Literature DB >> 29052027

Four new diterpenoid alkaloids from Aconitum japonicum subsp. subcuneatum.

Hiroshi Yamashita1, Keiko Takeda1, Machiko Haraguchi1, Yuki Abe1, Natsumi Kuwahara1, Shota Suzuki1, Ayaka Terui1, Takumi Masaka1, Naoko Munakata1, Mariko Uchida1, Masashi Nunokawa1, Kyousuke Kaneda1, Masuo Goto2, Kuo-Hsiung Lee2,3, Koji Wada4.   

Abstract

Diterpenoid alkaloids with remarkable chemical properties and biological activities are frequently found in plants of the genera Aconitum, Delphinium, and Garrya. Accordingly, several diterpenoid alkaloid constituents of Aconitum and Delphinium plants as well as their derivatives exhibited cytotoxic activity against lung, prostate, nasopharyngeal, and vincristine-resistant nasopharyngeal cancer cell lines. Four new C19-diterpenoid alkaloids, 14-anisoyllasianine (1), 14-anisoyl-N-deethylaconine (2), N-deethylaljesaconitine A (3), and N-deethylnevadensine (4), together with 17 known C19- and C20-diterpenoid alkaloids, were isolated in a phytochemical investigation of rhizoma of Aconitum japonicum THUNB. subsp. subcuneatum (NAKAI) KADOTA. Their structures were elucidated by extensive spectroscopic methods including NMR (1D and 2D), IR, and MS (HRMS). Eight known diterpenoid alkaloids, lipoaconitine, lipomesaconitine, aconine, nevadenine, talatisamine, nevadensine, ryosenamine, and dehydrolucidusculine, were isolated the first time from A. japonicum subsp. subcuneatum. Three of the new C19-diterpenoid alkaloids (1, 3, 4) and six of the known diterpenoid alkaloids were evaluated for cytotoxic activity against five human tumor cell lines.

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Keywords:  14-Anisoyl-N-deethylaconine; 14-Anisoyllasianine; Aconitum japonicum subsp. subcuneatum; Cytotoxicity; N-deethylaljesaconitine A; N-deethylnevadensine

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Year:  2017        PMID: 29052027     DOI: 10.1007/s11418-017-1139-9

Source DB:  PubMed          Journal:  J Nat Med        ISSN: 1340-3443            Impact factor:   2.343


  6 in total

1.  The C19-diterpenoid alkaloids.

Authors:  Feng-Peng Wang; Qiao-Hong Chen
Journal:  Alkaloids Chem Biol       Date:  2010

2.  [Chemical studies on crude drug processing. II. Aconiti tuber (1). On the constituents of "chuan-wu", the dried tuber of Aconitum carmichaeli Debx].

Authors:  I Kitagawa; Z L Chen; M Yoshihara; M Yoshikawa
Journal:  Yakugaku Zasshi       Date:  1984-08       Impact factor: 0.302

3.  Development of a novel class of tubulin inhibitor from desmosdumotin B with a hydroxylated bicyclic B-ring.

Authors:  Kyoko Nakagawa-Goto; Akifumi Oda; Ernest Hamel; Emika Ohkoshi; Kuo-Hsiung Lee; Masuo Goto
Journal:  J Med Chem       Date:  2015-02-26       Impact factor: 7.446

4.  Evaluation of Aconitum diterpenoid alkaloids as antiproliferative agents.

Authors:  Koji Wada; Emika Ohkoshi; Yu Zhao; Masuo Goto; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  Bioorg Med Chem Lett       Date:  2015-02-18       Impact factor: 2.823

5.  The structures of condelphine, isotalatizidine, and talatizidine.

Authors:  S W Pelletier; L H Keith; P C Parthasarathy
Journal:  J Am Chem Soc       Date:  1967-08-02       Impact factor: 15.419

Review 6.  [Studies on structural elucidation of Aconitum diterpenoid alkaloid by LC-APCI-MS and effects of Aconitum diterpenoid alkaloid on cutaneous blood flow].

Authors:  Koji Wada
Journal:  Yakugaku Zasshi       Date:  2002-11       Impact factor: 0.302

  6 in total
  1 in total

1.  Aconitine linoleate, a natural lipo-diterpenoid alkaloid, stimulates anti-proliferative activity reversing doxorubicin resistance in MCF-7/ADR breast cancer cells as a selective topoisomerase IIα inhibitor.

Authors:  Shangxian Luan; Yingying Gao; Xiaoxia Liang; Li Zhang; Qiang Wu; Yunkai Hu; Lizi Yin; Changliang He; Shixi Liu
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  2021-11-02       Impact factor: 3.000

  1 in total

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