Eremophilane-type sesquiterpene lactones from Ligularia hodgsonii Hook

Huang, Han-Ching; Xu, Yali; Liu, Hongli; Liu, Xiaoqing; Shang, Ji-Ning; Han, Guang-Tian; Yao, Mingjun; Yuan, Chengqian

doi:10.1016/j.phytochem.2011.01.008

Cited by 27 publications

(13 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is reported that many plants used in traditional medicine systems contain a variety of compounds responsible for their healing properties. A large part of these compounds are sesquiterpenoid hydroxylactones [ 1 , 2 , 3 , 4 , 5 , 6 ], substances of high biological activity. Hydroxylactones exhibit a number of biological properties, showing e.g., hepaprotective [ 7 ], cytotoxic [ 8 , 9 , 10 , 11 , 12 , 13 , 14 ], antiplasmodial [ 15 ], antifungal [ 16 ], antibacterial [ 17 ], antitumor and anti-inflammatory activity [ 18 ], acting as phytotoxic agents [ 19 ], and having an inhibitory effect on NO production [ 20 ] and against activity of some enzymes [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Lactones with Methylcyclohexane Systems Obtained by Chemical and Microbiological Methods and Their Antimicrobial Activity

et al. 2015

View full text Add to dashboard Cite

Abstract:Eight new lactones (δ-chloro-, δ-bromo-and δ-iodo-γ-lactones), each with a methylcyclohexane ring, were obtained by chemical means from (4-methylcyclohex-2-en-1-yl) acetic acid or (6-methylcyclohex-2-en-1-yl) acetic acid. Whole cells of ten fungal strains (Fusarium species, Syncephalastrum racemosum and Botrytis cinerea) were tested on their ability to convert these lactones into other products. Some of the tested fungal strains transformed chloro-, bromo-and iodolactone with a methyl group at C-5 into 2-hydroxy-5-methyl-9-oxabicyclo[4.3.0]nonan-8-one during hydrolytic dehalogenation. When the same lactones had the methyl group at C-3, no structural modifications of halolactones were observed. In most cases, the optical purity of the product was low or medium, with the highest rate for chlorolactone (45.4%) and iodolactone (45.2% and 47.6%). All of the obtained compounds were tested with reference to their smell. Seven halolactones and the hydroxylactone obtained via biotransformation of halolactones with 5-methylcyclohexane ring were examined for their antimicrobial activity. These compounds were capable of inhibiting growth of some bacteria, yeasts and fungi. OPEN ACCESSMolecules 2015, 20 3336

show abstract

Section: Introductionmentioning

confidence: 99%

Lactones with Methylcyclohexane Systems Obtained by Chemical and Microbiological Methods and Their Antimicrobial Activity

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Another most common counterfeit introduced to the market is an artificial complex consisting of caterpillars and the plant stem of L. hodgsonii as the stromata. The roots of L. hodgsonii contain sesquiterpenes and pyrrolizidine alkaloids (Huang et al, 2011). However, the pyrrolizidine alkaloid clivorine isolated from L. hodgsonii is toxic to the human liver (Ji et al, 2008) (Wang & Yao, 2011;Zhang et al, 2012).…”

Section: Discussionmentioning

confidence: 99%

“…Considering its high cost, O. sinensis has been produced using various counterfeit versions with very similar morphology, thereby causing confusion in market management and challenging the safe use of O. sinensis. These counterfeits are in the form of natural counterfeits, such as Ophiocordyceps robertsii, Cordyceps gunnii, Cordyceps militaris, and Cordyceps cicadae Au et al, 2012), and artificial complexes, which can cause illness or even death when improperly used (Ji et al, 2008;Huang et al, 2011). Studies have shown that O. sinensis can be identified from its counterfeits or closely related species based on its macroscopic and microscopic properties Au et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

DNA barcoding the commercial Chinese caterpillar fungus

Song

Xin

et al. 2013

FEMS Microbiol Lett

View full text Add to dashboard Cite

Chinese caterpillar fungus (Ophiocordyceps sinensis) has been widely used as tonic in Asian medicine. Considering its curative effect and high cost, various counterfeit versions of O. sinensis have been introduced and are commercially available. These counterfeits have morphological characteristics that are difficult to distinguish based on morphology alone, thereby causing confusion and threatening its safe use. In this study, internal transcribed spacer (ITS) sequences as a DNA barcode were analyzed and assessed for rapid and accurate identification of 131 O. sinensis samples and 12 common counterfeits and closely related species. Results showed that sufficient ITS sequence differences, also known as 'barcode gaps', existed to distinguish between O. sinensis and counterfeit species. ITS sequence correctly identified 100% of the samples at the species and genus level using the Basic Local Alignment Search Tool 1 and the nearest distance method. Furthermore, O. sinensis, counterfeits, and closely related species can be successfully identified using tree-based methods including maximum parsimony, neighbor-joining, and maximum likelihood analysis. These results indicated that DNA barcoding could be used as a fast and accurate identification method to distinguish O. sinensis from counterfeits and closely related species to ensure its safe use.

show abstract

“…1.77 (m, H 2 -9), 1.80 (quint, J = 1.5 Hz, H 3 -5′ or 5′′′), 1.82 (quint, J = 1.5 Hz, H 3 -5′ or 5′′′), 1.85 (quint, J = 1.5 Hz, H 3 -5′′), 1.89 (dq, J = 7.2, 1.5 Hz, H 3 -4′ or 4′′′), 1.90 (dq, J = 7.2, 1.5 Hz, H 3 -4′ or 4′′′), 1.94 (dq, J = 7.2, 1.5 Hz, H 3 -4′′), 2.71 (t, J = 5.8 Hz, H-10), 2.88 (dd, J = 11.7, 7.6 Hz, H-6), 3.42 (d, J = 0.8 Hz, H-4), 5.24 (s, H-14), 5.32 (s, H-14), 5.39 (dd, J = 9.0, 3.4 Hz, H-8), 5.46 (d, J = 7.6 Hz, H-5), 5.82 (d, J = 11.7 Hz, H-1), 6.01 (qq, J = 7.2, 1.5 Hz, H-3′ or 3′′′), 6.02 (qq, J = 7.2, 1.5 Hz, H-3′ or 3′′′), 6.11 (qq, J = 7.2, 1.5 Hz, H-3′′). 13…”

Section: Isolation Of Compoundsmentioning

confidence: 99%

“…Eremophilanes have been isolated from L. hodgsonii in Japan [8,9] and China [10][11][12][13], as well as related sesquiterpenes such as bakkenolide A [9] and an eudesmane [12]. An eremophilane dimer has also been obtained [13]. In the course of our continuous study on Ligularia, we isolated furanoeremophilanes from both Japanese and Chinese samples [14].…”

mentioning

confidence: 99%