Dr DAVID S. RYCROFT School of Chemistry Joseph Black Building University of Glasgow GLASGOW G12 8QQ Telephone 0141 330 4479 Fax 0141 330 4888 Email David.Rycroft@glasgow.ac.uk

Areas of interest Liverwort chemistry and chemosystematics Structural elucidation of natural products using NMR spectroscopy Publications Miscellaneous
Liverwort chemistry and chemosystematics Liverworts grow prolifically in Scotland, especially in the west. Oil bodies generally assumed to contain terpenoid and/or aromatic compounds are produced within the cells of liverworts, and a wide variety of terpenoid skeletal types has been found,including some which are unique to liverworts.
We have developed an NMR profiling method based on direct extraction of plant material with the NMR solvent CDCl3. Complementary NMR and GC-MS experiments (with Dr Cole) using the same solutions have enabled us to identify characteristic compounds in several species that are available in small quantities only and to compare gatherings of the same species from different parts of the world, in some cases using herbarium material over eighty years old.
In collaboration with groups in Germany, we have investigated the systematics of the large and morphologically difficult genus Plagiochila. Secondary metabolites revealed by NMR profiling prompted morphological and phytochemical investigation of disjunct populations (in North America, the Neotropics and Europe with Macaronesia) and resulted in the discovery of important range extensions, for example of Plagiochila retrorsa Gottsche and Plagiochila papillifolia Steph.

SEM of elaters from the sporophyte of the Neotropical liverwort Plagiochila retrorsa, now known from Madeira and the Azores as well as the USA (where it was known as P. sharpii H.L.Blomq.), Costa Rica and Mexico.

SEM of the papillose leaf surface of Plagiochila papillifolia, now known from the Azores as well as the Neotropics.

In the case of Plagiochila atlantica F.Rose, a European endemic, atlanticol and plagiochiline C have served as chemical pointers to a systematic relationship with Neotropical species notable for the presence of leaf surface waxes, supported by the subsequent discovery of leaf surface waxes in P. atlantica itself. The more recent synomymization of P. atlantica with the Neotropical P. heterophylla by Heinrichs was confirmed through phylogenetic reconstruction based on analysis of DNA sequence variation.

Further information

Structural elucidation of natural products using NMR spectroscopy

Further information.

Publications

Representative publications

• Reinstatement of Plagiochila maderensis (Jungermanniopsida: Plagiochilaceae) based on chemical evidence and nrDNA ITS sequences.
  D.S. Rycroft, H. Groth, J. Heinrichs. Journal of Bryology, 2004, 26, 37-45.
• Phytochemical, morphological, and molecular evidence for the occurrence of the Neotropical liverwort Plagiochila stricta in the Canary Islands, new to Macaronesia.
  D.S. Rycroft, W.J. Cole, J. Heinrichs, H.Groth, C. Renker, T. Pröschold. The Bryologist, 2002, 105, 363-372. [PDF]
• Plagiochila in Europe (and beyond).
  D.S. Rycroft. Bulletin of the British Bryological Society, 2002, 78, 21-25.
• Plagiochila virginica A.Evans rather than P. dubia Lindenb. & Gottsche occurs in Macaronesia; placement in sect. Contiguae Carl is supported by ITS sequences of nuclear ribosomal DNA.
  J. Heinrichs, T. Pröschold, C. Renker, H.Groth, D.S. Rycroft. Plant Systematics and Evolution, 2002, 230, 221-230.
• Plagiochila rutilans (Hepaticae): a poorly known species from tropical America.
  HEINRICHS, J., GROTH, H., GRADSTEIN, S.R., RYCROFT, D.S., COLE, W.J., ANTON, H. (2001) The Bryologist, 104, 350-361.
• Leaf surface waxes and lipophilic secondary metabolites place the endemic European liverwort Plagiochila atlantica F.Rose in the Neotropical Plagiochila sect. Bursatae Carl.
  HEINRICHS, J., RYCROFT, D.S. (2001) Cryptogamie, Bryologie, 22, 95-103.
• Hydroquinone derivatives and monoterpenoids from the Neotropical liverwort Plagiochila rutilans.
  RYCROFT, D.S., COLE, W.J. (2001) Phytochemistry, 57, 479-488.
• A phytochemical and morphological study of the liverwort Plagiochila retrorsa Gottsche, new to Europe.
  RYCROFT, D.S., HEINRICHS, J., COLE, W.J., ANTON, H. (2001) Journal of Bryology, 23, 23-34.
• Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: stereoselective total synthesis of herbertenediol and mastigophorenes A and B.
  BRINGMANN, G., PABST, T., HENSCHEL, P., KRAUS, J., PETERS, K., PETERS, E.-M., RYCROFT, D.S., CONNOLLY, J.D. (2000) Journal of the American Chemical Society, 122, 9127-9133. [PDF]
• Killarniensolide, methyl orsellinates and 9,10-dihydrophenanthrenes from the liverwort Plagiochila killarniensis from Scotland and the Azores.
  RYCROFT, D.S., COLE, W.J., ASLAM, N., LAMONT, Y.M., GABRIEL, R. (1999) Phytochemistry, 50, 1167-1173. [PDF]
• Atlanticol, an epoxybicyclogermacrenol from the liverwort Plagiochila atlantica F. Rose.
  RYCROFT, D.S., COLE, W.J. (1998) Phytochemistry, 49, 1641-1644.
• Fingerprinting of plant extracts using NMR spectroscopy: application to small samples of liverworts.
  RYCROFT, D.S. (1996) Chemical Communications, 1287-1288. [PDF]
• Revised structure of haemoventosin.
  RYCROFT, D.S., CONNOLLY, J.D., HUNECK, S., HIMMELREICH, U. (1995) Z. Naturforsch., 50b, 1557-1563.

Miscellaneous