Home Isolation of secondary metabolites from Stenochlaena palustris stems and structure-activity relationships of 20-hydroxyecdysone derivatives on antitermite activity
Article
Licensed
Unlicensed Requires Authentication

Isolation of secondary metabolites from Stenochlaena palustris stems and structure-activity relationships of 20-hydroxyecdysone derivatives on antitermite activity

  • Antoni Pardede , Morina Adfa , Arif Juliari Kusnanda , Masayuki Ninomiya and Mamoru Koketsu EMAIL logo
Published/Copyright: May 24, 2018
Become an author with De Gruyter Brill

Abstract

Stenochlaena palustris is an edible fern, belonging to the Blechnaceae family and is called kelakai in South Kalimantan, Indonesia. The effects of fractions of S. palustris stems and isolated constituents on termite mortality and paper disc consumption by Coptotermes curvignathus have been studied. Treatment of the ethyl acetate (EtOAc) fraction on paper discs greatly induced death of C. curvignathus within 6 days. Our phytochemical investigation of S. palustris stems led to the isolation of major constituents and 20-hydroxyecdysone exerted the highest termiticidal activity, followed by stenopalustroside A and ajugasterone C. Moreover, the structure-activity relationships (SAR) of synthetic derivatives from 20-hydroxyecdysone and ajugasterone C suggested that a 2,3-diol has considerable effect on their antitermite properties against C. curvignathus.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Employment or leadership: None declared.

  4. Honorarium: None declared.

References

Adfa, M., Livandri, F., Meita, N.V., Manaf, S., Ninomiya, M., Gustian, I., Putranto, A.M.H., Supriati, R., Koketsu, M. (2015) Termitical activity of Acorus calamus Linn, rhizomes and its main constituents against Coptotermes curvignathus Holmgren. J. Asia Pac. Entomol. 18:47–50.10.1016/j.aspen.2014.10.012Search in Google Scholar

Adfa, M., Kusnanda, A.J., Livandri, F., Rahmad, R., Darwis, W., Efdi, M., Ninomiya, M., Koketsu, M. (2017) Insecticidal activity of Toona sinensis against Coptotermes curvignathus Holmgren. Rasayan J. Chem. 10:153–159.Search in Google Scholar

Chai, T.T., Kwek, M.T., Ong, H.C., Wong, F.C. (2015) Water fraction of edible medicinal fern Stenochlaena palustris is a potent α-glucosidase inhibitor with concurrent antioxidant activity. Food Chem. 186:26–31.10.1016/j.foodchem.2014.12.099Search in Google Scholar

Chang, S.T., Cheng, S.S. (2002) Antitermite activity of leaf essential oil and compounds from Cinnammum asmophleum. J. Agric. Food Chem. 50:1389–1392.10.1021/jf010944nSearch in Google Scholar

Chear, N.J.Y., Khaw, K.Y., Murugaiyah, V., Lai, C.S. (2016) Cholinesterase inhibitory activity and chemical constituents of Stenochlaena palustris fronds at two different stages of maturity. J. Food Drug Anal. 24:358–366.10.1016/j.jfda.2015.12.005Search in Google Scholar

Giron, M.Y., San Pablo, M.R. (2004) Resistance of some forest vines to wood-​destroying fungi. FPRDI J. 26:58–67.Search in Google Scholar

Hiramatsu, Y., Adfa, M., Ninomiya, M., Yoshimura, T., Koketsu, M. (2013) Effects of 2,2-dimethylchromenes against the feeding behavior of Coptotermes formosanus Shiraki. J. Pestic. Sci. 38:228–231.10.1584/jpestics.D13-050Search in Google Scholar

Kadir, R., Hale, M.D. (2012) Comparative termite resistance of 12 Malaysian timber species in laboratory tests. Holzforschung 66:127–130.10.1515/HF.2011.116Search in Google Scholar

Kadir, R., Ali, N.M., Soit, Z., Khamaruddin, Z. (2014) Anti-termitic potential of heartwood and bark extract and chemical compounds isolated from Madhuca utilis Ridl. H. J. Lam and Neobalanocarpus heimii King P. S. Ashton. Holzforschung 68:713–720.10.1515/hf-2013-0101Search in Google Scholar

Little, N.S., Schultz, T.P., Nicholas, D.D. (2010) Termite-resistantheartwood. Effect of antioxidants on termite feeding deterrence and mortality. Holzforschung 64:395–398.10.1515/hf.2010.053Search in Google Scholar

Liu, H., Orjala, J., Rali, T., Sticher, O. (1998) Glycosides from Stenochlaena palustris. Phytochemistry 49:2403–2408.10.1016/S0031-9422(98)00352-5Search in Google Scholar

Liu, H., Orjala, J., Sticher, O., Rali, T. (1999) Acylated flavonol glycosides from leaves of Stenochlaena palustris. J. Nat. Prod. 62:70–75.10.1021/np980179fSearch in Google Scholar PubMed

Ninomiya, M., Aoki, T., Adfa, M., Yoshimura, T., Koketsu, M. (2014) Comparison of antitermite properties of 2-thioxocoumarins against Coptotermes formosanus Shiraki. Holzforschung 68:361–365.10.1515/hf-2013-0099Search in Google Scholar

Oramahi, H.S., Yoshimura, T. (2013) Antifungal and antitermite activities of wood vinegar from Vitex pubesscens Vahl. J. Wood Sci. 59:344–350.10.1007/s10086-013-1340-8Search in Google Scholar

Pardede, A., Adfa, M., Kusnanda, A.J., Ninomiya, M., Koketsu, M. (2017) Flavonoid rutinosides from Cinnamomum parhenoxylon leaves and their hepatoprotective and antioxidant activity. Med. Chem. Res. 26:2074–2079.10.1007/s00044-017-1916-8Search in Google Scholar

Roszaini, K., NorAzah, M.A., Mailina, J., Zaini, S., Faridz, Z.M. (2013) Toxicity and antitermite activity of the essential oils from Cinnamomum camphora, Cymbopogon nardus, Melaleuca cajuputi and Dipterocarpus sp. against Coptotermes curvignathus. Wood Sci. Technol. 47:1273–1284.10.1007/s00226-013-0576-1Search in Google Scholar

Sowmya, S.N., Calistus, J.A.L., Deepa, M. (2016) Antitermite properties of four selected species of Zingiberaceae extracts. J. Zool. St. 3:24–29.Search in Google Scholar

Su, N.Y., Monteagudo, E.J. (2017) Hyperecdysonism in the Formosan subterranean termite and Eastern subterranean termite (Isoptera: Rhinotermitidae). J. Econ. Entomol. 110:1736–1739.10.1093/jee/tox178Search in Google Scholar

Suksamrarn, A., Pattanaprateep, P. (1995) Selective acetylation of 20-hydroxyecdysone partial synthesis of some minor ecdysteroids and analogues. Tetrahedron 51:10633–10650.10.1016/0040-4020(95)00635-LSearch in Google Scholar

Suksamrarn, A., Yingyongnarongkul, B. (1996) Synthesis and biological activity of 2-deoxy-20-hydroxyecdysone and derivatives. Tetrahedron 52:12623–12630.10.1016/0040-4020(96)00750-8Search in Google Scholar

Ves’kina, N.A., Odinokov, V.N. (2012) Transformations of ecdysteroids in the synthesis of their structural analogs and minor phytoecdysteroids. Russian J. Org. Chem. 48:1141–1165.10.1134/S1070428012090011Search in Google Scholar

Zuraini, Z., Sasidharan, S., Kaur, S.R., Nithiyayini, M. (2010) Antimicrobial and antifungal activities of local edible fern Stenochlaena palustris (Burm. F) Bedd. Pharmacologyonline 1:233–237.Search in Google Scholar


Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/hf-2017-0212).


Received: 2017-12-18
Accepted: 2018-04-24
Published Online: 2018-05-24
Published in Print: 2018-10-25

©2018 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 24.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/hf-2017-0212/html?lang=en
Scroll to top button