Symplocosionosides A-C, Three Megastigmane Glycosides, a Neolignan Glucoside, and Symplocosins A and B, Two Triterpene Glycosyl Esters from the Leaves of Symplocos cochinchinensis var. Philippinensis
Wen-Hu Cai, Katsuyoshi Matsunami, Hideaki Otsuka, Yoshio Takeda
.
DOI: 10.4236/ajps.2011.24072   PDF    HTML     5,698 Downloads   10,182 Views   Citations

Abstract

From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Symplocos cochinchinensis var. philippinensis, 12 compounds were isolated. Spectroscopic analyses of compounds 1 - 3 established their structures to be megastig-mane glycosides, named symplocosionosides A-C. The absolute structure of 1 was determined by the modified Mosher’s method. Compound 4 was found to be a neolignan glucoside and named symplocosneolignan. The structures of com-pounds 5 and 6, named symplocosins A and B, were elucidated to be the saponins of hederagenin sugar esters. The structures of the remaining known compounds (7 - 12) were identified by comparison of spectroscopic data with those reported in the literature.

Share and Cite:

W. Cai, K. Matsunami, H. Otsuka and Y. Takeda, "Symplocosionosides A-C, Three Megastigmane Glycosides, a Neolignan Glucoside, and Symplocosins A and B, Two Triterpene Glycosyl Esters from the Leaves of Symplocos cochinchinensis var. Philippinensis," American Journal of Plant Sciences, Vol. 2 No. 4, 2011, pp. 609-618. doi: 10.4236/ajps.2011.24072.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] S. Hatusima, “Flora of the Ryukyus. Added and Corrected,” The Biological Society of Okinawa, Naha, 1975, p. 476.
[2] C. Sunil and S. Ignacimuthu, “In vivo and in vitro Antioxidant Activity of Symplocos cochinchinensis S. Moore Leaves Containing Phenolic Compounds,” Food and Chemical Toxicology, Vol. 49, No. 7, 2011, pp. 1604-1609. doi:10.1016/j.fct.2011.04.010
[3] C. Sunil, S. Ignacimuthu and P. Agastian, “Antidiabetic Effect of Symplocos cochinchinensis (Lour.) S. Moore in Type 2 Diabetic Rats,” Journal of Ethnopharmacology, Vol. 134, No. 2, 2011, pp. 298-304. doi:10.1016/j.jep.2010.12.018
[4] M. R. Khan, M. Kihara and A. D. Ornoloso, “Antimicrobial Activity of Symplocos cochinensis,” Fitoterapia, Vol. 72, No. 7, 2001, pp. 825-828. doi:10.1016/S0367-326X(01)00314-8
[5] H. Otsuka, Ya. Takeda, K. Yamasaki and Yo. Takeda, “Structural Eelucidation of Dendranthemosides A and B: Two New β-Ionone Glucoside from Dendranthema shiwogiku,” Planta Medica, Vol. 58, No. 4, 1992, pp. 373-375. doi:10.1055/s-2006-961489
[6] A. G. González, J. A. Guillermo, A. G. Ravelo, I. A. Jimenez and M. P. Gupta, “4,5-Dihydroblumenol A, a New Nor-Isoprenoid from Perrottetia multiflora,” Journal of Natural Products, Vol. 57, No. 3, 1994, pp. 400-402. doi:10.1021/np50105a013
[7] H. Otsuka, K. Kamada, C. Ogimi, E. Hirata, A. Takushi and Y. Takeda, “Alangionosides A and B, Ionol Glycosides from Leaves of Alangium premnifolium,” Phytochemistry, Vol. 35, No. 5, 1994, pp. 1331-1334. doi:10.1016/S0031-9422(00)94848-9
[8] A. Inada, Y. Nakamura, M. Konishi, H. Murata, F. Kitamura, H. Toya and T. Nakanishi, “A New Ionone Glucoside and a New Phenylpropanoid Rhamnoside from Stems of Ampelopsis brevipedunculata (Maxim.) Trautv.,” Chemical and Pharmaceutical Bulletin, Vol. 39, No. 9, 1991, pp. 2437-2439.
[9] K. Umehara, I. Hattori, T. Miyase, A .Ueno, S. Hara and C. Kageyama, “Studies on the Constituents of Leaves of Citrus unshiu Marcov.,” Chemical and Pharmaceutical Bulletin, Vol. 36, No. 12, 1988, pp. 5004-5008.
[10] T. Seto, T. Tanaka, O. Tanaka and N. Naruhashi, “β-Gluco-syl Esters of 19α-Hydroxyursolic Acid Derivatives in Leaves of Rubus Species,” Phytochemistry, Vol. 23, No. 12, 1984, pp. 2829-2834. doi:10.1016/0031-9422(84)83023-X
[11] T. Morikawa, L. -B. Wang, K. Ninomiya, S. Nakamura, H. Matsuda, O. Muraoka, L. -J. Wu and M. Yoshikawa, “Medicinal Flowers. XXX. Eight New Glycosides, Everlastosides F-M, from the Flowers of Helichrysum arenarium,” Chemical and Pharmaceutical Bulletin, Vol. 57, No. 8, 2009, pp. 853-859. doi:10.1248/cpb.57.853
[12] R. Kasai, M. Suzuno, J. Asakawa and O. Tanaka, “Carbon-13 Chemical Shifts of Isoprenoid-β-D-glucopy-rano-sides and -β-D-mannopyranosides. Stereochemical Influences of Aglycone Alcohols,” Tetrahedron Letter, Vol. 18, No. 2, 1977, pp. 175-178. doi:10.1016/S0040-4039(01)92581-X
[13] I. Ohtani, T. Kusumi, Y. Kashman and H. Kakisawa, “High-Field FT NMR Application of Mosher’s Method. The Absolute Configurations of Marine Terpenoids,” Journal of American Chemical Society, Vol. 113, No. 11, 1991, pp. 4092-4096. doi:10.1021/ja00011a006
[14] K. Matsunami, H. Otsuka and Y. Takeda, “Structural Revisions of Blumenol C Glucoside and Byzantionoside B,” Chemical and Pharmaceutical Bulletin, Vol. 58, No. 3, 2010, pp. 438-441. doi:10.1248/cpb.58.438
[15] A. C. H. Braga, S. Zacchino, H. Badano, M. G. Sierra and E. A. Rúveda, “13C NMR Spectral and Conformational Analysis of 8-O-4′ Neolignans,” Phytochemistry, Vol. 23, No. 9, 1984, pp. 2025-2028.
[16] C. Huo, H. Liang, Y. Zhao, B. Wang and Q. Zhang, “Neo-Lignan Glycosides from Symplocos caudata,” Phytochemistry, Vol. 69, No. 3, 2008, pp. 788-795. doi:10.1016/j.phytochem.2007.08.022
[17] A. Arnoldi and L. Merlini, “Asymmetric Synthesis of 3-Methyl-2-phenyl-1,4-Benzodioxanes. Absolute Configuration of the Neolignans Eusiderin and Eusiderin C and D,” Journal of Chemical Society Perkin Transaction I, No. 6, 1985, pp. 2555-2557. doi:10.1039/p19850002555
[18] K. Kónya, T. Kurtán, A. Kiss-Szikszai, L. Juhász and S. Antus, “A General CD-Method for the Configurational Assignment of Erythro-8,4'-Oxyneolign-8'-Enes,” Arkivoc, Vol. 8, 2004, pp. 72-78.
[19] C. Sunil, S. Ignacimuthu and P. Agastian, “Antidiabetic Effect of Symplocos cochinchinensis (Lour.) S. Moore. in Type 2 Diabetic Rats,” Journal of Ethnopharmacology, Vol. 134, No. 2, 2011, pp. 298-304. doi:10.1016/j.jep.2010.12.018
[20] T. Ishii and M. Yanagisawa, “Synthesis, Separation and NMR Spectral Analysis of Methyl Apiofuranosides,” Carbohydrate Research, Vol. 313, No. 3-4, 1998, pp. 189-192. doi:10.1016/S0008-6215(98)00262-6
[21] T. Tanaka, T. Nakashima, T. Ueda, K. Tomii and I. Kouno, “Facile Discrimination of Aldose Enantiomers by Reversed-Phase HPLC,” Chemical and Pharmaceutical Bulletin, Vol. 55, No. 6, 2007, pp. 899-901. doi:10.1248/cpb.55.899

Copyright © 2024 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.