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07.03.2019 | Note

New vasorelaxant indole alkaloids, taberniacins A and B, from Tabernaemontana divaricata

verfasst von: Yusuke Hirasawa, Xin Dai, Jun Deguchi, Shota Hatano, Tadahiro Sasaki, Ruri Ohtsuka, Alfarius Eko Nugroho, Toshio Kaneda, Hiroshi Morita

Erschienen in: Journal of Natural Medicines | Ausgabe 3/2019

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Abstract

Taberniacins A (1) and B (2), new indole alkaloids, were isolated from the stems of Tabernaemontana divaricata (Apocynaceae). Structure elucidation of 1 and 2 was based on spectroscopic methods and total synthesis. Each alkaloid showed vasorelaxant activity against phenylephrine-induced contraction of isolated rat aorta.

Pratchayasakul W, Pongchaidecha A, Chattipakorn N, Chattipakorn S (2008) Ethnobotany & ethnopharmacology of Tabernaemontana divaricata. Indian J Med Res 127:317–335PubMed

Tarseli MA, Raehal KM, Brasher AK, Streicher JM, Groer CE, Cameron MD, Bohn LM, Micalizio GC (2011) Synthesis of conolidine, a potent non-opioid analgesic for tonic and persistent pain. Nat Chem 3:449–453CrossRef

Dagnino D, Schripsema J, Verpoorte R (1993) Comparison of terpenoid indole alkaloid production and degradation in two cell lines of Tabernaemontana divaricata. Plant Cell Rep 13:95–98CrossRef

Kam TS, Loh KY, Lim LH, Loong WL, Chuah CH, Wei C (1992) New alkaloids from the leaves of Tabernaemontana divaricata. Tetrahedron Lett 33:969–972CrossRef

Kam TS, Loh KY, Wei C (1993) Conophylline and conophyllidine:new dimeric alkaloids from Tabernaemontana divaricata. J Nat Prod 56:1865–1871CrossRef

Kam TS, Anuradha S (1995) Alkaloids from Tabernaemontana divaricata. Phytochemistry 40:313–316CrossRef

Kam TS, Pang HS, Lim TM (2003) Biologically active indole andbisindole alkaloids from Tabernaemontana divaricata. Org Biomol Chem 1:1292–1297CrossRef

Kam TS, Choo YM, Komiyama K (2004) Biologically active iboganand vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers 1:646–656CrossRef

Raj K, Shoeb A, Kapil RS, Popli SP (1974) Alkaloids of Tabernaemontana divaricata. Phytochemistry 13:1621–1622CrossRef

10.

Schripsema J, Peltenburg-Looman A, Erkelens C, Verpoorte R (1991) Nitrogen metabolism in cultures of Tabernaemontana divaricata. Phytochemistry 30:3951–3954CrossRef

11.

van Beek TA, Verpoorte R, Svendsen AB, Leeuwenberg AJ, Bisset NG (1984) Tabernaemontana L. (Apocynaceae): a review of its taxonomy, phytochemistry, ethnobotany and pharmacology. J Ethnopharmacol 10:1–156CrossRef

12.

Hirasawa Y, Miyama S, Hosoya T, Koyama K, Rahman A, Kusumawati I, Zaini NC, Morita H (2009) Alasmontamine A, a first tetrakis monoterpene indole alkaloid from Tabernaemontana elegans. Org Lett 11:5718–5721CrossRef

13.

Nugroho AE, Moue M, Sasaki T, Shirota O, Hadi AHA, Morita H (2018) Yohimbine-related alkaloids from Tabernaemontana corymbosa. Nat Prod Commun 13:347–350

14.

Nugroho AE, Hashimoto A, Wong CP, Yokoe H, Tsubuki M, Kaneda T, Hadi AHA, Morita H (2018) Ceramicines M-P from Chisocheton ceramicus: isolation and structure-activity relationship study. J Nat Med 72:64–72CrossRef

15.

Nugroho AE, Inoue D, Wong CP, Hirasawa Y, Kaneda T, Shirota O, Hadi AHA, Morita H (2018) Reinereins A and B, new onocerane triterpenoids from Reinwardtiodendron cinereum. J Nat Med 72:588–592CrossRef

16.

Kaneda T, Matsumoto M, Sotozono Y, Nugroho AE, Hirasawa Y, Hadi AHA, Morita H (2019) Cycloartane-triterpenoid, (23R, 24E)-23-acetoxy-mangiferonic acid inhibited proliferation and migration in B16-F10 melanoma via MITF downregulation caused by inhibition of both β-catenin and c-Raf-MEK1-ERK signaling axis. J Nat Med 73:47–58CrossRef

17.

Kaneda T, Nakajima Y, Koshikawa S, Nugroho AE, Morita H (2019) Cyclolinopeptide F, a cyclic peptide from flaxseed inhibited RANKL-induced osteoclastogenesis via downergulation of RANK expression. J Nat Med. https://doi.org/10.1007/s11418-019-01292-w

18.

Prema, Wong CP, Awouafack MD, Nugroho AE, Win YY, Win NN, Ngwe H, Morita H, Morita H (2019) Two new quassinoids and other constituents from the Picrasma javanica wood and their biological activities. J Nat Med. https://doi.org/10.1007/s11418-018-01279-z

19.

McLean S, Murray DG (1970) Isolation of indole (β-carboline), pyridine, and indole-pyridine alkaloids from Nauclea diderrichii. Can J Chem 48:867–868CrossRef

20.

Murray DG, Szakolcia A, McLean S (1972) The constituents of Nauclea diderrichii. Part II. Isolation and classification of constituents; simple β-carboline and pyridine alkaloids. Can J Chem 50:1486–1495CrossRef

21.

Mukhtar MR, Osman N, Awang K, Hazni H, Qureshi AK, Hadi AHA, Zaima K, Morita H, Litaudon M (2012) Neonaucline, a new indole alkaloid from the leaves of Ochreinauclea maingayii (Hook. f.) Ridsd. (Rubiaceae). Molecules 17:267–274CrossRef

22.

Ahmad K, Thomas NF, Hadi AHA, Mukhtar MR, Mohamad K, Nafiah MA, Takeya K, Morita H, Litaudon M, Arai H, Awang K (2010) Oppositinines A and B: new vasorelaxant β-carboline alkaloids from Neisosperma oppositifolia. Chem Pharm Bull 58:1085–1087CrossRef

23.

Suckling CJ, Murphy JA, Khalaf AI, Zhou S, Lizos DE, Nhien AN, Yasumatsu H, McVie A, Young LC, McCraw C, Waterman PG, Morris BJ, Pratt JA, Harvey AL (2007) M4 agonists/5HT7 antagonists with potential as antischizophrenic drugs: serominic compounds. Bioorg Med Chem Lett 17:2649–2655CrossRef

24.

Cai L, Liu X, Tao X, Shen D (2004) Efficient microwave-assisted cyanation of aryl bromide. Synth Commun 34:1215–1221CrossRef

25.

Schareina T, Zapf A, Magerlein W, Muller N, Beller M (2007) A state-of-the-art cyanation of aryl bromides: a novel and versatile copper catalyst system inspired by nature. Chem Eur J 13:6249–6254CrossRef

26.

Weissman SA, Zewge D, Chen C (2005) Ligand-free palladium-catalyzed cyanation of aryl halides. J Org Chem 70:1508–1510CrossRef

27.

Baliski R, Kaczmarek L (1993) Mild and efficient conversion of nitriles to amides with basic urea-hydrogen peroxide adduct. Synth Commun 23:3149–3155CrossRef

28.

Mukhtar MR, Nafiah MA, Awang K, Thomas NF, Zaima K, Morita H, Litaudon M, Hadi AHA (2009) α’-Oxoperakensimines A-C, new bisbenzylisoquinoline alkaloids from Alseodaphne perakensis (Gamble) Kosterm. Heterocycles 78:2085–2092CrossRef

Titel: New vasorelaxant indole alkaloids, taberniacins A and B, from Tabernaemontana divaricata
verfasst von: Yusuke Hirasawa
Xin Dai
Jun Deguchi
Shota Hatano
Tadahiro Sasaki
Ruri Ohtsuka
Alfarius Eko Nugroho
Toshio Kaneda
Hiroshi Morita
Publikationsdatum: 07.03.2019
Verlag: Springer Singapore
Erschienen in: Journal of Natural Medicines / Ausgabe 3/2019
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-019-01293-9

Springer Medizin

Abstract

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