ABSTRACT
Sesquiterpene dimers are mainly found in the Asteraceae family. However, conflicting reports on the structures of these compounds can be found in the literature. Herein, we describe ten sesquiterpene dimers isolated from the flowers of Inula japonica, including configurational revisions of japonicone H (1-1), japonicone D (2-1), inulanolide A (4-1), japonicone X (5-1), and inulanolide F (5-2) to compounds 1, 2, 4, and 5, respectively. Five new related metabolites (3 and 6-9) are also described. Application of GIAO NMR/DP4+ analyses and ECD/OR calculations enabled us to revise the absolute configurations of an additional 13 sesquiterpene dimers isolated from plants of the genus Inula. Compounds 1, 2, 4, and 6 exhibited inhibition of nitric oxide production in lipopolysaccharide activated RAW264.7 macrophages with IC50 values of 4.07-10.00 µM.
Subject(s)
Flowers , Inula , Nitric Oxide , Sesquiterpenes , Flowers/chemistry , Sesquiterpenes/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Inula/chemistry , Mice , Animals , RAW 264.7 Cells , Molecular Structure , Nitric Oxide/biosynthesis , Nitric Oxide/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Macrophages/drug effects , DimerizationABSTRACT
In the quest to search and discover bioactive compounds from nature, terpenoids have emerged as one of the most interesting and researched classes of compounds. Secoiridoid, a type of the terpenoid, has also been extensively studied, especially their chemical structures and pharmacological effects. Oleaceae is a family of woody dicotyledonous plants with broad economic and medicinal values. This family contains a large number of flavonoids, monoterpenoids, iridoids, secoiridoids and phenylethyl alcohols, of which the secoiridoids have various biological activities. The purpose of this review is to summarize the phytochemical and pharmacological of the secoiridoids (glycosides, aglycones, derivatives and dimers) in the Oleaceae family from 1987 to 2018. This review will also serve as a reference for further studies.
Subject(s)
Iridoids/chemistry , Iridoids/pharmacology , Oleaceae/chemistry , Animals , Flavonoids , Glycosides , Humans , Molecular Structure , Monoterpenes , Phytochemicals/chemistry , Phytochemicals/pharmacologyABSTRACT
1. Corydaline, an isoquinoline alkaloid obtained from the rhizomes of Corydalis yanhusuo, exhibits anti-acetylcholinesterase, anti-angiogenic, anti-allergic and gastric-emptying activities. In this study, a rapid and reliable ultra-performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry (UPLC-Q/TOF-MS) method was developed and employed for the comprehensive study of the metabolites of corydaline in rats. 2. Altogether, 43 metabolites were identified in the plasma (11), bile (9), urine (34) and feces (21) of rats after oral administration of corydaline at a dose of 4.5mg/kg. 3. It was demonstrated that demethylation, hydroxylation, sulfation and glucuronidation were the major metabolic transformation pathways. Among these, two metabolites were identified as tetrahydropalmatine and isocorybulbine, and 33 phase I and phase II products were inferred to be new metabolites arising from the in vivo metabolism of corydaline. 4. Importantly, this research provides scientific and reliable support for full understanding of the metabolic profiles of corydaline and the results could help to elucidate its safety and efficacy.
Subject(s)
Berberine Alkaloids/metabolism , Enzyme Inhibitors/metabolism , Animals , Bile , Chromatography, Liquid , Feces , Metabolome , Plasma , RatsABSTRACT
The matured, ripen, and dried seeds of Scaphium affine (Mast.) Pierre, known as Pangdahai (PDH) in Chinese and recorded as Sterculia lychnophora Hance (scientific synonym) in the 2015 edition of the Chinese Pharmacopeia, have been widely used in traditional Chinese medicine, Japanese folk medicine, Vietnamese traditional medicine, traditional Thai medicine and Indian traditional medicine. The decoctions of the seeds are used as a remedy for pharyngitis, laryngitis, constipation, cough, menorrhagia, and pain management. This review is aimed at fully collating and presenting a systematic and comprehensive overview of the ethnopharmacological uses of PDH, its phytochemical constituents, pharmacological activities, and toxicological profile. Additionally, this review aims to reveal the therapeutic potentials as well as the important scientific gaps in the research of this traditional medicine that need to be filled so as to provide a comprehensive data for its development, utilization and application. From our extensive review of literatures, the teas (water decoctions) of PDH, which largely contain very polar constituents like polysaccharides, are used in the treatment of constipation, pharyngitis, and pain traditionally and ethno-medicinally and their use have been justified by pharmacological studies carried out on the polysaccharides and aqueous extracts. Additionally, this review has revealed that the organic (ethanolic and methanolic) extracts of PDH possess diverse pharmacological (anti-inflammatory, anti-ulcer, anti-pyretic, anti-microbial, anti-obesity and analgesic) effects, yet have received little attention. Most studies on PDH have been focused on the polysaccharides (large molecular weight metabolites), resulting in a major scientific gap in our knowledge on PDH. Furthermore, this review has also shown that few studies have been done in the areas of quality control, pharmacokinetics, and toxicological studies of PDH.
Subject(s)
Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Sterculia/chemistry , Animals , Ethnopharmacology , Humans , Pharmacology , Seeds/chemistryABSTRACT
Two novel physalins, including a 22,26-seco physalin, physalin X (1), and a 11,15-cyclo-9(10),14(17),22(26)-triseco physalin with an unprecedented aromatic ring, aromaphysalin B (2), were isolated from Physalis angulata L. Their structures were determined by IR, UV, HRESIMS, and 2D NMR spectra as well as theoretical calculations. Compounds 1 and 2 exhibited inhibitory activities on NO production with IC50 values of 68.50 and 29.69 µM, respectively. A plausible biosynthetic pathway for 2 is also discussed.
Subject(s)
Anti-Inflammatory Agents/pharmacology , Nitric Oxide/antagonists & inhibitors , Physalis/chemistry , Withanolides/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Dose-Response Relationship, Drug , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Macrophages/metabolism , Molecular Conformation , Molecular Docking Simulation , Nitric Oxide/biosynthesis , Structure-Activity Relationship , Withanolides/chemistry , Withanolides/isolation & purificationABSTRACT
Paeonol, an active constituent in the root bark of Paeonia suffruticosa Andrews, is used to treat inflammation, headache and other diseases in clinic. Though the data on pharmacological researches of paeonol abounds, its metabolic profile is not so clear. It is essential to systematically characterize the in vivo metabolites in order to better understand its mechanism of action. In this study, ultra performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q/TOF-MS) with an integrative strategy was developed for analysis of paeonol metabolites. As a result, based on seven reference substances isolated or synthesized, twenty-five metabolites were detected and identified in urine, feces, bile and plasma of rats after oral administration of paeonol. To the best of our knowledge, 14 of these metabolites have not been reported previously. In addition, the dominating metabolic fates were oxidation, demethylation, hydrogenation, glucuronic acid and sulfate conjugations, and hydrogenation of paeonol was reported for the first time. This research provides scientific and reliable support for full understanding of the metabolic profiling of paeonol.
Subject(s)
Acetophenones/analysis , Acetophenones/chemistry , Chromatography, High Pressure Liquid/methods , Spectrometry, Mass, Electrospray Ionization/methods , Tandem Mass Spectrometry/methods , Acetophenones/metabolism , Animals , Bile/chemistry , Feces/chemistry , Male , Rats , Rats, Sprague-DawleyABSTRACT
ETHNOPHARMACOLOGICAL RELEVANCE: Notopterygium incisum Ting ex H.T. Chang, known in Chinese as 'Qianghuo' is a traditional Chinese medicinal herb with the rhizome and roots associated with meridians of the kidney and urinary bladder. It is pungent, bitter and warm in nature. It has been used over the years to disperse cold, prevent painful obstructions from wind, damp and warm pain. It has also been used with other herbs to treat wind-cold exterior syndrome and wind-cold-damp bi-syndromes and has been known to grow well in regions of high altitude such as Gansu, Tibet etc. THE AIM OF THE REVIEW: This systematic review focuses on the ethnopharmacological uses of this herb, including recent advances on the phytochemical and pharmacological study of N. incisum. Recent analytical methods developed for the quantitative and qualitative determination of constituents in this herb have also been reviewed. Additionally, future trends and prospects in the study of this herb have been proposed. MATERIALS AND METHOD: Various literature and electronic databases such as Pubmed, Science Direct, Springer, Wiley etc were searched and data obtained. Other online academic libraries such as Google Scholar and ethnopharmacological literature were searched systematically for more information on the herb. RESULTS: This review focuses on the ethnopharmacological uses of N. incisum and also the various chemical constituents present in the herb and their various therapeutic effects such as analgesic, anti-inflammatory, anti-cancer and antioxidants effects. Analytical methods developed for the quantitative and qualitative determination of various compounds in this herb were further reviewed. CONCLUSION: In this paper, we have reviewed various researches conducted on N. incisum especially in areas of its ethnopharmacological use, phytochemicals, pharmacology and developed analytical methods. This herb has been used over the years in treating headache, rheumatoid arthritis, cold, diaphoretic etc, prompting many types of research into identifying which compounds are responsible for these activities and their mechanism of action. More research is needed in the area of pharmacokinetics and toxicology to give further information on the clinical use and control the quality of the herb.
Subject(s)
Apiaceae/chemistry , Ethnopharmacology , Phytotherapy , Plant Extracts/pharmacology , Animals , China , Drugs, Chinese Herbal , Humans , Medicine, Chinese Traditional , Plant Extracts/chemistry , TibetABSTRACT
The genus Vitex, which belongs to the Verbenaceae family, includes approximately 250 species. Some species of the genus Vitex have traditionally been used for the treatment of headaches, ophthalmodynia, coughs, asthma, premenopausal syndrome, etc. Chemical investigations indicate that the characteristic constituents of the genus Vitex are terpenes, and 210 of these compounds, including monoterpenoids, sesquiterpenoids, diterpenoids and triterpenoids, have been obtained from 12 species. Pharmacological studies had shown that these terpenes possess anti-inflammatory, antitumor, antibacterial, antioxidant activities, and so on. In this paper, the identity of these terpenes and their pharmacological effects are reviewed, which can provide references for further research regarding the chemistry and utilization of the Vitex species.