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Studies On The Bioactive Constituents From Holothuria Fuscocinerea Jaeger And Pseudocolochirus Violaceus Theel

Posted on:2006-07-27Degree:DoctorType:Dissertation
Country:ChinaCandidate:S Y ZhangFull Text:PDF
GTID:1104360155450730Subject:Medicinal chemistry
Abstract/Summary:PDF Full Text Request
Holothuria fuscocinerea and Pseudocolochirus violaceus are abundant sea cucumbers distributed in South China Sea. No chemical works have been performed on these sea cucumbers up to date. Guided by Pyricularia oryzae bioassay model, the anticancer and antifungal constituents of H. fuscocinerea and P. violaceus have been investigated by various chromatography methods including LPLC, MPLC, HPLC on silica gel, ODS RP C18 and Zorbax SB C18 respectively. Twenty-four compounds were isolated and chemical structures of twenty-one were elucidated by chemical and spectral analysis (IR, EI-MS, ESI-MS, HRESI-MS, 1H NMR, 13C NMR, 1H-1H COSY, DQCOSY, TOCSY, HMQC, HMBC, NOESY, etc).From the ethanolic extracts of H. fuscocinerea, ten compounds were isolated and identified, including six triterpene glycosides: 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3) -β-O-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfate-β-D-xylo-pyranosyl]-holosta-9(11)-ene-3β, 12α-diol (HF-1, pervicoside C), 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl]-25-acetoxy-holosta-9(11)-ene-22-one-3β, 12α-diol (HF-2), 3-O- [3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovo-pyranosyl-(1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl]-holosta-9(11)-ene-22-one-3β, 12α -diol (HF-3), 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl]-22,25-epoxy-holosta-9(11)-ene-3β, 12α-diol (HF-4), 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-gluco-pyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl]-22,25-epoxy-holosta-9(11)-ene-3β, 12α, 17α-triol (HF-5, holothurin A) and 3-O-[β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-22,25-epoxy-holosta-9(11)-ene-3β,12α, 17α-triol (HF-6, DS-holothurin B); and four other type compounds: uracil (HF-7), thymine (HF-8), thymidine (HF-10) and 2'-deoxyuridine (HF-11).From the ethanolic extracts of P. violaceus, the chemical structures of eleven compounds were elucidated, including seven triterpene glycosides: 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-(1→2)-quinovopyranosyl-4-O-sodiumsulfate-β-D-xylopyranosyl]-16p-acetoxy-holosta-7, 24-diene-3β-ol (PV-1, philinop-side A), 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl]-16β-acetoxy-holosta-7, 24-diene-3β-ol (PV-2), 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→...
Keywords/Search Tags:Holothuria fuscocinerea, Pseudocolochirus violaceus, triterpene glycosides, cytotoxicity, Pyricularia oryzae, anti-fungus
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