The chemical components of the essential oil obtained from Chrysanthemum indicum L. were analyzed by GC-MS. Seventy-three compounds accounting for 96.65% of the extracted essential oil were identified. The main compounds in the oil were alpha-pinene (4.4%), 1,8-cineole (10.4%), alpha-thujone (6.05%), camphor (10.12%), terpinen-4-ol (3.4%), bornyl acetate (6.1%), borneol (3.6%), cis-chrysanthenol (3.4%), beta-caryophyllene (5.1%), germacrene D (10.6%), and alpha-cadinol (3.0%). The essential oil of C. indicum exhibited stronger antibacterial activity against all oral bacteria tested (MICs, 0.1 to 1.6 mg/ml; MBCs, 0.2 to 3.2 mg/ml) than their major compounds. Furthermore, the MICs/MBCs were reduced to one half ~ one sixteenth as a result of the combinations included the essential oil with ampicillin or gentamicin for all oral bacteria. A strong bactericidal effect was exerted in drug combinations. The in vitro data suggest that the essential oil of C. indicum with other antibiotics may be microbiologically beneficial and synergistic.
Accounting ; Ampicillin ; Anti-Bacterial Agents ; Bacteria ; Bornanes ; Camphor ; Chrysanthemum ; Cyclohexanols ; Drug Combinations ; Gentamicins ; Monoterpenes ; Sesquiterpenes ; Sesquiterpenes, Germacrane ; Terpenes

OBJECTIVETo analyze the chemical components of the essential oil extracted from six cultivars' Juhua (Zaogongju, Wangongju, Huangyaoju, Chuju, Xiaoboju and Daboju) produced in Anhui province of China, which were breed from Chrysanthemum morifolium, and to provide scientific basis for quality control.

METHODThe essential oils of the six cultivars'Juhua were extracted by water-steam distillation and separated by GC capillary column chromatography. The components were quantitatively determined with normalization method, and identified by GC-MS.

RESULTFrom Zaogongju, Wangongju, Huangyaoju, Chuju, Xiaoboju and Daboju, 247, 226, 246, 182, 216 and 122 chromatographic peaks were detected, among them 75, 54, 78, 50, 53 and 43 components were identified,which were composed of 85.67%, 82.80%, 81.38%, 73.22%, 71.51% and 72.87% of the total essential oil, respectively.

CONCLUSIONMonoterpenoid compounds were higher more than sesquiterpenoid compounds in the five juhua except for Chuju. There was no difference in the constituents of essential oil of Zaogongju and Wangongju. And verbenyl acetate was the main chemical constituent and composed of 32.10% and 37.85% of the total essential oil, respectively. (1R)-Camphor and bisabolol oxide A were the main chemical constituents in Huangyaoju, which were composed of 28.70% and 12.58% of the total essential oil, respectively. beta-Selinene and borneol were the main chemical constituents in Chuju, which were composed of 17.85% and 12.84% of the total essential oil, respectively. Eucalyptol was the main chemical constituent in Xiaoboju, which were composed of 21.33%. Verbene oxides and chrysanthenone were composed of 25.32% and 8.26% of the total essential oil, respectively, in the Daboju. The common chemical constituents were camphene, borneol, bornyl aceate, (1R)-camphor, (-)-4-terpineol, alpha-terpineol, eucalyptol, cis-caryophyllene, caryophyllene oxide, juniper camphor, beta-sesquiphellandrene, alpha-curcumene and beta-farnesene in the six cultivars' Juhua produced in Anhui province of China. The resultant data provided the further evidences to distinguish Juhua' cultivars and scientific basis for quality control of Juhua.

Boranes ; chemistry ; Bornanes ; chemistry ; Camphor ; chemistry ; China ; Chrysanthemum ; chemistry ; Cyclohexanols ; chemistry ; Gas Chromatography-Mass Spectrometry ; Monoterpenes ; chemistry ; Oils, Volatile ; chemistry ; Sesquiterpenes ; chemistry ; Terpenes ; chemistry ; Tetrahydronaphthalenes ; chemistry

The genus Chloranthus has 13 species and 5 varieties in China, which can be found in the southwest and northeast regions. Phytochemical studies on Chloranthus plants have reported a large amount of terpenoids, such as diterpenoids, sesquiterpenoids, and sesquiterpenoid dimers. Their anti-inflammation, anti-tumor, antifungal, antivirus, and neuroprotection activities have been confirmed by previous pharmacological research. Herein, research on the chemical constituents from Chloranthus plants and their biological activities over the five years was summarized to provide scientific basis for the further development and utilization of Chloranthus plants.
Diterpenes ; Phytochemicals/pharmacology* ; Plants ; Sesquiterpenes/pharmacology* ; Terpenes

Genome mining for the search and discovery of two new globin-like enzymes, TriB fromFusarium poae and TutaA from Schizophyllum commne, are involved in the synthesis of two linear terpenes tricinonoic acid (1) and 2-butenedioic acid (3). Both in vivo heterologous biosynthesis and in vitro biochemical assays showed that these two enzymes catalyzed the C-C double bond cleavage of a cyclic sesquiterpene precursor (-)-germacrene D (7) and a linear diterpene backbone schizostain (2), respectively. Our work presents an unusual formation mechanism of linear terpenes from fungi and expands the functional skills of globin-like enzymes in the synthesis of terpene compounds.
Terpenes/chemistry* ; Alkyl and Aryl Transferases ; Globins ; Diterpenes

Sesquiterpenoids are comprised of three C₅ units and derived from farnesyl diphosphate. In these C₁₅ family of terpenoids, drimane-type sesquiterpenoids are unique as their chemical structure of decahydronaphthalene along with the methyl group decorations resemble the A/B rings of labdane derived diterpenoids and the eastern part of many meroterpenoids. In the past decades, based on their chemical structural features and diverse bioactivities, great efforts have been made to perform chemical and biological research on this family of natural products, leading to the characterization of a large of new compounds and a few biosynthetic pathways. In this review, we collected 164 new drimane-type sesquiterpenoids from fungi between January 2004 and October 2021 and classified them into three major subfamilies, so as to highlight their diverse chemical structures, biological activities, and biosynthetic pathways,.
Polycyclic Sesquiterpenes ; Sesquiterpenes/chemistry* ; Fungi ; Terpenes/chemistry* ; Diterpenes

Phytocannabinoids are bioactive terpenoids that are exclusive to Cannabis sativa L. The main pharmacologically active phytocannabinoids are Δ9-tetrahydrocannabinol and cannabidiol, both target endogenous cannabinoid receptors. Δ9-tetrahydrocannabinol and cannabidiol have extensive therapeutic potential due to their participation in many physiological and pathological processes in human body by activating the endocannabinoid system. At present, Δ9-tetrahydrocannabinol, cannabidiol and their analogues or combination preparations are used to treat epilepsy, vomiting in patients with cancer chemotherapy, spasticity in multiple sclerosis and relieve neuropathic pain and pain in patients with advanced cancer. With the further exploration of the application value of Δ9-tetrahydrocannabinol and cannabidiol as well as the increasing demand for standardization of pharmaceutical preparations, it is imminent to achieve large-scale production of Δ9-tetrahydrocannabinol and cannabidiol in the pharmaceutical industry. In this article, pharmacological research progress of phytocannabinoids in recent years, biosynthetic pathways of phytocannabinoids and the mechanism of key enzymes as well as various product development strategies of cannabinoids in pharmaceutical industry are reviewed. By exploring the potential of synthetic biology as an alternative strategy for the source of phytocannabinoids, it will provide a theoretical basis for the research and development of microbial engineering for cannabinoids synthesis, and promote the large-scale production of medicinal cannabinoids.
Cannabidiol ; Cannabinoids/biosynthesis* ; Cannabis ; Humans ; Receptors, Cannabinoid

Terpenoids are main bioactive components in Tripterygium wilfordii,but the contents of some terpenoids are relatively low. In order to provide scientific evidence for the regulation of terpenoids in T. wilfordii,this research explored the effect of GR24 on accumulations of four diterpenoids( triptolide,tripterifordin,triptophenolide,and triptinin B) in T. wilfordii suspension cells by biological technology and UPLC-QQQ-MS/MS. The results indicated that 100 μmol·L-1 GR24 inhibited the accumulations of triptolide,tripterifordin,triptophenolide,and triptinin B to different degrees. Compared with the control group,the contents of 4 diterpenoids( in the induced group) were down to 96.59%,63.80%,61.02% and 33.59% in 240 h,respectively. Among them,the accumulation of triptinin B iswas significantly inhibited. In addition,the key time point of inhibitory effect was 120 h after induction with GR24 in some diterpenoids. This is the first systematic study focusing on the effect of GR24 on the accumulations of diterpenoids in T. wilfordii suspension cells. The dynamic accumulation ruleregularity of four diterpenoids after induced by GR24 was summarized,which laid a foundation for further study on the chemical response mechanism of terpenoids to GR24.
Cells, Cultured ; Diterpenes ; pharmacokinetics ; Humans ; Lactones ; pharmacology ; Tandem Mass Spectrometry ; Terpenes ; Tripterygium ; chemistry

Five new terpenoids, including two vibsane-type diterpenoids (1, 2) and three iridoid allosides (3-5), together with eight known ones, were isolated from the leaves and twigs of Viburnum odoratissimum var.sessiliflorum. Their planar structures and relative configurations were determined by spectroscopic methods, especially 2D NMR techniques. The sugar moieties of the iridoids were confirmed as β-D-allose by GC analysis after acid hydrolysis and acetylation. The absolute configurations of neovibsanin Q (1) and dehydrovibsanol B (2) were determined by quantum chemical calculation of their theoretical electronic circular dichroism (ECD) spectra and Rh₂(OCOCF₃)₄-induced ECD analysis. The anti-inflammatory activities of compounds 1, 3, 4, and 5 were evaluated using an LPS-induced RAW264.7 cell model. Compounds 3suppressed the release of NO in a dose-dependent manner, with an IC₅₀ value of 55.64 μmol·L^-1. The cytotoxicities of compounds 1-5 on HCT-116 cells were assessed and the results showed that compounds 2 and 3 exhibited moderate inhibitory activities with IC₅₀ values of 13.8 and 12.3 μmol·L^-1, respectively.
Terpenes/pharmacology* ; Viburnum/chemistry* ; Molecular Structure ; Diterpenes/chemistry* ; Plant Leaves/chemistry*

OBJECTIVES: To establish a high performance liquid chromatographic （HPLC） method for simultaneous determination of three effective constituents, including tetrahydrocannabinol （THC）, cannabidiol （CBD） and cannabinol （CBN） in Cannabis plants. METHODS: A C₁₈ column was used in this study, and acetonitrile-phosphate buffer （0.015 mol/L KH₂PO₄） was used as mobile phase at a flow rate of 1.0 mL/min. At a detection wavelength of 220 mm, UV absorption spectra were collected at the wavelength range of 190-400 nm, and the spectra and retention time were counted as qualitative evidence. RESULTS: THC, CBD and CBN could be well separated by this method. Three components had good linear relationship in the range of 0.4-40 μg/mL （R²≥0.999 3）. The recoveries were over 87%. The limits of detection were 1.8 ng, 2.0 ng and 1.3 ng, respectively. The relative standard deviation （RSD） were less than 5% for both inter-day and intra-day precisions. CONCLUSIONS Reversed-phase HPLC method is simple, rapid and accurate, and it is suitable for the qualitative and quantitative detection of THC, CBD and CBN in Cannabis plants.
Cannabidiol/analysis* ; Cannabinol/analysis* ; Cannabis/chemistry* ; Chromatography, High Pressure Liquid ; Dronabinol/analysis*

OBJECTIVETo compare the contents of diterpenoid pigments in the different processed products of Gardenia jasminoides.

METHODThe separation of Crocin 1, Crocin 2, Crocin 3, Crocetin were determined simultaneously by HPLC on a kromasil C18 column at 35 degrees C with the m methanol-acetonitrile-0.3% formic acid anhydrous in gradient elution as the mobile phrase. The detection wavelength was set at 440 nm and the flow rate was 1.0 mL x min(-1).

RESULTThe obtained linearity of the four components was better over 0.9995 and the average recoveries were 97.77%, 100.05% , 98.40%, 101.02%, respectively.

CONCLUSIONThe method is simple, accurate with good reproducibility. The results showed that the remarkable variation regulations appear among the different processed products.

Carotenoids ; chemistry ; Chromatography, High Pressure Liquid ; Diterpenes ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Gardenia ; chemistry ; Reproducibility of Results