1.Research progress on chemical constituents and pharmacological activities of halogenated sesquiterpenes from natural sources.
Hua-Wei LYU ; Ji-Ye ZHANG ; Hai CAI ; Hui-Min LIANG ; Xing-Nuo LI
China Journal of Chinese Materia Medica 2023;48(18):4919-4941
Halogenated sesquiterpenes are important derivatives of sesquiterpenes, referring to chemical components of sesquiterpenes that contain halogens such as chlorine, bromine, and iodine. Halogenated sesquiterpenes have attracted attention from researchers in China and abroad because of their diverse structures, unique halogen elements, and extensive pharmacological activities. Studies have shown that halogenated sesquiterpenes exhibit significant antimicrobial, anti-inflammatory, anticancer, insecticidal, hypoglycemic, and enzyme inhibitory activities. In order to better explore the potential pharmaceutical value of halogenated sesquiterpenes, this paper reviewed the structural characteristics and pharmacological activities of halogenated sesquiterpenes in the past two decades, aiming to provide references for further research and development of this class of compounds.
Sesquiterpenes/chemistry*
;
Anti-Inflammatory Agents/pharmacology*
;
China
2.Polyhydroxylated eudesmane sesquiterpenoids and sesquiterpenoid glucoside from the flower buds of Tussilago farfara.
Yu-Peng LI ; Kang YANG ; Hui MENG ; Tao SHEN ; Hua ZHANG
Chinese Journal of Natural Medicines (English Ed.) 2022;20(4):301-308
Chemical fractionation of the n-BuOH partition, which was generated from the EtOH extract of the flower buds of Tussilago farfara, afforded a series of polar constituents including four new sesquiterpenoids (1-4), one new sesquiterpenoid glucoside (5) and one known analogue (6) of the eudesmane type, as well as five known quinic acid derivatives (7-11). Structures of the new compounds were unambiguously characterized by detailed spectroscopic analyses, with their absolute configurations being established by X-ray crystallography, electronic circular dichroism (ECD) calculation and induced ECD experiments. The inhibitory effect of all the isolates against LPS-induced NO production in murine RAW264.7 macrophages was evaluated, with isochlorogenic acid A (7) showing significant inhibitory activity.
Animals
;
Flowers/chemistry*
;
Glucosides/pharmacology*
;
Mice
;
Sesquiterpenes/pharmacology*
;
Sesquiterpenes, Eudesmane/pharmacology*
;
Tussilago/chemistry*
3.Research progress of chemical constituents and biological activities of essential oil of Pistacia lentiscus.
Wei LIU ; Yu-Shuang LIU ; Yu CHEN ; Yan-Ru QI ; Tao YUAN
China Journal of Chinese Materia Medica 2019;44(17):3684-3694
Pistacia lentiscus,which belongs to foreign medicine resources,is widely distributed in the Mediterranean and Middle Eastern area. The essential oils are a mixture of several volatile compounds mainly monoterpenes and sesquiterpenes obtained from different parts of P. lentiscus by hydrodistillation. The variability of chemical composition,biological activities and content of essential oil is strongly affected by extraction technology,environmental and sex factors. It is indicated that essential oils of P. lentiscus have kinds of biological activities such as antibacterial,anticancer,anti-atherogenesis,antioxidant,anti-inflammatory and insecticidal activities.Many scholars hold the opinion that combination of different components with synergistic and/or additive actions should account for their biological activities. Due to its diverse efficacy and special taste,the essential oil of P. lentiscus has been extensively used in medicine,food and cosmetics industries. A mini review of chemical constituents and biological activities of essential oil of P. lentiscus in the past20 years is made here to provide valuable reference for the construction of " the Belt and Road".
Monoterpenes
;
chemistry
;
pharmacology
;
Oils, Volatile
;
chemistry
;
pharmacology
;
Pistacia
;
chemistry
;
Plant Oils
;
chemistry
;
pharmacology
;
Sesquiterpenes
;
chemistry
;
pharmacology
4.Dysideanones F-G and dysiherbols D-E, unusual sesquiterpene quinones with rearranged skeletons from the marine sponge Dysidea avara.
Hong-Yan LIU ; Mi ZHOU ; Ru-Yi SHANG ; Li-Li HONG ; Guang-Hui WANG ; Wen-Jing TIAN ; Wei-Hua JIAO ; Hai-Feng CHEN ; Hou-Wen LIN
Chinese Journal of Natural Medicines (English Ed.) 2022;20(2):148-154
Four new sesquiterpene quinone meroterpenoids, dysideanones F-G (1-2) and dysiherbols D-E (3-4), were isolated from the marine sponge Dysidea avara collected from the South China Sea. The new structures were elucidated by extensive analysis of spectroscopic data including HR-MS and 1D and 2D NMR spectra, and their absolute configurations were assigned by single-crystal X-ray diffraction and ECD calculations. Anti-inflammatory evaluation showed that dysiherbols D-E (3-4) exhibited moderate inhibitory activity on TNF-α-induced NF-κB activation in human HEK-293T cells with IC50 values of 10.2 and 8.6 μmol·L-1, respectively.
Animals
;
Dysidea/chemistry*
;
Porifera
;
Quinones/pharmacology*
;
Sesquiterpenes/pharmacology*
;
Skeleton
5.A new sesquiterpene from stems of Buddleja lindleyana.
Zhao-Chan CHEN ; Yun-Shuang CAI ; Shi-Shan YU
China Journal of Chinese Materia Medica 2022;47(20):5537-5543
The present study investigated the chemical constituents from the stems of Buddleja lindleyana. Ten compounds were isolated from the 95% EtOH extract of B. lindleyana stems by means of some techniques including polyamide, silica gel, MCI, Sephadex LH-20 column chromatography, and semi-preparative high-performance liquid chromatography(HPLC). Their structures were identified by spectral analysis and single-crystal X-ray diffraction as buddledin F(1), 6-O-4″-hydroxy-3″-methoxy-benzoyl ajugol(2), negundoin G(3),(+)-dihydrocubebin(4), 7-O-ethylguaiacylglycerol(5),(-)-jatrointelignan B(6), threo-1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol(7), vomifoliol(8), hinokinin(9), and isovanillic acid(10). Compound 1 was a new sesquiterpene named buddledin F. Compounds 3-8 were isolated from the Buddleja plant for the first time. The anti-inflammatory activities of compounds 1-10 in vitro were investigated, and the results failed to show the inhibitory activities of these compounds on the production of inflammatory factor NO.
Buddleja/chemistry*
;
Sesquiterpenes/pharmacology*
;
Chromatography, High Pressure Liquid
6.Spectral characteristics of sesquiterpene pyridine alkaloids from Tripterygium plants.
Jian-Gong YAN ; Xian-Fu WU ; Ming-Hui CHEN ; Zhong DAI ; Ya-Dan WANG ; Shuang-Cheng MA
China Journal of Chinese Materia Medica 2022;47(16):4292-4304
Sesquiterpene pyridine alkaloids are important components in Tripterygium plants, possessing a wide range of pharmacological activities, such as anti-inflammation immunosuppression, anti-tumor, anti-virus, and deinsectization, and are of great research value. They are composed of highly oxidized dihydro-β-furansquiterpene and pyridine dicarboxylic acid through ester bonds. According to the structural characteristics of pyridine dicarboxylic acid fragments, they can be divided into various structural subtypes. Up to now, more than 110 sesquiterpene pyridine alkaloids have been isolated and identified from Tripterygium plants. This study reviewed the structural features and spectral(i.e., UV, IR, MS, and NMR) characteristics of sesquiterpene pyridine alkaloids and summarized the structural elucidation process in detail to provide references for their further research and development.
Alkaloids/pharmacology*
;
Drugs, Chinese Herbal/pharmacology*
;
Molecular Structure
;
Pyridines/pharmacology*
;
Sesquiterpenes
;
Tripterygium/chemistry*
7.New bisabolane-type phenolic sesquiterpenoids from the marine sponge Plakortis simplex.
Jie WANG ; Li LIU ; Li-Li HONG ; Kai-Xuan ZHAN ; Zheng-Jiang LIN ; Wei-Hua JIAO ; Hou-Wen LIN
Chinese Journal of Natural Medicines (English Ed.) 2021;19(8):626-631
Six new bisabolane-type phenolic sesquiterpenoids, including plakordiols A-D (1-4), (7R, 10R)-hydroxycurcudiol (5) and (7R, 10S)-hydroxycurcudiol (6) were isolated from the marine sponge Plakortis simplex collected from the South China Sea. Their structures were determined based on extensive analysis of spectroscopic data. Their configurations were assigned by coupling constant analysis, NOESY correlations, and the modified Mosher's method. Furthermore, their cytotoxic and antibacterial activities were evaluated.
Animals
;
Anti-Bacterial Agents/pharmacology*
;
China
;
Molecular Structure
;
Monocyclic Sesquiterpenes/pharmacology*
;
Pacific Ocean
;
Plakortis/chemistry*
8.Research progress on sesquiterpenes and its pharmacological activities in genus Carpesium.
Di-Lu CHEN ; Xuan LI ; Xiao-Jiang ZHOU
China Journal of Chinese Materia Medica 2020;45(1):37-51
The genus Carpesium plants contain many kinds of sesquiterpenes. Up to now, more than 201 sesquiterpene compounds have been isolated and identified, including 86 germacranolides, 30 eudesmanolides, 29 guaianolides, 23 sesquiterpene dimers, 9 pseudoguaianes, 9 carabranolides, 7 xanthanolides, 6 sesquiterpenes without lactone, 1 eremophilane and 1 tricyclo dodecane sesquiterpene. The reported sesquiterpenes possess a series of pharmacological properties, such as anti-tumor, anti-inflammatory, antibacterial, antiparasitic, insecticidal, and antiviral activities. This paper summarizes the 201 chemical structures and biological activities of sesquiterpenes in genus Carpesium, and provides the scientific basis for the further development and utilization.
Anti-Bacterial Agents
;
Anti-Inflammatory Agents
;
Asteraceae/chemistry*
;
Lactones
;
Molecular Structure
;
Phytochemicals/pharmacology*
;
Sesquiterpenes/pharmacology*
9.Clavuridins A and B, two new trinor-guaiane sesquiterpenes isolated from the Xisha soft coral Clavularia viridis.
Yuan GAO ; Wei XIAO ; Hong-Chun LIU ; Jian-Rong WANG ; Li-Gong YAO ; Ping-Kai OUYANG ; De-Cai WANG ; Yue-Wei GUO
Chinese Journal of Natural Medicines (English Ed.) 2017;15(11):855-859
In the present study, two new trinor-guaiane sesquiterpenes, named clavuridins B (1), and A (2), along with three known sesquiterpenes (3-5), were isolated from the Xisha soft coral Clavularia viridis. Their structures and absolute configurations were determined on the basis of spectroscopic analysis, X-ray diffraction analysis with Cu Kα radiation and by comparison with related model compounds. Compounds 1 and 3-5 were evaluated for their cytotoxic activity.
Animals
;
Anthozoa
;
chemistry
;
Biological Products
;
chemistry
;
pharmacology
;
Magnetic Resonance Spectroscopy
;
Molecular Structure
;
Sesquiterpenes, Guaiane
;
chemistry
;
isolation & purification
;
pharmacology
10.Advances in studies on chemical constituents of Senecio.
China Journal of Chinese Materia Medica 2003;28(2):97-100
The large cosmopolitan genus Senecio, a perennial medicinal herb of the family compositae, has been utilized as a anthmicrobial agent. A variety of pyrrolizidine alkaloids and furanoeremophilanes are widespread in the genus Senecio, which are responsible for the hepatotoxic and carchnogenic effects. Some of them have been screened for anti-tumour activity, but their liver toxicity renders their use in chemotherapy. This article reviews the recent advances in chemical constituents, identification methods and pharmacological activities of it.
Animals
;
Anti-Bacterial Agents
;
pharmacology
;
Antineoplastic Agents, Phytogenic
;
pharmacology
;
Chromatography, High Pressure Liquid
;
methods
;
Humans
;
Molecular Structure
;
Plants, Medicinal
;
chemistry
;
Pyrrolizidine Alkaloids
;
chemistry
;
isolation & purification
;
pharmacology
;
Senecio
;
chemistry
;
Sesquiterpenes
;
chemistry
;
isolation & purification
;
pharmacology
;
Sesquiterpenes, Eudesmane
;
chemistry
;
isolation & purification