1.Research progress in strigolactones and application prospect in medicinal plants.
Yi-Ying CAO ; Yu-Chao CHEN ; Sheng-Hu GUO ; Xiao-Yan GAN ; Li TIAN ; Lu-Qi HUANG ; Yuan YUAN
China Journal of Chinese Materia Medica 2023;48(12):3132-3139
Strigolactones(SLs) are a class of sesquiterpenoids derived from the carotenoid biosynthesis pathway with the core carbon skeleton consisting of tricyclic lactone(ABC tricyclic ring) and α,β-unsaturated furan ring(D ring). SLs are widely distributed in higher plants and are symbiotic signals between plants and Arbuscular mycorrhiza(AM), which play key roles in the evolution of plant colonizing terrestrial habitats. As a new type of plant hormone, SLs possess such important biological functions as inhibiting shoot branching(tillers), regulating root architecture, promoting secondary growth, and improving plant stress resistance. Therefore, SLs have attracted wide attention. The biological functions of SLs are not only closely related to the formation of "excellent shape and quality" of Chinese medicinal materials but also have important practical significance for the production of high-quality medicinal materials. However, SLs have been currently widely studied in model plants and crops such as Oryza sativa and Arabidopsis thaliana, and few related studies have been reported on SLs in medicinal plants, which need to be strengthened. This review focused on the latest research progress in the isolation and identification, biological and artificial synthesis pathways, biosynthesis sites and transport modes, signal transduction pathways and mechanisms, and biological functions of SLs, and prospected the research on the regulation mechanism of SLs in the growth and development of medicinal plants and their related application on targeted regulation of Chinese herbal medicine production, which is expected to provide some references for the in-depth research on SLs in the field of Chinese medicinal resources.
Arabidopsis
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Lactones
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Plants, Medicinal
2.New Meroterpenoids from a Penicillium sp. Fungus
Ji Yeon HWANG ; Min Jung YOU ; Dong Chan OH ; Ki Bong OH ; Jongheon SHIN
Natural Product Sciences 2018;24(4):253-258
Two meroterpenoids (1 and 2) along with twelve known compounds (3 – 14) were isolated from the culture broth of a Penicillium sp. fungus collected from Chuja-do, Korea. Based on the results of a combination of spectroscopic analyses, the new compounds, preaustinoids E (1) and F (2), were determined to be epimeric austin-type penta-cyclic lactones.
Fungi
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Korea
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Lactones
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Penicillium
3.Germacrene-derived sesquiterpene lactones:opportunities and challenges for biosynthesis.
Qiang ZHANG ; Dong-Mei XIE ; Lei ZHANG ; Guo-Kai WANG
China Journal of Chinese Materia Medica 2021;46(8):2020-2028
Sesquiterpene lactones are a kind of widely distributed natural organic compounds with anti-tumor, anti-malarial and other significant biological activities. Based on their carbocylic skeletons, sesquiterpene lactones are classified into germacranolide, guaia-nolide, xanthanolide, pseudo-guaianolide, elemonolide and eudesmanolide, etc. In recent years, with the development of various omics and synthetic biology technologies, the biosynthetic pathways of sesquiterpene lactone compounds of different structural types have gradually been resolved. Among them, the researches on germacrene-derived sesquiterpene lactones are relatively more than others. Therefore, this article focused on the germacrene-derived sesquiterpene lactone biosynthesis pathways and their key enzyme genes, which can lay the foundation for in-depth analysis of sesquiterpene lactone biosynthetic pathways, functional gene mining and heterologous synthesis of active ingredients.
Biosynthetic Pathways
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Lactones
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Sesquiterpenes
4.A new seco-prezizaane-type sesquiterpene lactone from stems and branches of Illicium ternstroemioides.
Jian-Pei ZHANG ; Wen-Rui LI ; Jin-Yao YONG ; Jia YANG ; Shuang-Gang MA
China Journal of Chinese Materia Medica 2021;46(22):5848-5852
Three seco-prezizaane-type sesquiterpene lactones, one phenylpropanoid, and two lignans were isolated from the 95% ethanol extract of stems and branches of Illicium ternstroemioides with silica gel column chromatography, ODS column chromatography, and preparative HPLC. Based on the spectral data, they were identified as burmanicumolide D(1), veranisatin A(2), veranisatin B(3), dihydroconiferylalcohol(4), pinoresinol(5),(-)-matairesinol(6), respectively. Among them, compound 1 was a new seco-prezizaane-type sesquiterpene lactone, and 2-6 were obtained from this plant for the first time. None of these compounds display antiviral or cytotoxic activities.
Antiviral Agents
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Illicium
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Lactones
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Molecular Structure
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Phytochemicals
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Sesquiterpenes
5.Cytotoxic Lactones from the Pericarps of Litsea japonica
Quynh Mai Thi NGO ; Thao Quyen CAO ; Mi Hee WOO ; Byung Sun MIN
Natural Product Sciences 2019;25(1):23-27
From the pericarps of Litsea japonica (Thunb.) Jussieu, eighteen butanolide derivatives (1 – 18) were evaluated for their cytotoxic activity against HeLa, HL-60, and MCF-7 cells. Compounds 1 – 9 with 2-alkylidene-3-hydroxy-4-methylbutanolides structure exhibited cytotoxic activities against cancer-cell lines. Among them, compound 8 (litsenolide D₂) exhibited the most potent cytotoxicity against the tested cell lines, including HeLa, HL-60, and MCF-7, with IC₅₀ values of 17.6 ± 1.3, 4.2 ± 0.2, and 12.8 ± 0.0 µM, respectively. Compound 8 induced apoptosis in a dose-dependent manner. Annexin V/Propidium Iodide (PI) double staining confirmed that 8 effectively induced apoptosis in MCF-7 cells. To the best of our knowledge, we have reported cytotoxic activity of butanolides from L. japonica against these cancer-cell lines for the first time.
Apoptosis
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Cell Line
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Lactones
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Lauraceae
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Litsea
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MCF-7 Cells
6.Two new diterpenoid lactones isolated from Andrographis paniculata.
Gui-Yang WANG ; Ting WEN ; Fei-Fei LIU ; Hai-Yan TIAN ; Chun-Lin FAN ; Xiao-Jun HUANG ; Wen-Cai YE ; Ying WANG
Chinese Journal of Natural Medicines (English Ed.) 2017;15(6):458-462
In the present study, two new diterpenoid lactones, 3-deoxy-andrographoside (1) and 14-deoxy-15-methoxy-andrographolide (2), were isolated from the aerial parts of Andrographis paniculata. Their structures were elucidated by combination of NMR, MS, and chemical methods. The configurations of 1 and 2 were established based on the analysis of ROESY data and single crystal X-ray diffraction experiment.
Andrographis
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chemistry
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Diterpenes
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chemistry
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isolation & purification
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Lactones
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chemistry
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isolation & purification
7.Advance in biosynthesis and metabolic regulation of ginkgolides.
China Journal of Chinese Materia Medica 2021;46(13):3288-3297
Ginkgolides,the unique terpenoids in Ginkgo biloba,have a significant effect on the prevention and treatment of cardiovascular and cerebrovascular diseases. Metabolic regulation and synthetic biology strategies are efficient methods to obtain high-quality ginkgolides. The present study reviewed the cloning and functions of genes related to the biosynthetic pathway of ginkgolides,as well as relevant studies of omics,genetic transformation,and metabolic regulation in recent years,and predicted the research trends and prospects,aiming to provide a reference for discovering the key genes related to the biosynthetic pathway and the biosynthesis of ginkgolides.
Ginkgo biloba/genetics*
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Ginkgolides
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Humans
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Lactones
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Plant Extracts
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Terpenes
8.Preparation and quality evaluation of orodispersible film containing ginkgolide B novel nanosuspension lyophilized powder.
Jing WANG ; Jun-Jun ZHU ; Bao-De SHEN ; Ting ZHANG ; Bo DAI ; Ya-Ning ZHU ; Hai-Long YUAN
China Journal of Chinese Materia Medica 2020;45(22):5504-5510
To prepare a new dosage form that can improve the drug loading of the film--ginkgolide B nanosuspension lyophilized powder orodispersible film(GB-NS-LP-ODF) and to evaluate its quality. Firstly, ginkgolide B nanosuspension(GB-NS) was prepared by media milling method, and then ginkgolide B nanosuspension lyophilized powder(GB-NS-LP) was prepared with freeze-drying method. The mannitol was used as lyoprotectant and its dosage was also investigated. GB-NS-LP-ODF was prepared by solvent casting method and its formulation was screened by single factor test method and optimized by orthogonal test. The appearance, mechanical properties, content uniformity and in vitro dissolution of the optimized GB-NS-LP-ODF were investigated. The particle size of prepared GB-NS was about 201 nm, and the optimal dosage of mannitol was 8%. According to the optimal formula, the GB-NS-LP-ODF was prepared with GB-NS-LP 35.6%, PVA 0588 49.4%, PEG 400 10.7% and CMS-Na 4.3%, and completely disintegrated in about 30 s, and the particle size of reconstituted GB nanoparticles from ODF was about 210 nm. The film with smooth appearance and good mechanical properties was stable within 30 days and the content uniformity(A+2.2 S<15) conformed to the regulations. Scanning electron microscope(SEM) showed that GB-NS-LP-ODFs were evenly distributed and the particle size was about 200 nm. X-rays diffraction(XRD) showed that its crystallinity was significantly lower than that of GB raw drug and GB-ODF. The results of in vitro release test showed that the drug film was completely dissoluted within 10 minutes. These results indicated that nanosuspension lyophilized powder was prepared by freeze drying of nanosuspensions, and then loaded into the orodispersible film to effectively increase the drug loading of the ODF and have broad application prospects.
Ginkgolides
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Lactones
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Nanoparticles
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Particle Size
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Powders
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Solubility
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Suspensions
9.Optimized preparation of ginkgolides A and B long-circulating solid lipid nanoparticles by central composite design and response surface method.
Min LIU ; Jian-hai CHEN ; Fu-rong DONG ; Yuan LIU
Journal of Southern Medical University 2008;28(5):700-703
OBJECTIVETo optimize the formulation of long-circulating solid lipid nanoparticles (LSLN) carrying ginkgolides A and B (GAB) extracted from traditional Chinese medicinal herbs.
METHODSGAB-LSLN was prepared by high pressure homogenization. The effects of such factors as the contents of glycerol monostearate, soybean lecithin and Myrj 59 on the mean diameter, entrapment efficiency and drug loading were investigated using central composite design and response surface method. The data were analyzed using multi-linear equation and second-order polynomial equation for selecting the optimal conditions for LSLN preparation.
RESULTSThe method of second-order polynomial equation was superior to multi-linear equation method in view of the multiple correlation coefficients. Under the optimal conditions, the mean diameter, entrapment efficiency, and drug loading of the GAB-LSLN were 169.5 nm, 92.3% and 5.1%, respectively.
CONCLUSIONThe optimized process for GAB-LSLN preparation is stable, feasible and allows high inclusion rate in the large-scale production of GAB-LSLN.
Delayed-Action Preparations ; chemical synthesis ; chemistry ; Drug Compounding ; methods ; Ginkgolides ; chemistry ; Lactones ; chemistry ; Liposomes ; Nanoparticles ; chemistry
10.Simultaneous determination of five sesquiterpene lactones in Carpesium abrotanoides by HPLC.
China Journal of Chinese Materia Medica 2015;40(9):1783-1786
An HPLC method was established to simultaneously determine the five sesquiterpene lactones, carabrone, carabrol, 2-desoxy-4-epi-pulchellin, telekinand 11(13)-dehydroivaxillin in Carpesium abrotanoides. Samples were analyzed on a kromasil C18 column (4.6 mm x 250 mm, 5 µm); mobile phase: A was acetonitrile, B was water, with gradient elution; flow speed: 1.0 mL · min(-1); detection was carried out using a photodiode array detector at 211 nm; temperatureof column: 30 °C. The five sesquiterpene lactones were well separated with good linear correlations in the range of 0.270-2.700 (r = 0.999 7 ), 1.336-13.360 (r = 0.999 6), 0.258-2.580 (r = 0.999 7), 0.238-2.380 (r = 0.999 9), 0.490-4.900 µg (r = 0.999 9) for carabrone, carabrol, 2-desoxy-4-epi-pulchellin, telekin and 11 (13) -dehydroivaxillin. The average recoveries of these five sesquiterpene lactoneswere 96.78%-98.41% (RSD 1.3%-2.9%). The method was simple, repeatable and stable, which could be used for quality control of C. abrotanoide.
Asteraceae
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chemistry
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Chromatography, High Pressure Liquid
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methods
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Drugs, Chinese Herbal
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analysis
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Lactones
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analysis
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Sesquiterpenes
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analysis