Acutudaurin from Cultured Roots of Menispermum dauricum

Abstract

A new alkaloid, acutudaurin, was isolated from cultured roots of Menispermum dauricum, a rich source of the chlorine-containing alkaloid acutumine and its dechlorinated analogue dechloroacutumine. The structure of acutudaurin was determined to be 2′,3′-dihydro-5-hydroxy-4,6′,7′-trimethoxy-1′-methylspiro[3-cyclohexene-1,10′-[3a,7a]propano[1H]indole]-2,5′(4′H)-dione by spectroscopic methods.

References

• 1 Engvild K C. Chlorine-containing natural compounds in higher plants.  Phytochemistry. 1986;  25 781-91
• 2 Goto K, Sudzuki H. Sinomenine and disinomenine. Part IX. On acutumine and sinactine.  Bulletin of the Chemical Society of Japan. 1929;  4 220-4
• 3 Barton D HR, Kirby AJ,  W. Phenol oxidation and biosynthesis. Part XVII. Investigations on the biosynthesis of sinomenine. Journal of the Chemical Society (C) 1968: 929-36
• 4 Tomita M, Okamoto Y, Kikuchi T, Osaki K, Nishikawa M, Kamiya K, Sasaki Y, Matoba K, Goto K. Studies on the alkaloids of Menispermaceous plants. CCLIX. Alkaloids of Menispermum dauricum DC. (suppl. 7). Structures of acutumine and acutumidine, chlorine-containing alkaloids with a novel skeleton.  Chemical and Pharmaceutical Bulletin. 1971;  19 770-91
• 5 Doskotch R W, Knapp J E. Alkaloids from Menispermum canadense .  Lloydia. 1971;  34 292-300
• 6 Tomita M, Okamoto Y, Kikuchi T, Osaki K, Nishikawa M, Kamiya K, Sasaki Y, Matoba K, Goto K. Acutumine and acutumidine, chlorine containing alkaloids with a novel skeleton (1): X-ray analysis of acutumine. Tetrahedron Letters 1967: 2421-4
• 7 Tomita M, Okamoto Y, Kikuchi T, Osaki K, Nishikawa M, Kamiya K, Sasaki Y, Matoba K, Goto K. Acutumine and acutumidine, chlorine containing alkaloids with a novel skeleton (2): Chemical proof. Tetrahedron Letters 1967: 2425-30
• 8 Sugimoto Y, Uchida S, Inanaga S, Kimura Y, Hashimoto M, Isogai A. Early steps of dauricine biosynthesis in cultured roots of Menispermum dauricum .  Bioscience, Biotechnology and Biochemistry. 1996;  60 503-5
• 9 Sugimoto Y, Inanaga S, Kato M, Shimizu T, Hakoshima T, Isogai A. Dechloroacutumine from cultured roots of Menispermum dauricum .  Phytochemistry. 1998;  49 1293-7
• 10 Babiker H AA, Sugimoto Y, Saisho T, Inanaga S, Hashimoto M, Isogai A. Biosynthetic relationship between acutumine and dechloroacutumine in Menispermum dauricum root cultures.  Bioscience, Biotechnology and Biochemistry. 1999;  63 515-8
• 11 Nishikawa M, Kamiya K, Tomita M, Okamoto Y, Kikuchi T, Osaki K, Tomiie Y, Nitta I, Goto K. The X-ray analyses of acutumine and its acetate; A trial of a short cut in the structure elucidation. Journal of the Chemical Society (B) 1968: 652-8
• 12 Okamoto Y, Yuge E, Nagai Y, Katsuta R, Kishimoto A, Kobayashi Y, Kikuchi T, Tomita M. Acutuminine, a new alkaloid from the leaves of Menispermum dauricum DC. Tetrahedron Letters 1969: 1933-5
• 13 Berthou S, Leboeuf M, Cavé A, Mahuteau J, David B, Guinaudeau H. Limalongine, a modified hasubanan type alkaloid, and clolimalongine, its chlorinated derivative.  The Journal of Organic Chemistry. 1989;  54 3491-3
• 14 Sugimoto Y, Yoshida A, Uchida S, Inanaga S, Yamada Y. Dauricine production in cultured roots of Menispermum dauricum .  Phytochemistry. 1994;  36 679-83