Isolation and characterization of triterpenoids from the stem barks of Pinus massoniana

Chuan-Ling Si; Yue Gao; Lei Wu; Rui Liu; Guanhua Wang; Lin Dai; Xionghui Li; Yimei Hong

doi:10.1515/hf-2016-0228

Article

Isolation and characterization of triterpenoids from the stem barks of Pinus massoniana

Chuan-Ling Si , Yue Gao , Lei Wu , Rui Liu , Guanhua Wang , Lin Dai , Xionghui Li and Yimei Hong

Published/Copyright: April 19, 2017

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From the journal Holzforschung Volume 71 Issue 9

Abstract

Tree barks, residues in forestry and the pulp industry, could be a rich source of novel biologically or pharmaceutically active substances. In the current work, chemical constituents of extracts obtained from stem barks of Pinus massoniana have been analyzed. A novelty is the isolation of a new ursane-type triterpene saponin, which was characterized as ursolic acid 3-O-[β-d-glucopyranosyl (1′′→6′)]-β-d-glucopyranoside-28-O-β-d-glucopyranoside (IV). Moreover, three already known triterpenoid compounds ursolic acid (I), oleanolic acid (II) and oleanolic acid 3-O-β-d-glucopyranoside (III) are described. The elucidation of chemical structures of the isolated extractives was carried out mainly by a combination of 1D ¹H, ¹³C and various 2D NMR experiments as well as by IR, UV and MS spectroscopic techniques. It is the first report about four triterpenoids found in bark of P. massoniana.

Keywords: extractives; Pinus massoniana; spectroscopic techniques; stem barks; structural elucidation; triterpenoids; ursolic acid 3-O-[β-d-glucopyranosyl (1′′→6′)]-β-d-glucopyranoside-28-O-β-d-glucopyranoside

Acknowledgement

This work was financially supported by the open fund of state key laboratory of tree genetics and breeding (Chinese Academy of Forestry) (grant no. TGB2016002), Science Foundation for Young Doctors of Jiangxi Academy of Science (2016-YYB-07), Jiangsu Province Biomass Energy and Materials Laboratory in Institute of Chemical Industry of Forest Products, CAF (JSBEM201601), State Key Laboratory of Pulp and Paper Engineering (South China University of Technology) (201611, 201503, 201211), Natural Science Foundation of Tianjin City (16JCQNJC05900) and the Innovation Foundation for Young Teachers in Tianjin University of Science and Technology (no. 2016LG20).

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Received: 2016-12-13

Accepted: 2017-3-21

Published Online: 2017-4-19

Published in Print: 2017-8-28

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https://doi.org/10.1515/hf-2016-0228

Keywords for this article

extractives; Pinus massoniana; spectroscopic techniques; stem barks; structural elucidation; triterpenoids; ursolic acid 3-O-[β-d-glucopyranosyl (1′′→6′)]-β-d-glucopyranoside-28-O-β-d-glucopyranoside