Bioactive phthalides from Ligusticum sinense Oliv cv. Chaxiong

Qian, Wei; Yang, Jun; Ren, Jin; Wang, Aiguo; Ji, Tengfei; Su, Ya‐Lun

doi:10.1016/j.fitote.2014.01.010

Cited by 23 publications

(12 citation statements)

References 8 publications

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“…The GC/MS characterization was therefore performed to show the profile of chemicals comprised in LHE, which has no publication on its compositions. A high percentage of phthalides, such as 3- N -butylphthalide and butylidene phthalide found in LHE was corresponded to those of many studies previously reported phthalides as the main biological components of L. sinense rhizome, besides phenolic acids and polysaccharide [ 51 – 55 ]. Chemical characterization by a similar technique, like GC/MS, of other products from L. sinense , such as essential oils, demonstrated variations in type and amount of compound substances.…”

Section: Discussionsupporting

confidence: 80%

Remarkable repellency of Ligusticum sinense (Umbelliferae), a herbal alternative against laboratory populations of Anopheles minimus and Aedes aegypti (Diptera: Culicidae)

Sanghong

Junkum

Chaithong

et al. 2015

Malar J

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BackgroundFor personal protection against mosquito bites, user-friendly natural repellents, particularly from plant origin, are considered as a potential alternative to applications currently based on synthetics such as DEET, the standard chemical repellent. This study was carried out in Thailand to evaluate the repellency of Ligusticumsinense hexane extract (LHE) against laboratory Anopheles minimus and Aedes aegypti, the primary vectors of malaria and dengue fever, respectively.MethodsRepellent testing of 25% LHE against the two target mosquitoes; An. minimus and Ae. aegypti, was performed and compared to the standard repellent, DEET, with the assistance of six human volunteers of either sex under laboratory conditions. The physical and biological stability of LHE also was determined after keeping it in conditions that varied in temperature and storage time. Finally, LHE was analysed chemically using the qualitative GC/MS technique in order to demonstrate a profile of chemical constituents.ResultsEthanol preparations of LHE, with and without 5% vanillin, demonstrated a remarkably effective performance when compared to DEET in repelling both An. minimus and Ae. aegypti. While 25% LHE alone provided median complete-protection times against An. minimus and Ae. aegypti of 11.5 (9.0–14.0) hours and 6.5 (5.5–9.5) hours, respectively, the addition of 5% vanillin increased those times to 12.5 (9.0–16.0) hours and 11.0 (7.0–13.5) hours, respectively. Correspondingly, vanillin added to 25% DEET also extended the protection times from 11.5 (10.5–15.0) hours to 14.25 (11.0–18.0) hours and 8.0 (5.0–9.5) hours to 8.75 (7.5–11.0) hours against An. minimus and Ae. aegypti, respectively. No local skin reaction such as rash, swelling or irritation was observed during the study period. Although LHE samples kept at ambient temperature (21–35°C), and 45°C for 1, 2 and 3 months, demonstrated similar physical characteristics, such as similar viscosity and a pleasant odour, to those that were fresh and stored at 4°C, their colour changed from light- to dark-brown. Interestingly, repellency against Ae. aegypti of stored LHE was presented for a period of at least 3 months, with insignificantly varied efficacy. Chemical analysis revealed that the main components of LHE were 3-N-butylphthalide (31.46%), 2, 5-dimethylpyridine (21.94%) and linoleic acid (16.41%), constituting 69.81% of all the extract composition.ConclusionsLHE with proven repellent efficacy, no side effects on the skin, and a rather stable state when kept in varied conditions is considered to be a potential candidate for developing a new natural alternative to DEET, or an additional weapon for integrated vector control when used together with other chemicals/measures.

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Section: Discussionsupporting

confidence: 80%

Remarkable repellency of Ligusticum sinense (Umbelliferae), a herbal alternative against laboratory populations of Anopheles minimus and Aedes aegypti (Diptera: Culicidae)

Sanghong

Junkum

Chaithong

et al. 2015

Malar J

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“…Their ability to produce structurally diverse and biologically significant monomeric and dimeric phthalide metabolites is well documented [1,2]. Previous pharmacological activity studies revealed that these compounds display anti-proliferative [3,4], anti-inflammatory [5][6][7], anti-thrombus [8], neuroprotective [9][10][11], anti-tumor [12,13], and anti-spasmodic effects. In recent years, the bioactivities of these compounds have attracted a great interest and extensive research has been carried out to characterize the molecular mechanism(s) behind their activity.…”

Section: Introductionmentioning

confidence: 99%

Neuroprotective and Cytotoxic Phthalides from Angelicae Sinensis Radix

Gong

Zhou

et al. 2016

Molecules

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Seven phthalides, including a new dimeric one named tokinolide C (7), were isolated from Angelicae Sinensis Radix and characterized. The structures of these compounds were elucidated on the basis of comprehensive analysis of spectroscopic data and comparison with literature data. All of the compounds were evaluated for their cytotoxic activities against the A549, HCT-8, and HepG2 cancer cell lines. Riligustilide (4) showed cytotoxicity against three cancer cell lines, with IC 50 values of 13.82, 6.79, and 7.92 µM, respectively. Tokinolide A (6) and tokinolide C (6) exerted low cytotoxicity in these cancer cell lines, while the remaining compounds were inactive. Flow cytometry analysis was employed to evaluate the possible mechanism of cytotoxic action of riligustilide (4). We observed that compound 4 was able to arrest the cell cycle in the G1, S phases and induce apoptosis in a time-dependent manner in HCT-8 cell lines. In addition, these compounds were evaluated for neuroprotective effect against SH-SY5Y cells injured by glutamate. The result showed that ligustilide (1), Z-butylidenephthalide (3) and tokinolide A (6) exhibited significant neuroprotective effects.

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“…IR spectra were acquired using a Varian 660-IR spectrometer (equipped with Gladi-ATR), using thin film solid method. NMR experiments ( 1 H, 13 C, NOE, COSY, HETCOR and HMBC) were recorded on a Varian Mercury 300 spectrometer with CDCl 3 as solvent. Chemical shifts were reported relative to CHCl 3 (7.27 ppm for 1 H) and CDCl 3 (77.0 ppm for 13 C).…”

Section: Generalmentioning

confidence: 99%

“…Phthalides and derivatives thereof are a group of secondary metabolites produced by, for example, marine fungi [1e3] and several genera of the Apiaceae family of hollow stemmed plants [4]. Many examples of these synthetic and naturally occurring bicyclic compounds were found to possess a wide range of bioactivities [5,6] such as anti-inflammatory [7], antibacterial [8], insecticide [9], anticancer [10], phytotoxic [11], fungicide [12] and protective effect against neural injury [13]. Several representative examples of these molecules are presented in Fig.…”

Section: Introductionmentioning

confidence: 99%