Biphenanthrenes from Bletilla striata

Dihydrophenanthrenes from Bletilla formosana

“…The ethyl acetate and n-butanol-soluble fractions were separatedly subjected to silica gel column chromatography. Fractions rich in polyphenolic compounds were combined and purified by Sephadex LH-20 column to give three new dihydrophenanthrenes, 4-methoxy-9,10-dihydrophenanthrene-1,2,7-triol (1), 1-(4-hydroxybenzyl)-4,7-dimethoxy-9,10-dihydrophenanthrene-2-ol (2), and 1,3,6-tri(4-hydroxylbenzyl)-4-methoxydihydrophenanthrene-2,7-diol (3), along with seven known phenanthrene derivatives, 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol (4), 3) 1,6-di(4-hydroxylbenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol (5), 4) 1,3-di(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol (6), 3,4) 1-(4-hydroxybenzyl)-4-methoxyphenanthrene-2,7-diol (7), 4) 1-(4-hydroxybenzyl)-4,8-di-methoxyphenanthrene-2,7-diol (8), 5) 1,8-bi(4-hydroxybenzyl)-4-methoxyphenanthrene-2,7-diol (9), 6) and blestriarene B (10), 7) a bibenzyl, 2Ј,6Ј-bis(p-hydroxybenzyl)-3,3Ј-dihydroxy-5-methoxybibenzyl (11), 8) six known flavonoids, 8-C-p-hydoxybenzylkaempferol (12), 9) apigenin (13), 10) 6-methoxykaempferol (14), 11) kaempferol (15), 12) isorhamnetin (16), 13) kaempferol 7-O-glucoside (17), 12) 3,4-dihydroxybenzaldehyde (18), 14) protocatechuic acid (19), 12) p-(hydroxymethyl)phenyl-b-D-glucoside (20). 15) Compound 1 was isolated as a pale yellow amorphous powder with a molecular formular C 15 .…”

Bioactive Constituents from Chinese Natural Medicines. XVII. Constituents with Radical Scavenging Effect and New Glucosyloxybenzyl 2-Isobutylmalates from Gymnadenia conopsea

“…O 2 Ϫ (IC 50 ϭ13.3 mg/ml) without exhibiting any inhibitory activity on xanthine oxidase (IC 50 Ͼ100 mg/ml). The MeOH-eluted fraction was subjected to ordinary and reversed-phase silica gel column chromatography and finally HPLC to furnish gymnosides VIII (1, 0.0003% from the natural medicine), IX (2, 0.013%), and X (3, 0.0005%) together with dactylorhin A (4, 0.12%), 1,14) gymconopins A (5, 0.0006%) 13) and B (6, 0.0003%), 13) 2-methoxy-9,10-dihydrophenanthrene-4,5-diol (7, 0.0010%), 13) 4-methoxy-9,10-dihydrophenanthrene-2,7-diol (8, 0.0012%), 13) 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol (9, 0.0013%), 13) 1-(4-hydroxybenzyl)-4-methoxyphenanthrene-2,7-diol (10, 0.0003%), 13) blestriarenes A (11, 0.0004%), 13) B 15) (0.0001%), and C 15) (0.0001%), batatacin III (12, 0.0016%), 13) 3Ј,5-dihydroxy-2-(4-hydroxybenzyl)-3-methoxybibenzyl (13, 0.0009%), 13) 3,3Ј-dihydroxy-2-(4-hydroxybenzyl)-5-methoxybibenzyl (14, 0.0008%), 13) 3,3Ј-dihydroxy-2,6-bis(4-hydroxybenzyl)-5-methoxybibenzyl (15, 0.0003%), 13) (0.0006%) and B 14) (0.0003%), thymidine 20,37) (0.0005%), and 5-hydroxymethylfuraldehyde 38) (0.0004%).…”

Chemical Constituents from the Aerial Parts of Cyrtopodium paniculatum

“…The last set of compounds were the dimers, occurring as either homo-(two units of 9,10-dihydrophenanthrene or phenanthrene) or as heterodimers (combinations of a 9,10-dihydrophenanthrene and a phenanthrene unit) having a C-C bond linkage. These biphenanthrene derivatives occur mostly in species of the genus Bletilla [33,41,71,[78][79][80], Bulbophyllum [55,[81][82][83] and Cremastra [54,[84][85][86][87][88]. The existence of dimers together their respective monomers in the same species provides support for a proposed biogenetic pathway for biaryl-derived compounds occurring from their corresponding monomers as a result of free radical [56] or an enzymatic oxidative phenolic coupling reaction [82,[89][90][91].…”

“…The alcoholic crude extract was suspended in water and sequentially extracted with cyclohexane, CH2Cl2 and n-BuOH. The CH2Cl2 extract was concentrated to dryness and subjected to silica gel column chromatography, Sephadex LH-20 and preparative thin layer chromatography (PTLC) to afford eight new compounds 1-8 ( Figure 1) together with 28 previously described compounds 9-35 which were identified as para-ethoxybenzyl alcohol (9) [18,19], 3,4,6-trimethoxyl-9,10-dihydrophenanthrene-2,7-diol (10) [20], confusarin (11) [21], erianthridin (12) [22], para-hydroxybenzaldehyde (13) [18], nudol (14) [23], cephathrene-B (15) [24], gigantol (16) [25], batatasin III (17) [26], ephemeranthoquinone (18) [27], coelonin (19) [28], 2,4-dimethoxyphenanthrene-3,7-diol (20) [29], lusianthridin (21) [30], densiflorol B (22) [31], denthyrsinin (23) [32], bleformins A (24) and B (25) [33], chrysoeriol (26) [34,35], vanillic alcool (27) [36], gastrodigenin (28) [37,38], 1-(4-hydroxybenzyl)-4-methoxyl-9,10-dihydrophenanthrene-2,7-diol (29) [39], shancidin (30) [40], blestriarenes A (32) and B (31) [41], velutin (33) [42], (+)-syringaresinol (34) [43] and (+)-balanophonin (35) [44], respectively, by comparison of their UV, MS, and NMR data with literature data.…”