Skip to main content
Erschienen in: Journal of Natural Medicines 3/2018

05.03.2018 | Note

Four new resin glycosides, murasakimasarins I–IV, from the tuber of Ipomoea batatas

verfasst von: Masateru Ono, Sena Teramoto, Saori Naito, Asuka Takahashi, Akito Yoneda, Masato Shinkai, Naoki Taga, Sin Yasuda, Ryota Tsuchihasi, Masafumi Okawa, Junei Kinjo, Hitoshi Yoshimitsu, Toshihiro Nohara

Erschienen in: Journal of Natural Medicines | Ausgabe 3/2018

Einloggen, um Zugang zu erhalten

Abstract

Four new resin glycosides having macrolactone structures (jalapins), murasakimasarins I–IV, were isolated from the tubers of Ipomoea batatas (L.) Lam. (‘Murasakimasari’, Convolvulaceae), along with three known glycosides. Their structures were determined on the basis of spectroscopic data as well as chemical evidence. Murasakimasarin III is the first representative of a resin glycoside with 10-methylundecanoic acid as the component organic acid.
Literatur
1.
Zurück zum Zitat Shellard EJ (1961) The chemistry of some convolvulaceous resins part 1. Vera cruz jalap. Plant Med 9:102–116CrossRef Shellard EJ (1961) The chemistry of some convolvulaceous resins part 1. Vera cruz jalap. Plant Med 9:102–116CrossRef
2.
Zurück zum Zitat Pereda-Miranda R, Rosas-Ramírez D, Castańeda-Gómez J (2010) Resin glycosides from morning glory family. In: Kinghorn AD, Falk H, Kobayashi J (eds) Progress in the chemistry of organic natural products. Springer, Berlin, pp 77–153 (92) Pereda-Miranda R, Rosas-Ramírez D, Castańeda-Gómez J (2010) Resin glycosides from morning glory family. In: Kinghorn AD, Falk H, Kobayashi J (eds) Progress in the chemistry of organic natural products. Springer, Berlin, pp 77–153 (92)
3.
Zurück zum Zitat Yoshikawa K, Yagi C, Hama H, Tanaka M, Arihara S, Hashimoto T (2010) Ipomotaosides A-D, resin glycosides from the aerial parts of Ipomoea batatas and their inhibitory activity against COX-1 and COX-2. J Nat Prod 73:1763–1766CrossRef Yoshikawa K, Yagi C, Hama H, Tanaka M, Arihara S, Hashimoto T (2010) Ipomotaosides A-D, resin glycosides from the aerial parts of Ipomoea batatas and their inhibitory activity against COX-1 and COX-2. J Nat Prod 73:1763–1766CrossRef
4.
Zurück zum Zitat Figueroa-González G, Jacobo-Herrera N, Zentella-Dehesa A, Pereda-Miranda R (2012) Reversal of multidrug resistance by morning glory resin glycosides in human breast cancer cells. J Nat Prod 75:93–97CrossRef Figueroa-González G, Jacobo-Herrera N, Zentella-Dehesa A, Pereda-Miranda R (2012) Reversal of multidrug resistance by morning glory resin glycosides in human breast cancer cells. J Nat Prod 75:93–97CrossRef
5.
Zurück zum Zitat Ono M, Takigawa A, Kanemaru Y, Kawakami G, Kabata K, Okawa M, Kinjo J, Yokomizo K, Yoshimitsu H, Nohara T (2014) Calysolins V–IX, resin glycosides from Calystegia soldanella and their antiviral activity toward herpes. Chem Pharm Bull 62:97–105CrossRef Ono M, Takigawa A, Kanemaru Y, Kawakami G, Kabata K, Okawa M, Kinjo J, Yokomizo K, Yoshimitsu H, Nohara T (2014) Calysolins V–IX, resin glycosides from Calystegia soldanella and their antiviral activity toward herpes. Chem Pharm Bull 62:97–105CrossRef
6.
Zurück zum Zitat Noda N, Yoda S, Kawasaki T, Miyahara K (1992) Simonins I–V, ether-soluble resin glycosides (jalapins) from the roots of Ipomoea batatas (cv. Simon). Chem Pharm Bull 40:3163–3168CrossRef Noda N, Yoda S, Kawasaki T, Miyahara K (1992) Simonins I–V, ether-soluble resin glycosides (jalapins) from the roots of Ipomoea batatas (cv. Simon). Chem Pharm Bull 40:3163–3168CrossRef
7.
Zurück zum Zitat Escalante-Sánchez E, Pereda-Miranda R (2007) Batatins I and II, ether-type dimers of acylated pentasaccharides from the resin glycosides of sweet potato. J Nat Prod 70:1029–1034CrossRef Escalante-Sánchez E, Pereda-Miranda R (2007) Batatins I and II, ether-type dimers of acylated pentasaccharides from the resin glycosides of sweet potato. J Nat Prod 70:1029–1034CrossRef
8.
Zurück zum Zitat Yin Y-Q, Kong L-Y (2008) Ether-soluble resin glycosides from the roots of Ipomoea batatas. J Asian Nat Prod Res 10:233–238CrossRef Yin Y-Q, Kong L-Y (2008) Ether-soluble resin glycosides from the roots of Ipomoea batatas. J Asian Nat Prod Res 10:233–238CrossRef
9.
Zurück zum Zitat Yin Y, Li Y, Kong L (2008) Pentasaccharide glycosides from the tubers of sweet potato (Ipomoea batatas). J Agric Food Chem 56:2363–2368CrossRef Yin Y, Li Y, Kong L (2008) Pentasaccharide glycosides from the tubers of sweet potato (Ipomoea batatas). J Agric Food Chem 56:2363–2368CrossRef
10.
Zurück zum Zitat Escalante-Sánchez E, Rosas-Rameírez D, Linares E, Bye R, Pereda-Miranda R (2008) Batatinosides II–VI, acylated lipooligosaccharides from the resin glycosides of sweet potatao. J Agric Food Chem 56:9423–9428CrossRef Escalante-Sánchez E, Rosas-Rameírez D, Linares E, Bye R, Pereda-Miranda R (2008) Batatinosides II–VI, acylated lipooligosaccharides from the resin glycosides of sweet potatao. J Agric Food Chem 56:9423–9428CrossRef
11.
Zurück zum Zitat Noda N, Horiuchi Y (2008) The resin glycosides from the sweet potato (Ipomoea batatas L. Lam.). Chem Pharm Bull 56:1607–1610CrossRef Noda N, Horiuchi Y (2008) The resin glycosides from the sweet potato (Ipomoea batatas L. Lam.). Chem Pharm Bull 56:1607–1610CrossRef
12.
Zurück zum Zitat Yin Y, Huang X, Kong L, Niwa M (2008) Three new pentasaccharide resin glycosides from the roots of sweet potato (Ipomoea batatas). Chem Pharm Bull 56:1670–1674CrossRef Yin Y, Huang X, Kong L, Niwa M (2008) Three new pentasaccharide resin glycosides from the roots of sweet potato (Ipomoea batatas). Chem Pharm Bull 56:1670–1674CrossRef
13.
Zurück zum Zitat Rosas-Ramírez D, Escalante-Sánchez E, Pereda-Miranda R (2011) Batatins III–VI, glycolipid ester-type dimers from Ipomoea batatas. Phytochemistry 72:773–780CrossRef Rosas-Ramírez D, Escalante-Sánchez E, Pereda-Miranda R (2011) Batatins III–VI, glycolipid ester-type dimers from Ipomoea batatas. Phytochemistry 72:773–780CrossRef
14.
Zurück zum Zitat Rosas-Ramírez D, Pereda-Miranda R (2013) Resin glycosides from the yellow-skinned variety of sweet potato (Ipomoea batatas). J Agric Food Chem 61:9488–9494CrossRef Rosas-Ramírez D, Pereda-Miranda R (2013) Resin glycosides from the yellow-skinned variety of sweet potato (Ipomoea batatas). J Agric Food Chem 61:9488–9494CrossRef
15.
Zurück zum Zitat Rosas-Ramírez D, Pereda-Miranda R (2015) Batatins VIII–XI, glycolipid ester-type dimers from Ipomoea babatas. J Nat Prod 78:26–33CrossRef Rosas-Ramírez D, Pereda-Miranda R (2015) Batatins VIII–XI, glycolipid ester-type dimers from Ipomoea babatas. J Nat Prod 78:26–33CrossRef
16.
Zurück zum Zitat Ono M, Oda S, Yasuda S, Mineno T, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T, Miyahara K (2017) Acylated glycosidic acid methyl esters generated from the convolvulin fraction of Rhizoma Jalapae Braziliensis by treatment with indium(III) chloride in methanol. Chem Pharm Bull 65:107–111CrossRef Ono M, Oda S, Yasuda S, Mineno T, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T, Miyahara K (2017) Acylated glycosidic acid methyl esters generated from the convolvulin fraction of Rhizoma Jalapae Braziliensis by treatment with indium(III) chloride in methanol. Chem Pharm Bull 65:107–111CrossRef
17.
Zurück zum Zitat Takigawa A, Setoguchi H, Okawa M, Kinjo J, Miyashita H, Yokomizo K, Yoshimitsu H, Nohara T, Ono M (2011) Identification and characterization of component organic and glycosidic acids of crude resin glycoside fraction from Calystegia soldanella. Chem Pharm Bull 59:1163–1168CrossRef Takigawa A, Setoguchi H, Okawa M, Kinjo J, Miyashita H, Yokomizo K, Yoshimitsu H, Nohara T, Ono M (2011) Identification and characterization of component organic and glycosidic acids of crude resin glycoside fraction from Calystegia soldanella. Chem Pharm Bull 59:1163–1168CrossRef
18.
Zurück zum Zitat Ono M, Kawasaki T, Miyahara K (1989) Resin glycosides. V. identification and characterization of the component organic and glycosidic acids of the ether-soluble crude resin glycosides (“jalapin”) from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 37:3209–3213CrossRef Ono M, Kawasaki T, Miyahara K (1989) Resin glycosides. V. identification and characterization of the component organic and glycosidic acids of the ether-soluble crude resin glycosides (“jalapin”) from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 37:3209–3213CrossRef
19.
Zurück zum Zitat Ono M (2017) Resin glycosides from convolvulaceae plants. J Nat Med 71:591–604CrossRef Ono M (2017) Resin glycosides from convolvulaceae plants. J Nat Med 71:591–604CrossRef
20.
Zurück zum Zitat Ono M, Nishi M, Kawasaki T, Miyahara K (1990) Resin glycosides. IX. operculins I, II, V, VII and VIII, new ether-soluble resin glycosides of Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 38:2986–2991CrossRef Ono M, Nishi M, Kawasaki T, Miyahara K (1990) Resin glycosides. IX. operculins I, II, V, VII and VIII, new ether-soluble resin glycosides of Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 38:2986–2991CrossRef
Metadaten
Titel
Four new resin glycosides, murasakimasarins I–IV, from the tuber of Ipomoea batatas
verfasst von
Masateru Ono
Sena Teramoto
Saori Naito
Asuka Takahashi
Akito Yoneda
Masato Shinkai
Naoki Taga
Sin Yasuda
Ryota Tsuchihasi
Masafumi Okawa
Junei Kinjo
Hitoshi Yoshimitsu
Toshihiro Nohara
Publikationsdatum
05.03.2018
Verlag
Springer Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 3/2018
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-018-1197-7

Weitere Artikel der Ausgabe 3/2018

Journal of Natural Medicines 3/2018 Zur Ausgabe