Evaluation of in vitro anticancer activity of sphaeropsidins A–C, fungal rearranged pimarane diterpenes, and semisynthetic derivatives

• Published in: Phytochemistry letters Vol. 5; no. 4; pp. 770 - 775
• Main Authors: Lallemand, Benjamin, Masi, Marco, Maddau, Lucia, De Lorenzi, Manuela, Dam, Ricard, Cimmino, Alessio, Moreno y Banuls, Laetitia, Andolfi, Anna, Kiss, Robert, Mathieu, Véronique, Evidente, Antonio
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01-12-2012
• Subjects: antineoplastic agents; Botryosphaeriaceae; Diplodia; Diplodia cupressi; diterpenoids; fungi; In vitro anticancer activity; in vitro studies; phytotoxins; Sphaeropsidins; structure-activity relationships; Unrearranged pimarane diterpenes; Diplodia cupressi; Unrearranged pimarane diterpenes; In vitro anticancer activity; Sphaeropsidins; Botryosphaeriaceae
• ISSN: 1874-3900; 1876-7486
• DOI: 10.1016/j.phytol.2012.08.011

Sphearopsidins A (1), B and C, phytotoxins produced by Diplodia cupressi were tested together their semisynthetic derivatives for their in vitro anticancer activity on five human and one mouse cancer cell lines. 1 and its 6-O-acetyl- and 15,16-dihydro-derivatives showed a significant anticancer activity. [Display omitted]
► Sphaeropsidins A–C fungal phytoxins and semisynthetic derivatives. ► In vitro anticancer activity against five human and mouse cancer cell lines. ► Structure–activity relationships.
Sphaeropsidins A (1), B (7) and C (10), three fungal phytotoxins, unrearranged pimarane diterpenes produced by Diplodia cupressi and 10 semisynthetic derivatives were evaluated for their in vitro anticancer activities. Among these 13 compounds, sphaeropsidin A and two derivatives (2 and 6) thereof display 50% growth-inhibitory concentration in the low micromolar range for all cell lines analyzed. Structure activity relationship paralleled the phytopathogenic and antimicrobial ones except regarding the vinyl group at C-13 that does not seems to be required as it is for their antipathogenic activity.