gracillin
gracillin Basic information
- Product Name:
- gracillin
- Synonyms:
-
- 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)-Spirost-5-en-3β-yl]2-O-(6-deoxy-α-L-mannopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranoside
- [(25R)-Spirosta-5-ene-3β-yl]3-O-β-D-glucopyranosyl-2-O-α-L-rhamnopyranosyl-β-D-glucopyranoside
- Diosgenin 3-O-β-gracillimatrioside
- Gracilline
- Diosgenin 3-O-beta-gracillimatrioside
- DulcaMarinC
- CAS:
- 19083-00-2
- MF:
- C45H72O17
- MW:
- 885.04
- Product Categories:
-
- chemical reagent
- pharmaceutical intermediate
- phytochemical
- reference standards from Chinese medicinal herbs (TCM).
- standardized herbal extract
- Mol File:
- 19083-00-2.mol
gracillin Chemical Properties
- Melting point:
- 290-293℃ (DEC.)
- Density
- 1.42
- storage temp.
- under inert gas (nitrogen or Argon) at 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
gracillin Usage And Synthesis
Description
Gracillin is a steroidal saponin that has been found in C. speciosus and has diverse biological activities. 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). 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. 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 in mice.
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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