| Pleione bulbocodioides (Franch.) Rolfe, which is a species of the Orchidaceae family and its dry tuber is one of the main sources of traditional Chinese medicine "shan-ci-gu". The herbal of shan-ci-gu was first recorded in "Bencaoshiyi" According to Chinese Pharmacopeia(the2010Edition), The tubers of three orchidaceous plants, Cremastra appendiculata (D. Don) Makino, Pleione bulbocodioides (Franch.) Rolfe and Pleione yunnanensis Rolfe can be used as it. Pleione bulbocodioides is sweet, pungent in taste and cool in nature. It has actions of removing heat and counteracting toxicity, dissipating phlegm and eliminating stagnation, usually be applied in the treatment of edema, crewels, snake and insert bite.In this dissertation systematic investigation of the ethyl acetate portion of the95%ethanolic extract of Pleione bulbocodioides has been taken, combined with various chromatographic techniques35compoumds were isolated and compounds1-12were new. The isolates were elucidated on the basis of spectroscopic analysis and chemical methods as well.Among these isolates twenty-five compounds were phenanthrenes and its deri-vatives, including two phenanthrenequinone derivatives:2,7,9-trihydroxy-4-methoxy-9-acetonyl-phenanthren-10-one (1),2,7,10-trihydroxy-4-methoxy-10-acetonyl-phenant-hren-9-one (2); Four Benzylphenanthrenequinone derivatives:1-p-hydroxyl-benzyl-2,7,9-trihydroxy-4-methoxy-9-acetonyl-phenanthren-10-one (3),1,3-bis(p-hydroxybenzyl)-2,7,9-trihydroxy-4-methoxy-9-acetonyl-phenanthren-10-one (4),1,9-bis(p-hydroxybe-nzyl)-2,7,9-trihydroxy-4-methoxy-phenanthren-10-one (5),1,10-bis(p-hydroxybenzyl)-2,7-dihydroxy-4-methoxy-phenanthren-9-one (6); Four biphenanthrenes:2,7,2’,6’-tetra hydroxy-4,9,4’,6’-tetramethoxy-1,1’-biphenanthrene (7),2,7,2’,7’-tetrahydroxy-4,4’,9,9’-tetramethoxy-1,1’-biphenanthrene (8), monbarbatain A (13),2,7,2’-trihydroxy-4,4’,7’-trimethoxy-1,1’-biphenanthrene (14); Two dimers which contained phenanthrene and dihydrophenanthrene:2,2’,7,7’-tetrahydroxy-4,9,4’-trimethoxy-9’,10’-dihydro-1,1’-biphe-nanthrene (9),2,2’,7’-trihydroxy-4,7,4’-trimethoxy-9’,10’-dyhydro-1,1-biphenanthrene (10); Two bidihydrophenanthrenes:blestriarene A (15), blestrianol A (16); One dimer which contained phenanthrene and bibenzyl:5’,3"-dihydroxy1-3’-methoxy-bib-enzyl)-4-methoxy-2,7-dihydroxy-9,10-dihydrophenanthrene (11); Six dimers which contained phenanthrene and phenylpropanoids:(7’S,8’R)-7-hydroxy-7’-(4’-hydroxy-3’,5’-dimethoxy-phenyl)-8’-hydroxymethyl-5-methoy-9,10,7’,8’-tetra-hydro-phenanthrene-[2,3-b]furan(12), pleionesin E (19), shanciol H (20),7-hydroxy-7’-(4’-hydroxy-3’- methoxy-phenyl)-4-methoxy-9,10,7’,8’-tetrahydrophenanthrene-[2,3-b] furan-8’-yl-met-hyl acetate (21), pleionesin B (22), pleionesin D (23); One Benzyldihydrophenant-hrene:1-p-hydroxybenzyl-4-methoxy-9,10-dihydrophenanthrene-2,7-diol (17); One Be-nzylphenanthrene:1-p-hydroxybenzyl-4-methoxy-phenanthrene-2,7-diol (18); Two dihydrophenanthrenes:hircinol (24), coelonin (25). Three compoumds were bibenz-yls:3,3’-dihydroxy-2,6-bis(p-hydroxybenzyl)-5-methoxybibenzyl (26), gigantol (27), batatasin Ⅲ (28); Three compoumds were sterol:ergosta-4,6,8(14),22-tetraen-3-one (29), β-sitosterol (30), daucosterol (31); A lignin:syringaresinol (32) and three simple aromatic compounds:5-hydroxymethylfurfural (33), p-hydroxybenzoic acid (34), p-hydroxybenzaldehyde (35). Compounds13-16,24,29,32were isolated from this genus for the first time.Twenty-five phenanthrenes and its derivatives combined with three bibenzyls compounds were investigated for several biological activity assay in vitro, we found that compound1and2exhibited significant antioxidant activity in DPPH radical scavenging at the concentration of10-6M; Compound3-5,7-10,13-14,20-25,27showed potent DPPH radical scavenging activity at the concentration of10-5M.Compound6and compound19,22showed selectived cytotoxic activity to the human pancreatic cancer cells (SW-1990) and human ovarian cancer cells (A2780) at the concentration of10-6M. Compound25showed a potent activity against the production of NO in mouse peritoneal marcophage and compound21,28showed a potent neurotoxicity activity to the rat hippocampal neurons cells (SY-SH-5Y) at the concentration of10-5M.The above researches enrich the contents of chemical constituents from Pleione bulbocodioides in a certain extent and establish good foundation for next research of the tumor cytotoxic and other activitivies constituents. |
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