Sains Malaysiana 50(1)(2021): 101-107

http://dx.doi.org/10.17576/jsm-2021-5001-11

Structural Diversity, Anti-Fungal Activity and Chemosystematics of Bornean Liverwort Bazzania harpago (De Not.) Schiffner

(Kepelbagaian Struktur, Aktiviti Anti-Kulat dan Kemosistematik Lumut Hati Borneo Bazzania harpago (De Not.) Schiffner)

SHEAN-YEAW NG¹, LEE-PING ANG¹, VUI-LUN HAU¹, MONICA SULEIMAN¹, CHARLES SANTHANARAJU VAIRAPPAN¹ & TAKASHI KAMADA^1,2*

¹Institute for Tropical Biology and Conservation, Universiti Malaysia Sabah, Jalan UMS, 88400 Kota Kinabalu, Sabah, Malaysia

²Department of Materials and Life Science, Faculty of Science and Technology, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan

Received: 12 December 2019/Accepted: 2 July 2020

ABSTRACT

Two terpenes; cneorubin X (1), (-)-gymnomitr-3(15)-en-4β-ol (2) as well as one benzoic compound; caffeic acid (3) were isolated from Bazzania harpago collected from Mt. Trus Madi, Sabah, Malaysia. The structures of these secondary metabolites were elucidated based on spectroscopic data (Infra-Red (IR), 1D and 2D Nuclear Magnetic Resonance (NMR), and Mass Spectrum (MS)). This is the first record that cneorubin X (1) was isolated from non-vascular plants and it exhibited active anti-fungal activity against Haliphthoros sabahensis and Haliphthoros milfordensis. Chemosystematics finding suggests that the Marchantiophyta (liverworts) genus Bazzania might have a closer chemical relationship to its sister group Bryophyta (mosses) genus Brachythecium, Kindbergia and Mnium, as well as Anthocerophyta (hornworts) genus Anthoceros in their evolutionary history.

Keywords: Bazzania harpago; Borneo; chemosystematics; liverwort; secondary metabolite

ABSTRAK

Dua terpena; cneorubin X (1), (-)-gymnomitr-3(15)-en-4β-ol (2) dan satu sebatian benzoik; asid kaffeik (3) telah diasingkan daripada Bazzania harpago yang diambil dari Gunung Trus Madi, Sabah, Malaysia. Struktur metabolit sekunder ini telah dijelaskan berdasarkan data spektroskopi (Infra-merah (IR), 1D and 2D Resonans Magnet Nukleus (NMR) dan Spektrum Jisim (MS)). Kajian ini merupakan rekod pertama cneorubin X (1) yang diasingkan daripada tumbuhan bukan vaskular serta menunjukkan aktiviti anti-kulat yang aktif terhadap Haliphthoros sabahensis dan Haliphthoros milfordensis. Hasil kajian mencadangkan bahawa Marchantiophyta (lumut hati) genus Bazzania mempunyai hubungan kimia yang lebih rapat dengan kumpulan kembarnya, briofit (lumut hati) genus Brachythecium, Kindbergia dan Mnium, begitu juga dengan Anthocerophyta (lumut tanduk) genus Anthoceros dalam sejarah evolusi mereka.

Kata kunci: Bazzania harpago; Borneo; lumut hati; metabolit sekunder; sistematik kimia

REFERENCES

Adio, A.M., Paul, C., König, W.A. & Muhle, H. 2002. Volatile components from European liverworts Marsupella emarginata, M. aquatic and M. alpina. Phytochemistry 61(1): 79-91.

Ariyanti, N.S., Bos, M.M., Kartawinata, K., Tjitrosoedirdjo, S.S., Guhardja, E. & Gradstein, S.R. 2008. Bryophytes on tree trunks in natural forest, selectively logged forests and cacao agroforests in Central Sulawesi, Indonesia. Biological Conservation 141(10): 2516-2527.

Asakawa, Y. 2004. Chemosystematics of the Hepaticae. Phytochemistry 65(6): 623-669.

Asakawa, Y. 1995. Chemical constituents of the Bryophytes. In Progress in the Chemistry of Organic Natural Products, edited by Herz, W., Kirby, G.W., Moore, R.E., Steglich, W. & Tamm, Ch. Vienna: Springer. pp. 1-618.

Asakawa, Y. 1982. Chemical constituents of Hepaticae. In Progress in the Chemistry of Organic Natural Products, edited by Herz, W., Grisebach, H. & Kirby, G.W. Vienna: Springer. pp. 1-285.

Asakawa, Y., Ludwiczuk, A. & Nagashima, F. 2013a. Phytochemical and biologica studies of bryophytes. Phytochemistry 91: 52-80.

Asakawa, Y., Ludwiczuk, A. & Nagashima, F. 2013b. Chemical constituents of bryophytes. In Progress in the Chemistry of Organic Natural Products, edited by Kinghorn, A.D., Falk, H. & Kobayashi, J. Vienna: Springer. pp. 1-796.

Brochini, C.B. & Roque, N.F. 2000. Two new cneorubin related diterpenes from the leaves of Guarea guidonia (Meliaceae). Journal of the Brazillian Chemical Society 11(4): 361-364.

Chuah-Petiot, M.S. 2011. A checklist of Hepaticae and Anthocerotae of Malaysia. Polish Botanical Journal 56(1): 1-44.

Crandall-Stotler, B.J., Stotler, R.E. & Long, D.G. 2009. Phylogeny and classification of the Marchantiophyta. Edinburgh Journal of Botany 66(1): 1-44.

Frahm, J.P., Frey, W., Kürschner, H. & Menzel, M. 1990. Mosses and Liverworts of Mt. Kinabalu. Kota Kinabalu: Sabah Parks Trustees. pp. 12(2): 1-91.

Hernandez, V., De Leo, M., Cotugno, R., Braca, A., De Tommasi, N. & Severino, L. 2018.  New tirucallane-type triterpenoids from Guarea guidonia. Planta Medica 84(9-10): 716-720.

Jocković, N., Andrade, P.B., Valentão, P. & Sabovljević, M. 2008. HPLC-DAD of phenolics in bryophytes Lunularia cruciata, Brachytheciastrum velutinum and Kindbergia praelonga. Journal of the Serbian Chemical Society 73(12): 1161-1167.

Ludwiczuk, A. & Asakawa, Y. 2010. Chemosystematics of selected liverworts collected in Borneo. Tropical Bryology 31: 33-42.

Menzel, M. 1988. Annotated catalogue of the Hepaticae and Anthocerotae of Borneo. Journal of Hattori Botanical Laboratory 65: 145-206.

Mulholland, D.A. & Mahomed, H.A. 2000. Isolation of Cneorubin X, an unusual diterpenoid from Ptaeroxylon obliquum (Ptaeroxylaceae). Biochemical Systematics and Ecology 28(7): 713-716.

Munchan, C., Hatai, K., Takagi, S. & Yamashita, A. 2009. In vitro and in vivo effectiveness of itraconazole against Ochroconis humicola isolated from fish. Aquaculture Science 57(3): 399-404.

Ng, S.Y., Kamada, T. & Vairappan, C.S. 2017. New pimarane-type diterpenoid and ent-eudesmane-type sesquiterpenoid from Bornean liverwort Mastigophora diclados. Records of Natural Products 11(6): 508-513.

Ng, S.Y., Kamada, T., Suleiman, M. & Vairappan, C.S. 2016. A new Seco-Clerodane-type diterpenoid from Bornean liverwort Schistochila acuminata. Natural Product Communications 11(8): 1071-1072.

Soares, A.D.O., Ferreira, A.G.L., Soares, L.R., Corsino, J., Garcez, F.R. & Garcez, W.S. 2014. Chemical study of leaves of Trichilia silvatica (Meliaceae). Química Nova 37: 1487-1490.

Trautmann, D., Epe, B., Oelberman, U. & Mondon, A. 1980. Diterpene aus Cneoraceen, I. Konstitution und Konfiguration der Cneorubine. Chemische Berichte 113(12): 3848-3865.

*Corresponding author; email: takashi.kamada800@gmail.com