Sesquiterpene constituents from the essential oils of the liverworts Mylia taylorii and Mylia nuda

Phytochemistry

Volumn 65, Issue 15, 2004, Pages 2277-2291

  Von Reuß, Stephan H ^a   Wu, Chia Li ^b   Muhle, Hermann ^c   König, Wilfried A ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b TAMKANG UNIVERSITY   (Taiwan)

^c UNIVERSITY OF ULM   (Germany)

Author keywords

Liverworts; Mylia nuda; Mylia taylorii; Sesquiterpenoids; Structure elucidation

Indexed keywords

7 EPIBOURBON 3 EN 5,11 OXIDE; ALPHA TAYLORIONE; AROMADENDRA 1(10),4(15) DIENE; AROMADENDRA 4,10(14) DIENE; AROMADENDRA 4,9 DIENE; ESSENTIAL OIL; FURAN DERIVATIVE; GUAI 3,10(14) DIEN 5,11 OXIDE; GUAI 3,9 DIEN 5,11 OXIDE; HYDROCARBON; MYLI 4(15) EN 3 ONE; MYLI 4(15) ENE; PYRAN DERIVATIVE; SESQUITERPENE; SESQUITERPENE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; DRUG ISOLATION; DRUG STRUCTURE; GAS CHROMATOGRAPHY; LIVERWORT; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS;

GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HEPATOPHYTA; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OILS, VOLATILE; SESQUITERPENES;

MARCHANTIOPHYTA; MYLIA; MYLIA TAYLORII; NUDA;

EID: 4344684941     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2004.04.039     Document Type: Article

References (32)

1. Adio A.M., Paul C., König W.A., Muhle H. Volatile components from European liverworts Marsupella emarginata, M. aquatica and M. alpina. Phytochemistry. 61:2002;79-91
2. Adio, A.M., 2004. Unpublished results
3. Andersen N.H., Bissonette P., Liu C.B., Shunk B., Ohta Y., Tseng C.L.W., Moore A., Huneck S. Sesquiterpenes of nine European liverworts from the genera Anastrepta, Bazzania, Jungermannia, Lepidozia and Scapania. Phytochemistry. 16:1977;1731-1751
4. Andersen N.H., Ohta Y., Moore A., Tseng C.L.W. Anastreptene, a commonly encoutered sesquiterpene of the liverworts (Hepaticae). Tetrahedron. 34:1978;41-46
5. Asakawa Y. Chemical constituents of the bryophytes. Herz W., Kirby W.B., Moore R.E., Steglich W., Tamm C. Progress in the Chemistry of Organic Natural Products. vol. 65:1995;1-618 Springer, Wien
6. Benesova V., Sedmera P., Herout V., Sorm F. The structure of a tetracyclic sesquiterpenic alcohol from liverwort Mylia taylorii (Hook.) Gray. Tetrahedron Letters. 28:1971;2679-2682
7. Benesova V., Sedmera P., Herout V., Sorm F. The structure of myliol, a tetracyclic sesquiterpenic alcohol from the liverwort Mylia taylorii (Hook.) Gray. Collection of Czechoslovak Chemical Communications. 38:1973;1084-1090
8. Bernart M.W., Kashman Y., Tischler M., Cardellina J.H., Boyd M.R. Bershacolone, an unprecedented diterpene cyclobutene from Maprounea africana. Tetrahedron Letters. 34:1993;4461-4464
9. Friedel H.D., Matusch R. Neue Aromadendran-Derivate aus Tolu-Balsam. Helvetica Chimica Acta. 70:1987;1753-1759
10. Hardt I., König W.A. Preparative enantiomer separation with modified cyclodextrins as chiral stationary phases. Journal of Chromatography A. 666:1994;611-615
11. Hirota H., Tanahashi Y., Takahashi T. Structure of a guaiane-type sesquiterpene ether from "san-shion" Tetrahedron Letters. 51:1975;4579-4582
12. Hirota H., Tanahashi Y., Takahashi T. Structure of a guaioxide-type sesquiterpene from "san-shion" Bulletin of the Chemical Society of Japan. 53:1980;785-788
13. Hochmuth, D.H., Joulain, D., König, W.A., 2003. MassFinder 2.3, Terpenoids and Related Constituents of Essential Oils (www.chemie.uni-hamburg. de/oc/koenig/massfinder.html)
14. Joulain D., König W.A. The Atlas of Spectral Data of Sesquiterpene Hydrocarbons. 1998;E.B.-Verlag, Hamburg
15. König, W.A., Adio, A.M., von Reuß, S.H., 2003. unpublished results
16. Liu H.J., Wu C.L., Hashimoto T., Asakawa Y. Nudenoic acid: a novel tricyclic sesquiterpenoid from the Taiwanese liverwort Mylia nuda. Tetrahedron Letters. 37:1996;9307-9308
17. Matsuo A., Sato S., Nakayama M., Hayashi S. Taylorione, a novel carbon skeletal sesquiterpene ketone. Tetrahedron Letters. 42:1974;3681-3684
18. Matsuo A., Nozaki H., Nakayama M., Kushi Y., Hayashi S., Kamijo N., Benesova V., Herout V. X-ray crystal and molecular structure of the p-bromobenzoate of (-)-myliol, a novel tetracyclic sesquiterpene alcohol from Mylia taylorii (liverwort) containing two conjugated cyclopropane rings. Revision of a proposed structure. Journal of the Chemical Society, Chemical Communications. 1976;1006-1007
19. Matsuo A., Nozaki H., Shigemori M., Nakayama M., Hayashi S. (-)-Dihydromylione A, a novel tetracyclic sesquiterpene ketone containing two conjugated cyclopropane rings, from Mylia taylorii (liverwort). Experientia. 33:1977;991-992
20. Matsuo A., Sato S., Nakayama M., Hayashi S. Structure and absolute configuration of (-)-taylorione, a novel carbon skeletal sesquiterpene ketone of ent 1,10-seco-aromadendrane form from Mylia taylorii (liverwort). Journal of the Chemical Society Perkin Transcations I. 1979;2652-2656
21. Matsuo A., Takaoka D. Structures of new sesquiterpenoids from the liverwort Mylia taylorii. Zinsmeister H.D., Mues R. Bryophytes, Their Chemistry and Chemical Taxonomy. 1990;59-69 Claredon Press, Oxford
22. Nagashima F., Asakawa Y. Chemical constituents of the liverworts Jungermannioideae and Myliioideae (Jungermanniaceae). Pandalai S.G. Recent Research Developments in Phytochemistry, Part II. vol. 2:1998;327-382 Research Signpost, India
23. Nakayama M., Ohira S., Shinke S., Matsushita Y., Matsuo A., Hayashi S. Synthesis of (-)-taylorione, a sesquiterpene ketone of ent-1,10-seco- aromadendrane skeleton. Chemistry Letters. 1979;1245-1246
24. Nozaki H. Structure and absolute stereochemistry of the sesquiterpene alcohol (-)-myliol: X-ray analysis of the p-bromobenzoate. Journal of the Chemical Society Perkin Transactions II. 1979;514-518
25. Oyedeji A.O., Ekundayu O., Mekem Sonwa M., Fricke C., König W.A. (-)-Eudesma-1,4(15),11-triene from the essential oil of Callitris intratropica. Phytochemistry. 48:1998;657-660
26. Takaoka D., Matsuo A., Kuramoto J., Nakayama M., Hayashi S. (-)-Myltaylenol, a tricyclic sesquiterpene alcohol with a novel carbon skeleton from the liverwort Mylia taylorii. Journal of the Chemical Society Chemical Communications. 482:1985;483
27. Takaoka D., Tani H., Matsuo A. Cyclomytaylenol, a novel tetracyclic sesquiterpenoid from the liverwort Mylia taylorii. Journal of Chemical Research (Synopsis). 1988;130-131
28. Takaoka D., Kouyama N., Tani H., Matsuo A. Structures of three novel dimeric sesquiterpenoids from the liverwort Mylia taylorii. Journal of Chemical Research (Synopsis). 1991;180-181
29. Warmers U., Wihstutz K., Bülow N., Fricke C., König W.A. Sesquiterpene constituents of the liverwort Calypogeia muelleriana. Phytochemistry. 49:1998;1723-1731
30. Wu C.-L. Highlights of phytochemistry of liverworts from Taiwan and mainland China. Youji Huaxue. 17:1997;28-37
31. Wu C.-L., Asakawa Y. The chemical constituents of the liverwort Mylia nuda. Journal of the Chinese Chemical Society. 34:1987;219-223
32. Wu C.-L., Chang S.-J. Cyclomyltaylane, a tetracyclic sesquiterpene hydrocarbon from Bazzania tridens. Phytochemistry. 31:1992;2150-2152