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ABSTRACT: Thirty three C19-diterpenoid alkaloids, twenty-two prepared from known C19-diterpenoid alkaloids and eleven isolated from Aconitum and Delphinium spp. were evaluated for their cardiac activity in the isolated bullfrog heart assay. Among them, eleven compounds exhibited cardiac activity, with average rate of amplitude increase in the range of 16-118%. Compound 7, mesaconine (17), hypaconine (25), and beiwutinine (26) exhibited strong cardiac activities relative to the reference drug. The structure-activity relationship data acquired indicated that an alpha-hydroxyl group at C-15, a hydroxyl group at C-8, an alpha-methoxyl or hydroxyl group at C-1, and a secondary amine or N-methyl group in ring A are important structure features necessary for the cardiac activities of the aconitine-type C19-diterpenoid alkaloids without any ester groups. In addition, an alpha-hydroxyl group at C-3 is also helpful for the cardiac activity of these alkaloids.
Natural product communications 06/2012; 7(6):713-20. · 1.24 Impact Factor
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ABSTRACT: A series of new bisbenzylisoquinoline alkaloids was partially synthesized from tetrandrine and fangchinoline and evaluated for their ability to reverse P-glycoprotein-mediated multidrug resistance (MDR) in cancer cells. All the test compounds increased the intracellular accumulation rate of rhodamine 123 in MDR cells (Bel7402 and HCT8), and most exhibited more potent MDR-reversing activity relative to the reference compound verapamil. Compounds 8, 10, 13, and 14 enhanced intracellular accumulation of doxorubicin in Bel7402 and HCT8 cells.
Journal of Asian natural products research 06/2012; 14(6):564-76. · 0.61 Impact Factor
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ABSTRACT: The relative reactivity of three hydroxyl groups in aconitine toward acetylation, chlorination, sulfonylation, and oxidation has been studied in this paper. The reduction of C-3 ketone and C-15 ketone derivatives of aconitine was also investigated. It was found that (1) the relative reactivity of three hydroxyl groups toward acetylation, chlorination, and sulfonylation is 3-OH>13-OH>15-OH; (2) 3-OH is much more reactive than 15-OH toward oxidation; and (3) reduction of the carbonyl group at C-3 with NaBH(4) generated a pair of C-3 epimers, while the reduction products of the carbonyl group at C-15 depend largely on the specific reducing agent and the absolute configuration of 16-OCH(3). When the substrate has 16β-OCH(3), its carbonyl group at C-15 can be reduced with NaBH(4) to yield exclusively the 15α-OH-containing product. Upon replacement of reducing agent NaBH(4) with LiAlH(4), the C-15 carbonyl group can be reduced to yield a pair of C-15 epimers. On the other hand, when the substrate has 16α-OCH(3), C-15 carbonyl group can only be reduced to generate 15α-OH-containing product.
Journal of Asian natural products research 05/2012; 14(7):665-77. · 0.61 Impact Factor
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ABSTRACT: The O-acyl group at C-1 of two C₁₉-diterpenoid alkaloids 2 and 5 was transferred to the secondary amine nitrogen to form amides 3 and 6 in the basic condition. This kind of O-to-N intramolecular acyl migration could be caused by the near distance between the nucleophilic nitrogen atom and the carbonyl group of the ester at C-1 in the C₁₉-diterpenoid alkaloids, which is consistent with the conformation of rings A and E in the C₁₉-diterpenoid alkaloids.
Journal of Asian natural products research 05/2012; 14(6):586-91. · 0.61 Impact Factor
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ABSTRACT: Bioassay-guided fractionation of an n-BuOH extract of the lateral roots of Aconitum carmichaeli. led to the isolation of 5 cardioactive C(19)-diterpenoid alkaloids: N-deethylaconine (1), beiwutinine (2), hypaconine (3), mesaconine (4), and 15α-hydroxyneoline (5). N-Deethylaconine and beiwutinine are new aconitine-type C(19)-diterpenoid alkaloids. Hypaconine was isolated from this species for the first time. Among them, mesaconine, hypaconine, and beiwutinine showed the strongest cardiac actions on the isolated perfused bullfrog heart. Furthermore, mesaconine has protective effects, including improved inotropic effect and left ventricular diastolic function, on myocardial ischemia-reperfusion injury in rat at a dose of 10(-9) mol/L. However, mesaconine has almost no effect on heart rate.
Chemical & pharmaceutical bulletin 01/2012; 60(1):144-9. · 1.70 Impact Factor
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ChemInform 05/2010; 33(43):218 - 218.
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ABSTRACT: A new aconitine-type C19-diterpenoid alkaloid, longzhoushansine (1), along with fourteen known alkaloids, were isolated from the roots of Aconitum longzhoushanense. Their structures were established by spectral analysis and chemical methods.
Natural product communications 02/2009; 4(1):19-22. · 1.24 Impact Factor
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ABSTRACT: A new C(19)-diterpenoid alkaloid, ouvrardiantine (1) and two new C(20)-diterpenoid alkaloids, ouvrardiandines A (2) and B (3) were isolated from the root of Aconitum ouvrardianum HAND.-MAZZ. The structure of the new alkaloids was established on the basis of spectral data (1D- and 2D-NMR, HR-MS).
CHEMICAL & PHARMACEUTICAL BULLETIN 08/2007; 55(7):1090-2. · 1.59 Impact Factor
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ABSTRACT: Five new C18-diterpenoid alkaloids, anthriscifolcines A (1), B (2), C (3), D (4), and E (5), together with a known C19-diterpenoid alkaloid delcorine (6), were isolated from the whole herb of Delphinium anthriscifolium var. savatieri. The structures of these new alkaloids were established on the basis of spectral data (1D- and 2D-NMR, HR-ESI-MS).
CHEMICAL & PHARMACEUTICAL BULLETIN 07/2007; 55(6):918-21. · 1.59 Impact Factor
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ABSTRACT: Four new diterpenoid alkaloids: tiantaishansine (1), tiantaishannine (2), tiantaishanmine (3), and tiantaishandine (4) have been isolated from the roots of Delphinium tiantaishan. Their structures were elucidated by chemical evidence and spectral analyses, including ESI-MS, HR-EI-MS, 1D- and 2D-NMR.
Molecules 02/2007; 12(3):353-60. · 2.39 Impact Factor
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ABSTRACT: Two new C19-diterpenoid alkaloids, kongboentine A (1) and kongboentine B (3), were isolated from the roots of Aconitum kongboense Lauener and their structures were elucidated by spectral data.
Journal of Asian Natural Products Research 07/2004; 6(2):151-4. · 0.94 Impact Factor
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ABSTRACT: A new franchetine-type (leueandine 1) and two new lycoctonine-type [potanisines F (3) and G (5)] C19-diterpenoid alkaloids have been isolated from the roots of Aconitum hemsleyanum var. leueanthus and Delphinium potaninii, respectively, and their structures were established on the basis of spectral data.
Journal of Asian Natural Products Research 10/2003; 5(3):209-13. · 0.94 Impact Factor
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ChemInform 07/2003; 34(28).
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ABSTRACT: A novel approach to the highly functionalized taxane ABC ring system through chemical conversion of the C19-diterpenoid alkaloid deltaline (1) was achieved in six steps (1→17) in 18% overall yield mainly by Grob fragmentation, fission of the Δ9(14) double bond, followed by aldol condensation, and Pelletier's cleavage process.Graphical abstract
Tetrahedron. 64(32):7594-7604.
