Blestriarene A

Phenanthrenes from Arundina graminifolia and in vitro evaluation of their antibacterial and anti-haemolytic properties.[Pubmed:28553728]

Nat Prod Res. 2018 Mar;32(6):707-710.

Chemical investigation and activity test of Arundina graminifolia led to the isolation of six phenanthrenes: Blestriarene A (1), shancidin (2), densiflorol B (3), ephemeranthoquinone (4), coelonin (5) and lusianthridin (6). The isolated compounds demonstrated antibacterial and anti-haemolytic activities. It was found that compounds 1 and 2 had medium antibacterial activity against Staphylococcus aureus, Bacillus subtilis and Escherichia coli, with MICs of 20-40 mug/mL and MBCs of 40-320 mug/mL. Bactericidal mechanisms were explored. Rupture of cell wall and membrane and leakage of nuclear mass were observed by transmission electron microscopy (TEM). Moreover, compounds 1-3 attenuated the erythrocyte damage. Compounds 1 and 2 showed significant anti-haemolytic activity with inhibition rate about 50% at 16 mug/mL.

[Chemical Constituents from Cremastra appendiculata].[Pubmed:26415404]

Zhong Yao Cai. 2015 Feb;38(2):298-301.

OBJECTIVE: To study the chemical constituents of Cremastra appendiculata. METHODS: The compounds were isolated by repeated column chromatography with silica gel, Sephadex LH-20 and ODS-HPLC. The structures were elucidated by analysis of spectroscopic data(1H-NMR and 13C-NMR). RESULTS: Ten compounds were isolated from the EtOAc extract in the tuber of Cremastra appendiculata. Their structures were identified as shancigusin I (I), 4-O-beta-D-glucopyranosyl cinnamate (II), bulbocodin D (III), Blestriarene A (IV), 7-hydroxy-2,4-dimethoxy phenanthrene (V), coelonin (VI), militarine (VII), gastrodine (VIII), 3-hydroxyphenylpropionic acid (IX) and cinnamic acid (X). CONCLUSION: Compounds I-III, IX and X are isolated from Cremastra appendiculata for the first time.

[Chemical constituents from Pleione yunnanensis].[Pubmed:25204178]

Zhongguo Zhong Yao Za Zhi. 2014 Mar;39(5):851-6.

This study was to investigate the chemical constituents from pseudobulbs of Pleione yunnanensis, one of the source of traditional Chinese medicine "Shancigu". The chemical constituents were isolated by various chromatography methods, including silica gel, ODS, Sephadex LH-20, and semi-preparative HPLC. Fourteen compounds were isolated and identified from the EtOAc fraction of 90% ethanol extract, including five dihydrophenanthrenes, four bibenzyls, two triterpenoids, and three phenylacrylic acids. Their structures were identified on the basis of the spectral data as 4, 7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene (1), 4, 7-dihydroxy-1-(p-hydroxybenzyl)-2-methoxy-9,10-dihydrophenanthrene (2), (2,3-trans)-2-(4-hydroxy-3-methoxyphenyl) -3-hydroxymethyl-10-methoxy-2,3,4,5-tetrahydro-phenanthro[2,1-b]furan-7-ol (3), pleionesin B (4), Blestriarene A (5), batatasin III (6), 3, 3'-dihydroxy-2-(p-hydroxybenzyl) -5-methoxybibenzyl (7), 3', 5-dihydroxy-2-(p-hydroxybenzyl) -3-methoxybibenzyl (8), 3,3'-dihydroxy-2,6-bis(4-hydroxybenzyl) -5-methoxybibenzyl (9), triphyllol (10), pholidotin (11), (E) -p-hydroxycinnamic acid (12), (E)-ferulic acid (13), and (E)-ferulic acid hexacosyl ester (14). Compounds 5,10-14 were separated from this plant for the first time.

[Chemical constituents from Pleione bulbocodioides].[Pubmed:24946545]

Zhongguo Zhong Yao Za Zhi. 2014 Feb;39(3):442-7.

Fourteen compoumds were isolated from the ethyl acetate portion of the 95% ethanolic extract of Pleione bulbocodioides by a combination of various chromatographic techniques including silica gel, ODS, macroporous adsorbent resin, Sephadex LH-20, and preparative HPLC, of which ten compoumds were phenanthrenes and dihydrophenanthrenes, two compoumds were bibenzyls, one was lignan and a sterol. Their structures were identified on the basis of spectroscopic data as monbarbatain A(1), 2, 7, 2'-trihy-droxy-4, 4', 7'-trimethoxy-1, 1'- biphenanthrene(2), Blestriarene A(3), pleionesin B(4), shanciol H(5), 17-hydroxy-7'-(4'-hy-droxy-3 '-methoxyphenyl)- 4-methoxy-9, 10, 7', 8'-tetrahydrophenanthro[2, 3-b]furan-8'-yl methyl acetate(6), 1-p-hydroxybenzyl-4-methoxy phenanthrene-2, 7-diol(7), 1-p-hydroxybenzyl-4-met-hoxy-9, 10-dihydrophenanthrene-2, 7-diol(8), hircinol(9), coelonin( 10), gigantol(11), batatasin 11 (12), syringaresinol(13) and ergosta4, 6, 8 ( 14) , 22-tetraen-3-one (14). Compounds 1-3, 9, 13 and 14 were isolated from this genus for the first time.

Antiallergic phenanthrenes and stilbenes from the tubers of Gymnadenia conopsea.[Pubmed:15386193]

Planta Med. 2004 Sep;70(9):847-55.

The methanolic extract from the tubers of Gymnadenia conopsea showed an antiallergic effect on ear passive cutaneous anaphylaxis reactions in mice. From the methanolic extract, three new dihydrophenanthrenes, gymconopins A ( 1), B ( 2), and C ( 3), and a new dihydrostilbene, gymconopin D ( 4), were isolated together with 10 known phenanthrene and stilbene constituents. The structures of the new compounds were determined on the basis of physicochemical evidence. Next, the inhibitory effects of the principal constituents on the release of beta-hexosaminidase, as a marker of degranulation, in RBL-2H3 cells were examined and five phenanthrenes, gymconopin B ( 2), 4-methoxy-9,10-dihydrophenanthrene-2,7-diol ( 6), 1-(4-hydroxybenzyl)-4-methoxyphenanthrene-2,7-diol ( 7), 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol ( 8), and Blestriarene A ( 9), and six dihydrostilbenes, gymconopin D ( 4), batatacin III ( 10), 3'- O-methylbatatacin III ( 11), 3,3'-dihydroxy-2-(4-hydroxybenzyl)-5-methoxybibenzyl ( 12), 3',5-dihydroxy-2-(4-hydroxybenzyl)-3-methoxybibenzyl ( 13), and 3,3'-dihydroxy-2,6-bis(4-hydroxybenzyl)-5-methoxybibenzyl ( 14) were found to inhibit the antigen-induced degranulation by 65.5 to 99.4 % at 100 microM in RBL-2H3 cells.