6 production in LPS-induced BV2 cells at a concentration of 20 μmol·L-1 in the in vitro bioassay,with inhibition rates of 51. 26% ± 4. 13%,67. 82% ± 3. 77% and85. 81%±1. 19%,respectively.
Anti-Inflammatory Agents/pharmacology*
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Cinnamomum
;
Cinnamomum camphora
;
Plant Leaves
7.Effects of drought stress on physiological and biochemical and chemical components of Cinnamomum cassia seedlings.
Lei ZHONG ; Pei-Ran LIAO ; Chang-Zheng LIU ; Jia-Ping QIAN ; Wan-Cong HE ; Bi LUO ; Quan YANG
China Journal of Chinese Materia Medica 2021;46(9):2158-2166
Six month old Cinnamomum cassia seedlings were used to simulate drought stress with polyethylene glycol(PEG 6000). The physiological indicators(osmotic substances, antioxidant enzymes, etc.) and chemical components of seedlings under different drought levels and the correlation between the two were studied. The results showed that the chlorophyll content and relative water content decreased gradually with the increase of PGE 6000(0, 5%, 10%, 15%) concentration and time(3, 5, 7 d), while the soluble protein content, soluble sugar content and catalase(CAT) activity increased, but the rising rate slowed down with the time. The activities of peroxidase(POD), superoxide dismutase(SOD), malondialdehyde(MDA) and proline content increased at first and then decreased. The content of coumarin, cinnamaldehyde, cinnamic acid and dimethoxycinnamaldehyde decreased, while the content of cinnamyl alcohol continued to increase.Under drought stress, the fluorescence signals of reactive oxygen species and no contents in roots of C. cassia seedlings were significantly stronger than those of the control.Further correlation analysis showed that coumarin content, di-methoxycinnamaldehyde content and osmoregulation substance content were significantly negatively correlated(P<0.05), cinnamic acid content was significantly negatively correlated with POD and SOD activities(P<0.01).It was found that C. cassia seedlings showed a certain degree of drought tolerance under short-term or mild drought stress, but if the drought exceeded a certain degree, the physiological metabolism of the seedlings would be unbalanced.
Catalase
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Cinnamomum aromaticum
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Droughts
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Malondialdehyde
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Seedlings
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Stress, Physiological
;
Superoxide Dismutase
8.Bioactive sesquineolignans from the twigs of Litsea cubeba.
Huan XIA ; Gui-Yang XIA ; Ling-Yan WANG ; Min WANG ; Ya-Nan WANG ; Peng-Cheng LIN ; Sheng LIN
Chinese Journal of Natural Medicines (English Ed.) 2021;19(10):796-800
In a continuing search for biological natural products with structure diversity from traditional Chinese herbs, five new sesquineolignans (1-5) were isolated from an ethyl acetate extract of the twigs of Litsea cubeba. Their structures were elucidated based on MS, 1D and 2D NMR spectroscopic data, as well as experimental electronic circular dichroism (ECD) spectra. Compounds 1-5 showed moderate inhibitory effects against LPS-induced NO production in RAW264.7 macrophages, with IC
Litsea
;
Macrophages
;
Molecular Structure
9.Advances in quality research of Cinnamomum cassia.
Ya-Ling YANG ; Bi LUO ; Hong ZHANG ; Wen-Jun ZHENG ; Miao-Li WU ; Shao-Ying LI ; Hong-Yang GAO ; Qing LI ; Yue-Wei GE ; Quan YANG
China Journal of Chinese Materia Medica 2020;45(12):2792-2799
Cinnamomum cassis is one of the commonly used traditional Chinese medicines in China. Its genuine producing areas distribute in Guangdong and Guangxi provinces. As an important edible herb and export variety of China, the quality control and internationalization of quality standards of C. cassis is extremely significant. In the recent years, with the development of the cinnamon industry, relevant academic research and the upgrade of the international standards, it is necessary to summarize the quality-related progress of C. cassis. In the present review, the germplasm resources, specific quality marker(Q-marker) and quality standards of C. cassis were summarized on the basis of published research during the last 10 years.
China
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Cinnamomum
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Cinnamomum aromaticum
;
Cinnamomum zeylanicum
;
Medicine, Chinese Traditional
10.Banana anaphylaxis in Thailand: case series
Ratchataporn THONGKHOM ; Supa ONCHAM ; Mongkhon SOMPORNRATTANAPHAN ; Wannada LAISUAN
Asia Pacific Allergy 2020;10(1):4-
BACKGROUND: Banana fruit has been recognized as an important food allergen source. Nowadays banana hypersensitivity had been reported more frequently with various presentations from oral allergy syndrome to anaphylaxis.OBJECTIVE: This study aims to describe the pattern of banana hypersensitivity and the sensitivity of diagnostic test.METHODS: Six patients who experienced banana hypersensitivity were recruited from adult allergy clinic, Ramathibodi Hospital, Mahidol University between 2015–2018. Demographic data, pattern of banana allergy consisted of the onset of reaction, symptoms, severity, cross-reactivity to kiwi, avocado, latex including type and amount of banana were collected. Skin test, serum specific IgE to banana and open-label food challenge test had been applied.RESULTS: All patients experienced multiple episodes of banana anaphylaxis. Regarding the diagnostic investigation, prick-to-prick skin test had higher sensitivity (sensitivity, 100%; 95% confidence interval [CI], 54.07%–100%) than the commercial banana extract (sensitivity, 83.33%; 95% CI, 35.88%–99.58%) and serum specific IgE to banana (sensitivity, 50%; 95% CI, 11.81%–88.19%). The discordance between skin prick test using commercial banana extract and skin test was reported. The cross-reactivity between the species of banana, kiwi, the avocado was documented in all patients. Latex skin prick test and application test were applied with negative results. From the oral food challenge test, a case of banana anaphylaxis patient can tolerate heated banana.CONCLUSION: The various phenotypes of banana hypersensitivity were identified. The prick-to-prick test showed the highest sensitivity for diagnosis of banana allergy. However, component resolved diagnostics might be needed for conclusive diagnosis.
Adult
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Anaphylaxis
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Diagnosis
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Diagnostic Tests, Routine
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Food Hypersensitivity
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Fruit
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Hot Temperature
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Humans
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Hypersensitivity
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Hypersensitivity, Immediate
;
Immunoglobulin E
;
Latex
;
Musa
;
Persea
;
Phenotype
;
Skin
;
Skin Tests
;
Thailand

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