Isolation, structural elucidation, and chemical synthesis of 2-hydroxy-3-octadecyl-5-methoxy-1,4-benzoquinone (irisoquin), a cytotoxic constituent of Iris missouriensis

• Published in: Journal of pharmaceutical sciences Vol. 74; no. 10; p. 1114
• Main Authors: Wong, S M, Pezzuto, J M, Fong, H H, Farnsworth, N R
• Format: Journal Article
• Language: English
• Published: United States 01.10.1985
• Subjects: Animals; Antineoplastic Agents, Phytogenic - analysis; Antineoplastic Agents, Phytogenic - chemical synthesis; Antineoplastic Agents, Phytogenic - pharmacology; Benzoquinones; Cell Line; Chemical Phenomena; Chemistry; Humans; KB Cells - pathology; Leukemia P388 - pathology; Mice; Plants, Medicinal - analysis; Quinones - analysis; Quinones - chemical synthesis; Quinones - pharmacology; Spectrophotometry, Ultraviolet; Structure-Activity Relationship
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600741023

As part of a continuing effort to provide novel agents of potential value in cancer chemotherapy, 2-hydroxy-3-octadecyl-5-methoxy-1,4-benzoquinone (irisoquin) was identified as a component of Iris missouriensis. This novel species demonstrated cytotoxic activity with cultured KB and P-388 cells (ED50 = 1.8 and 0.03 microgram/mL, respectively). The structure was assigned on the basis of spectral analyses and The structure was assigned on the basis of spectral analyses and confirmed by chemical synthesis. The latter provides a facile method for the production of irisoquin and structural derivatives that may be of value for the examination of structure-activity relationships. A closely related compound, 3-octadecyl-5-methoxy-1,4-benzoquinone (deoxyirisoquin), was also isolated from Iris missouriensis, prepared synthetically, and found to be devoid of cytotoxic activity.