New Phenanthrenes and Stilbenes from Dendrobium loddigesii

• Published in: Chemical & Pharmaceutical Bulletin Vol. 58; no. 5; pp. 628 - 633
• Main Authors: Ito, Masanobu, Matsuzaki, Keiichi, Wang, Jue, Daikonya, Akihiro, Wang, Nai-Li, Yao, Xin-Sheng, Kitanaka, Susumu
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.05.2010; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: 2,2-diphenyl-1-picrylhydrazyl radical scavenging; Animals; Cell Line; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Dendrobium - chemistry; Dendrobium - classification; Dendrobium loddigesii; Inhibitory Concentration 50; Life Sciences & Biomedicine; loddigesiinol; Macrophages - drug effects; Magnetic Resonance Spectroscopy; Mice; nitric oxide; Pharmacology & Pharmacy; phenanthrene; Phenanthrenes - chemistry; Phenanthrenes - pharmacology; Physical Sciences; Plant Components, Aerial - chemistry; Science & Technology; stilbene; Stilbenes - chemistry; nitric oxide; NOBILE; 2,2-diphenyl-1-picrylhydrazyl radical scavenging; loddigesiinol; BIBENZYL DERIVATIVES; stilbene; 9,10-DIHYDROPHENANTHRENE; CANDIDUM; Dendrobium loddigesii; SPECTRA; phenanthrene
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.58.628

New phenanthrenes, loddigesiinols A (1) and B (7), and stilbenes, loddigesiinols C (8) and D (9), were isolated from 80% ethanol extract of Dendrobium loddigesii ROLFE (Orcharedceae) along with known compounds, including five phenanthrenes, three stilbenes, two lignans, and three sterols. Their structures were determined by spectroscopic studies. These compounds were evaluated for their inhibitory activities against nitric oxide (NO) production and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging. Phenanthrenes (1—3, 7) and dihydrophenanthrenes (4—6) showed significant inhibitory activity against NO production. In particular, 2 showed stronger inhibitory activity against NO production than 5 and 6. This suggested that this phenanthrene is a stronger inhibitor of NO production than dihydrophenanthrene. The new phenanthrenes, loddigesiinols A (1) and B (7), significantly inhibited NO production with IC50 values of 2.6 and 10.9 μM, respectively. One new dihydrostilbene, loddigesiinol D (9), showed weak inhibitory activity against NO production with an IC50 value of 69.7 μM, but the other new dihydrostilbene, loddigesiinol C (8), did not show this activity at 100 μM.