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Published in: Journal of Natural Medicines 3/2019

01-06-2019 | Note

Four limonoids from the seeds extract of Sandoricum koetjape

Authors: Miranti B. Bumi, Leny Heliawaty, Elvira Hermawati, Yana M. Syah

Published in: Journal of Natural Medicines | Issue 3/2019

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Abstract

Three andirobin- and one trijugin-class limonoids, named koetjapins A-D (14), have been isolated from the seed extracts of Sandoricum koetjape. The structures of these compounds were determined by extensive NMR and mass spectral data, and the chemotaxonomic significance of these limonoids in the family Meliaceae is highlighted. Preliminary biological activity showed that only compound 4 has significant inhibitory activity against P-388 cells, while antibacterial tests showed that none of these compounds were active.
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Literature
1.
go back to reference Muellner AN, Samuel R, Chase MW, Coleman A, Stuessy TF (2008) An evaluation of tribe and generic relationship in Melioideae (Meliaceae) based on nuclear ITS Ribosomal DNA. Taxon 57:98–108 Muellner AN, Samuel R, Chase MW, Coleman A, Stuessy TF (2008) An evaluation of tribe and generic relationship in Melioideae (Meliaceae) based on nuclear ITS Ribosomal DNA. Taxon 57:98–108
2.
go back to reference Kaneda N, Pezzuto JM, Kinghorn D, Farnsworth NR (1992) Plant anticancer agents, L. Cytotoxic triterpenes from Sandoricum koetjape stems. J Nat Prod 55:654–659CrossRef Kaneda N, Pezzuto JM, Kinghorn D, Farnsworth NR (1992) Plant anticancer agents, L. Cytotoxic triterpenes from Sandoricum koetjape stems. J Nat Prod 55:654–659CrossRef
3.
go back to reference King FE, Morgan JWW (1960) The chemistry of extractives from hardwoods. Part XXX. The constitution of katonic acid, a triterpene from Sandoricum indicum. J Chem Soc 0:4738–4747 King FE, Morgan JWW (1960) The chemistry of extractives from hardwoods. Part XXX. The constitution of katonic acid, a triterpene from Sandoricum indicum. J Chem Soc 0:4738–4747
4.
go back to reference Sim KY, Lee HT (1972) Triterpenoid and other constituents from Sandoricum indicum. Phytochemistry 11:3341–3343CrossRef Sim KY, Lee HT (1972) Triterpenoid and other constituents from Sandoricum indicum. Phytochemistry 11:3341–3343CrossRef
5.
go back to reference Kosela S, Yulizar Y, Chairul Tori M, Asakawa Y (1995) Secomultiflorane-type triterpenoid acids from stem bark of Sandoricum Koetjape. Phytochemistry 38:691–694CrossRef Kosela S, Yulizar Y, Chairul Tori M, Asakawa Y (1995) Secomultiflorane-type triterpenoid acids from stem bark of Sandoricum Koetjape. Phytochemistry 38:691–694CrossRef
6.
go back to reference Tanaka T, Koyano T, Kowithayakorn T, Fujimoto H, Okuyama E, Hayashi M, Komiyama K, Ishibashi M (2001) New multiflorane-type triterpenoid acids from Sandoricum indicum. J Nat Prod 64:1243–1245CrossRef Tanaka T, Koyano T, Kowithayakorn T, Fujimoto H, Okuyama E, Hayashi M, Komiyama K, Ishibashi M (2001) New multiflorane-type triterpenoid acids from Sandoricum indicum. J Nat Prod 64:1243–1245CrossRef
7.
go back to reference Ismail IS, Ito H, Mukainaka T, Higashihara H, Enjo F, Tokuda H, Nishino H, Yoshida T (2003) Ichthyotoxic and anticarcinogenic effects of triterpenoids from Sandoricum koetjape Bark. Biol Pharm Bull 26:1351–1353CrossRef Ismail IS, Ito H, Mukainaka T, Higashihara H, Enjo F, Tokuda H, Nishino H, Yoshida T (2003) Ichthyotoxic and anticarcinogenic effects of triterpenoids from Sandoricum koetjape Bark. Biol Pharm Bull 26:1351–1353CrossRef
8.
go back to reference Efdi M, Ninomiya M, Suryani E, Tanaka K, Ibrahim S, Watanabe K, Koketsu M (2012) Sentulic acid: a cytotoxic ring A-seco triterpenoid from Sandoricum koetjape Merr. Bioorg Med Chem Lett 22:4242–4245CrossRef Efdi M, Ninomiya M, Suryani E, Tanaka K, Ibrahim S, Watanabe K, Koketsu M (2012) Sentulic acid: a cytotoxic ring A-seco triterpenoid from Sandoricum koetjape Merr. Bioorg Med Chem Lett 22:4242–4245CrossRef
9.
go back to reference Powell RG, Mikolajczak KL, Zilkowski BW (1991) Limonoid antifeedants from seed of Sandoricum koetjape. J Nat Prod 54:241–246CrossRef Powell RG, Mikolajczak KL, Zilkowski BW (1991) Limonoid antifeedants from seed of Sandoricum koetjape. J Nat Prod 54:241–246CrossRef
10.
go back to reference Ismail IS, Ito H, Hatano T, Taniguchi S, Yoshida T (2003) Modified limonoids from the leaves of Sandoricum koetjape. Phytochemistry 64:1345–1349CrossRef Ismail IS, Ito H, Hatano T, Taniguchi S, Yoshida T (2003) Modified limonoids from the leaves of Sandoricum koetjape. Phytochemistry 64:1345–1349CrossRef
11.
go back to reference 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 52:1145–1147CrossRef 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 52:1145–1147CrossRef
12.
go back to reference Nagakura Y, Nugroho AE, Hirasawa Y, Hosoya T, Rahman A, Kusumawati I, Zaini NC, Morita H (2012) Sanjecumins A and B: new limonoids from Sandoricum koetjape. J Nat Med 67:381–385CrossRef Nagakura Y, Nugroho AE, Hirasawa Y, Hosoya T, Rahman A, Kusumawati I, Zaini NC, Morita H (2012) Sanjecumins A and B: new limonoids from Sandoricum koetjape. J Nat Med 67:381–385CrossRef
13.
go back to reference Rasadah MA, Khozirah S, Aznie AA, Nik MM (2004) Anti-inflammatory agents from Sandoricum koetjape Merr. Phytomedicine 11:261–263CrossRef Rasadah MA, Khozirah S, Aznie AA, Nik MM (2004) Anti-inflammatory agents from Sandoricum koetjape Merr. Phytomedicine 11:261–263CrossRef
14.
go back to reference Sun DA, Starck SR, Locke EP, Hecht HM (1999) DNA polymerase β-inhibitors from Sandoricum koetjape. J Nat Prod 62:1110–1113CrossRef Sun DA, Starck SR, Locke EP, Hecht HM (1999) DNA polymerase β-inhibitors from Sandoricum koetjape. J Nat Prod 62:1110–1113CrossRef
15.
go back to reference Ning J, Di Y-T, Fanf X, He H-P, Wang Y-Y, Li Y, Li S-L, Hao X-J (2010) Limonoids from the leaves of Cipadessa baccifera. J Nat Prod 73:1327–1331CrossRef Ning J, Di Y-T, Fanf X, He H-P, Wang Y-Y, Li Y, Li S-L, Hao X-J (2010) Limonoids from the leaves of Cipadessa baccifera. J Nat Prod 73:1327–1331CrossRef
16.
go back to reference Di Y-T, He H-P, Liu H-Y, Yi P, Zhang Z, Ren Y-L, Wang J-S, Sun Q-Y, Yang F-M, Fanf X, Li S-L, Zhu H-J, Hao X-J (2007) Trijugin-type limonoids from the leaves of Cipadessa cineascens. J Nat Prod 70:1352–1355CrossRef Di Y-T, He H-P, Liu H-Y, Yi P, Zhang Z, Ren Y-L, Wang J-S, Sun Q-Y, Yang F-M, Fanf X, Li S-L, Zhu H-J, Hao X-J (2007) Trijugin-type limonoids from the leaves of Cipadessa cineascens. J Nat Prod 70:1352–1355CrossRef
17.
go back to reference Tan Q-G, Luo X-D (2011) Meliaceous limonoids: chemistry and biological activities. Chem Rev 111:7437–7522CrossRef Tan Q-G, Luo X-D (2011) Meliaceous limonoids: chemistry and biological activities. Chem Rev 111:7437–7522CrossRef
18.
go back to reference Pennington TD, Styles BT (1975) A generic monograph of the Meliaceae. Blumea 22:419–540 Pennington TD, Styles BT (1975) A generic monograph of the Meliaceae. Blumea 22:419–540
19.
go back to reference Fang X, Di Y-T, Li C-S, Geng L-Z, Zhang Z, Zhang Y, Yang S-Y, Hao X-J (2009) Tetranortriterpenoids from the leaves of Cipadessa cinerascens. J Nat Prod 72:714–718CrossRef Fang X, Di Y-T, Li C-S, Geng L-Z, Zhang Z, Zhang Y, Yang S-Y, Hao X-J (2009) Tetranortriterpenoids from the leaves of Cipadessa cinerascens. J Nat Prod 72:714–718CrossRef
20.
go back to reference Chiruvella KK, Mohammed A, Dampuri G, Ghanta RG, Raghavan SC (2007) Phytochemical and antimicrobial studies of methyl angolensate and luteolin-7-O-glucoside isolated from callus cultures of Soymida febrifuga. Int J Biomed Sci 3:269–278PubMedPubMedCentral Chiruvella KK, Mohammed A, Dampuri G, Ghanta RG, Raghavan SC (2007) Phytochemical and antimicrobial studies of methyl angolensate and luteolin-7-O-glucoside isolated from callus cultures of Soymida febrifuga. Int J Biomed Sci 3:269–278PubMedPubMedCentral
21.
go back to reference Muhtadi Hakim EH, Juliawaty LD, Syah YM, Achmad SA, Latif J, Ghisalberti EL (2006) Cytotoxic resveratrol oligomers from the tree bark of Dipterocarpus hasseltii (Dipterocarpaceae). Fitoterapia 77:550–555CrossRef Muhtadi Hakim EH, Juliawaty LD, Syah YM, Achmad SA, Latif J, Ghisalberti EL (2006) Cytotoxic resveratrol oligomers from the tree bark of Dipterocarpus hasseltii (Dipterocarpaceae). Fitoterapia 77:550–555CrossRef
22.
go back to reference Windayani N, Juliawaty LD, Hakim EH, Ruslan K, Syah YM (2015) An acetylated triterpene glycoside and lignans from Phyllanthus myrtifolius and their antibacterial activities. Nat Prod J 5:152–157 Windayani N, Juliawaty LD, Hakim EH, Ruslan K, Syah YM (2015) An acetylated triterpene glycoside and lignans from Phyllanthus myrtifolius and their antibacterial activities. Nat Prod J 5:152–157
Metadata
Title
Four limonoids from the seeds extract of Sandoricum koetjape
Authors
Miranti B. Bumi
Leny Heliawaty
Elvira Hermawati
Yana M. Syah
Publication date
01-06-2019
Publisher
Springer Singapore
Published in
Journal of Natural Medicines / Issue 3/2019
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-019-01303-w

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