Physicochemical properties and antitumor activities for sulfated derivatives of lentinan

Carbohydr Res. 2009 Nov 2;344(16):2209-16. doi: 10.1016/j.carres.2009.04.033. Epub 2009 Jul 30.


Five fractions of lentinan, a beta-(1-->3)-D-glucan bearing beta-(1-->6)-d-glucopyranosyl branches, were treated with chlorosulfonic acid for 90 min at 60 degrees C in pyridine medium to synthesize water-soluble sulfated derivatives having the substitution degree of 1.44-1.76. The (13)C NMR spectra of the sulfated beta-glucans indicated that the C-6 position was preferentially substituted by the sulfate groups. The values of the weight-average molecular weight (M(w)), radius of gyration (s(2)(z)(1/2)), and intrinsic viscosity ([eta]) of the sulfated lentinan fractions were determined by size-exclusion chromatography with multi-angle laser light scattering (SEC-MALLS) and viscometry in 0.15 M aq NaCl at 25 degrees C, respectively. The dependence of [eta] on M(w) for the sulfated lentinan was found to be [eta]=8.93 x 10(-3)M(w)(0.73+/-0.02) (mL/g) in 0.15 M aq NaCl (for M(w) ranging from 14.6 x 10(4) to 50.4 x 10(4)). On the basis of the Yamakawa-Fujii-Yoshizaki (YFY) theory, the conformational parameters of the sulfated lentinan were calculated as 950 nm(-1) for the molar mass per unit contour length (M(L)), 4.8 nm for the persistence length (q), and 13.9 for the characteristic ratio (C(infinity)), indicating relatively extended single flexible chains in solution. The sulfated glucan fractions exhibited in vitro antiproliferative activities against sarcoma 180 (S-180) cells, and their inhibition ratios were lower than that of the triple-helix lentinan, but higher than that for the one with single random-coil lentinan chains.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Carbohydrate Conformation
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Chemical Phenomena*
  • Lentinan / chemistry*
  • Lentinan / pharmacology*
  • Molecular Weight
  • Solubility
  • Sulfonic Acids / chemistry*
  • Ultrasonics
  • Water / chemistry


  • Antineoplastic Agents
  • Sulfonic Acids
  • Water
  • chlorosulfonic acid
  • Lentinan