Studies On The Bioactive Constituents From Bohadschia Marmorata Jaeger & Holothuria (Microthele) Axiloga H.L.Clark

Bohadschia marmorata Jaeger and Holothuria (Microthele) axiloga H.L.Clark are abundant sea cucumbers distributed in South China Sea. Japanese researchers had reported the structures and antifungal activityes of four new triterpene glycosides isolated from the sea cucumber Bohadschia bivittata Mitsukuri. But no chemical works have been performedon the sea cucumber Holothuria (Microthele) axiloga H.L.Clark up to date. The antifungalconstituents of B. marmorata and H. axiloga have been investigated by various chromatographymethods including LPLC, MPLC, HPLC on silica gel and ODS respectively. Fifty-seventriterpene glycosides were isolated, then the chemical structures of the twenty-eightnew compounds were elucidated by chemical reactions, spectral analysis (IR, ¹H NMR, ¹³C NMR, ¹H-¹H COSY, HMQC, HMBC, TOCSY, NOESY) and ESI-MS.From the ethanolic extracts of B. marmorata, thirty-six triterpene glycosides were isolated and the structures were identified as the below, BM-1: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 25 (26)-holostene-3β, 12α-diol (named: 25,26-dehydro bivittoside D); BM-2: 3-O-{( 3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-gmcopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β, 12α, 17α-triol (named: 17-hydroxy impatiensideA); BM-3: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyr anosyl-(1-4)]-β-D-xylopyranosyl}-9 (11), 23 (24)-holostene-3β, 12a, 25-triol (named: marmoroside A); BM-4: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-25-acetoxy-9 (11)-holostene-3β, 12α-diol (named: 25-acetoxy bivittoside D); BM-5: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3) -β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyran osyl)-(1→3)-β- D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene -3β, 12α-diol(impatienside A); BM-6: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosy 1)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11)-holostene-3β, 12α-diol (bivittoside D); BM-7: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyrano- syl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-12-one-9 (11)-holostene-3β-ol (named: marmoroside E);BM-8: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl -(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glu copyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β,12α, 22-triol (named:22-hydroxy impatienside A); BM-9: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3) -β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyran osyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11)-holostene-3β,12α, 17α-triol (named: marmoroside D); BM-10: 3-O-{(3-O-methyl-β-D-glucopy-ranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9(11)-holostene-3β,12α, 17α, 25-tetrol (named: marmoroside F); BM-11: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (named: marmoroside G); BM-12: 3-O-{(β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-2 2, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (named: marmoroside H); BM-13: 3-O-{( 3-O-methyl-β-D-glucopyranosyl)-(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-xylop yranosyl}-9 (11), 24 (25)-holostene-3β, 12α-diol (named: marmoroside I); BM-14: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-24-one-9 (11)-holostene-3β, 12α-diol (named: 24-one bivittoside D); BM-15: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-16-acetoxy-9 (11), 24 (25)-holostene-3β, 12α, 17α-triol (named: marmoroside J); BM-16: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (named: 17-dehydroxy marmoroside G); BM-17: 3-O-{(3-O-methyl-β-D-glucopyranosyl) -(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl -(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11), 24 (25)-holostene-3β, 12α-diol (named: marmoroside K); BM-18: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)] -β-D-xylopyrano syl}-23-acetoxy-9 (11), 24 (25)-holostene-3β,12α, 17α-triol (named: 17-hydroxy marmoroside K);BM-19: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xyIopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β,12α-diol (named: 17-dehydroxy holothurinoside A); BM-20:3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurinoside A); BM-21: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-so diumsulfato-β-D-xylopyranosyl]-22-one-9 (11)-holostene-3β,12α-diol (fuscocineroside B );BM-22:3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22-one-25-acetoxy-9 (11)-holostene-3β,12α-diol (fuscocineroside A); BM-23: 3-O-[(3-O-methyl-β-D-gluco-pyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodium sulfato-β-D-xylopyranosyl]-22-one-25-acetoxy-9 (11)-holostene-3β, 12α, 17α-triol (named: marmoroside C); BM-24: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyr anosyl]-9 (11)-holostene-3β, 12α-diol(pervicoside C); BM-25: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-so diumsulfato-β-D-xylopyranosyl]-22-one-9 (11)-holostene-3β,12α, 17α-triol (named: 17-hydroxy fuscocineroside B); BM-26: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22-one-9 (11)-holostene-3β, 12α, 25-triol (named: 25-hydroxy fuscocineroside B); BM-27: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurin A); BM-28: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (fuscocineroside C); BM-29: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D -quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-25-acetoxy-9 (11)-holostene-3β, 12α-diol (pervicoside A); BM-30: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-9 (11), 24 (25)-holostene-3β, 12α-diol (named: 24,25-dehydro marmoroside L); BM-31: 3-O-[(3 -O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-9 (11)-holostene-3β, 12α-diol (named: marmoroside L); BM-32:3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D -quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol(DS-holothurin A); BM-33: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (named: marmoroside B); BM-34: 3-O-{β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyra nosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β,12α-diol(named: 24, 25-dehydro bivittoside B); BM-35: 3-O-{β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11)-holostene -3β,12α-diol (bivittoside B); BM-36: 3-O-[β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β,12α, 17α-triol (named:holothurin B).From the ethanolic extracts of H. axiloga, twenty-one triterpene glycosides were isolatedand the structures were identified as the below, HA-1: 3-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-acetoxy-7(8),25 (26)-holostene-3β-ol (stichloroside B2); HA-2: 3-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-acetoxy-7 (8)-holostene-3β-ol (stichloroside B1); HA-3: 3-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-acetoxy-7 (8), 25 (26)-holostene-3β-ol (stichloroside C2); HA-4: 3-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-acetoxy-7 (8)-holostene-3β-ol (stichloroside C1); HA-5: 3-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-acetoxy-7 (8)-holostene-3β-ol (named: axilogoside B); HA-6: 3-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-glu- copyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8)-holostene-3β-ol (named: axilogoside C); HA-7: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (marmoroside G); HA-8: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-xylopy -ranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11)-holostene-3β,12α-diol (named: axilogoside D); HA-9: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11), 24 (25)-holostene-3β, 12α-diol (marmoroside K); HA-10: 3-O-{(3-Omethyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β, 12α-diol (named: axilogoside E); HA-11: 3-O-{(β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (axilogoside F); HA-12: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3) -β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-9 (11)-holostene-3β, 12α, 17α, 22-tetrol (holothurin A1); HA-13: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-9 (11)-holostene-3β, 12α, 17α-triol (echinoside A); HA-14: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-9(11)-holostene-3β, 12α-diol (pervicoside C); HA-15: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glu-copyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl] -22-one-9 (11)-holostene-3β, 12α-diol(fuscocineroside B); HA-16: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-so diumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurin A);HA-17: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (ruscocineroside C); HA-18: 3-O-[(3-O-methyl-β-D-glucop-yranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22-one-25-acetoxy-9 (11)-holostene-3β, 12α-diol (fuscocineroside A);HA-19: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-25-acetoxy-9 (11)-holostene-3β, 12α-diol (pervicoside A); HA-20: 3-O-[β-D-quinovopyranosyl-(1→2 )-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurin B); HA-21: 3-O-[β-D-quinovopyranosyl-(1→2)-4-O-sulfo-β-D-xylopyranosyl] -22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (axilogoside A).BM-1; BM-2; BM-3; BM-4; BM-7; BM-8; BM-9; BM-10; BM-11; BM-12; BM-13; BM-14; BM-15; BM-16; BM-17; BM-18; BM-19; BM-23; BM-25; BM-26; BM-30; B-31; BM-33; BM-34 are novel triterpene glycosides isolated from B. marmorata. HA-5; HA-6; HA-8; HA-10; HA-21 are novel triterpene glycosides isolated from H. axiloga.The antifungal active assay of these saponins indicated that BM-1; BM-2; BM-5; BM-6; BM-7; BM-13; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Candida albicans. BM-1; BM-2; BM-4; BM-5; BM-6; BM-7; BM-13; BM-17; BM-19; BM-20; BM-24; BM-27; BM-30; BM-31; BM-34; BM-35; BM-36; HA-13; HA-14; HA-16; HA-20 exhibit significant antifungal activities against Cryptococcusneoformans. BM-1; BM-2; BM-5; BM-6; BM-13; BM-17; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Aspergillusfumigatus. BM-1; BM-4; BM-5; BM-6; BM-9; BM-11; BM-17; BM-19; BM-20; BM-24; BM-30; BM-31; BM-32; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Trichophyton rubrum. BM-1; BM-2; BM-5; BM-6; BM-7; BM-13; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Candida tropicalis. BM-2; BM-5; BM-6; BM-7; BM-13; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Candida krusei, MIC₈₀≤4μg/ml.The studied of the cytotoxic activities indicated that BM-1; BM-2; BM-5 and BM-6exhibit significant cytotoxic active against A549, while BM-24 exhibit considerable cytotoxicactive. BM-1; BM-2; BM-5 and BM-6 exhibit considerable cytotoxic active against MOLT-4.Our studies focused on bioactive constituents of B. marmorata and H. axiloga have established a foundation for further research and development of these two sea cucumbers with abundant resources in South China Sea, and provided important leading compounds for the development of new antifungal drugs.