Skip to main content
Erschienen in: Journal of Natural Medicines 4/2017

Open Access 01.10.2017 | Review

Resin glycosides from Convolvulaceae plants

verfasst von: Masateru Ono

Erschienen in: Journal of Natural Medicines | Ausgabe 4/2017

Einloggen, um Zugang zu erhalten

Abstract

Resin glycosides are well known as purgative ingredients, which are characteristic of certain crude drugs such as Mexican Scammony Radix, Orizabae Tuber, and Jalapae Tuber, all of which originate from Convolvulaceae plants. Depending on their solubility in ether, these are roughly classified into two groups—jalapin (soluble) and convolvulin (insoluble). Almost all jalapins hitherto isolated and characterized had common intramolecular macrocyclic ester structures. These are composed of 1 mol of oligoglycoside of hydroxyl fatty acid (glycosidic acid) partially acylated by some organic acids at the sugar moiety, some examples of which are ester-type dimers. On the other hand, convolvulin is regarded as an oligomer of a variety of acylated glycosidic acids. This review describes the isolation and structural elucidation of resin glycosides from some Convolvulaceae plants, including Ipomoea operculata, Pharbitis nil, Quamoclit pennata, Calystegia soldanella, and I. muricata.
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 Mayer W (1855) Ueber die sogenannten jalappaharze. Justus Liebigs Ann Chem 95:129–176CrossRef Mayer W (1855) Ueber die sogenannten jalappaharze. Justus Liebigs Ann Chem 95:129–176CrossRef
3.
Zurück zum Zitat Mannich C, Schumann P (1938) Jalap resin and its principal constituent, convolvulin. Arch Pharm 276:211–226CrossRef Mannich C, Schumann P (1938) Jalap resin and its principal constituent, convolvulin. Arch Pharm 276:211–226CrossRef
4.
Zurück zum Zitat Noda N, Ono M, Miyahara K, Kawasaki T (1987) Resin glycosides. I. Isolation and structure elucidation of orizabin-I, II, III and IV, genuine resin glycosides from the root of Ipomoea orizabensis. Tetrahedron 43:1389–3902CrossRef Noda N, Ono M, Miyahara K, Kawasaki T (1987) Resin glycosides. I. Isolation and structure elucidation of orizabin-I, II, III and IV, genuine resin glycosides from the root of Ipomoea orizabensis. Tetrahedron 43:1389–3902CrossRef
5.
Zurück zum Zitat Noda N, Tsuji K, Kawasaki T, Miyahara K, Hanazono H, Yang C-R (1995) A novel resin glycoside, meremin (tuguajalapin × dimer), from Merremia hungaiensis. Chem Pharm Bull 43:1061–1063CrossRef Noda N, Tsuji K, Kawasaki T, Miyahara K, Hanazono H, Yang C-R (1995) A novel resin glycoside, meremin (tuguajalapin × dimer), from Merremia hungaiensis. Chem Pharm Bull 43:1061–1063CrossRef
6.
Zurück zum Zitat Bah M, Pereda-Miranda R (1997) Isolation and structural characterization of new glycolipid ester-type dimers from the resin of Ipomoea tricolor (Convolvulaceae). Tetrahedron 53:9007–9022CrossRef Bah M, Pereda-Miranda R (1997) Isolation and structural characterization of new glycolipid ester-type dimers from the resin of Ipomoea tricolor (Convolvulaceae). Tetrahedron 53:9007–9022CrossRef
7.
Zurück zum Zitat Escalante-Sánchez E, Pereda-Miranda R (2007) Batatins I and II, ester-type dimers of acylated pentasaccarides from the resin glycosides of sweet potato. J Nat Prod 70:1029–1034CrossRef Escalante-Sánchez E, Pereda-Miranda R (2007) Batatins I and II, ester-type dimers of acylated pentasaccarides from the resin glycosides of sweet potato. J Nat Prod 70:1029–1034CrossRef
8.
Zurück zum Zitat Castañeda-Gómez J, Pereda-Miranda R (2011) Resin glycosides from the herbal drug jalap (Ipomoea purga). J Nat Prod 74:1148–1153CrossRef Castañeda-Gómez J, Pereda-Miranda R (2011) Resin glycosides from the herbal drug jalap (Ipomoea purga). J Nat Prod 74:1148–1153CrossRef
9.
Zurück zum Zitat Rosas-Rameírez D, Escalante-Sánchez E, Pereda-Miranda R (2011) Batatins III–VI, glycolipid ester-type dimers from Ipomoea batatas. Phytochemistry 72:773–780CrossRef Rosas-Rameírez D, Escalante-Sánchez E, Pereda-Miranda R (2011) Batatins III–VI, glycolipid ester-type dimers from Ipomoea batatas. Phytochemistry 72:773–780CrossRef
10.
Zurück zum Zitat Castañeda-Gómez J, Figueroa-González G, Jacobo N, Pereda-Miranda R (2013) Purgin II, a resin glycoside ester-type dimer and inhibitor of multidrug efflux pumps from Ipomoea purga. J Nat Prod 76:64–71CrossRef Castañeda-Gómez J, Figueroa-González G, Jacobo N, Pereda-Miranda R (2013) Purgin II, a resin glycoside ester-type dimer and inhibitor of multidrug efflux pumps from Ipomoea purga. J Nat Prod 76:64–71CrossRef
11.
Zurück zum Zitat Rosas-Raíez D, Pereda-Miranda R (2013) Resin glycosides from the yellow-skinned variety of sweet potato (Ipomoea batatas). J Agri Food Chem 61:9488–9494CrossRef Rosas-Raíez D, Pereda-Miranda R (2013) Resin glycosides from the yellow-skinned variety of sweet potato (Ipomoea batatas). J Agri Food Chem 61:9488–9494CrossRef
12.
Zurück zum Zitat Rosas-Raíez D, Pereda-Miranda R (2015) Batatins VIII–XI, glycolipid ester-type dimers from Ipomoea batatas. J Nat Prod 78:26–33CrossRef Rosas-Raíez D, Pereda-Miranda R (2015) Batatins VIII–XI, glycolipid ester-type dimers from Ipomoea batatas. J Nat Prod 78:26–33CrossRef
13.
Zurück zum Zitat Corona-Castañeda B, Rosas-Ramírez D, Castañeda-Gómez J, Aparico-Cuevas MA, Fragoso-González G, Pereda-Miranda R (2016) Resin glycosides from Ipomoea wolcottiana as modulators of the multidrug resistance phenotype in vitro. Phytochemistry 123:48–57CrossRef Corona-Castañeda B, Rosas-Ramírez D, Castañeda-Gómez J, Aparico-Cuevas MA, Fragoso-González G, Pereda-Miranda R (2016) Resin glycosides from Ipomoea wolcottiana as modulators of the multidrug resistance phenotype in vitro. Phytochemistry 123:48–57CrossRef
14.
Zurück zum Zitat Graf E, Dahlke E (1964) Structure elucidation of exogonic acid. Chem Ber 97:2785–2797CrossRef Graf E, Dahlke E (1964) Structure elucidation of exogonic acid. Chem Ber 97:2785–2797CrossRef
15.
Zurück zum Zitat Graf E, Dahlke E, Voigtlander HW (1965) Convolvulin; new fragment units and differentiation reactions. Arch Pharm Ber Dtsch Pharm Ges 298:81–91CrossRef Graf E, Dahlke E, Voigtlander HW (1965) Convolvulin; new fragment units and differentiation reactions. Arch Pharm Ber Dtsch Pharm Ges 298:81–91CrossRef
16.
Zurück zum Zitat Wagner H, Kazmaier P (1977) Structure of the operculinic acid from the resin of Ipomoea operculata. Phytochemistry 16:711–714CrossRef Wagner H, Kazmaier P (1977) Structure of the operculinic acid from the resin of Ipomoea operculata. Phytochemistry 16:711–714CrossRef
17.
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
18.
Zurück zum Zitat Dale JA, Mosher HS (1973) Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmanndelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc 95:512–519CrossRef Dale JA, Mosher HS (1973) Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmanndelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc 95:512–519CrossRef
19.
Zurück zum Zitat Ono M, Kubo K, Miyahara K, Kawasaki T (1989) Operculin I and II, new ether-soluble resin glycosides (“jalapin”) with fatty acid ester groups from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 37:241–244CrossRef Ono M, Kubo K, Miyahara K, Kawasaki T (1989) Operculin I and II, new ether-soluble resin glycosides (“jalapin”) with fatty acid ester groups from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 37:241–244CrossRef
20.
Zurück zum Zitat Ono M, Yamada F, Noda N, Kawasaki T, Miyahara K (1993) Resin glycosides. XVIII. Determination by Mosher’s method of the absolute configurations of mono- and dihydroxyfatty acids originated from resin glycosides. Chem Pharm Bull 41:1023–1026CrossRef Ono M, Yamada F, Noda N, Kawasaki T, Miyahara K (1993) Resin glycosides. XVIII. Determination by Mosher’s method of the absolute configurations of mono- and dihydroxyfatty acids originated from resin glycosides. Chem Pharm Bull 41:1023–1026CrossRef
21.
Zurück zum Zitat Shibuya H, Kawashima K, Baek NI, Narita N, Yoshikawa M, Kitagawa I (1989) Synthesis of (11S)-(+)- and (11R)-(−)-jalapinolic acids. A revision of chemical structure of merremosides B and D. Chem Pharm Bull 37:260–262 Shibuya H, Kawashima K, Baek NI, Narita N, Yoshikawa M, Kitagawa I (1989) Synthesis of (11S)-(+)- and (11R)-(−)-jalapinolic acids. A revision of chemical structure of merremosides B and D. Chem Pharm Bull 37:260–262
22.
Zurück zum Zitat Okabe H, Koshito N, Tanaka K, Kawasaki T (1971) Studies on resin glycosides. II. Unhomogeneity of “pharbitin” and isolation and partial structures of pharbitic acids C and D, the major constituents of “pharbitic acid”. Chem Pharm Bull 19:2394–2403CrossRef Okabe H, Koshito N, Tanaka K, Kawasaki T (1971) Studies on resin glycosides. II. Unhomogeneity of “pharbitin” and isolation and partial structures of pharbitic acids C and D, the major constituents of “pharbitic acid”. Chem Pharm Bull 19:2394–2403CrossRef
23.
Zurück zum Zitat Ono M, Nishioka H, Fukushima T, Kunimatu H, Mine A, Kubo H, Miyahara K (2009) Components of ether-insoluble resin glycoside (rhamonvolvulin) from Rhizoma Jalapae Braziliensis. Chem Pharm Bull 57:262–268CrossRef Ono M, Nishioka H, Fukushima T, Kunimatu H, Mine A, Kubo H, Miyahara K (2009) Components of ether-insoluble resin glycoside (rhamonvolvulin) from Rhizoma Jalapae Braziliensis. Chem Pharm Bull 57:262–268CrossRef
24.
Zurück zum Zitat Jakob B, Gerlach H (1996) Relative and absolute configuration of 3,12-dihydroxypalmitic acids. Liebings Ann 1996:2123–2129CrossRef Jakob B, Gerlach H (1996) Relative and absolute configuration of 3,12-dihydroxypalmitic acids. Liebings Ann 1996:2123–2129CrossRef
25.
Zurück zum Zitat Ono M, Fukunaga T, Kawasaki T, Miyahara K (1990) Resin glycosides. VIII. Four new glycosidic acids, operculinic acids D, E, F and G, of the ether-soluble crude resin glycosides (“jalapin”) from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 38:2650–2655CrossRef Ono M, Fukunaga T, Kawasaki T, Miyahara K (1990) Resin glycosides. VIII. Four new glycosidic acids, operculinic acids D, E, F and G, of the ether-soluble crude resin glycosides (“jalapin”) from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 38:2650–2655CrossRef
26.
Zurück zum Zitat Hara S, Okabe H, Mihashi K (1987) Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates. Chem Pharm Bull 35:501–506CrossRef Hara S, Okabe H, Mihashi K (1987) Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates. Chem Pharm Bull 35:501–506CrossRef
27.
Zurück zum Zitat Aritomi M, Kawasaki T (1970) Partial methylation with diazomethane of the sugar moiety of some C- and O-d-glucopyranosides. Chem Pharm Bull 18:677–686CrossRef Aritomi M, Kawasaki T (1970) Partial methylation with diazomethane of the sugar moiety of some C- and O-d-glucopyranosides. Chem Pharm Bull 18:677–686CrossRef
28.
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
29.
Zurück zum Zitat Ono M, Kawasaki T, Miyahara K (1991) Resin glycosides. XI. Operculins III, IV, IX, X, XVI, XVII and XVIII, new ether-soluble resin glycosides of Rhizoma Jalapae Braziliensis (the root of Ipomoea operculata). Chem Pharm Bull 39:2534–2539CrossRef Ono M, Kawasaki T, Miyahara K (1991) Resin glycosides. XI. Operculins III, IV, IX, X, XVI, XVII and XVIII, new ether-soluble resin glycosides of Rhizoma Jalapae Braziliensis (the root of Ipomoea operculata). Chem Pharm Bull 39:2534–2539CrossRef
30.
Zurück zum Zitat Ono M, Fujimoto K, Kawata M, Fukunaga T, Kawasaki T, Miyahara K (1992) Resin glycosides. XIII. Operculins VI, XI, XII, XIII, XIV and XV, the ether-soluble resin glycosides (jalapin) from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 40:1400–1403CrossRef Ono M, Fujimoto K, Kawata M, Fukunaga T, Kawasaki T, Miyahara K (1992) Resin glycosides. XIII. Operculins VI, XI, XII, XIII, XIV and XV, the ether-soluble resin glycosides (jalapin) from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 40:1400–1403CrossRef
31.
Zurück zum Zitat Lawson EN, Jamie JF, Kitching W (1992) Absolute stereochemistry of exogonic acid. J Org Chem 57:353–358CrossRef Lawson EN, Jamie JF, Kitching W (1992) Absolute stereochemistry of exogonic acid. J Org Chem 57:353–358CrossRef
32.
Zurück zum Zitat Mineno T, Kansui H (2006) High yielding methyl esterification catalyzed by indium(III) chloride. Chem Pharm Bull 54:918–919CrossRef Mineno T, Kansui H (2006) High yielding methyl esterification catalyzed by indium(III) chloride. Chem Pharm Bull 54:918–919CrossRef
33.
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
34.
Zurück zum Zitat Asahina Y, Terada S (1919) Constituents of the seeds of Pharbitis nil chois. Yakugaku Zasshi 452:821–836 Asahina Y, Terada S (1919) Constituents of the seeds of Pharbitis nil chois. Yakugaku Zasshi 452:821–836
35.
Zurück zum Zitat Asahina Y, Shimizu T (1922) Constituents of the seeds of Pharbitis nil chois. II. Yakugaku Zassh 479:1–18 Asahina Y, Shimizu T (1922) Constituents of the seeds of Pharbitis nil chois. II. Yakugaku Zassh 479:1–18
36.
Zurück zum Zitat Asahina Y, Nakanishi Y (1925) Constituents of the seeds of Pharbitis nil chois. III. Yakugaku Zasshi 520:515–520CrossRef Asahina Y, Nakanishi Y (1925) Constituents of the seeds of Pharbitis nil chois. III. Yakugaku Zasshi 520:515–520CrossRef
37.
Zurück zum Zitat Okabe H, Kawasaki T (1970) Structures of pharbitic acids C and D. Tetrahedron Lett 11:3123–3126CrossRef Okabe H, Kawasaki T (1970) Structures of pharbitic acids C and D. Tetrahedron Lett 11:3123–3126CrossRef
38.
Zurück zum Zitat Kawasaki T, Okabe H, Nakatsuka I (1971) Studies on resin glycosides. I. Reinvestigation of the components of pharbitin, a resin glycoside of the seeds of Pharbitis nil CHOISY. Chem Pharm Bull 19:1144–1149CrossRef Kawasaki T, Okabe H, Nakatsuka I (1971) Studies on resin glycosides. I. Reinvestigation of the components of pharbitin, a resin glycoside of the seeds of Pharbitis nil CHOISY. Chem Pharm Bull 19:1144–1149CrossRef
39.
Zurück zum Zitat Okabe H, Kawasaki T (1972) Studies on resin glycosides. III. Complete structures of phabitic acids C and D. Chem Pharm Bull 20:514–520CrossRef Okabe H, Kawasaki T (1972) Studies on resin glycosides. III. Complete structures of phabitic acids C and D. Chem Pharm Bull 20:514–520CrossRef
40.
Zurück zum Zitat Ono M, Noda N, Kawasaki T, Miyahara K (1990) Resin glycosides. VII. Reinvestigation of the component organic and glycosidic acids of pharbitin, the crude ether-insoluble resin glycoside (“convolvulin”) of Pharbitidis Semen (seeds of Pharbitis nil). Chem Pharm Bul 38:1892–1897CrossRef Ono M, Noda N, Kawasaki T, Miyahara K (1990) Resin glycosides. VII. Reinvestigation of the component organic and glycosidic acids of pharbitin, the crude ether-insoluble resin glycoside (“convolvulin”) of Pharbitidis Semen (seeds of Pharbitis nil). Chem Pharm Bul 38:1892–1897CrossRef
41.
Zurück zum Zitat Ono M, Takagi-Taki Y, Honda-Yamada F, Noda N, Miyahara K (2010) Components of ether-insoluble resin glycoside (convolvulin) from seeds of Quamoclit pennata. Chem Pharm Bull 58:666–672CrossRef Ono M, Takagi-Taki Y, Honda-Yamada F, Noda N, Miyahara K (2010) Components of ether-insoluble resin glycoside (convolvulin) from seeds of Quamoclit pennata. Chem Pharm Bull 58:666–672CrossRef
42.
Zurück zum Zitat Ono M, Takigawa A, Mineno T, Yoshimitsu H, Nohara T, Ikeda T, Fukuda-Teramachi E, Noda N, Miyahara K (2010) Acylated glycosides of hydroxy fatty acid methyl esters generated from the crude resin glycoside (pharbitin) of seeds of Pharbitis nil by treatment with indium(III) chloride in methanol. J Nat Prod 73:1846–1852CrossRef Ono M, Takigawa A, Mineno T, Yoshimitsu H, Nohara T, Ikeda T, Fukuda-Teramachi E, Noda N, Miyahara K (2010) Acylated glycosides of hydroxy fatty acid methyl esters generated from the crude resin glycoside (pharbitin) of seeds of Pharbitis nil by treatment with indium(III) chloride in methanol. J Nat Prod 73:1846–1852CrossRef
43.
Zurück zum Zitat Ono M, Kuwabata K, Kawasaki T, Miyahara K (1992) Resin glycosides. XIV. Quamoclins I–IV, new ether-soluble resin glycosides (“jalapin”) from the seeds of Quamoclit pennata. Chem Pharm Bull 40:2674–2680CrossRef Ono M, Kuwabata K, Kawasaki T, Miyahara K (1992) Resin glycosides. XIV. Quamoclins I–IV, new ether-soluble resin glycosides (“jalapin”) from the seeds of Quamoclit pennata. Chem Pharm Bull 40:2674–2680CrossRef
44.
Zurück zum Zitat Ono M, Takaki Y, Takatsuji M, Akiyama K, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T (2012) Three new resin glycosides and a new tetrahydropyran derivative from the seeds of Quamoclit pennata. Chem Pharm Bull 60:1083–1087CrossRef Ono M, Takaki Y, Takatsuji M, Akiyama K, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T (2012) Three new resin glycosides and a new tetrahydropyran derivative from the seeds of Quamoclit pennata. Chem Pharm Bull 60:1083–1087CrossRef
45.
Zurück zum Zitat Ono M, Imao M, Miyahara K (2010) Two new glycosidic acids, quamoclinic acids G and H, of the resin glycosides (convolvulin) from the seeds of Quamoclit pennata. Chem Pharm Bull 58:1232–1235CrossRef Ono M, Imao M, Miyahara K (2010) Two new glycosidic acids, quamoclinic acids G and H, of the resin glycosides (convolvulin) from the seeds of Quamoclit pennata. Chem Pharm Bull 58:1232–1235CrossRef
46.
Zurück zum Zitat Akiyama K, Mineno T, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T, Ono M (2013) Three acylated glycosidic acid methyl esters and two acylated methyl glycosides generated from the convolvulin fraction of seeds of Quamoclit pennata by treatment with indium(III) chloride in methanol. Chem Pharm Bull 61:952–961CrossRef Akiyama K, Mineno T, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T, Ono M (2013) Three acylated glycosidic acid methyl esters and two acylated methyl glycosides generated from the convolvulin fraction of seeds of Quamoclit pennata by treatment with indium(III) chloride in methanol. Chem Pharm Bull 61:952–961CrossRef
47.
Zurück zum Zitat Akiyama K, Yamamoto K, Mineno T, Okawa M, Kinjo J, Yoshimitsu H, Nohara T, Ono M (2014) Five new resin glycoside derivatives isolated from the convolvulin fraction of seeds of Quamoclit pennata after treatment with indium(III) chloride in methanol. Chem Pharm Bull 62:125–133CrossRef Akiyama K, Yamamoto K, Mineno T, Okawa M, Kinjo J, Yoshimitsu H, Nohara T, Ono M (2014) Five new resin glycoside derivatives isolated from the convolvulin fraction of seeds of Quamoclit pennata after treatment with indium(III) chloride in methanol. Chem Pharm Bull 62:125–133CrossRef
48.
Zurück zum Zitat Ono M, Akiyama K, Yamamoto K, Mineno T, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T (2014) Four new acylated glycosidic acid methyl esters isolated from the convolvulin fraction of seeds of Quamoclit pennata after treatment with indium(III) chloride in methanol. Chem Pharm Bull 62:830–835CrossRef Ono M, Akiyama K, Yamamoto K, Mineno T, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T (2014) Four new acylated glycosidic acid methyl esters isolated from the convolvulin fraction of seeds of Quamoclit pennata after treatment with indium(III) chloride in methanol. Chem Pharm Bull 62:830–835CrossRef
49.
Zurück zum Zitat Miyahara K, Du X-M, Watanabe M, Sugiura C, Yahara S, Nohara T (1996) Resin glycosides. XXIII. Two novel acylated trisaccharides related to resin glycoside from the seeds of Cuscuta chiensis. Chem Pharm Bull 44:481–485CrossRef Miyahara K, Du X-M, Watanabe M, Sugiura C, Yahara S, Nohara T (1996) Resin glycosides. XXIII. Two novel acylated trisaccharides related to resin glycoside from the seeds of Cuscuta chiensis. Chem Pharm Bull 44:481–485CrossRef
50.
Zurück zum Zitat Gasper EM (1999) New pentasaccharide macrolactone from the European convolvulaceae Calysegia soldanella. Tetrahedron Lett 40:6861–6864CrossRef Gasper EM (1999) New pentasaccharide macrolactone from the European convolvulaceae Calysegia soldanella. Tetrahedron Lett 40:6861–6864CrossRef
51.
Zurück zum Zitat Gasper EM (2001) Soldanelline B: the first acylated nonlinear tetrasaccharide macrolactone from the Europeane Convolvulaceae plant Calystegia soldanella. Eur J Org Chem 2:369–373CrossRef Gasper EM (2001) Soldanelline B: the first acylated nonlinear tetrasaccharide macrolactone from the Europeane Convolvulaceae plant Calystegia soldanella. Eur J Org Chem 2:369–373CrossRef
52.
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
53.
Zurück zum Zitat Takigawa A, Muto H, Kabata K, Okawa M, Kinjo J, Yoshimitsu H, Nohara T, Ono M (2011) Calysolins I—IV, resin glycosides from Calystegia soldanella. J Nat Prod 74:2414–2419CrossRef Takigawa A, Muto H, Kabata K, Okawa M, Kinjo J, Yoshimitsu H, Nohara T, Ono M (2011) Calysolins I—IV, resin glycosides from Calystegia soldanella. J Nat Prod 74:2414–2419CrossRef
54.
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
55.
Zurück zum Zitat Ono M, Kawakami G, Takigawa A, Kabata K, Okawa M, Kinjo J, Yokomizo K, Yoshimitsu H, Nohara T (2014) Calysolins X–XIII, resin glycosides from Calystegia soldanella and their antiviral activity toward herpes simplex virus. Chem Pharm Bull 62:839–844CrossRef Ono M, Kawakami G, Takigawa A, Kabata K, Okawa M, Kinjo J, Yokomizo K, Yoshimitsu H, Nohara T (2014) Calysolins X–XIII, resin glycosides from Calystegia soldanella and their antiviral activity toward herpes simplex virus. Chem Pharm Bull 62:839–844CrossRef
56.
Zurück zum Zitat Ono M, Takigawa A, Muto H, Kabata K, Okawa M, Kinjo J, Yokomizo K, Yoshimitsu H, Nohara T (2015) Antiviral activity of four new resin glycosides calysolins XIV–XVII from Calystegia soldanella against herpes simplex virus. Chem Pharm Bull 63:641–648CrossRef Ono M, Takigawa A, Muto H, Kabata K, Okawa M, Kinjo J, Yokomizo K, Yoshimitsu H, Nohara T (2015) Antiviral activity of four new resin glycosides calysolins XIV–XVII from Calystegia soldanella against herpes simplex virus. Chem Pharm Bull 63:641–648CrossRef
57.
Zurück zum Zitat Noda N, Kobayashi H, Miyahara K, Kawasaki T (1988) Resin glycosides. II. Identification and characterization of the component organic and glycosidic acids of the crude resin glycoside from the seeds of Ipomoea muricata. Chem Pharm Bull 36:627–633CrossRef Noda N, Kobayashi H, Miyahara K, Kawasaki T (1988) Resin glycosides. II. Identification and characterization of the component organic and glycosidic acids of the crude resin glycoside from the seeds of Ipomoea muricata. Chem Pharm Bull 36:627–633CrossRef
58.
Zurück zum Zitat Noda N, Nishi M, Miyahara K, Kawasaki T (1988) Resin glycosides. IV. Two new resin glycosides, muricatins VII and VIII, from the seeds of Ipomoea muricata. Chem Pharm Bull 36:1707–1713CrossRef Noda N, Nishi M, Miyahara K, Kawasaki T (1988) Resin glycosides. IV. Two new resin glycosides, muricatins VII and VIII, from the seeds of Ipomoea muricata. Chem Pharm Bull 36:1707–1713CrossRef
59.
Zurück zum Zitat Noda N, Kobayashi H, Miyahara K, Kawasaki T (1988) Resin glycosides. III. Isolation and structural study of the genuine resin glycosides, muricatins I–VI, from the seeds of Ipomoea muricata. Chem Pharm Bull 36:920–929CrossRef Noda N, Kobayashi H, Miyahara K, Kawasaki T (1988) Resin glycosides. III. Isolation and structural study of the genuine resin glycosides, muricatins I–VI, from the seeds of Ipomoea muricata. Chem Pharm Bull 36:920–929CrossRef
60.
Zurück zum Zitat Ono M, Taketomi S, Kakiki Y, Yauda S, Okawa M, Kinjo J, Yoshimitsu H, Nohara T (2016) A new resin glycoside, muricatin IX, from the seeds of Ipomoea muricata. Chem Pharm Bull 64:1408–1410CrossRef Ono M, Taketomi S, Kakiki Y, Yauda S, Okawa M, Kinjo J, Yoshimitsu H, Nohara T (2016) A new resin glycoside, muricatin IX, from the seeds of Ipomoea muricata. Chem Pharm Bull 64:1408–1410CrossRef
61.
Zurück zum Zitat Ono M, Nakagawa K, Kawasaki T, Miyahara K (1993) Resin glycosides. XIX. Woodrosins I and II, ether-insoluble resin glycosides from the stems of Ipomoea tuberosa. Chem Pharm Bull 41:1925–1932CrossRef Ono M, Nakagawa K, Kawasaki T, Miyahara K (1993) Resin glycosides. XIX. Woodrosins I and II, ether-insoluble resin glycosides from the stems of Ipomoea tuberosa. Chem Pharm Bull 41:1925–1932CrossRef
Metadaten
Titel
Resin glycosides from Convolvulaceae plants
verfasst von
Masateru Ono
Publikationsdatum
01.10.2017
Verlag
Springer Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 4/2017
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-017-1114-5

Weitere Artikel der Ausgabe 4/2017

Journal of Natural Medicines 4/2017 Zur Ausgabe