New Cytotoxic Diarylheptanoids from the Rhizomes of Alpinia officinarum

Abstract

Bioassay-guided fractionation of the cytotoxic MeOH extract from the rhizomes of Alpinia officinarum Hance led to the isolation of two new diarylheptanoids named alpinoid D (1) and E (2), together with fifteen known diarylheptanoids (3 - 17). The structures of compounds 1 and 2 were elucidated on the basis of spectroscopic data and chemical evidence. The cytotoxic activity of the isolated diarylheptanoids was evaluated against the IMR-32 human neuroblastoma cell line. Among the tested compounds, 11, 12 and 14 exhibited the most potent activities with IC₅₀ values of 0.83, 0.23 and 0.11 μM, respectively.

Key words

Alpinia officinarum - Zingiberaceae - diarylheptanoids - cytotoxicity - neuroblastoma cell line

References

• 1 Jiangsu new medicinal college. The Encyclopedia of Chinese Materia Medica. Shanghai; Science and Technical Press 1978: 1907-9
• 2 Yokosuka A, Mimaki Y, Sakagami H, Sashida Y. New diarylheptanoids and diarylheptanoid glucosides from the rhizomes of Tacca chantrieri and their cytotoxic activity.  J Nat Prod. 2002;  65 283-9
• 3 Yang Y, Kinoshita K, Koyama K, Takahashi T, Kondo S, Watanabe K. Structure-antiemetic-activity of some diarylheptanoids and their analogues.  Phytomedicine. 2002;  9 146-52
• 4 Claeson P, Pongprayoon U, Sematong T, Tuchinda P, Reutrakul V, Soontornsaratune P. et al . Non-phenolic linear diarylheptanoids from Curcuma xanthorrhiza. A novel type of topical anti-inflammatory agents. Structure-activity relationship.  Planta Med. 1996;  62 236-40
• 5 Ali M S, Banskota A H, Tezuka Y, Saiki I, Kadota S. Antiproliferative activity of diarylheptanoids from the seeds of Alpinia blepharocalyx. .  Biol Pharm Bull. 2001;  24 525-8
• 6 Li G, Xu M -L, Choi H -G, Lee S -H, Jahng Y -D, Lee C -S. et al . Four new diarylheptanoids from the roots of Juglans mandshurica. .  Chem Pharm Bull. 2003;  51 262-4
• 7 Kusumi T, Ooi T, Ohkubo Y, Yabuuchi T. The modified Mosher’s method and the sulfoximine method.  Bull Chem Soc Jpn. 2006;  79 965-80
• 8 Gomès L M. Synthèse de dérivés du naphto-[2.3-b]furanne.  Sci Chim. 1970;  270 750-3
• 9 Shin D, Kinoshita K, Koyama K, Takahashi K. Antiemetic principles of Alpinia officinarum. .  J Nat Prod. 2002;  65 1315-8
• 10 Hashimoto T, Tori M, Asakawa Y. Five new diarylheptanoids from the male flower of Alnus sieboldiana. .  Chem Pharm Bull. 1986;  34 1846-9
• 11 Itokawa H, Morita H, Midorikawa I, Aiyama R, Morita M. Diarylheptanoids from the rhizome of Alpinia officinarum Hance.  Chem Pharm Bull. 1985;  33 4889-93
• 12 Itokawa H, Morita M, Mihashi S. Two new diarylheptanoids from Alpinia officinarum Hance.  Chem Pharm Bull. 1981;  29 2383-5
• 13 Kiuchi F, Shibuya M, Sankawa U. Inhibitors of prostaglandin biosynthesis from Alpinia officinarum. .  Chem Pharm Bull. 1982;  32 2279-82
• 14 Lee K S, Li G, Kim S H, Lee C S, Woo M H, Lee S H. et al . Cytotoxic diarylheptanoids from the roots of Juglans mandshurica. .  J Nat Prod. 2002;  65 1707-8
• 15 Girija K, Hari K KB, Chandrasekharan G, Ramadasan K. Antitumor, anti-invasion, and antimetastatic effects of curcumin.  Adv Exp Med Biol. 2007;  595 173-84