Abstract
The definitive identification of the first lignans to be found in humans and animals is described. Gas chromatography--mass spectrometry, n.m.r. spectroscopy, i.r. spectroscopy and chemical techniques were employed to establish the structures of two lignans as trans-2,3-bis(3-hydroxybenzyl)-gamma-butyrolactone and 2,3-bis(3-hydroxybenzyl)butane-1,4-diol. Both compounds are essetially racemic. Evidence was also found for several methoxy analogues of these lignans in the vervet monkey.
Full text
PDF![447](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/2c13dc60099c/biochemj00395-0199.png)
![448](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/54c280a9b982/biochemj00395-0200.png)
![449](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/48e75d42737b/biochemj00395-0201.png)
![450](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/d3ba6e098c77/biochemj00395-0202.png)
![451](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/87db4eca2526/biochemj00395-0203.png)
![452](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/27aa756de902/biochemj00395-0204.png)
![453](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/34d6544a5451/biochemj00395-0205.png)
![454](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/9e7469124a2c/biochemj00395-0206.png)
![455](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/d862997f276c/biochemj00395-0207.png)
![456](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/e3fccdc1e381/biochemj00395-0208.png)
![457](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/2e23066a44ba/biochemj00395-0209.png)
![458](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7fd1/1163145/994d48864523/biochemj00395-0210.png)
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Axelson M., Setchell K. D. Conjugation of lignans in human urine. FEBS Lett. 1980 Dec 15;122(1):49–53. doi: 10.1016/0014-5793(80)80399-1. [DOI] [PubMed] [Google Scholar]
- Axelson M., Sjövall J. Analysis of unconjugated steroids in plasma by liquid-gel chromatography and glass capillary gas chromatography mass spectrometry. J Steroid Biochem. 1977 Jun;8(6):683–692. doi: 10.1016/0022-4731(77)90297-7. [DOI] [PubMed] [Google Scholar]
- Determann H., Walter I. Source of aromatic affinity to "Sephadex" dextran gels. Nature. 1968 Aug 10;219(5154):604–605. doi: 10.1038/219604a0. [DOI] [PubMed] [Google Scholar]
- Reimendal R., Sjövall J. Analysis of steroids by off-line computerized gas chromatography-mass spectrometry. Anal Chem. 1972 Jan;44(1):21–29. doi: 10.1021/ac60309a014. [DOI] [PubMed] [Google Scholar]
- Rutten G. A., Luyten J. A. Analysis of steroids by high resolution gas-liquid chromatography. I. Preparation of apolar columns. J Chromatogr. 1972 Dec 20;74(2):177–193. doi: 10.1016/s0021-9673(01)86148-3. [DOI] [PubMed] [Google Scholar]
- Setchell K. D., Almé B., Axelson M., Sjövall J. The multicomponent analysis of conjugates of neutral steroids in urine by lipophilic ion exchange chromatography and computerised gas chromatography-mass spectrometry. J Steroid Biochem. 1976 Aug;7:615–629. doi: 10.1016/0022-4731(76)90086-8. [DOI] [PubMed] [Google Scholar]
- Setchell K. D., Bull R., Adlercreutz H. Steroid excretion during the reporductive cycle and in pregnanacy of the vervet monkey (Cercopithecus aethiopus pygerythrus). J Steroid Biochem. 1980 Jan;12:375–384. doi: 10.1016/0022-4731(80)90296-4. [DOI] [PubMed] [Google Scholar]
- Setchell K. D., Lawson A. M., Mitchell F. L., Adlercreutz H., Kirk D. N., Axelson M. Lignans in man and in animal species. Nature. 1980 Oct 23;287(5784):740–742. doi: 10.1038/287740a0. [DOI] [PubMed] [Google Scholar]
- Setchell K. D., Shackleton C. H. The group separation of plasma and urinary steroids by column chromatography on sephadex LH-20. Clin Chim Acta. 1973 Sep 14;47(3):381–388. doi: 10.1016/0009-8981(73)90270-2. [DOI] [PubMed] [Google Scholar]
- Shackleton C. H., Whitney J. O. Use of Sep-pak cartridges for urinary steroid extraction: evaluation of the method for use prior to gas chromatographic analysis. Clin Chim Acta. 1980 Nov 6;107(3):231–243. doi: 10.1016/0009-8981(80)90451-9. [DOI] [PubMed] [Google Scholar]
- Stitch S. R., Toumba J. K., Groen M. B., Funke C. W., Leemhuis J., Vink J., Woods G. F. Excretion, isolation and structure of a new phenolic constituent of female urine. Nature. 1980 Oct 23;287(5784):738–740. doi: 10.1038/287738a0. [DOI] [PubMed] [Google Scholar]