Caragasinin C: a new oligostilbene from the roots of Caragana sinica.

A new oligostilbene, caragasinin C (1), and seven known compounds, betulinic acid (2), 4-hydroxybenzaldehyde (3), (‒)-medicarpin (4), wistin (5), (2E,4S)-4-hydroxy-2-nonenoic acid (6), pallidol (7), and (+)-α-viniferin (8), were isolated from the roots of Caragana sinica. The structure of caragasinin C was established on the basis of spectroscopic techniques, including HRESIMS, 1D and 2D-NMR.

Hydroxyl octadecenoic acids biosynthesized by crown galls of Panax quinquefolium induced by artermisinic acid.

OBJECTIVE: To investigate the effect of artermisinic acid on the secondary metabolites production of Panax quinquefolium crown galls. METHODS: Artemisinic acid was added into the suspended cells of Panax quinquefolium crown galls and co-culture for two days. Products were isolated with chromatographic method. RESULTS: Three hydroxyl octadecenoic acids [9,12,13-trihydroxy-10-octadecenoic acid (1), 11,12,13-trihydroxy-9-octadecenoic acid (2) and 11-hydroxy-12,13-epoxy-9-octadecenoic acid (3)] were isolated from crown galls of Panax quinquefolium. CONCLUSION: Artermisinic acid as one of the new type of phytohormones that might induce the production of 13-lipoxygenases in crown galls of Panax quinquefolium.

[Studies on the chemical constituents of Codonopsis pilosula].

OBJECTIVE: To study the chemical constituents of Codonopsis pilosula. METHODS: The compounds were isolated and purified by column chromatography and their structures were elucidated through spectroscopic techniques (NMR) and physicochemical properties. RESULTS: The compounds were isolated as hesperidin(I), n-hexyl beta-sophoroside(II), atractylenolide III (III), lobetyolin(IV), lobetyolinin(V), taraxerol(VI), taraxeryl acetate(VII), alpha-spinasterol(VIII),9,10,13-trihydroxy-(E)-11-octadecenoic acid (IX),beta-sitosterol(X),beta-daucosterol(XI)and sugar(XII). CONCLUSION: Compounds 1 -2 and 9 are isolated from this plant for the first time.

Two new compounds from transgenic Panax quinquefolium.

A new ceramide and a new poly-hydroxyl octadecenoic acid were isolated from transgenic crown galls of Panax quinquefolium. Their structures were elucidated as (2S, 3S, 4R, 20E)-2-[(2'R)-2'-hydroxyl-palmitoyl-amino]-20-hexacosene-1, 3, 4-triol (1) and 12, 13, 15-trihydroxy-9-octadecenoic acid (2) respectively on the basis of spectroscopic and chemical methods.

Phytochemical constituents from Salsola tetrandra.

The new norisoprenoid 3beta-hydroxy-5alpha,6alpha-epoxy-beta-ionone-2alpha-O-beta-d-glucopyranoside (1) and the long-chain hydroxy fatty acids 9,12,13-trihydroxyoctadeca-10(E),15(Z)-dienoic acid (2) and 9,12,13-trihydroxyoctadeca-10(E)-dienoic acid (3) were isolated from Salsola tetrandra aerial parts, together with 3,4,5-trimethoxyphenyl-beta-d-glucopyranoside (4), 9-hydroxylinaloyl glucoside (5), taxiphyllin (6), trans-N-feruloyltyramine (7), and S-(-)-trans-N-feruloyloctopamine (8). Their structures were elucidated by extensive spectroscopic analysis and chemical methods. Compounds 6 and 8 displayed mild antibacterial activity against Staphylococcus aureus, whereas compound 6 showed the highest activity in the Artemia salina bioassay.

GC-MS analysis of compounds extracted from buds of Populus balsamifera and Populus nigra.

The composition of hexane and ether extracts from buds of two poplar species (Populus balsamifera and P. nigra) was investigated by GC-MS method. In hexane extracts, 54 "neutral" compounds were recorded. The greatest amounts of them are sesquiterpenes and n-alkanes. Among 56 components of ether extracts, many aliphatic acids and hydroxyacids were detected. However, the main fraction consists of phenolcarboxylic acids, substituted cinnamic acids, and their esters. It was established that chemotaxonomic differences between Populus balsamifera and P. nigra are observed in the case of both hexane and ether bud extracts.

A new (E)4-hydroxy-dodec-2-enedioic acid from the stem bark of Albizzia julibrissin.

A new unsaturated hydroxy acid was isolated from the stem bark extract of Albizzia julibrissin through repeated silica gel and Sephadex LH-20 column chromatography. The chemical structure of the new acid was determined as (E)-4-hydroxy-dodec-2-enedioic acid on the basis of several spectral data including 2D-NMR. The stereochemical feature of the double bond was determined to be E on the basis of the coupling pattern of related proton signals in the 1H-NMR and COSY experiments.

Plant constituents interfering with human sex hormone-binding globulin. Evaluation of a test method and its application to Urtica dioica root extracts.

A test system is described, which allows the search for compounds interfering with human sex hormone-binding globulin (SHBG) even in complex plant extracts. The method has been evaluated and applied to Urtica dioica root extracts. The lignan secoisolariciresinol (5) as well as a mixture of isomeric (11 E)-9,10,13-trihydroxy-11-octadecenoic and (10 E)-9,12,13-trihydroxy-10-octadecenoic acids (3 and 4, resp.) were demonstrated to reduce binding activity of human SHBG. Methylation of the mixture of 3 and 4 increased its activity about 10-fold.

Dietary supplementation with ethyl ester concentrates of fish oil (n-3) and borage oil (n-6) polyunsaturated fatty acids induces epidermal generation of local putative anti-inflammatory metabolites.

Clinical reports have attributed the amelioration of chronic inflammatory skin disorders to the presence of certain polyunsaturated fatty acids (PUFA) in dietary oils. To test the hypothesis of a local modulatory effect of these PUFA in the epidermis, the basal diet of normal guinea pigs was supplemented with ethyl esters of either fish oil [rich in eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)] or borage oil [rich in gamma-linolenic acid (GLA)]. Our data demonstrated that dietary oils influence the distribution of PUFA in epidermal phospholipids and the epidermal levels of PUFA-derived hydroxy fatty acids. Specifically, animals supplemented with ethyl esters of fish oil markedly incorporated EPA and DHA into epidermal phospholipids, which paralleled the epidermal accumulation of 15-hydroxyeicosapentaenoic acid (15-HEPE) and 17-hydroxydocosahexaenoic acid (17-HDoHE). Similarly, animals supplemented with esters of borage oil preferentially incorporated dihomogammalinolenic acid (DGLA), the epidermal elongase product of GLA, into the epidermal phospholipids, which also was accompanied by epidermal accumulation of 15-hydroxyeicosatrienoic acid (15-HETrE). By factoring the epidermal levels of the 15-lipoxygenase products and their relative inhibitory potencies, we evolved a measure of the overall potential of dietary oils to exert local anti-inflammatory effect. For example, the leukotriene inhibition potentials (LIP) of both fish oil and borage oil were greatly enhanced when compared to controls. Thus, the altered profiles of epidermal 15-lipoxygenase products generated from particular dietary oils may be responsible, at least in part, for reported ameliorative effects of oils on chronic inflammatory skin disorders.

Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean (Vicia faba L.).

Incubation of linoleic acid with the 105,000g particle fraction of the homogenate of the broad bean (Vicia faba L.) led to the formation of the following products: 13(S)-hydroxy-9(Z),11(E)-octadecadienoic acid, 9,10-epoxy-12(Z)-octadecenoic acid (9(R),10(S)/9(S)/10(R), 80/20), 12,13-epoxy-9(Z)-octadecenoic acid (12(S),13(R)/12(R)/13(S), 64/36), and 9,10-epoxy-13(S)-hydroxy-11(E)-octadecenoic acid (9(S),10(R)/9(R),10(S), 91/9). Oleic acid incubated with the enzyme preparation in the presence of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid or cumene hydroperoxide was converted into 9,10-epoxyoctadecanoic acid (9(R),10(S)/9(S),10(R), 79/21). Two enzyme activities were involved in the formation of the products, an omega 6-lipoxygenase and a hydroperoxide-dependent epoxygenase. The lipoxygenase, but not the epoxygenase, was inhibited by low concentrations of 5,8,11,14-eicosatetraynoic acid and nordihydroguaiaretic acid. In contrast, the epoxygenase, but not the lipoxygenase, was readily inactivated in the presence of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid. Studies with 18O2-labeled 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid showed that the epoxide oxygens of 9,10-epoxyoctadecanoic acid and of 9,10-epoxy-13(S)-hydroxy-11(E)-octadecenoic acid were derived from hydroperoxide and not from molecular oxygen.