Policosanol profiles and adenosine 5'-monophosphate-activated protein kinase (AMPK) activation potential of Korean wheat seedling extracts according to cultivar and growth time.

Policosanols is a health promoting aliphatic alcohol known as lipid-lowing agent. To enable maximising the functional properties of wheat, this research investigates the policosanol profiles and adenosine 5'-monophosphate-activated protein kinase (AMPK) activation potential of Korean wheat seedlings according to cultivars and growth times. GC-MS revealed six policosanols that differed markedly in content between 17 cultivars, especially, octacosanol (8) showed the most predominant component (49-83%), varying significantly in average concentrations with growth times as 361.4 (3 days) â†’ 613.0 (6 days) â†’ 203.1 (9 days) â†’ 196.5 (12 days) â†’ 50.9 mg/100 g (19 days). The highest average policosanol (738.7 mg/100 g) exhibited after 6 days, while the lowest was 104.4 mg/100 g on 19 days. Moreover, the wheat cultivars including Shinmichal 1, Anbaek, Namhae, and Joah at 6 days may be recommended as potential sources because of high policosanols (921.7-990.6 mg/100 g). Western blot analysis revealed markedly higher AMPK activation in cells treated with the hexane extracts (150-370% at 100 µg/ml) and octacosanol (8) possessed potent AMPK activator (control; 100 â†’ 280% at 200 µg/ml). It is confirmed that the AMPK activation by wheat seedlings are positively related to the highest policosanol content at the 6 days of growth time, independent of the cultivar. Our results may be contributed to enhance the wheat value regarding development of new cultivars and functional foods.

Anti-melanin deposition activity and active constituents of Jatropha multifida stems.

Jatropha multifida is a medicinal plant that belongs to the Euphorbiaceae family. Our investigation revealed that the chloroform extract of J. multifida stems showed anti-melanin deposition activity against α-melanocyte stimulating hormone (α-MSH)- and 3-isobutyl-1-methylxanthine (IBMX)-induced melanogenesis in the mouse melanoma cell line (B16-F10). Further fractionation and purification of the major constituents led to the isolation of two coumarins (1 and 2) and seven known lignoids (3-9). All isolated compounds exhibited anti-melanin deposition activities against the mouse melanoma cell line (B16-F10) with IC50 values ranging from 37.5 to 560.1 µM, without any cytotoxicity even at high concentrations, except for 8. Further mechanistic studies suggested that 9 downregulated tyrosinase mRNA expression, while the anti-melanin deposition activities of 4 and 8 appeared to be unrelated to tyrosinase inhibition and the downregulated expression of the key melanogenesis-associated mRNAs. These results suggested that J. multifida could possess potent skin whitening ingredients.

Lignans with melanogenesis effects from Premna serratifolia wood.

Three new lignoids, premnan A (1), premnan B (2), and tauntangyiol C (3), were isolated from Premna serratifolia wood, a traditional cosmetic plant in Myanmar, together with a new lignoid, premnan C (4) assumed to be an artifact, one natural new lignoid (5), and three known lignoids (6-8). The structures of the new compounds 1-4 were elucidated based on 1D and 2D NMR, IR spectroscopy, and HRESIMS. The absolute configurations of 1-4 were also determined by optical rotation, circular dichroism (CD) data analyses, and comparisons with the reported literature. All isolated compounds were tested for their melanogenesis activities against the B16-F10 mouse melanoma cell line. Compounds 1 and 4 showed melanogenesis enhancing activities of 31% and 50%, respectively, at a 50 µM concentration. Compounds 2, 3, and 6 increased melanin production by 67%, 30%, and 45%, respectively, at a 100 µM concentration, without any cytotoxicity.

Tetrahydrofuran lignans: Melanogenesis inhibitors from Premna integrifolia wood collected in Myanmar.

Two new tetrahydrofuran lignans, taungtangyiols A (1) and B (2), and eight known furofuran lignans (3-10), were isolated from the chloroform extract of Premna integrifolia wood collected in Myanmar. Their structures were elucidated by extensive spectroscopic techniques. The X-ray crystal structure of 1 clearly indicated its relative configuration. Taungtangyiols A (1) and B (2) inhibited the deposition of melanin in B16F10 mouse melanoma cells, with IC50 values of 50.7 and 40.9 µM, respectively, without notable cytotoxicity. An SAR study demonstrated that the furofuran and dioxymethylene moieties of the lignans play a vital role in inhibiting melanogenesis.

Two new pyrrolo-2-aminoimidazoles from a Myanmarese marine sponge, Clathria prolifera.

Marine organisms such as marine sponges and soft corals are valuable sources of pharmacologically active secondary metabolites. In our ongoing research on the discovery of new secondary metabolites from marine organisms, two new pyrrolo-2-aminoimidazoles, clathriroles A (1) and B (2), were isolated from the water-soluble portion prepared from the methanol and acetone (2:1) extract of the marine sponge, Clathria prolifera, collected in Myanmar. The chemical structures of the isolated compounds were determined using extensive spectroscopic techniques, including NMR, HRESIMS, IR, and optical rotation, and comparisons with the reported literature. The spectroscopic analyses of 1 and 2 suggested that 1 is an enantiomer of antifungal N-methylmanzacidin C isolated from the marine sponge Axinella brevistyla, whereas 2 is a diastereomer of manzacidin D at C-11 isolated from the marine sponge Astrosclera willeyana. To the best of our knowledge, this is the first report of the isolation of the pyrrolo-2-aminoimidazole compounds from C. prolifera. Furthermore, in contrast to the potency of N-methylmanzacidin C against Saccharomyces cerevisiae, the antifungal assay revealed that 1 and 2 lack any activity against this strain. Thus, these observations may suggest that the absolute configurations at both C-9 and C-11 play an important role in controlling the antifungal activity of this type of compound.

Anti-influenza virus activity of extracts from the stems of Jatropha multifida Linn. collected in Myanmar.

BACKGROUND: To contribute to the development of novel anti-influenza drugs, we investigated the anti-influenza activity of crude extracts from 118 medicinal plants collected in Myanmar. We discovered that extract from the stems of Jatropha multifida Linn. showed anti-influenza activity. J. multifida has been used in traditional medicine for the treatment of various diseases, and the stem has been reported to possess antimicrobial, antimalarial, and antitumor activities. However, the anti-influenza activity of this extract has not yet been investigated. METHODS: We prepared water (H2O), ethyl acetate (EtOAc), n-hexane (Hex), and chloroform (CHCl3) extracts from the stems of J. multifida collected in Myanmar, and examined the survival of Madin-Darby canine kidney (MDCK) cells infected with the influenza A (H1N1) virus, and the inhibitory effects of these crude extracts on influenza A viral infection and growth in MDCK cells. RESULTS: The H2O extracts from the stems of J. multifida promoted the survival of MDCK cells infected with the influenza A H1N1 virus. The EtOAc and CHCl3 extracts resulted in similar, but weaker, effects. The H2O, EtOAc, and CHCl3 extracts from the stems of J. multifida inhibited influenza A virus H1N1 infection; the H2O extract possessed the strongest inhibitory effect on influenza infection in MDCK cells. The EtOAc, Hex, and CHCl3 extracts all inhibited the growth of influenza A H1N1 virus, and the CHCl3 extract demonstrated the strongest activity in MDCK cells. CONCLUSION: The H2O or CHCl3 extracts from the stems of J. multifida collected in Myanmar demonstrated the strongest inhibition of influenza A H1N1 viral infection or growth in MDCK cells, respectively. These results indicated that the stems of J. multifida could be regarded as an anti-influenza herbal medicine as well as a potential crude drug source for the development of anti-influenza compounds.

Piscroside C, a novel iridoid glycoside isolated from Pseudolysimachion rotundum var. subinegrum suppresses airway inflammation induced by cigarette smoke.

ETHNOPHARMACOLOGICAL RELEVANCE: Pseudolysimachion rotundum var. subintegrum (Speedwell, Plantaginaceae) is used as a traditional herbal medicine for treating bronchitis, cough and asthma in Korea, China, Russia, and Europe. AIM OF THE STUDY: In this study, we investigated the protective effects of the novel iridoid glycoside, piscroside C (compound 1) isolated from the methanolic extract of P. rotundum var. subintegrum against inflammatory responses using a cigarette smoke induced chronic obstructive pulmonary disease (COPD) and TNF-α-stimulated human airway epithelial NCI-H292 cells. MATERIALS AND METHODS: The novel iridoid glycoside piscroside C was isolated from the methanolic extract of P. rotundum var. subintegrum. The chemical structure was established by NMR, HRESIMS, and optical rotation. In in vivo experiment, the mice received 1h of cigarette smoke for 3 days. Piscroside C was administered to mice by oral gavage 1h before cigarette smoke exposure for 3 days. In in vitro experiment, we evaluated the effect of piscroside C on proinflammatory mediators in H292 cells stimulated with TNF-α. RESULTS: Piscroside C significantly reduced the neutrophil influx, reactive oxygen species production, IL-6, TNF-α, and elastase activity in bronchoalveolar lavage fluid in COPD animals. In addition, piscroside C attenuated NF-κB and IκB phosphorylation, leading to reduced recruitment of inflammatory cells into the lung tissue. Consistent with the results of in vivo experiment, piscroside C significantly inhibited the expression of inflammatory cytokines (IL-6, IL-8 and IL-1ß) by inhibiting NF-κB activation, as resulting decrease in the phosphorylation of IKKß, IκBα and TAK1 in TNF-α-stimulated H292 cells. CONCLUSION: These findings indicate that piscroside C effectively inhibits inflammatory responses, which is an important process in the development of COPD through suppression of IKK/NF-κB activation. Our study suggest that piscroside C might represent a useful therapeutic for the treatment of inflammatory airway disease.