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01.04.2013 | Note

Sanjecumins A and B: new limonoids from Sandoricum koetjape

verfasst von: Yuta Nagakura, Alfarius Eko Nugroho, Yusuke Hirasawa, Takahiro Hosoya, Abdul Rahman, Idha Kusumawati, Noor Cholies Zaini, Hiroshi Morita

Erschienen in: Journal of Natural Medicines | Ausgabe 2/2013

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Abstract

Two new limonoids, sanjecumins A (1) and B (2), have been isolated from the leaves of Sandoricum koetjape, together with sandoripins A (3) and B (4). Their structures and absolute configurations were elucidated on the basis of NMR and CD data. Sandoripins A (3) and B (4) moderately inhibited nitric oxide production in mouse macrophage-like cell line J774.1 stimulated by lipopolysaccharide.

Powell RG, Mikolajczak KL, Zilkowski BW, Mantus EK, Cherry D, Clardy J (1991) Limonoid antifeedants from seed of Sandoricum koetjape. J Nat Prod 54:241–246PubMedCrossRef

Kaneda N, Pezzuto JM, Kinghorn AD, Farnsworth NR, Santisuk T, Tuchinda P, Udchachon J, Reutrakul V (1992) Plant anticancer agents, L. Cytotoxic triterpenes from Sandoricum koetjape stems. J Nat Prod 55:654–659PubMedCrossRef

Kosela S, Yulizar Y, Chairul, Tori M, Asakawa Y (1995) Secomultiflorane-type triterpenoid acids from stem bark of Sandoricum koetjape. Phytochemistry 38:691–694CrossRef

Ismail IS, Ito H, Hatano T, Taniguchi S, Yoshida T (2003) Modified limonoids from the leaves of Sandoricum koetjape. Phytochemistry 64:1345–1349PubMedCrossRef

Ismail IS, Ito H, Hatano T, Taniguchi S, Yoshida T (2004) Two new analogues of trijugin-type limonoids from the leaves of Sandoricum koetjape. Chem Pharm Bull (Tokyo) 52:1145–1147CrossRef

Rasadah MA, Khozirah S, Aznie AA, Nik MM (2004) Anti-inflammatory agents from Sandoricum koetjape Merr. Phytomedicine 11:261–263PubMedCrossRef

Pancharoen O, Pipatanapatikarn A, Charles Taylor W, Bansiddhi J (2009) Two new limonoids from the leaves of Sandoricum koetjape. Nat Prod Res 23:10–16PubMedCrossRef

Morita H, Oshimi S, Hirasawa Y, Koyama K, Honda T, Ekasari W, Indrayanto G, Zaini NC (2007) Cassiarins A and B, novel antiplasmodial alkaloids from Cassia siamea. Org Lett 9:3691–3693PubMedCrossRef

Oshimi S, Deguchi J, Hirasawa Y, Ekasari W, Widyawaruyanti A, Wahyuni TS, Zaini NC, Shirota O, Morita H (2009) Cassiarins C–E, antiplasmodial alkaloids from the flowers of Cassia siamea. J Nat Prod 72:1899–1901PubMedCrossRef

10.

Mohamad K, Hirasawa Y, Litaudon M, Awang K, Hadi AHA, Takeya K, Ekasari W, Widyawaruyanti A, Zaini NC, Morita H (2009) Ceramicines B–D, new antiplasmodial limonoids from Chisocheton ceramicus. Bioorg Med Chem 17:727–730PubMedCrossRef

11.

Hirasawa Y, Hara M, Nugroho AE, Sugai M, Zaima K, Kawahara N, Goda Y, Awang K, Hadi AHA, Litaudon M, Morita H (2010) Bisnicalaterines B and C, atropisomeric bisindole alkaloids from Hunteria zeylanica, showing vasorelaxant activity. J Org Chem 75:4218–4223PubMedCrossRef

12.

Koyama K, Hirasawa Y, Hosoya T, Hoe TC, Chan K-L, Morita H (2010) Alpneumines A–H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora. Bioorg Med Chem 18:4415–4421PubMedCrossRef

13.

Taha H, Hadi AHA, Nordin N, Najmuldeen IA, Mohamad K, Shirota O, Nugroho AE, Piow WC, Kaneda T, Morita H (2011) Pseuduvarines A and B, two new cytotoxic dioxoaporphine alkaloids from Pseuduvaria rugosa. Chem Pharm Bull (Tokyo) 59:896–897CrossRef

14.

Hosoya T, Yamasaki F, Nakata A, Rahman A, Kusumawati I, Zaini NC, Morita H (2011) Inhibitors of nitric oxide production from Stemona javanica. Planta Med 77:256–258PubMedCrossRef

15.

Wong CP, Shimada M, Nugroho AE, Hirasawa Y, Kaneda T, Hadi AH, Osamu S, Morita H (2012) Ceramicines J–L, new limonoids from Chisocheton ceramicus. J Nat Med (in press)

16.

Yamasaki F, Machida S, Nakata A, Nugroho AE, Hirasawa Y, Kaneda T, Shirota O, Hagane N, Sugizaki T, Morita H (2012) Haworforbins A–C, new phenolics from Haworthia cymbiformis. J Nat Med (in press)

17.

Zaima K, Deguchi J, Matsuno Y, Kaneda T, Hirasawa Y, Morita H (2012) Vasorelaxant effect of FR900359 from Ardisia crenata on rat aortic artery. J Nat Med (in press)

18.

Zaima K, Takeyama Y, Koga I, Saito A, Tamamoto H, Azziz SS, Mukhtar MR, Awang K, Hadi AH, Morita H (2012) Vasorelaxant effect of isoquinoline derivatives from two species of Popowia perakensis and Phaeanthus crassipetalus on rat aortic artery. J Nat Med (in press)

19.

Zaima K, Koga I, Iwasawa N, Hosoya T, Hirasawa Y, Kaneda T, Ismail IS, Lajis NH, Morita H (2012) Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. J Nat Med (in press)

20.

Morita H, Mori R, Deguchi J, Oshimi S, Hirasawa Y, Ekasari W, Widyawaruyanti A, Hadi AH (2012) Antiplasmodial decarboxyportentol acetate and 3,4-dehydrotheaspirone from Laumoniera bruceadelpha. J Nat Med (in press)

21.

Hosoya T, Nakata A, Yamasaki F, Abas F, Shaari K, Lajis NH, Morita H (2012) Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors. J Nat Med 66:166–176PubMedCrossRef

22.

Pancharoen O, Haboonmee P, Taylor WC (2005) Chemical constituents from the leaves of Sandoricum koetjape. Acta Hortic 677:51–55

23.

TURBOMOLE V6.3 2011, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989–2007; TURBOMOLE GmbH, since 2007. http://www.turbomole.com

24.

Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 38:3098–3100PubMedCrossRef

25.

Lee C, Yang W, Parr RG (1988) Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B Condens Matter 37:785–789PubMedCrossRef

26.

Schäfer A, Horn H, Ahlrichs R (1992) Fully optimized contracted Gaussian basis sets for atoms Li to Kr. J Chem Phys 97:2571–2577CrossRef

27.

Eichkorn K, Treutler O, Öhm H, Häser M, Ahlrichs R (1995) Auxiliary basis sets to approximate Coulomb potentials. Chem Phys Lett 240:283–290CrossRef

28.

Halgren TA (1990) Maximally diagonal force constants in dependent angle-bending coordinates. II. Implications for the design of empirical force fields. J Am Chem Soc 112:4710–4723CrossRef

29.

Halgren TA (1992) The representation of van der Waals (vdW) interactions in molecular mechanics force fields: potential form, combination rules, and vdW parameters. J Am Chem Soc 114:7827–7843CrossRef

30.

Halgren TA (1996) Merck molecular force field. II. MMFF94 van der Waals and electrostatic parameters for intermolecular interactions. J Comput Chem 17:520–552CrossRef

31.

Halgren TA (1996) Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J Comput Chem 17:490–519CrossRef

32.

Mohamadi F, Richards NGJ, Guida WC, Liskamp R, Lipton M, Caufield C, Chang G, Hendrickson T, Still WC (1990) MacroModel—an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J Comput Chem 11:440–467CrossRef

Titel: Sanjecumins A and B: new limonoids from Sandoricum koetjape
verfasst von: Yuta Nagakura
Alfarius Eko Nugroho
Yusuke Hirasawa
Takahiro Hosoya
Abdul Rahman
Idha Kusumawati
Noor Cholies Zaini
Hiroshi Morita
Publikationsdatum: 01.04.2013
Verlag: Springer Japan
Erschienen in: Journal of Natural Medicines / Ausgabe 2/2013
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-012-0677-4

Springer Medizin

Abstract

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