Three new sesquiterpene glycosides from Dendrobium nobile with immunomodulatory activity

J Nat Prod. 2001 Sep;64(9):1196-200. doi: 10.1021/np0102612.

Abstract

Dendroside A (1) and dendronobilosides A and B (2 and 3), three new sesquiterpene glycosides, have been isolated from the stems of Dendrobium nobile, a plant used in Chinese traditional medicine. Their structures and stereochemistry were determined as 10beta,12,14-trihydroxyalloaromadendrane 14-O-beta-D-glucopyranoside (1), 10,12-dihydroxypicrotoxane 10,12-di-O-beta-D-glucopyranoside (2), and 6alpha,10,12-trihydroxypicrotoxane 10-O-beta-D-glucopyranoside (3), respectively, on the basis of spectroscopic and chemical methods. Quantum chemistry calculations were used in support of the structural determination of 1. Compounds 1 and 2 were found to stimulate the proliferation of murine T and B lymphocytes in vitro, while compound 3 showed inhibitory activity in this same assay.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adjuvants, Immunologic / chemistry
  • Adjuvants, Immunologic / isolation & purification*
  • Adjuvants, Immunologic / pharmacology
  • Animals
  • B-Lymphocytes / drug effects
  • B-Lymphocytes / immunology
  • B-Lymphocytes / metabolism
  • Chromatography, Thin Layer
  • Concanavalin A / pharmacology
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification
  • Drugs, Chinese Herbal / pharmacology
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • In Vitro Techniques
  • Lipopolysaccharides / pharmacology
  • Lymphokines / chemistry
  • Lymphokines / isolation & purification*
  • Lymphokines / pharmacology
  • Magnetic Resonance Spectroscopy
  • Medicine, Chinese Traditional
  • Mice
  • Molecular Structure
  • Plant Lectins
  • Plant Stems / chemistry
  • Plants, Medicinal / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Spectrophotometry, Infrared
  • Spleen / cytology
  • Spleen / drug effects
  • Spleen / immunology
  • Spleen / metabolism
  • T-Lymphocytes / drug effects
  • T-Lymphocytes / immunology
  • T-Lymphocytes / metabolism

Substances

  • Adjuvants, Immunologic
  • Drugs, Chinese Herbal
  • Glucosides
  • Glycosides
  • Lipopolysaccharides
  • Lymphokines
  • Plant Lectins
  • Sesquiterpenes
  • dendronobiloside A
  • dendronobiloside B
  • dendroside A
  • lymphocyte proliferation potentiating factors
  • Concanavalin A