Description
Steviolbioside is extracted from the leaves of Stevia rebaudia. It belongs to a terpenoid compound and is a rare natural sweetener. It shows antibacterial effects and has been used in trials studying the treatment of HIV-1 infection. It also displays moderate antituberculosis activity against M. tuberculosis strain H37RV in vitro. It inhibits human breast cancer cell MDA-MB-231, hepatocarcinoma cell Hep3B and pancreatic cancer cell BxPC-3 remarkably. It may be used to treat human breast cancer potentially.
Synonyms
13-[(2-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid; (4α)-13-[(2-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid; Kaur-16-en-18-oic acid, 13-((2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-, (4alpha); 13-O-beta-sophorosyl-steviol
IUPAC Name
(1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
Molecular Formula
C32H50O13
Canonical SMILES
CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)(C)C(=O)O
InChI
InChI=1S/C32H50O13/c1-15-11-31-9-5-18-29(2,7-4-8-30(18,3)28(40)41)19(31)6-10-32(15,14-31)45-27-25(23(38)21(36)17(13-34)43-27)44-26-24(39)22(37)20(35)16(12-33)42-26/h16-27,33-39H,1,4-14H2,2-3H3,(H,40,41)/t16-,17-,18?,19?,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31-,32+/m1/s1
InChIKey
OMHUCGDTACNQEX-YXHQYMSVSA-N
Boiling Point
847.3±65.0 °C(Predicted)
Melting Point
190 °C (methanol )
Density
1.45±0.1 g/cm3 (20 °C 760 Torr)
Solubility
DMSO (Slightly), methanol (Slightly)
Application
Sweetening Agents
Storage
Hygroscopic, -20°C Freezer, Under inert atmosphere
Uses
Steviolbioside is a terpenoid compound which is converted into antituberculotic and antibacterial agents. In addition it is used as a natural sweetener.