History

Brief history of marine natural product chemistry

The genesis of marine natural product chemistry was initiated by the late Professor Bergman work (1950s) on the discovery of the non-ribose nucleosides spongothymidine and spongouridine from the West Indian sponge Cryptotethia crypta [1−3]. Almost at the same time, late Professor Scheuer had developed research on the sea urchin pigment by using chemotaxonomy strategy and had isolated spinochrome M [4], a napthoquinone type molecule. Professor Scheuer also introduced the phrase ‘marine natural products’, thus giving the emerging field an identity in the scientific community [5]. Still in 1950s, studies on marine toxins became the major feature of marine natural product researches. The intriguing marine toxin phenomenon has attracted giant chemists in the field to pursue it: Professors Hirata [6,7], Scheuer, Moore [8−10], and Hashimoto [11]. The work of marine toxin was followed by studying marine chemical ecology lead by Scheuer [12] and Faulkner [13]. Moreover, the first systematic study of a range of marine animals, both invertebrates as well as vertebrates, was reported in 1970 by Professor Pettit [14] and was expanded by Professor Rinehart with his bioassay-directed collections and onboard screening [15]. Led by Professor William Fenical, the study of marine microorganisms has rapidly become a major focus in recent years [16].

From the above explanation, marine natural product chemistry is an emerging field and recognized as a major subdiscipline of organic chemistry. In order to have a strong understanding on marine natural product chemistry, we need to equip our knowledge and skill from field–learning of biology aspect of marine organism to laboratory−concluding the chemical structures isolated from those marine organisms with interesting functions.

The diversity of chemicals and biological activities can provide excellent tools for other scientific fields, including biology, agriculture, medicine, materials, energy, and the environment. These facts have made marine organisms attractive targets for research endeavors.

References

  1. Bergmann, W.; Feeney, R.J. Isolation of a new thymine pentoside from sponges. J. Am. Chem. Soc. 1950, 72, 2809–2810, doi: 10.1021/ja01162a543.
  2. Bergmann, W.; Feeney, R.J. Contributions to the study of marine products XXXII. The nucleosides of sponges. I. J. Org. Chem. 1951, 16, 981–987, doi: 10.1021/jo01146a023.
  3. Bergmann, W.; Burke, D.C. Contributions to the study of marine products XXXIX. The nucleosides of sponges. III. Spongothymidine and spongouridine. J. Org. Chem. 1955, 20, 1501–1507, doi: 10.1021/jo01146a023.
  4. Chang, C.W.J.; Moore, R.E.; Scheuer, P. J.  The structure of spinochrome M. J. Am. Chem. Soc. 1964, 86, 2959−2961, doi: 10.1021/ja01068a056.
  5. Higa, T.; Okuda, R.K. Festschrift Issue of Tetrahedron in Honor of Paul Josef Scheuer, Professor Emeritus of Chemistry, The University of Hawai’i at Manoa. Tetrahedron 2000, 56, vii-ix.
  6. Goto, T.; Kishi, Y.; Takahashi, S.; Hirata, Y. Tetrodotoxin. Tetrahedron 1965, 21, 2059–2088, doi: 10.1016/S0040-4020(01)98344-9.
  7. Uemura, D.; Ueda, K.; Hirata, Y.; Naoki, H.; Iwashita, T. Further studies on palytoxin. II. structure of palytoxin. Tetrahedron Lett. 1981, 22, 2781−2784, doi: 10.1016/S0040-4039(01)90551-9.
  8. Moore, R.E.; Scheuer, P.J. Palytoxin: New marine toxin from a coelenterate. Science 1971, 172, 495–498, doi: 10.1126/science.172.3982.495.
  9. Moore, R.E.; Bartolini, G.  Structure of palytoxin. J. Am. Chem. Soc. 1981, 103, 2491–2494, doi: 10.1021/ja00399a093.
  10. Moore, R.E.; Bartolini, G.; Barchi, J.; Bothner-By, A.A.; Dadok, J.; Ford, J. Absolute stereochemistry of palytoxin. J. Am. Chem. Soc. 1982, 104, 3776–3779, doi: 10.1021/ja00377a064.
  11. Scheuer, P. J. In memoriam Yoshiro Hashimoto (1920−1976). Toxicon 1978, 16, 10−11, doi: 10.1016/0041-0101(78)90054-5
  12. Scheuer, P. J. Across two oceans onto the reef−The genesis of marine natural products. The Chemical Intelligencer, 1997, 3, 46−57.
  13. Faulkner, D.J. Highlights of marine natural products chemistry (1972−1999). Nat. Prod. Rep. 2000, 17, 1−6, doi: 10.1039/a909113k.
  14. Pettit, G.R.; Day, J.F.; Hartwell, J.L.; Wood, H.B. Antineoplastic components of marine animals. Nature 1970, 227, 962–963, doi: 10.1038/227962a0.
  15. Rinehart, K.L. Jr.; Shaw, P.D.; Shield, L.S.; Gloer, J.B.; Harbour, G.C.; Koker, M.E.S.; Samain, D.; Schwartz, R.E.; Tymiak, A.A.; Weller, D.L.; Carter, G.T.; Munro, M.H.G. Marine natural products as sources of antiviral, antimicrobial, and antineoplastic agents. Pure Appl. Chem. 1981, 53, 795–817, doi: 10.1351/pac198153040795.
  16. Blunt, J.W.; Copp, B.R.; Hu, W.-P.; Northcote, P.T.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2009, 26,170–244, doi: 10.1039/b805113p.

Brief history of international of summer course on marine natural products (ISCMNP)

First international summer course on marine natural products (ISCMNP) has been held since summer 2019. The course was featured by renowned chemists and biologist such as Profs. Lik Tong Tan, Masaki Kita, and Nicole J de Voogd. The course was very exciting since we direclty studied the marine organisms and marine ecology in the field (Kepulauan Seribu, Jakarta) using scuba or snorkeling from Prof. de Voogd, an expert of marine sponges. We also did experiment how to isolate marine natural products from sample collection. How to identify marine organisms roughly by seeing their morphology. Understanding of marine organism’s (macro and micro) taxonomy, spatial distributions, chemical and biological-including ecological and genetic as well as medicinal- perspectives is required for those who are studying marine natural product chemistry. Having more skilled and knowledge in biology and chemistry in hand, students or researchers can appreciate the biodiversity, otherwise we simply do not care with our environment. The ISCMNP 2019 has attracted a lot of students and researchers from Indonesia, the Netherlands, Japan, Singapore, France, India, Brazil, Taiwan, The Philippines, Kongo, China and Ethiopia to study marine natural product chemistry together in Indonesia. Finally, social activity was held in Bogor Botanical Garden with the impressive out-of-town Bogor Presidential palace fronting it. Here is some pictures of ISCMNP 2019.