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A new cytotoxic anthraquinone glucoside, pulmatin, 1,8-dihydroxy-3-methyl-anthraquinone-1-O-β-D-glucoside, and its congeners, chrysophanein and physcionin, have been isolated as minor components from the root of Rheum pulmatum, an Indonesian Jamu (medicinal plant) known as ‘kelembak’ by recycling high performance liquid chromatography (R-HPLC). These anthraquinone glycosides exhibited moderate cytotoxic activity against several types of carcinoma cells. Their structures were established by means of spectroscopic methods, in particular, the NMR data.

cytotoxicity, Rheum pulmatum, Polygonaceae, roots, anthraquinone glycosides, pulmatin, recycling HPLC

Publication DOI: 10.1016/0031-9422(92)80078-S
Journal NLM ID: 0151434
Publisher: Elsevier
Institutions: Division of Entomology and Parasitology College of Natural Resources, University of California, Berkeley, USA, Inter University Center, Life Sciences Institute of Technology of Bandung, Bandung, Indonesia
Methods: 13C NMR, 1H NMR, IR, FAB-MS, GPC, UV, extraction, RP-HPLC, cell growth, melting point determination, cytotoxicity assay, MTT

The inhibitory activity of stilbenes isolated from medicinal plants on cell adhesion molecules on the surface of THP-1 human monocytic cell lines was investigated. Among ten stilbenes tested, four stilbenes displayed a significant inhibitory activity on the expression of both intercellular adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1). A cell-to-cell adhesion assay showed that 3,5-dihydroxy-4'-methoxystilbene and 2,3,4',5-tetrahydroxystilbene-2-O-β-D-glucopyranoside as well as resveratrol blocked significantly TNF-alpha-inducing cell-cell adhesion between human umbilical vein endothelial cells (HUVEC) and THP-1 cells.

cytotoxicity, inhibitory activity, stilbenes, THP1 cells

NCBI PubMed ID: 11105570
Publication DOI: 10.1055/s-2000-8634
Journal NLM ID: 0066751
Publisher: George Thieme
Correspondence: Lee HK
Institutions: Immunomodulator Research Laboratory, Korea Research Institute of Bioscience and Biotechnology, Taejeon, South Korea, Korea Research Institute of Chemistry and Technology, Taejeon, South Korea
Methods: ELISA, cell growth, cell viability assay, cytotoxicity assay, adhesion assays

Two new anthraquinone glucosides [chrysophanol 8-O-β-d-(6′-galloyl)-glucopyranoside, aloe-emodin 1-O-β-d-glucopyranoside] together with various known stilbenes and their glucosides, anthraquinone glucosides, and a naphthalene glucoside were isolated from the rhizome of Rheum undulatum L. Three stilbenes (rhapontigenin, piceatannol, resveratrol), a naphthalene glucoside (torachrysone 8-O-β-d-glucopyranoside), and two stilbene glucoside gallates (rhaponticin 2′′-O-gallate, rhaponticin 6′′-O-gallate) showed inhibitory activity of NO production in lipopolysaccharide-activated macrophages. (IC50=11–69 μM). The oxygen functions (-OH,-OCH3) at the benzene ring were found to be essential to show the activity. Whereas, the glucoside moiety reduced the activity, while the α,β-double bond did not affect the activity. Furthermore, the active stilbenes (rhapontigenin, piceatannol, resveratrol) inhibited iNOS induction.

stilbene glucosides, Rheum undulatum, rhubarb, anthraquinone glucosides, inhibition of NO production

NCBI PubMed ID: 10714491
Publication DOI: 10.1016/s0960-894x(99)00702-7
Journal NLM ID: 9107377
Publisher: Elsevier
Correspondence: Yoshikawa M
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan

cytotoxicity, inhibitory activity, stilbenes, THP1 cells

Stilbene glucosides are naturally occurring phytoalexins, found in a variety of medicinal plants. Among the stilbene derivatives, resveratrol 3-O-D-glucoside (piceid) is found in grapes and wine. We studied the effects of stilbene glucosides isolated from medicinal plants and grapes on tumour growth and lung metastasis in mice bearing highly metastastic Lewis lung carcinoma (LLC) tumours. We also studied the inhibitory effects of stilbene glucosides on differentiation of human umbilical vein endothelial cells (HUVECs) to form a capillary network. Tumour growth in the right hind paw and lung metastasis were inhibited by oral administration of the stilbene glucosides, piceid and 2,3,5,4′-tetrahydroxystilbene-2-O-D-glucoside for 33 consecutive days, in LLC-bearing mice. As the number of CD8+ and NK1.1+ T cells in the spleen was not affected, the inhibitory effects of these stilbene glucosides on tumour growth and lung metastasis could not be explained by natural killer or cytotoxic T lymphocyte activation. Piceid inhibited the DNA synthesis in LLC cells at a concentration of 1000 μm, but not at lower concentrations (10–100 μM). 2,3,5,4′-Tetra-hydroxystilbene-2-O-D-glucoside also inhibited DNA synthesis in LLC cells (IC50 81 μM). In addition, both stilbene glucosides inhibited the formation of capillary-like tube networks (angiogenesis) of HUVECs at concentrations of 100 to 1000 μM. We suggest that the antitumour and antimetastatic activity of the stilbene glucosides, piceid and 2,3,5,4′-tetrahydroxystilbene-2-O-D-glucoside, might be due to the Polygonum multifloriuminhibition of DNA synthesis in LLC cells and angiogenesis of HUVECs.

Lewis lung carcinoma, antitumour activity, piceid, stilbene glucosides

NCBI PubMed ID: 11092574
Publication DOI: 10.1211/0022357001777270
Journal NLM ID: 0376363
Publisher: London: Pharmaceutical Society of Great Britain; West Sussex: Wiley
Correspondence: yokim@m.ehime-u.ac.jp
Institutions: Second Department of Medical Biochemistry, School of Medicine, Ehime University, Shigenobu-cho, Japan
Methods: biological assays, radiolabeling, fluorescence labeling, antitumor activity assay, centrifugation