Aristolone

Chemical constituents of essential oils from the leaves, stems, roots and fruits of Alpinia polyantha.[Pubmed:25920286]

Nat Prod Commun. 2015 Feb;10(2):367-8.

The essential oils obtained from the leaves, stems, roots and fruits of Alpinia polyantha D. Fang (Zingiberaceae) have been studied. The leaf oil was comprised mainly of camphor (16.1%), alpha-pinene (15.2%) and beta-agarofuran (12.9%), while the major constituents of the stem oil were alpha-pinene (12.4%), beta-cubebene (10.6%), beta-agarofuran (10.3%) and globulol (8.8%). However, beta-cubebene (12.6%), fenchyl acetate (10.8%), beta-maaliene (9.0%), Aristolone (8.8%) and alpha-pinene (8.2%) were the compounds occurring in higher amounts in the root oil. The quantitatively significant compounds of the fruit oil were delta-cadinene (10.9%), beta-caryophyllene (9.1%), beta-pinene (8.7%) and alpha-muurolene (7.7%).

Inhibitory effects of wild dietary plants on lipid peroxidation and on the proliferation of human cancer cells.[Pubmed:26408343]

Food Chem Toxicol. 2015 Dec;86:16-24.

Thirteen hydroalcoholic extracts of edible plants from Southern Italy were evaluated for their in vitro antioxidant and antiproliferative activity on three human cancer cell lines: breast cancer MCF-7, hepatic cancer HepG2 and colorectal cancer LoVo. After 48 h of incubation the most antiproliferative plant extract was rosemary (Rosmarinus officinalis L.) on LoVo cell line with IC50 of 16.60 microg/ml. Oregano (Origanum vulgare L. subsp. viridulum) showed a selective antiproliferative activity on hepatic cancer with IC50 of 32.59 microg/ml. All the extracts, with the exception of Diplotaxis tenuifolia (L.) DC., exerted antioxidant properties, the most active plants being dewberry (Rubus caesius L.) and "laprista" (Rumex conglomerates Murray) with IC50 of 4.91 and 5.53 microg/ml, respectively. Rumex conglomeratus contained the highest amount of flavonoids (15.5 mg/g) followed by Portulaca oleracea L. (11.8 mg/g). Rosmarinus officinalis contained the highest number of terpenes. Among them ketoursene (14.7%) and Aristolone (11.3%) were found to be the major constituents. P. oleracea and Raphanus raphanistrum L. subsp. landra contained the highest number of sterols.

Optimization of the extraction of the p-menthadienol isomers and aristolone contained in the essential oil from Elyonurus hensii using a 2(3) full factorial design.[Pubmed:28572969]

Food Sci Nutr. 2017 Feb 9;5(3):784-792.

The aim of this study was to optimize the extraction of p-menthadienol isomers and Aristolone from the essential oil of Elyonurus hensii by hydrodistillation. The study of the seasonal variation in the chemical composition has shown that the plant material has been subject to a natural selection regarding the biosynthesis of the p-menthadienol isomers: during periods of water stress, the extracts are rich in cis and trans-p-mentha-1(7),8-dien-2-ol and poor in cis and trans-p-mentha-2,8-dien-1-ol. Regarding the modeling, eight experiments were carried out by considering three easily interpretable factors (the extraction duration, the residual water content and the state of the division of the plant material). The average yield was 1.33% for the aerial part and 0.74% for the roots. The residual water content is the most important factor, which significantly influences the average yield of the essential oil and the content of the major constituents. Regarding the aerial part, a low residual water content of the plant material varies the essential oil yield (from 0.40% to 2.11%) and the content of cis and trans-p-mentha-2.8-dien-1-ol (from 15.87% to 23.24%). At the root level, the samples that have a very low residual water content provide extracts richer in Aristolone. The combined effects of the extraction duration, the state of division, and the residual water content influence greatly the extraction of Aristolone (from 36.68% to 54.55%). However, these interactions are more complex and difficult to assess.

A Simple and Rapid UPLC-PDA Method for Quality Control of Nardostachys jatamansi.[Pubmed:29202512]

Planta Med. 2018 May;84(8):536-543.

Nardostachys jatamansi is a well-documented herbal agent used to treat digestive and neuropsychiatric disorders in oriental medicinal systems. However, few simple, rapid, and comprehensive methods were reported for quality assessment and control of N. jatamansi. Herein, a UPLC with photodiode array detection method was developed for both fingerprint investigation of N. jatamansi and simultaneous quantitative analysis of the six serotonin transporter modulatory constituents in N. jatamansi. For chromatographic fingerprinting, 24 common peaks were selected as characteristic peaks to assess the consistency of N. jatamansi samples from different retail sources. Six of the common peaks (5, 7, 12: , and 16: - 18: ) were identified as desoxo-narchinol A, buddleoside, isonardosinone, nardosinone, kanshone H, and (-)-Aristolone, respectively, by phytochemical investigation. Five of the six compounds significantly either enhanced or inhibited serotonin transporter activity, while (-)-Aristolone (18: ) didn't show any serotonin transporter activity. In quantitative analysis, the six compounds showed good linearity (r > 0.999) within test ranges. The precision, expressed as relative standard deviation, was in the range of 0.25 - 2.77%, and the recovery of the method was in the range of 92 - 105%. The UPLC-photodiode array detection-based fingerprint analysis and quantitative methods reported here could be used for routine quality control of N. jatamansi.

Evaluation of the cytotoxic effects of Cyperus longus extract, fractions and its essential oil on the PC3 and MCF7 cancer cell lines.[Pubmed:26893742]

Oncol Lett. 2016 Feb;11(2):1353-1360.

Cyperus longus is one of the Iranian endemic species. However, to date, and to the best of our knowledge, there are no availale academic reports on the cytotoxicity of this plant. Thus, this study was carried out to examine the in vitro anti-proliferative and anti-apoptotic effects of Cyperus longus extract, fractions and essential oil (EO) on MCF7 and PC3 cell lines. The chemical constituents of EO were identified using gas chromatography (GC)-mass spectrometry (MS) analysis. The cells were cultured in RPMI-1640 medium and incubated with various concentrations of the plant extract and fractions. Cell viability was quantified by MTT assay following 24, 48 and 72 h of exposure to (12.5-200 microg/ml) of the methanol extract, the dichloromethane (CH2Cl2), ethyl acetate (EtOAc) and water fractions, as well as the EO of the plant. The percentage of apoptotic cells was determined using propidium iodide staining of DNA fragments by flow cytometry (sub-G1 peak). The most effective fraction in the MCF7 cell line was the CH2Cl2 fraction (IC50 after 48 h, 25.34+/-2.01). The EtOAc fraction (IC50 after 48 h, 35.2+/-2.69) and the methanol extract (IC50 after 48 h, 64.64+/-1.64) were also found to be effective. The IC50 values obtained for the PC3 cell line were 37.97+/-3.87, 51.57+/-3.87 and 70.33+/-2.36 for the CH2Cl2 fraction, the EtOAc fraction and the methanol extract, respectively. Based on these data and due to the partial polarity of the most effective fraction (the CH2Cl2 fraction), we also examined the cytotoxicity of the plant EO. The IC50 values after 48 h were 22.25+/-4.25 and 12.55+/-3.65 in the PC3 and MCF7 cell lines, respectively. DNA fragmentation assay also confirmed these data. Performing GC-MS analysis for the plant EO revealed that beta-himachalene (10.81%), alpha-caryophyllene oxide (7.6%), irisone (4.78%), beta-caryophyllene oxide (4.36%), humulene oxide (12%), viridiflorol (4.73%), Aristolone (6.39%) and longiverbenone (6.04%) were the main constituents. Our results demonstrated that two of the constituents of Cyperus longus, viridiflorol and longiverbenone, should be investigated further as possible promising chemotherapeutic agents in cancer treatment.

Terpenoids from Russula lepida and R. amarissima (Basidiomycota, Russulaceae).[Pubmed:22938994]

Phytochemistry. 2012 Dec;84:154-9.

Four aristolane sesquiterpenes were isolated from the fruiting bodies of Russula lepida and R. amarissima, namely (1R,2S)-1,2-dihydroxyAristolone (6), (2S,11S)-2,12-dihydroxy-Aristolone (7), (1R,2S,11S)-1,2,12-trihydroxyAristolone (8), (1S,2S,11S)-1,2,12-trihydroxy-Aristolone (9). In addition, a seco-cucurbitane triterpene, i.e. 3,4-secocucurbita-4,24E-diene-3-hydroxy-26-carboxylic acid (14) was isolated from both species. The configuration at C-2 of the already known rulepidol (2-hydroxyAristolone, 5) was corrected as S instead of R. Several more aristolane and nardosinane sesquiterpenes, as well as cucurbitane triterpenes, already reported both from European and Chinese samples of R. lepida, were also isolated. Compound 14 showed moderate cell growth inhibitory activity.

New bioactive secondary metabolites from Bornean red alga, Laurencia similis (Ceramiales).[Pubmed:23678792]

Nat Prod Commun. 2013 Mar;8(3):287-8.

A Bomean red algal population of Laurencia similis Nam et Saito was analyzed for its secondary metabolite composition. Seven compounds were identified: ent-1(10)-aristolen-9beta-ol (1), (+)-Aristolone (2), axinysone B (3), 9-aristolen-1alpha-ol (4), 2,3,5,6-tetrabromoindole (5), 1-methyl-2,3,5,6-tetrabromoindole (6), and 1-methyl-2,3,5-tribromoindole (7). Compound 1 was identified as a new optical isomer of 1(10)-aristolen-9beta-ol. Compounds 1, 4 and 5 exhibited good antibacterial activity against antibiotic resistant clinical bacteria and cytotoxic effects against selected cancer cell lines.