Dissertation
Dissertation > Medicine, health > Pharmacy > Drug basic science > Medicinal Chemistry

Studies on the Bioactive Constituents from Actinopuga.sp and Stichopus Variegates Semper

Author ZhangHongWei
Tutor YiYangHua
School Second Military Medical University
Course Medicinal Chemistry
Keywords Actinopuga.sp Stichopus variegatus Semper bioactive constituents triterpene glycoside anti-fungus
CLC R914
Type Master's thesis
Year 2009
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Actinopuga.sp and Stichopus variegatus Semper distributed abundantly in South China Sea especially in Guangdong and Fujian Province. Up to date , only few chemical works have been performed on these sea cucumbers.Guided by Pyricularia oryzae bioassay model, the anticancer and antifungal constituents of Actinopuga.sp and Stichopus variegatus Semper have been investigated by various chromatography methods including LPLC, MPLC, HPLC on silica gel, ODS RP C-18 and Zorbax SB C-18 respectively. Finally, nineteen compounds were isolated and elucidated by chemical and spectral analysis (IR, EI-MS, HREI-MS, ESI-MS; 1H NMR, 13C NMR, HMQC, TOCSY, 1H-1H COSY, DQF-COSY, HMBC, NOESY, etc) .From the Actinopuga.sp, seven compounds were isolated and identified, they are all triterpeneglycosides: 3-O-[3-Omethyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyran -os-yl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl]-holosta-9(11)-ene-3β,12α-diol(AC-1 pervicoside C),3-O-[3-O-methyl-β-D-glucopyr anosyl-(1→3)-β-D-xylopyranosyl(1→4)-β-D-xylopyr-anosyl(1→2)-β-D-quinovopyr anosyl(1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl]-holosta-7(8)ene-3β-ol(AC-2 fro -ndoside A),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-holos-ta-9(11)-ene-3β,12α,17α-triol(AC-3 holothurin A),3-O-[3-O-methyl-β-D-glucopyran-osyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsu-lfate-β-D-xylopyranosyl]-holosta-22-hydroxyholost-9(11)-ene-3β,12α,17α-triol (AC-4 holothurin A1) , 3-O-[β-D- quinovopyranosyl-(1→2)-4-O-Sodiu -msulfate-β-D-xylopyranosyl]-22,25-epoxy-holosta-9(11)-ene-3β,12α,17α-triol (AC-5 holothurin B),3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-gluc-opyranosyl- (1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl]-25- acetoxy-holosta-9(11)-ene-22-one-3β, 12a-diol (AC-6 fuscocineroside A ), 3-O-[3-O- methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovo-pyra nosyl-(1→2)-4-O-sodiumsulf-ate-β-D-xylopyranosyl]-holosta-9(11)-ene-22-one-3β,12α–diol(AC-7 fuscocineroside B).From the Stichopus variegatus Semper, even compounds were isolated and identified, including eleven triterpene glycosides and one aglycone as follows: 3β-O-{3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-gluco pyranosyl-(1→2)[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23(S)-acetoxyholosta-7, 25-diene(SV-1化合物F1). 3β-O-{3-O- methyl-β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-glucopyranosyl -(1→2)[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23(S)-acetoxyholosta-7-ene. (SV-2化合物F2). 3β-O-{3-O-methyl-β-D-glu copyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23(S)-acetoxyholosta-7, 25-diene(SV-3化合物G). 3β-O-[3-O-methyl-β-D-gluco pyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl]-22, 25-epoxy-holos-ta-9(11)-ene-3β, 12α, 17α-triol( SV-4 holothurin A). 3β-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyran osyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sulfato-β-D-xylopyranosyl]-22, 25- epoxy-holos-ta-9(11)-ene-3β, 12α, 17α-triol(SV-5 desnatrium-holothurin A). 3β-O- {3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23(S)-acetoxyholosta-7, 25-diene(SV-6 stichloroside A2). 3β-O- {3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23(S)-acetoxyholosta-7-ene(SV-7 stichloroside A1). 3β-O-{3-O- methyl-β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-glucopyranosyl -(1→2)[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23(S)-acetoxyholosta-7, 25-diene(SV-8 stichloroside B2). 3β-O-{3-O- methyl-β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-glucopyranosyl -(1→2)[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23(S)-acetoxyholosta-7-ene(SV-9 stichloroside B1). 3β-O-{3-O-methyl -β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23(S)-acetoxyholosta-7-ene(SV-10 stichloroside C1). 3β-O-{3-O-methyl-β- D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)[3-O -methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23(S)-acetoxyholosta-7-ene(SV-11化合物H). Holosta-23(S)- acetoxyholos ta-7-ene(SV-12化合物onenin).Our studies focused on bioactive constituents of Actinopuga.sp and Stichopus variegatus Semper have established a foundation for further research and development of the kind sea cucumber with abundant resources in South China Sea, and provided important lead- ing compounds for the development of new anti-cancer and anti-fungus drugs.

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