Sherburn's synthesis of (-)-Arctigenin

Origins

Arctigenin is a naturally occurring plant lignan found in certain plants of the Asteraceae family. [1] [2]

Lignans, which are a class of estrogen like compounds dubbed phytoestrogens, have been shown to have several promising anti-viral and anti-carcinogenic effects.

The lignan, Arctigenin, can be isolated from leaves of the plant Arctium lappa; more commonly known as the Burdock or Greater Burdock.

Use

Antiviral: Arctigenin is a known HIV-1 integrase and topoisomerase II inhibitor. In recent studies it has shown to inhibit both HIV protein production and reverse transcriptase activity by nearly 70% in some cases. However, conflicting reports suggest that due to its toxicity, arctigenin should not yet be used as an anti-viral treatment alone.

References

1. De Simone F, Aquino R, De Tomassi N, Mahmood N, Piacente S, Pizza C. Anti-HIV Aromatic Compounds from Higher Plants. In: Tringali C, editor. Bioactive Compounds from Natural Sources. London (UK): Taylor & Francis; 2001. 325-338 p.

2. Cavallito C J, Bailey J H, Kirchner F K. The Antibacterial Principle of Avctium minus. I. Isolation, Physical Properties and Antibacterial Action, Journal of the American Chemical Society 1945; 67: 948-950.�

3. Muhammad S, Hyoung J K, Muhammad S A, Yong S L. An update on bioactive plant lignans, Natural Product Reports 2005; 22: 696-716.��

4. Fischer J, Reynolds A J, Sharp L A, Sherburn M S. Radical Carboxyarylation Approach to Lignans. Total Synthesis of (-)-Arctigenin, (-)-Matairesinol, and Related Natural Products, Organic Letters 2004; 6 (9): 1345-1348.�

5. Mukund S P, Pingrong L, Jianguo J, Saumen H, Jian-xie C. Free-Radical-Mediated Conjugate Additions. Enantioselective Synthesis of Butyrolactone Natural Products: (-)-Enterolactone, (-)-Arctigenin, (-)-Isoarctigenin, (-)-Nephrosteranic Acid, and (-)-Roccellaric Acid, Journal of Organic Chemistry 2002; 67: 1738-1745.��

6.Eich E, Pertz H, Kaloga M, Schulz J, Fesen M, Mazumder A, Pommier Y. (-)-Arctigenin as a Lead Structure for Inhibitors of Human Immunodeficiency Virus Type-1 Integrase, Journal of Medical Chemistry 1996; 39: 86-95.

7. Charlton J L. Antiviral Activity of Lignans, Journal of Natural Products 1998; 61: 1447-1451.

8. Hausott B, Greger H, Marian B. Journal of Cancer Research and Clinical Oncology, Naturally occurring lignans efficiently induce apoptosis in colorectal tumor cells 2003; 129: 569-576.