Studies On The Bioactive Constituents From Pentacta Quadrangulasis And Structure Modification Of Philinopside A Analogues

Pentacta quadrangulasis Lesson distributed abundantly in South China Seaespecially in Guangdong and Fujian Province. Professor YI Yanghua team early foundPhilinopside A is a new triterpene glycoside with strong antitumor activity, which canbe as a leading compound. Two new triterpene glycosides, Philinopside E (1) and F (2),along with the previously isolated Philinopside A, B, C and D, have been found in thesea cucumber Pentacta quadrangulasis. Three new holostane-type triterpenoidaglycones named Philinopgenin A (3), B (4) and C (5) were isolated from the acidhydrolysate of the crude glycoside. Two new derivatives were obtained by structuremodification of philinopside A analogues and named CU-301 (6) and CU-305 (7)respectively. Finally, seven compounds were isolated and elucidated by chemical andspectral analysis (IR, EI-MS, HREI-MS, ESI-MS; H NMR, 1 13C NMR, HMQC,TOCSY, H-1H COSY, DQF-COSY, HMBC, NOESY) and elucidated as 3-O-{3''''- 1O-methyl-β-D-glucopyranosyl(1''''→3''')-β-D-xylopyranosyl(1'''→4'')-β-D-quinovopyranosyl(1''→2')-4'-O-sodiumsulfate-β-D-xylopyranosyl}-holosta-9(11),25-dien-16-one(1), 16β-acetoxyl-3-O-[3''''-O-methyl-β-D-glucopyranosyl(1''''→3''')-β-D-xylopyranosyl(1'''→3'')-β-D-glucopyranosyl(1''→2')-4'-O-sodium sulfate-β-D-xylopyranosyl]-holosta-7,24-diene-3β-ol (2), 16β-acetoxy-holosta-8(9),24(25)-diene-3β-ol (3), 18(16)-lactone-20,25-epoxylanosta-9(11)-ene-3β-ol (4),16β-acetoxy-holosta-9(11),24(25)-diene-3β-ol(5), 16β-acetoxy-3-O-[3''''-O-methyl-6''''-O-acetyl-β-D-glucopyranosyl(1''''→3''')-β-D-xylopy-ranosyl(1'''→3'')-β-D-glucopyranosyl(1''→2')-4'-O-sodium sulfate-β-D-xylo-pyranosyl]-holosta-7,22Z,24-triene-3β-ol(6),16β-acetoxy-3-O-[3''''-O-methyl-2′′′′,4′′′′,6′′′′-O-triacetyl-β-D-glucopyranosyl(1''''→3''')-2′′′,4′′′-O-diacetyl-β-D-xylopyranosyl(1'''→3'')-2′′,4′′-O-diacetyl-β-D-glucopyranosyl(1''→2')-4'-O-sodiumsulfate-2′-O-acetyl-β-D-xylopyrano-syl]-holosta-7,22Z,24-diene-3β-ol(7).These compounds showedmoderate cytotoxity in vitro against human tumor cell lines and some antitumor activityin intro against mouse caruncle cell. The derivatives significantly decrease hemolyticactivity in contrast with Philinopside A. The research has been supported by National High Technology Development Project .