- ORIGINAL ARTICLE
- Published:
Termite repellent sesquiterpenoids from Callitris glaucophylla heartwood
Journal of Wood Science volume 51, pages 514–519 (2005)
Abstract
Fractions of methanol and ethanol extracts from the heartwood of white cypress pine (Callitris glaucophylla Thompson et Johnson) were investigated for their repellent activity against subterranean termite Coptotermes formosanus Shiraki worker using a two-choice semicircular filter paper test at 0.5% (w/w) concentration. Fraction CY-E2 composed of (−)-citronellic acid, guaiol, α-, β-, and γ-eudesmol isomers as well as an unknown compound, showed the highest statistically significant repellency (97.8% ± 2.2 SEM) of all fractions tested. Bioactivity-guided fractionations using high-performance liquid chromatography led to the isolation of two, oxygenated eudesmane-type sesquiterpenes with α-methylene moieties, both termite-repellent compounds. These compounds were subsequently identified as ilicic acid methyl ester (IAME) and costic acid by means of spectroscopic analyses, electron impact mass spectrometry, and nuclear magnetic resonance spectroscopy. We report the isolation of both IAME and costic acid from C. glaucophylla heartwood for the first time.
References
J Thompson LAS Johnson (1986) ArticleTitleCallitris glaucophylla, Australia's ‘White Cypress Pine’ – a new name for an old species Telopea 2 731–736
R Tohya (1997) ArticleTitleAustralia no cypress jijou (in Japanese) Wood Ind 52 259–263
P Rudman (1965) ArticleTitleThe causes of natural durability in timber. Pt. XVII The causes of decay and termite resistance in Callitris columellaris F. Muell Holzforschung 19 52–57
Y Yazaki WE Hillis (1977) ArticleTitleComponents of the extractives from Callitris columellaris F. Muell. heartwood which affect termites Holzforschung 31 188–191
JRJ French PJ Robinson Y Yazaki WE Hillis (1979) ArticleTitleBioassays from white cypress pine (Callitris columellaris F. Muell.) against subterranean termites Holzforschung 33 144–148
L Doimo (2001) ArticleTitleAzulenes, costols and S61543-lactones from cypress-pines (Callitris columellaris, C. glaucophylla and C. intratropica) distilled oils and methanol extracts J Essent Oil Res 13 25–29
L Doimo RJ Fletcher BR D'Arcy (1999) ArticleTitleComparison in the S61543-lactone content of oils and extracts from white cypress pine (Callitris glaucophylla Thompson & Johnson) J Essent Oil Res 11 415–422
Watanabe Y, Mitsunaga T, Yoshimura T. Investigating antitermitic compounds from Australian white cypress heartwood (Callitris glaucophylla Thompson et Johnson) against Coptotermes sformosanus Shiraki. J Essent Oil Res (in press)
S Yuuya H Hagiwara T Suzuki M Ando A Yamada K Suda T Kataoka K Nagai (1999) ArticleTitleGuaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokko lactone, eremanthin and their derivatives J Nat Prod 62 22–30
IH Hall KH Lee CO Starnes O Muraoka Y Sumida TG Waddell (1980) ArticleTitleAntihyperlipidemic activity of sesquiterpene lactones and related compounds J Pharm Sci 69 694–697
Y Ohtani M Hazama K Sameshima (1996) ArticleTitleCrucial chemical factors for termiticidal activity of hinoki wood (Chamaecyparis obtusa) II. Variations in termiticidal activities among five individual samples of hinoki wood (in Japanese) Mokuzai Gakkaishi 42 1228–1233
W Herz H Chikamatsu LR Tether (1965) ArticleTitleConstituents of Ambrosia ilicifolia (Gray) Payne J Org Chem 31 1632–1634
JF Sanz G Castellano JA Marco (1990) ArticleTitleSesquiterpene lactones from Artemisia herba-alba Phytochemistry 29 541–545
AS Bawdekar GR Kelkar (1965) ArticleTitleTerpenoids-LXVIII. Structure and absolute configuration of costic acid – a new sesquiterpenic acid from costus root oil Tetrahedron 21 1521–1528
KV Rao FM Alvarez (1981) ArticleTitleAntibiotic principle of Eupatorium capillifolium J Nat Prod 44 252–256
RX Tan WZ Wang (1995) ArticleTitleA new eudesmenoic acid from Artemisia phaeolepis J Nat Prod 58 288–290
YH Kuo CH Chen (1997) ArticleTitleDiversifolol, a novel rearranged eudesmane sesquiterpene from the leaves of Tithonia diversifolia Chem Pharm Bull 45 1223–1224
RX Tan ZJ Jia ZQ Yan CH Deng (1995) ArticleTitleNew eudesmane acids from Artemisia hedinii Ostenf Indian J Chem 34B 565–568
WM Daniewski W Kroszczynski E Bloszyk B Drozdz J Nawrot U Rychlewska M Budesinsky M Holub (1986) ArticleTitleSesquiterpenenoids from Dittrichia ciscosa (L.) Greuter. Their structure and deterrent activity Collect Czech Chem Commun 51 1710–1721
M García ME Sosa OJ Donadel OS Giordano CE Tonn (2003) ArticleTitleAllelochemical effects of eudesmane and eremophilane sesquiterpenes on Tribolium castaneum larvae J Chem Ecol 29 175–187
Author information
Authors and Affiliations
Corresponding author
Additional information
Part of this paper was presented at the 47th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Tokyo, November 2003
Rights and permissions
About this article
Cite this article
Watanabe, Y., Mihara, R., Mitsunaga, T. et al. Termite repellent sesquiterpenoids from Callitris glaucophylla heartwood. J Wood Sci 51, 514–519 (2005). https://doi.org/10.1007/s10086-004-0683-6
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s10086-004-0683-6