InChI=1S/C38H62O13/c1-18(2)6-9-25(40)19(3)38(47)28(51-34-32(45)29(42)26(41)17-48-34)15-24-22-8-7-20-14-21(10-12-36(20,4)23(22)11-13-37(24,38)5)49-35-33(46)31(44)30(43)27(16-39)50-35/h7,18-19,21-24,26-35,39,41-47H,6,8-17H2,1-5H3/t19-,21-,22+,23-,24-,26-,27+,28-,29-,30+,31-,32+,33+,34-,35+,36-,37-,38+/m0/s1 |
NQDDCCOUDFVXKO-DAVJFRSBSA-N |
[H][C@@]12CC=C3C[C@H](CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])C[C@H](O[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)[C@]1(O)[C@@H](C)C(=O)CCC(C)C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |
|
Ornithogalum thyrsoides
(NCBI:txid484172)
|
Found in
bulb
(BTO:0000159).
See:
PubMed
|
Galtonia candicans
(NCBI:txid81751)
|
Found in
bulb
(BTO:0000159).
See:
PubMed
|
View more via ChEBI Ontology
Outgoing
|
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one
(CHEBI:65628)
has role
antineoplastic agent
(CHEBI:35610)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one
(CHEBI:65628)
has role
metabolite
(CHEBI:25212)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one
(CHEBI:65628)
is a
β-D-glucoside
(CHEBI:22798)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one
(CHEBI:65628)
is a
17-hydroxy steroid
(CHEBI:36838)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one
(CHEBI:65628)
is a
cholestanoid
(CHEBI:50401)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one
(CHEBI:65628)
is a
steroid saponin
(CHEBI:61655)
|
|
(3β,16β,20R)-16-(α-L-arabinopyranosyloxy)-17-hydroxy-22-oxocholest-5-en-3-yl β-D-glucopyranoside
|
Kuroda M, Mimaki Y, Yokosuka A, Hasegawa F, Sashida Y (2002) Cholestane glycosides from the bulbs of Ornithogalum thyrsoides and their cytotoxic activity against HL-60 leukemia cells. Journal of natural products 65, 1417-1423 [PubMed:12398536] [show Abstract] Twelve bisdesmosidic cholestane glycosides (1-12), including nine new ones (1-9), were isolated from the bulbs of Ornithogalum thyrsoides by monitoring the cytotoxic activity on HL-60 leukemia cells. The structural assignment of the new compounds was carried out by spectroscopic analysis and the results of hydrolytic cleavage. The 3-O-monoglucosides with an aromatic acyl group at the C-16 diglycoside moiety (1, 12) were extremely cytotoxic, with respective IC(50) values of 0.00016 and 0.00013 microg/mL, and the other compounds, except for 2, 5, and 8, also showed cytotoxic activity as potent as etoposide (IC(50) 0.30 microg/mL), used as a positive control. These cholestanes were concluded to contribute to the potent cytotoxicity of the crude O. thyrsoides bulb extract. | Kuroda M, Mimaki Y, Yokosuka A, Sashida Y (2001) Cholestane glycosides from the bulbs of Galtonia candicans and their cytotoxicity. Chemical & pharmaceutical bulletin 49, 1042-1046 [PubMed:11515577] [show Abstract] Further search for cytotoxic compounds contained in the bulbs of Galtonia candicans (Liliaceae) led to the isolation of four potent cytotoxic cholestane glycosides (1-4) based upon 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one, three of which (2-4) have not been reported previously. A new cholestane bisdesmoside (5) and a new rearranged cholestane glycoside (6) were also isolated. The structural assignment of the new constituents was carried out by spectroscopic analysis and a few chemical transformations. |
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