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 ; Korea ; Lactones ; Penicillium

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 ; Lactones ; Sesquiterpenes

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 ; Lactones ; Plants, Medicinal

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 ; Cell Line ; Lactones ; Lauraceae ; Litsea ; MCF-7 Cells

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 ; Lactones ; Nanoparticles ; Particle Size ; Powders ; Solubility ; Suspensions

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 ; chemistry ; Diterpenes ; chemistry ; isolation & purification ; Lactones ; chemistry ; isolation & purification

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* ; Ginkgolides ; Humans ; Lactones ; Plant Extracts ; Terpenes

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 ; Illicium ; Lactones ; Molecular Structure ; Phytochemicals ; Sesquiterpenes

OBJECTIVE: To evaluate the acute toxicity of rofecoxib during concurrent use with cisplatin-based chemoradiotherapy (CCRT) in patients with cervical cancer. METHODS: We evaluated 67 FIGO stage IB2-IVA cervical cancer patients treated with CCRT between June 2002 and July 2004. The study group included patients who received rofecoxib (N=30) and the control group included patients who received CCRT only (N=37). The patients' medical records were retrospectively reviewed for patient characteristics, toxicity related to CCRT and treatment results. RESULTS: There were no significant differences in toxicity between the two groups. The most common acute grade 3/4 toxicity was neutropenia (13.3% in the study group and 21.6% in the control group). Grade 3/4 late toxicity was observed in 2 (6.6%) patients in the study group and 3 (8.1%) in the control group. There was no treatment-related deaths in either group. Six (20.0%) patients in the study group had treatment failure. In the control group, 6 (16.2%) patients experienced treatment failure. Progression-free and overall survival was 55.8+/-4.2 and 59.0+/-2.8 months, respectively, in the study group, and 69.7+/-4.3 and 71.6+/-3.6 months, respectively, in the control group. There were no differences in progression-free and overall survival between the 2 groups. CONCLUSION: Our data indicate that rofecoxib, at a dose of 25 mg twice daily, has acceptable acute toxicity as a radiosensitizer during CCRT. Although rofecoxib was not efficacious as a radiosensitizer in the present study, the benefit of rofecoxib as a radiosensitizer should be further evaluated in a prospective study.
Chemoradiotherapy ; Cyclooxygenase 2 ; Humans ; Lactones ; Medical Records ; Neutropenia ; Retrospective Studies ; Sulfones ; Treatment Failure ; Uterine Cervical Neoplasms

OBJECTIVETo develop an UPLC-MS method for the simultaneously quantitation of adonifoline and senecinine in Senecio herbs.

METHODUPLC-Micro 2000 was used for quantification in SIR mode under ESI+. Monocrotaline was used as the internal standard. Chromatography was performed on a Shiseido Capcell Pak MG (2.0 mm x 50 mm, 3 microm) column at 30 degrees C using an gradient elution of acetonitrile-0.5% formic acid in water at the flow rate of 0.3 mL x min(-1). The injection volume was 2 microL.

RESULTGood linearity was obtained for quantitation of adonifoline over the range of 1.02-816.00 microg x L(-1) (r = 0.998 0). And recoveries at different concentration levels were between 95.73% and 103.0% with RSDs no more than 2.5%. For quantification of senecionine, the linear range was between 1.08-860.56 microg x L(-1) (r = 0.997 6). And recoveries at different concentration levels were between 95.67% and 101.5% with RSDs no more than 2.3%. Good reproducibility and precision were also achieved.

CONCLUSIONThe new developed UPLC method is sensitive, accurate and reliable enough for the quantitation of adonifoline and senecionine in Senecio herbs thus can be used for the limit detection of pyrrolizidne alkaloids in S. scandens. It can also be used for the identification of fake drugs of S. scandens such as S. vulgaris. The developed method was served for the quality evaluation of Herba Senecionis Scandentis.

Chromatography, Liquid ; methods ; Lactones ; analysis ; Mass Spectrometry ; methods ; Pyrrolizidine Alkaloids ; analysis ; Senecio ; chemistry