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Molecules 2016, 21(5), 619; doi:10.3390/molecules21050619

Identification and Synthesis of (Z,Z)-8,11-Heptadecadienyl Formate and (Z)-8-Heptadecenyl Formate: Unsaturated Aliphatic Formates Found in the Unidentified Astigmatid Mite, Sancassania sp. Sasagawa (Acari: Acaridae)

1
Faculty of Bioenvironmental Science, Kyoto Gakuen University, 1-1 Nanjo, Sogabe, Kameoka 621-8555, Japan
2
Institute of Applied Biochemistry, The University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
3
Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan
4
Asano Active Enzyme Molecule Project, JST, ERATO, Imizu, Toyama 939-0398, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 12 April 2016 / Revised: 4 May 2016 / Accepted: 5 May 2016 / Published: 11 May 2016
(This article belongs to the Section Natural Products)
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Abstract

We identified two aliphatic formates, (Z,Z)-8,11-heptadecadienyl formate and (Z)-8-heptadecenyl formate in the opisthonotal gland secretions of an unidentified acarid species, namely Sancassania sp. Sasagawa. Both compounds were isolated using silica gel column chromatography and the structures were elucidated by 1H-NMR and GC/FT-IR. Further information on the double bond positions was obtained by GC-MS analysis of the corresponding dimethyl disulfide derivatives. Based on the estimated structures of the two formates and using linoleic and oleic acids as the respective starting materials, a simple four-step synthesis was achieved via Barton decarboxylation as the key step. The aliphatic formates identified in acarids thus far are neryl formate ((Z)-3,7-dimethylocta-2,6-dienyl formate) and lardolure (1,3,5,7-tetramethyldecyl formate), and both have been reported to have pheromone functions. The biological function of the two formates isolated in this study is currently being investigated. Although we can speculate that the two compounds were biosynthesized from linoleic and oleic acid, there is a possibility that the synthetic processes featured a novel chain shortening and formic acid esterification mechanism. View Full-Text
Keywords: Sancassania sp. Sasagawa; mite; aliphatic formate; (Z,Z)-8,11-heptadecadienyl formate; (Z)-8-heptadecenyl formate; Barton decarboxylation Sancassania sp. Sasagawa; mite; aliphatic formate; (Z,Z)-8,11-heptadecadienyl formate; (Z)-8-heptadecenyl formate; Barton decarboxylation
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MDPI and ACS Style

Shimizu, N.; Sakata, D.; Miyazaki, H.; Shimura, Y.; Kuwahara, Y. Identification and Synthesis of (Z,Z)-8,11-Heptadecadienyl Formate and (Z)-8-Heptadecenyl Formate: Unsaturated Aliphatic Formates Found in the Unidentified Astigmatid Mite, Sancassania sp. Sasagawa (Acari: Acaridae). Molecules 2016, 21, 619.

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