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DOI: 10.1055/s-0036-1596757
Four new diterpenoid alkaloids from Aconitum japonicum
Publikationsverlauf
Publikationsdatum:
14. Dezember 2016 (online)
The constituents of Aconitum japonicum THUNB (Ranunculaceae) were investigated many years ago, and the isolation and structure elucidation of twenty-three diterpenoid alkaloids from rhizomes of Aconitum species have been reported [1 – 7]. The investigation on the constituents of this plant have now resulted in the isolation of four new C19-diterpenoid alkaloids, 14-anisoyl-N-deethylaconine (1), N-deethylaljesaconitine A (2), 14-anisoyllasianine (3), and N-deethylnevadensine (4), together with fifteen known C19-diterpenoid alkaloids. Alkaloids were isolated using standard column liquid chromatography and structures assigned by high resolution mass spectrometry combined with C13 and 1 and 2D proton NMR spectroscopy. Two of the new C19-diterpenoid alkaloids (2, 4) and three of the known diterpenoid alkaloids (aconine 5, virescenine 6, ryosenamine 7) were evaluated for cytotoxic activity against four human tumor cell lines [lung carcinoma (A549), triple-negative breast cancer (estrogen and progesterone receptors-negative/HER2-negative) (MDA-MB-231), nasopharyngeal (KB), and multidrug resistant KB subline expressing P-glycoprotein (KB-VIN)]. However, the five diterpenoid alkaloids (2, 4-7) were inactive (IC50 > 40µM) against four human tumor cell lines (A549, MDA-MB-231, KB, and KB-VIN). The presentation describes the isolation of four new aconitine- or lycoctonine-type C19-diterpenoid alkaloids (1-4) from the rhizomes of A. japonicum. The structures of 1-4 were elucidated from 1D and 2D NMR spectroscopic data. The structure of three new alkaloids, 14-anisoyl-N-deethylaconine (1), N-deethylaljesaconitine A (2), and N-deethylnevadensine (4), was unusual N-deethyl C19-diterpenoid alkaloids. 14-Anisoyllasianine (3) was the fourth natural C19-diterpenoid alkaloid possessing the amino group at C-8. Lipoaconitine, lipomesaconitine, aconine (5), 15α-hydroxyneoline, isotalatizidine, nevadenine, talatisamine, virescenine (6), nevadensine, ryosenamine (7), and dehydrolucidusculine were isolated the first time from this plant.
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Keywords: Aconitum japonicum, C19-diterpenoid alkaloid, 14-anisoyl-N-deethylaconine, N-deethylaljesaconitine A, 14-anisoyllasianine, N-deethylnevadensine.
References:
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[2] Mori T, Bando H, Kanaiwa Y, Wada K, Amiya T. Studies on the constituents of Aconitum Species. II. Structure of deoxyjesaconitine. Chem Pharm Bull 1983; 31:2884 – 2886
[3] Wada K, Bando H, Mori T, Wada R, Kanaiwa Y, Amiya T. Studies on the constituents of Aconitum Species. III. On the components of Aconitum subcuneatum NAKAI. Chem Pharm Bull 1985; 33: 3658 – 3661
[4] Bando H, Wada K, Watanabe M, Mori T, Amiya T. Studies on the constituents of Aconitum Species. IV. On the components of Aconitum japonicum THUNB. Chem Pharm Bull 1985; 33: 4717 – 4722
[5] Bando H, Wada K, Amiya T, Fujimoto Y, Kobayashi, K. Structures of secojesaconitine and subdesculine, two new diterpenoid alkaloids from Aconitum japonicum THUNB. Chem Pharm Bull 1988; 36: 1604 – 1606
[6] Bando H, Wada K, Amiya T, Fujimoto Y, Kobayashi K. Studies on the constituents of Aconitum Species. VII. On the components of Aconitum japonicum THUNB. Heterocycles 1988; 27: 2167 – 2174
[7] Wada K. Studies on structural elucidation of Aconitum diterpenoid alkaloid by LC-APCI-MS and effects of Aconitum diterpenoid alkaloid on cutaneous blood flow. Yakugaku Zasshi 2002; 122: 929 – 956
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Die Autoren geben an, dass kein Interessenkonflikt besteht.
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