Skip to main content
Top
Published in: Journal of Natural Medicines 3/2016

01-07-2016 | Original Paper

γ-Lactam alkaloids from the flower buds of daylily

Authors: Takahiro Matsumoto, Seikou Nakamura, Souichi Nakashima, Tomoe Ohta, Mamiko Yano, Junichiro Tsujihata, Junko Tsukioka, Keiko Ogawa, Masashi Fukaya, Masayuki Yoshikawa, Hisashi Matsuda

Published in: Journal of Natural Medicines | Issue 3/2016

Login to get access

Abstract

Four new alkaloids, hemerocallisamines IV–VII, were isolated from the methanol extract of flower buds of daylily. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. The absolute stereochemistry of the hemerocallisamines IV–VI was elucidated by the application of the modified Mosher’s method, HPLC analysis, and optical rotation. In the present study, the isolated alkaloids significantly inhibited the aggregation of Aβ42 in vitro. This is the first report about bioactive alkaloids with a γ-lactam ring from daylily. In addition, isolated nucleosides showed accelerative effects on neurite outgrowth under the non-fasting condition.
Appendix
Available only for authorised users
Literature
1.
go back to reference Ogawa Y, Konishi T (2009) N-Glycosides of amino acid amides from Hemerocallis fulva var. sempervirens. Chem Pharm Bull 57:1110–1112CrossRefPubMed Ogawa Y, Konishi T (2009) N-Glycosides of amino acid amides from Hemerocallis fulva var. sempervirens. Chem Pharm Bull 57:1110–1112CrossRefPubMed
2.
go back to reference Zhang Y, Cichewicz HR, Nair GM (2004) Lipid peroxidation inhibitory compounds from daylily (Hemerocallis fulva) leaves. Life Sci 75:753–763CrossRefPubMed Zhang Y, Cichewicz HR, Nair GM (2004) Lipid peroxidation inhibitory compounds from daylily (Hemerocallis fulva) leaves. Life Sci 75:753–763CrossRefPubMed
3.
go back to reference Nakamura S, Nakashima S, Tanabe G, Oda Y, Yokota N, Fujimoto K, Matsumoto T, Sakuma R, Ohta T, Ogawa K, Nishida S, Miki H, Matsuda H, Muraoka O, Yoshikawa M (2012) Medicinal flower XXXVII. Alkaloid constituents with melanogenesis inhibitory activity from flower buds and leaves of sacred Lotus (Nelumbo nucifera, Nymphaceaceae) in B16 melanoma cells. Bioorg Med Chem 21:779–787CrossRefPubMed Nakamura S, Nakashima S, Tanabe G, Oda Y, Yokota N, Fujimoto K, Matsumoto T, Sakuma R, Ohta T, Ogawa K, Nishida S, Miki H, Matsuda H, Muraoka O, Yoshikawa M (2012) Medicinal flower XXXVII. Alkaloid constituents with melanogenesis inhibitory activity from flower buds and leaves of sacred Lotus (Nelumbo nucifera, Nymphaceaceae) in B16 melanoma cells. Bioorg Med Chem 21:779–787CrossRefPubMed
4.
go back to reference Matsumoto T, Nakamura S, Nakashima S, Fujimoto K, Yoshikawa M, Ohta T, Ogawa K, Matsuda H (2014) Structures of lignan dicarboxylates and terpenoids from the flower buds of Cananga odorata and their inhibitory effects on melanogenesis. J Nat Prod 77:990–999CrossRefPubMed Matsumoto T, Nakamura S, Nakashima S, Fujimoto K, Yoshikawa M, Ohta T, Ogawa K, Matsuda H (2014) Structures of lignan dicarboxylates and terpenoids from the flower buds of Cananga odorata and their inhibitory effects on melanogenesis. J Nat Prod 77:990–999CrossRefPubMed
5.
go back to reference Matsumoto T, Nakamura S, Fujimoto K, Ohta T, Ogawa K, Yoshikawa M, Matsuda H (2014) Structure of constituents isolated from the flower buds of Cananga odorata and their inhibitory effects on aldose reductase. J Nat Med 68:709–716CrossRefPubMed Matsumoto T, Nakamura S, Fujimoto K, Ohta T, Ogawa K, Yoshikawa M, Matsuda H (2014) Structure of constituents isolated from the flower buds of Cananga odorata and their inhibitory effects on aldose reductase. J Nat Med 68:709–716CrossRefPubMed
6.
go back to reference Fujimoto K, Nakamura S, Nakashima S, Matsumoto T, Uno K, Ohta T, Miura T, Matsuda H, Yoshikawa M (2012) Medicinal flowers. XXXV. Nor-oleanane-type and acylated oleanane-type triterpene saponins from the flower buds of Chinese Camellia japonica and their inhibitory effects on melanogenesis. Chem Pharm Bull 60:1188–1194CrossRefPubMed Fujimoto K, Nakamura S, Nakashima S, Matsumoto T, Uno K, Ohta T, Miura T, Matsuda H, Yoshikawa M (2012) Medicinal flowers. XXXV. Nor-oleanane-type and acylated oleanane-type triterpene saponins from the flower buds of Chinese Camellia japonica and their inhibitory effects on melanogenesis. Chem Pharm Bull 60:1188–1194CrossRefPubMed
7.
go back to reference Nakamura S, Moriura T, Park S, Fujimoto K, Matsumoto T, Ohta T, Matsuda H, Yoshikawa M (2012) Melanogenesis inhibitory and fibroblast proliferation accelerating effects of noroleanane- and oleanane-type triterpene oligoglycosides from the flower buds of Camellia japonica. J Nat Prod 75:1425–1430CrossRefPubMed Nakamura S, Moriura T, Park S, Fujimoto K, Matsumoto T, Ohta T, Matsuda H, Yoshikawa M (2012) Melanogenesis inhibitory and fibroblast proliferation accelerating effects of noroleanane- and oleanane-type triterpene oligoglycosides from the flower buds of Camellia japonica. J Nat Prod 75:1425–1430CrossRefPubMed
8.
go back to reference Patching SG, Baldwin SA, Baldwin AD, Young JD, Gallagher MP, Henderson PJF, Herbert RB (2005) The nucleoside transport proteins, NupC and NupG, from Escherichia coli: specific structural motifs necessary for the binding of ligands. Org Biomol Chem 3:462–470CrossRefPubMed Patching SG, Baldwin SA, Baldwin AD, Young JD, Gallagher MP, Henderson PJF, Herbert RB (2005) The nucleoside transport proteins, NupC and NupG, from Escherichia coli: specific structural motifs necessary for the binding of ligands. Org Biomol Chem 3:462–470CrossRefPubMed
9.
go back to reference Shuto S, Itoh H, Ueda S, Imamura S, Fukukawa K, Tsujino M, Matsuda A, Ueda T (1988) A facile enzymatic synthesis of 5′-(3-sn-phosphatidyl)nucleosides and their antileukemic activities. Chem Pharm Bull 36:209–217CrossRefPubMed Shuto S, Itoh H, Ueda S, Imamura S, Fukukawa K, Tsujino M, Matsuda A, Ueda T (1988) A facile enzymatic synthesis of 5′-(3-sn-phosphatidyl)nucleosides and their antileukemic activities. Chem Pharm Bull 36:209–217CrossRefPubMed
10.
go back to reference Stueber D, Grant DM (2002) 13C and 15N chemical shift tensors in adenosine, guanosine dihydrate, 2′-deoxythymidine, and cytidine. J Am Chem Soc 124:10539–10551CrossRefPubMed Stueber D, Grant DM (2002) 13C and 15N chemical shift tensors in adenosine, guanosine dihydrate, 2′-deoxythymidine, and cytidine. J Am Chem Soc 124:10539–10551CrossRefPubMed
11.
go back to reference Inoue T, Konishi T, Kiyosawa S, Fujiwara Y (1994) 2,5-Dihydrofryl-γ-lactam derivatives from Hemerocallis fulva L. var. kwanso REGEL. II. Chem Pharm Bull 42:154–155CrossRef Inoue T, Konishi T, Kiyosawa S, Fujiwara Y (1994) 2,5-Dihydrofryl-γ-lactam derivatives from Hemerocallis fulva L. var. kwanso REGEL. II. Chem Pharm Bull 42:154–155CrossRef
12.
go back to reference Murai N, Yonaga M, Tanaka K (2012) Palladium-catalyzed direct hydroxymethylation of aryl halides and triflates with potassium acetoxymethyltrifluoroborate. Org Lett 14:3812–3813CrossRef Murai N, Yonaga M, Tanaka K (2012) Palladium-catalyzed direct hydroxymethylation of aryl halides and triflates with potassium acetoxymethyltrifluoroborate. Org Lett 14:3812–3813CrossRef
13.
go back to reference Matsumoto T, Nakamura S, Ohta T, Fujimoto K, Yoshikawa M, Ogawa K, Matsuda H (2014) A rare glutamine derivative from the flower buds of daylily. Org Lett 16:3076–3078CrossRefPubMed Matsumoto T, Nakamura S, Ohta T, Fujimoto K, Yoshikawa M, Ogawa K, Matsuda H (2014) A rare glutamine derivative from the flower buds of daylily. Org Lett 16:3076–3078CrossRefPubMed
14.
go back to reference Suchy M, Elehriki AAH, Hudson RHE (2011) A remarkably simple protocol for the N-formylation of amino acid esters and primary amines. Org Lett 13:3952–3955CrossRefPubMed Suchy M, Elehriki AAH, Hudson RHE (2011) A remarkably simple protocol for the N-formylation of amino acid esters and primary amines. Org Lett 13:3952–3955CrossRefPubMed
15.
go back to reference Ciuffreda P, Casati S, Manzocchi A (2007) Spectral assignments and reference data. Magn Reson Chem 45:781–784CrossRefPubMed Ciuffreda P, Casati S, Manzocchi A (2007) Spectral assignments and reference data. Magn Reson Chem 45:781–784CrossRefPubMed
16.
go back to reference Inoue T, Iwagoe K, Konishi T, Kiyosawa S, Fujiwara Y (1990) Novel 2,5-dihydrofuryl-γ-lactam derivatives from Hemerocallis fulva L. var. kwanzo Regel. Chem Pharm Bull 38:3187–3189CrossRef Inoue T, Iwagoe K, Konishi T, Kiyosawa S, Fujiwara Y (1990) Novel 2,5-dihydrofuryl-γ-lactam derivatives from Hemerocallis fulva L. var. kwanzo Regel. Chem Pharm Bull 38:3187–3189CrossRef
17.
go back to reference Miyamae Y, Kurisu M, Murakami K, Han J, Isoda H, Irie K, Shigemori H (2012) Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein. Bioorg Med Chem 20:5844–5849CrossRefPubMed Miyamae Y, Kurisu M, Murakami K, Han J, Isoda H, Irie K, Shigemori H (2012) Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein. Bioorg Med Chem 20:5844–5849CrossRefPubMed
18.
go back to reference Ohta T, Nakamura S, Nakashima S, Matsumoto T, Ogawa K, Fujimoto K, Fukaya M, Yoshikawa M, Matsuda H (2015) Acylated oleanane-type triterpene oligoglycosides from the flower buds of Camellia sinensis var. assamica. Tetrahedron 71:846–851CrossRef Ohta T, Nakamura S, Nakashima S, Matsumoto T, Ogawa K, Fujimoto K, Fukaya M, Yoshikawa M, Matsuda H (2015) Acylated oleanane-type triterpene oligoglycosides from the flower buds of Camellia sinensis var. assamica. Tetrahedron 71:846–851CrossRef
19.
go back to reference Oda Y, Nakashima S, Nakamura S, Yano M, Akiyama M, Imai K, Kimura T, Nakata A, Tani M, Matsuda H (2016) New potent accelerator of neurite outgrowth from Lawsonia inermis flower under non-fasting condition. J Nat Med (Submitted) Oda Y, Nakashima S, Nakamura S, Yano M, Akiyama M, Imai K, Kimura T, Nakata A, Tani M, Matsuda H (2016) New potent accelerator of neurite outgrowth from Lawsonia inermis flower under non-fasting condition. J Nat Med (Submitted)
20.
go back to reference Oda T, Kume T, Katsuki H, Niidome T, Sugimoto H, Akaike A (2007) Donepezil potentiates nerve growth factor-induced neurite outgrowth in PC12 cells. J Pharmacol Sci 104:349–354CrossRefPubMed Oda T, Kume T, Katsuki H, Niidome T, Sugimoto H, Akaike A (2007) Donepezil potentiates nerve growth factor-induced neurite outgrowth in PC12 cells. J Pharmacol Sci 104:349–354CrossRefPubMed
Metadata
Title
γ-Lactam alkaloids from the flower buds of daylily
Authors
Takahiro Matsumoto
Seikou Nakamura
Souichi Nakashima
Tomoe Ohta
Mamiko Yano
Junichiro Tsujihata
Junko Tsukioka
Keiko Ogawa
Masashi Fukaya
Masayuki Yoshikawa
Hisashi Matsuda
Publication date
01-07-2016
Publisher
Springer Japan
Published in
Journal of Natural Medicines / Issue 3/2016
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-015-0963-z

Other articles of this Issue 3/2016

Journal of Natural Medicines 3/2016 Go to the issue