研究業績2012-2015

原著 Original Article 2015

1. H. Ishida, S. Kimura, N. Kogure, M. Kitajima, and H. Takayama:
Total Synthesis of (±)-Lycoposerramine-R, a Novel Skeletal Type of Lycopodium Alkaloid.
Tetrahedron,71(1), 51-56 (2015).

2. M. Kitajima, T. Koyama, Y. Wu, N. Kogure, R. Zhang, and H. Takayama:
Kopsiyunnanines J1 and J2, New Strychnos-type Homo-Monoterpenoid Indole Alkaloids from Kopsia arborea.
Nat. Prod. Commun.,10(1), 49-51 (2015).

3. H. Ishida, S. Kimura, N. Kogure, M. Kitajima, and H. Takayama:
The First Asymmetric Total Synthesis of Lycoposerramine-R.
Org. Biomol. Chem.,13(28), 7762-7771 (2015).

4. N. A. Saidin, E. Holmes, H. Takayama, N. J. Gooderham:
The Cellular Toxicology of Mitragynine, the Dominant Alkaloid of the Narcotic-like Herb, Mitragyna speciosa Korth.
Toxicol. Res..4(5), 1173-1183 (2015).

5. R. Nakabayashi, H. Tsugawa, M. Kitajima, H. Takayama, K. Saito:
Boosting Sensitivity in Liquid Chromatography–Fourier Transform Ion Cyclotron Resonance–Tandem Mass Spectrometry for Product Ion Analysis of Monoterpene Indole Alkaloids.
Frontiers in plant science. DOI:10.3389/fpls.2015.01127 (2015).

総説・単行書等 Review, Monograph, etc 2015

1. M. Kitajima and H. Takayama:
Chemistry of Mitragyna Alkaloids.
“Kratom and Other Mitragynines: The Chemistry and Pharmacology of Opioids from a Non-Opium Source”, ed. by R. B. Raffa, CRC Press, Chapter 8 (p. 101-116) (2015).

2. H. Takayama and M. Kitajima:
Medicinal Chemistry Based on Mitragynine.
“Kratom and Other Mitragynines: The Chemistry and Pharmacology of Opioids from a Non-Opium Source”, ed. by R. B. Raffa, CRC Press, Chapter 9 (p. 117-134) (2015).

3. 北島満里子, 寺田祐子, 渡辺達夫, 堀江俊治, 高山廣光:
温度感受性TRPチャネルアンタゴニスト活性を有するVoacangine型アルカロイドの探索・合成と構造活性相関研究.
MEDCHEM NEWS, 25, 132-137 (2015).

4. H. Takayama:
Recent Progress in Total Synthesis of Lycopodium Alkaloids.
J. Synth. Org. Chem. Jpn., 73 (11), 1072-1080 (2015).

5. 寺田祐子, 堀江俊治, 北島満里子, 高山廣光, 渡辺達夫:
Voacanga africana由来アルカロイドvoacangineの温度感受性TRPチャネルに対する活性・阻害作用.
食品加工技術 (日本食品・機械研究会誌), 35 (2), 1-12 (49-60) (2015).

6. 高山廣光(分担執筆): 生薬の化学成分:アルカロイド, 漢方薬・生薬薬剤師講座テキスト4 第4版(日本薬剤師研修センター)142-154 (2015).

原著 Original Article 2014

1. M. Azuma, T. Yoshikawa, N. Kogure, M. Kitajima, and H. Takayama:
Biogenetically Inspired Total Syntheses of Lycopodium Alkaloids, (+)-Flabellidine and (–)-Lycodine.
J. Am. Chem. Soc.,136(33), 11618-11621 (2014).

2. M. Kitajima, Y. Murakami, N. Takahashi, Y. Wu, N. Kogure, R. Zhang, and H. Takayama:
Asymmetric Total Synthesis of Novel Pentacyclic Indole Alkaloid, Kopsiyunnanine E, Isolated from Kopsia arborea.
Org. Lett.,16(19), 5000-5003 (2014).

3. M. Kitajima, M. Anbe, N. Kogure, S. Wongseripipatana, and H. Takayama:
Indole alkaloids from Kopsia jasminiflora.
Tetrahedron,70(47) 9099-9106 (2014).

4. K. Matsumoto, M. Narita, N. Muramatsu, T. Nakayama, K. Misawa, M. Kitajima, K. Tashima, L. A. Devi, T. Suzuki, H. Takayama, and S. Horie:
Orally Active Opioid μ/δ Dual Agonist MGM-16, a Derivative of the Indole Alkaloid Mitragynine, Exhibits Potent Analgesic Effect on Neuropathic Pain in Mice.
J. Pharmacol. Exp. Ther., 348 (3), 383-392 (2014).


5. Y. Terada, S. Horie, H. Takayama, K. Uchida, M. Tominaga, and T. Watanabe:
Activation and Inhibition of Thermosensitive TRP Channels by Voacangine, an Alkaloid Present in Voacanga Africana, an African Tree.
J. Nat. Prod., 77 (2), 285-297 (2014).

6. H. Nishiyama, M. Ono, T. Sugimoto, T. Sasai, N. Asakawa, S. Ueno, Y. Tominaga, T. Yaegashi, M. Nagaoka, T. Matsuzaki, N. Kogure, M. Kitajima, and H. Takayama:
4-Chlorocolchicine Derivatives Bearing a Thiourea Side Chain at the C-7 Position as Potent Anticancer Agents.
Med. Chem. Commun.,5(4), 452-458 (2014).

7. Y. Terada, M. Kitajima, F. Taguchi, H. Takayama, S. Horie, and T. Watanabe:
Identification of Indole Alkaloid Structural Units Important for Stimulus-Selective TRPM8 Inhibition: SAR Study of Naturally Occurring Iboga Derivatives.
J. Nat. Prod.,77(8), 1831-1838 (2014).

8. M. A. Tan, C. N. L. Concepcion, G. J. D. Alejandro, and H. Takayama:
Chemotaxonomic Relevance of the Constituents from the Leaves of Rothmannia merrillii.
J. Chem. Pharm. Res.,6(6), 779-781 (2014).

9. M. A. Tan, G. F. M. Panghulan, M. M. Uy, and H. Takayama:
Chemical Constituents from Psychotria cadigensis and Their Chemotaxonomic Relevance.
Am. J. Essent. Oils Nat. Prod.,1(4), 18-19 (2014).

10. M. A. Tan, R. A. U. Villacorta, G. J. D. Alejandro, and H. Takayama:
Iridoids and a Norsesquiterpenoid from the Leaves of Villaria odorata.
Nat. Prod. Commun.,9(9), 1229-1230 (2014).

11. K. Yonekura-Sakakibara, R. Nakabayashi, S. Sugawara, T. Tohge, T. Ito, M. Koyanagi, M. Kitajima, H. Takayama, and K. Saito:
A Flavonoid 3-O-Glucoside: 2”-O-Glucosyltransferase Responsible for Terminal Modification of Pollen-specific Flavonols in Arabidopsis thaliana.
Plant J.,79(5), 769-782 (2014).

12. L. M. R. Al Muqarrabun, N. Ahmat, S. R. S. Aris, N. Shamsulrijal, S. N. Baharum, R. Ahmad, A. R. Rosandy, M. N. Suratman, and H. Takayama:
A New Sesquiterpenoid from Scaphium macropodum (Miq.) Beumee.
Nat. Prod. Res.,28(9), 597-605 (2014).

13. A. Wibowo, N. Ahmat, A. S. Hamzah, F. A. Latif, J. S. Norrizah, H. Y. Khong, H. Takayama:
Identification and Biological Activity of Secondary Metabolites from Dryobalanops beccarii.
Pytochemistry Lett.,9, 117-122 (2014).

原著 Original Article 2013

1. M. Kitajima, M. Iwai, N. Kogure, R. Kikura-Hanajiri, Y. Goda, and H. Takayama :
Aspidosperma-aspidosperma-type Bisindole Alkaloids from Voacanga africana.
Tetrahedron,69(2) , 796-801 (2013).

2. M. Kitajima, S. Ohara, N. Kogure, D. Santiarworn, and H. Takayama:
β-Carboline-type indole alkaloid glycosides from Ophiorrhiza trichocarpon.
Tetrahedron,69(45) , 9451-9456 (2013).

3. M. E. Bungihan, M. A. Tan, H. Takayama, T. E. E. dela Crus, and M. G. Nonato:
A New Macrolide isolated from the Endophytic Fungus Colletotrichum sp.
Phillippine Sci. Lett.,6(1), 57-73 (2013).

4. M. A. Tan, J. A. Eusebio, R. A. P. Villacorta, N. Kogure, H. Takayama, and G. J. D. Alejandro:
Isolation and Identification of Vomifoliol from Two Endemic Philippine Rubiaceae Species,
Psychotria gitingensis and Villaria odorata.
Asia-Pac. J. Sci. Math. Eng.,1(1), 1-3 (2013).

原著 Original Article 2012

1. A. Nakayama, M. Kitajima, and H. Takayama :
Syntheses of Fawcettimine-type Lycopodium Alkaloids Utilizing Pauson-Khand Reaction.
Synlett,23(14), 2014-2024 (2012) Invited Account.

2. M. Kitajima, S. Ohara, N. Kogure, Y. Wu, R. Zhang, and H. Takayama :
New Indole Alkaloids from Melodinus henryi.
Heterocycles,85(8), 1949-1959 (2012).

3. N. Kogure, Y. Suzuki, Y. Wu, M. Kitajima, R. Zhang, and H. Takayama :
Chemical Conversion of Strychnine into Kopsiyunnanine-I, a New Hexacyclic Indole Alkaloid from Yunnan Kopsia arborea.
Tetrahedron Lett.,53(48), 6523-6526 (2012).

4. H. Nishiyama, M. Ono, T. Sugimoto, T. Sasai, N. Asakawa, T. Matsumoto, T. Yaegashi, M. Nagaoka, T. Matsuzaki, N. Kogure, M. Kitajima, and H. Takayama :
Synthesis and Biological Evaluation of 4-Chlorocolchicine Derivatives as Potent Anticancer Agents with Broad Effective Dosage Ranges.
Med. Chem. Comm.,3(12), 1500-1504 (2012).

5. M. Harada, K. Asaba, M. Iwai, N. Kogure, M. Kitajima and H. Takayama :
Asymmetric Total Synthesis of an Iboga-Type Indole Alkaloid, Voacangalactone, Newly Isolated from Voacanga africana.
Org. Lett.,14(22), 5800-5803 (2012).

6. M. A. Tan, M. G. Nonato, M. Kitajima, N. Kogure, and H. Takayama :
Secondary Metabolites from Pandanus simplex.
Biochem. Syst. Ecol.,40, 4-5 (2012).

7. K. Matsumoto, M. Lo, T. Hosoya, K. Tashima, H. Takayama, T. Murayama, and S. Horie :
Experimental Colitis Alters Expression of 5-HT Receptors and Transient Receptor Potential Vanilloid 1 Leading to Visceral Hypersensitivity in Mice.
Lab. Invest.,92(5), 769-782 (2012).

8. A. H. Abou-Donia, E. A. Shawky, M. M. Mohy El-Din, H. Takayama, and A. A. Seif El Din :
Bio-guided Isolation of Acetylcholinesterase Inhibitory Alkaloids from the Bulbs of Crinum bulbispermum.
Natural Products: An Indian Journal,8(3), 107-114 (2012).

9. A. Wibowo, N. Ahmat, A. S. Hamzah, A. L. M. Low, S. A. S. Mohamad, H. Y. Khong, A. S. Sufian, N. Manshoor, H. Takayama :
Malaysianol B, an Oligostilbenoid Derivative from Dryobalanops lanceolata.
Fitoterapia,83(8), 1569-1575 (2012).

Review 2012

1. M. Kitajima and H. Takayama :
Lycopodium Alkaloids: Isolation and Asymmetric Synthesis.
Topics in Current Chemistry, “Alkaloid Synthesis”, ed. by H.-J. Knölker, Springer, 309, 1-32 (2012).