Four triterpene acetates, α-amyrin acetate (1a), β-amyrin acetate (2a), lupeol acetate (3a), and butyrospermol acetate (4a), and four triterpene cinnamates, α-amyrin cinnamate (1c), β-amyrin cinnamate (2c), lupeol cinnamate (3c), and butyrospermol cinnamate (4c), were isolated from the kernel fat (n-hexane extract) of the shea tree (Vitellaria paradoxa; Sapotaceae). Upon evaluation of these eight triterpene esters for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 μg/ear) in mice, all of the compounds tested exhibited marked anti-inflammatory activity, with ID50 values in the range of 0.15–0.75 μmol/ear, and among which compound 3c showed the highest activity with ID50 of 0.15 μmol/ear. Compound 3c (10 mg/kg) further exhibited anti-inflammatory activity on rat hind paw edema induced by carrageenan, with the percentage of inflammation at 1, 3, and 5 h of 35.4, 41.5, and 45.5%, respectively. The eight triterpene esters were then evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) in Raji cells as a primary screening test for inhibitors of tumor promoters. All the compounds showed moderate inhibitory effects. Furthermore, compound 3c exhibited inhibitory effect on skin tumor promotion in an in vivo two-stage carcinogenesis test using 7,12-dimethylbenz [a] anthracene (DMBA) as an initiator and TPA as a promoter. The biological activities of triterpene acetate and cinnamate esters, together with the exceptionally high levels of these triterpenes in shea fat, indicate that shea nuts and shea fat (shea butter) constitute a significant source of anti-inflammatory and anti-tumor promoting compounds.
The lipid and fatty acids of the Pacific oyster, Crassostrea gigas, collected both in Japan and France, were analyzed. Triacylglycerols and sterols were the major classes in the neutral lipids of both populations of C. gigas between the two countries, and they had significant levels of phospholipids (phosphatidylethanolamine and phosphatidylcholine) with ceramideaminoethylphosphonate in their polar tissue lipids. The differences of 18:3n-3 and 22:6n-3 (docosahexaenoic acid; DHA) levels in the depot triacylglycerols suggest the influence of dietary phytoplankton in different environments of the two countries. Although the levels of the fatty acids slightly differed, that of 20:5n-3 (icosapentaenoic acid; EPA, 20.5-24.8%) in the triacylglycerols was specifically the highest fatty acid in all the samples. The major polyunsaturated fatty acids in the polar lipids of all samples were EPA (13.2-17.8% for phosphatidylethanolamine and 13.4-22.7% for phosphatidylcholine) and DHA (18.9-26.8% for phosphatidylethanolamine and 13.1-22.5% for phosphatidylcholine). The fluctuation of total PUFA levels in the polar lipids between samples of both countries suggests the influence of diet. In addition, the consistently high EPA levels in the phospholipids may compensate for the variation in DHA levels.
In a unique attempt modification of only palm oil has been investigated. Triacylglycerols of palm oil has been randomized by chemical and biochemical means. Chemical randomization was carried out using sodium methoxide (NaOMe: 0.4 to 0.6 %, w/w) whereas the biochemical modifications were performed using five different commercial lipases from Amano Enzymes. It was observed that after chemical randomization (for 15 minutes at 90 °C) using sodium methoxide (0.5 %, w/w) catalyst the melting point of refined palm oil has risen from 32.0 °C to 40.1 °C. Chemical treatments for 15 minutes at 60 °C in miscella phase (60 %, w/v oil in hexane) using 0.5 %, w/v sodium methoxide resulted increase in melting point from 32.0 °C to 42.0 °C. After enzymatic treatment using lipases it was observed that the melting point may rise from 32.0 °C to 38.5 °C (in 15 minutes at 45.0 °C). All the five enzymes were found to be active in respect of randomization capacity and active at very low concentration 0.004 to 0.010 % (w/w).
It has been known that tissues of porpoise contain unique structured-lipids as combination of iso-valeric acid (iso-C5:0) and omega 3 polyunsaturated fatty acids (ω3 PUFAs). It is well known that ω3 PUFAs have lipid-lowering effects in animal and human studies. Although branched chain fatty acids have been interested in their unique functions, there is no data concerning the effect of iso-C5:0 on lipid metabolism. In this study we investigated the effect of structured-lipids from porpoise adipose tissue (porpoise oil) on lipid metabolism in Otsuka Long-Evans Tokushima Fatty (OLETF) rats. For 4 weeks, rats were fed semisynthetic diets containing either 10% corn oil or 5% corn oil plus 5% porpoise oil. After feeding period, the porpoise oil diet significantly alleviated hepatic triglyceride accumulation compared with the control diet in OLETF rats. Although serum triglyceride level increased, serum level of adiponectin that can protect liver function and alleviate abnormalities of lipid and glucose metabolism increased in rats fed porpoise oil diet. In conclusion, results from the present study suggest that porpoise oil feeding prevents the development of fatty liver disease through the enhancement of lipoprotein secretion and increase of adiponectin production in obese rats.
Water-distilled essential oils from flowers and stems of Tanacetum argyrophyllum var. argyrophyllum from Turkey were analyzed by GC and GC/MS. The flower oil of T. argyrophyllum var. argyrophyllum was characterized with camphor 29.7%, borneol 12.0%, 1,8-cineole 8.4% and bornyl acetate 6.1%. Stem oil was characterized with camphor 26.6%, 1,8-cineole 17.5%, and borneol 15.0%. Our previous research and literature on the essential oil of this plant reported oils with high thujone content unlike the present study. Antibacterial activity of the oils were evaluated for five Gram-positive and five Gram-negative bacteria by using a broth microdilution assay. The highest inhibitory activity was observed against Bacillus cereus for stem oil (125 μg/mL) when compared with positive control chloramphenicol it showed the same inhibition potency. However, the same oil showed lower inhibitory activity against B. subtilis. The flower oil did not show significant activity against the tested microorganisms. DPPH radical scavenging activity of the T. argyrophyllum var. argyrophyllum oil was investigated at 15 and 10 mg/mL concentrations. However, the oils did not show any significant activity when compared to positive control α-tocopherol. Both of the oils showed toxicity to Vibrio fischeri in the TLC-bioluminescence assay.
Melanogenesis is a well-known physiological response of human skin that may occur because of exposure to ultraviolet light, for genetic reasons, or due to other causes. In our efforts to find new skin lightening agents, palmitoleic acid was investigated for its ability to inhibit melanogenesis. In this study, palmitoleic acid’s effect on melanin formation was assessed. Results indicated that palmitoleic acid was shown to down-regulate melanin content in a dose-dependent pattern. To clarify the target of palmitoleic acid action in melanogenesis, we performed Western blotting for tyrosinase, tyrosinase-related protein-1 (TRP-1), TRP-2, and microphthalmia-associated transcription factor (MITF), which are key melanogenic enzymes. Palmitoleic acid inhibited tyrosinase, TRP-2, and MITF expressions in a dose-dependent manner. However, it did not inhibit TRP-1 expression. In order to assess its usefulness in future cosmetic product applications, the cytotoxic effects of the palmitoleic acid were also determined by colourimetric MTT assays using human keratinocyte HaCaT cells. Palmitoleic acid exhibited no cytotoxicity at 500 μM in a human cell line. Therefore, this study suggests that palmitoleic acid is a candidate anti-melanogenic agent, and it might be effective in hyperpigmentation disorders.
In the present study, a randomized, double-blind, placebo-controlled study was performed to evaluate the safety of an excessive intake and the efficacy of a long-term intake of polyphenols derived from apples for moderately underweight to moderately obese subjects (long-term intake: 94 subjects; excessive intake: 30 subjects). For each trial, the subjects were divided into the following two groups: a group that drank beverages with apple polyphenols (600 mg) (hereinafter referred to as the apple group) and a group that drank beverages without apple polyphenols (hereinafter referred to as the placebo group). For the long-term intake trial, the subjects were given a regular amount of the beverage (340 g) each day for 12 weeks. For the excessive intake trial, the subjects were given three times the regular amount of the beverage each day for 4 weeks. It is noteworthy that the visceral fat area (VFA) of subjects in the apple group for the long-term intake trial had decreased significantly by the 8- and 12-week marks (week 8: p < 0.05; week 12: p < 0.01) compared to the baseline (week 0). The degree of change in VFA experienced by subjects in the apple group compared to those in the placebo group was significantly lower by the 8- and 12-week marks (p < 0.01). Stratified analysis indicated that the VFA of subjects in the apple group that started with a high VFA (VFA > or = 100 cm2) had decreased significantly by the 8- and 12-week marks compared to the baseline (week 8: p < 0.05; week 12: p < 0.01). However, no significant change in the VFA of subjects in the apple group that started with a normal VFA (VFA < 100 cm2) was exhibited by the 8- and 12-week marks. No clinical problems arose in the blood examinations or physical examinations for the long-term intake trial or the excessive intake trial. No adverse reaction was observed in either trial. These results demonstrated the efficacy and the safety of the beverage with apple polyphenols.