Structure Elucidation of Two Triterpenoid Saponins from Leaves of Schimasuperba Gardn. et Champ
Two new oleanane-type triterpenoid saponins with two angeloyls at C-21, C-22, and a branch of tetrasaccharide moiety (Rha, Cal, Glc, GlcA, or Rha, Xyl, Glc, GlcA) at C-3 were isolated from leaves of Schima superba Gardn. et Champ. Their structures were es
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Structure Elucidation of Two Triterpenoid Saponins from Leaves of Schima superba Gardn. et Champ Guanghua Huo, Changling Zhang and Yingjun Zhang
Abstract Two new oleanane-type triterpenoid saponins with two angeloyls at C-21, C-22, and a branch of tetrasaccharide moiety (Rha, Cal, Glc, GlcA, or Rha, Xyl, Glc, GlcA) at C-3 were isolated from leaves of Schima superba Gardn. et Champ. Their structures were established using one- and two-dimensional NMR and high resolution electrospray ionization mass spectrometry as 21,22-di-Oangeloyl-R1-barrigenol-3-O–{b-D-glucopyranosyl-(1?2)-b-D-galactopyranosyl(1?2)-[a-L-rhamnopyranosyl-(1?4)]}-b-D-glucuronopyranoside, named schimasuoside A(1), 21,22-di-O-angeloyl-R1-barrigenol-3-O-{b-D–glucopyranosyl-(1 ?2)-b-D–xylopyranosyl-(1?2)-[a-L-rhamnopyranosyl-(1?4)]}-b-D-glucuronopyranoside, named schimasuoside B (2). There are strong antifungal effect of their mixture on Magnaporthe oryzae. Keywords Schima superba elucidation
Schimasuoside A Schimasuoside B Structure
98.1 Introduction Schima superba Gardn. et Champ (Theaceae) is mainly distributed in central and southern China. The plant is commonly cultivated as an ornamental tree, for timber production and as a firebreak planting. Its bark powder is used as a repellant agent to dispel wild pigs and birds from crops in Fujian mountain, to poison fish in G. Huo (&) C. Zhang College of Bioscience and Engineering, Jiangxi Agricultural University, 330045 Nanchang, People’s Republic of China e-mail: [email protected] Y. Zhang Kunming Institute of Botany, Chinese Academy of Sciences, 650204 Kunming, People’s Republic of China
T.-C. Zhang et al. (eds.), Proceedings of the 2012 International Conference on Applied Biotechnology (ICAB 2012), Lecture Notes in Electrical Engineering 250, DOI: 10.1007/978-3-642-37922-2_98, Ó Springer-Verlag Berlin Heidelberg 2014
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Taiwan, and as an arrow tip toxin by traditional hunters. A methanolic extract of its stem bark is used to kill snails [1], to induce apastia in Plutella xylostella, and Pieries rapae [2], and to control intestinal parasite. We recently found a strong antifungal effect of an ethanolic extract of S. superba leaves on Magnaporthe oryzae [3, 4]. The presence of a variety of chemical constituents in its stem such as saponins, flavonoids, lignanoids, have been reported [5, 6]. However, no report on the isolation and identification of saponins from the leaves of S. superba was available until now. The current study presents the isolation, structural elucidation of two new saponins from the leaves of S. superba in this paper.
98.2 Materials and Methods 98.2.1 General Experimental Procedures Optical rotations were measured with JASCOP-1020 digital polarimeter (Japan Jasco Pty Ltd). HRESI-MS spectra were acquired on API QSTAR Pulsa LC/TOF mass spectrometer (American AB corp). GC–MS spectra were obtained on Agilent 5973N with Shimadzu GC-14C column gas-mass spectrometer. One- and twodimensional NMR spectra were recorded on Bruker DRX-500 or Avance III 600 Fo
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