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Application of Residual Dipolar Couplings and Selective Quantitative NOE to Establish the Structures of Tetranortriterpenoids from Xylocarpus rumphii

Waratchareeyakul, W, Hellemann, E, Gil, RR, Chantrapromma, K, Langat, Moses and Mulholland, Dulcie (2017) Application of Residual Dipolar Couplings and Selective Quantitative NOE to Establish the Structures of Tetranortriterpenoids from Xylocarpus rumphii Journal of Natural Products, 80 (2). pp. 391-402.

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Abstract

Nine triterpenoid derivatives were isolated from the heartwood of X. rumphii and were identified as xylorumphiins E (1), C (2), L (3), and M-R (4-9). Compounds 4-9 have a hemiacetal group in the triterpenoid sidechain making them impossible to purify. Purification was achieved after acetylation and subsequent separation of the epimeric mixtures of acetates, however differentiaition of the R and S epimers was not possible using standard NMR techniques. In one case, the relative configuration of a remotely located stereocenter with respect to the stereocenters in the main skeleton was unambiguously determined using residual dipolar couplings (RDCs). Dipolar couplings were collected from the sample oriented in compressed poly (methyl methacrylate) (PMMA) gels swollen in CDCl3. In another case, the relative configuration was determined using 1D selective quantitative NOE experiments. Xylorumphiin K (10), xyloccensin E, taraxer-14-en-3-ol, (22S)-hydroxytirucalla-7,24-diene-3,23-dione and 25-hydroxy-(20S,24S)-epoxydammaran-3-one were isolated from the bark of the same plant. Compounds 3-10 are new compounds. Compounds 1-6 and xyloccensin E were tested at one concentration, 1 x 10-5 M, in the NCI59 cell one-dose screen but did not show significant activity.

Item Type: Article
Subjects : Chemistry
Divisions : Faculty of Engineering and Physical Sciences > Chemistry
Authors :
NameEmailORCID
Waratchareeyakul, WUNSPECIFIEDUNSPECIFIED
Hellemann, EUNSPECIFIEDUNSPECIFIED
Gil, RRUNSPECIFIEDUNSPECIFIED
Chantrapromma, KUNSPECIFIEDUNSPECIFIED
Langat, MosesM.Langat@surrey.ac.ukUNSPECIFIED
Mulholland, DulcieD.Mulholland@surrey.ac.ukUNSPECIFIED
Date : 25 January 2017
Identification Number : 10.1021/acs.jnatprod.6b00906
Copyright Disclaimer : Copyright © 2017 The American Chemical Society and American Society of Pharmacognosy
Related URLs :
Depositing User : Symplectic Elements
Date Deposited : 25 Jan 2017 18:12
Last Modified : 07 Jul 2017 10:35
URI: http://epubs.surrey.ac.uk/id/eprint/813370

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