| Identification | Back Directory | [Name]
gracillin | [CAS]
19083-00-2 | [Synonyms]
Gracilline
DulcaMarinC
LilioglycosideG
Gracillin 19083-00-2
Diosgenin 3-O-β-gracillimatrioside
Diosgenin 3-O-beta-gracillimatrioside
Gracillin, 98%, from Dioscorea opposita Thunb.
(25R)-3β-(2-O-α-L-Rhamnopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)spirosta-5-ene
[(25R)-Spirosta-5-ene-3β-yl]3-O-β-D-glucopyranosyl-2-O-α-L-rhamnopyranosyl-β-D-glucopyranoside
[(25R)-Spirost-5-en-3β-yl]2-O-(6-deoxy-α-L-mannopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranoside
β-D-Glucopyranoside, (3β,25R)-spirost-5-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]- | [Molecular Formula]
C15H20O3 | [MDL Number]
MFCD28978176 | [MOL File]
19083-00-2.mol | [Molecular Weight]
248.32 |
| Chemical Properties | Back Directory | [Melting point ]
290-293℃ (DEC.) | [density ]
1.42 | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Soluble in DMSO, methanol and pyridine | [form ]
powder | [pka]
12.78±0.70(Predicted) | [color ]
White | [InChI]
InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h9-10,13H,4-7H2,1-3H3 | [InChIKey]
RSDQBPGKMDFRHH-UHFFFAOYSA-N | [SMILES]
C12=C(C)CCC(=O)C1(C)CCC1C(C(=O)OC21)C |
| Hazard Information | Back Directory | [Description]
Gracillin is a steroidal saponin that has been found in C. speciosus and has diverse biological activities.1,2,3 It reduces cell growth in a panel of 58 leukemia, non-small cell lung, colon, CNS, prostate, melanoma, ovarian, renal, and breast cancer cell lines (GI50s = 0.58-2.44 μM).1 Gracillin reduces growth of fish Ich parasite (I. multifiliis) theronts (EC50 = 0.53 mg/L) and induces 100 and 92.5% mortality of I. multifiliis protomonts and encysted tomonts, respectively, when used at a concentration of 0.8 mg/L.2 It decreases the number of I. multifiliis-infected goldfish by approximately 75% when used at a concentration of 1 mg/L in tank water. Gracillin (100 mg/kg) reduces ear edema induced by arachidonic acid (Item No. 90010) in mice.3 | [Chemical Properties]
White powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from the rhizomes of Dioscorea zingiberensis and Dioscorea parviflora. | [Uses]
Gracillin is a steroidal glycoside from the rhizomes of the family Dioscoreaceae with potential anti-proliferative effects. | [Definition]
ChEBI: Gracillin is a triterpenoid. | [in vivo]
Gracillin (oral gavage, 10?mg/kg for xenografts and 20?mg/kg for PDX) inhibits tumor growth of xenograft tumors inoculating lung (H1299), prostate (DU145), and colorectum (HCT116) cancer cells, as well as patient-derived xenograft colon and lung tumors[1].
| [References]
[1] KE HU Xinsheng Y. The cytotoxicity of methyl protoneogracillin (NSC-698793) and gracillin (NSC-698787), two steroidal saponins from the rhizomes of Dioscorea collettii var. hypoglauca, against human cancer cells in vitro.[J]. Phytotherapy Research, 2003, 17 6: 620-626. DOI: 10.1002/ptr.1211
[2] WEI ZHENG. Antiparasitic efficacy of Gracillin and Zingibernsis newsaponin from Costus speciosus (Koen ex. Retz) Sm. against Ichthyophthirius multifiliis.[J]. Parasitology, 2015, 142 3: 473-479. DOI: 10.1017/s0031182014001358
[3] SUNG YONG KIM. Inhibition of mouse ear edema by steroidal and triterpenoid saponins[J]. Archives of Pharmacal Research, 1999, 22 3: 313-316. DOI: 10.1007/bf02976370 |
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