Showing papers on "Terpene published in 1973"
TL;DR: A novel C(35) terpene and its monounsaturated analogue were isolated from cultures of Acetobacter xylinum, together with traces of their C(36) homologues, found to be hopane derivatives substituted by a five-carbon chain bearing four vicinal hydroxyl groups.
Abstract: A novel C35 terpene and its monounsaturated analogue were isolated from cultures of Acetobacter xylinum, together with traces of their C36 homologues. These substances were found to be hopane derivatives substituted by a five-carbon chain bearing four vicinal hydroxyl groups. For the parent hydrocarbon the term bacteriohopane is proposed. The elucidation of the structures utilized high-resolution mass spectrometry of the terpenes, degradation to C32 hydrocarbons and detailed mass-spectrometric comparison of these with C32 hydrocarbons synthesized from known pentacyclic triterpenes. High-resolution mass-spectral data of the terpenes are presented. N.m.r. data are in agreement with the proposed structures, which are further supported by the isolation from the same organism of 22-hydroxyhopane and derivative hopene(s).
76 citations
TL;DR: It is concluded that the formation of diols is a common intermediate in the fungal metabolism of monocyclic terpenes.
Abstract: The transformation of three monocyclic terpenes by three soil microorganisms have been studied. The organisms were isolated on, and grew rapidly in, mineral salts medium containing the appropriate terpene substrates as sole carbon sources. These organisms belong to the class Fungi Imperfecti, and two of them have been tentatively identified as Cladosporium species. A Cladosporium species designated T(1) was isolated from terpene-soaked soil, using 1-menthene as the sole source of carbon. The major catabolic product isolated from the growth medium of this organism was found to be a cyclic 1,2-diol identified as trans-p-methane-1,2-diol. A similar but biochemically distinct Cladosporium sp. designated T(7) was isolated on D-limonene. After growth, the medium of this organism contained 1.5 g/liter of the analogous product, trans-limonene-1,2-diol. Minor quantities of the corresponding cis-1,2-diol were also isolated. The third organism, designated as laboratory culture T(8), was isolated on 3-menthene and yielded a diol identified as trans-p-menthane-3,4-diol. From these results it is concluded that the formation of diols is a common intermediate in the fungal metabolism of monocyclic terpenes.
43 citations
TL;DR: The chromatographic analysis of the volatile leaf oil of Pinus pinaster Ait showed 42% of monoterpene hydrocarbons and 23% of oxygenated compounds including esters (linalyl, bornyl, geranyl, neryl and farnesyl acetates) were also identified as discussed by the authors.
39 citations
TL;DR: The terpene alcohol linalool (3,7-dimethyl-1,6-octadien-3-ol) has been isolated from volatiles produced by Ips paraconfusus females and from frass produced by I. pini males, both insects boring in ponderosa pine.
32 citations
TL;DR: Squalene derived from mevalonate-2-14C in incorporation times of 1, 4 and 7 hours was degraded chemically and shown to be equivalently labelled, according to theory, in the isopentenyl pyrophosphate-derived and dimethylallyl pyrophophosphate -derived portions of the molecule.
23 citations
23 citations
19 citations
TL;DR: The major monoterpenoid hydrocarbons found to be present with only traces of camphene include alpha-pinene, beta-pinenes, delta(3)-carene, myrcene, linonene, and delta-phellandrene.
14 citations
7 citations
TL;DR: In this article, substituted esters (3c−h) and amides (4a−l) of thujic acid (3a) were prepared using acid chloride as intermediate and were screened for their insect repellent and attractant potential.
Abstract: Representatively substituted esters (3c–h) and amides (4a–l) of thujic acid (3a) were prepared using the acid chloride as intermediate and were screened for their insect repellent and attractant potential. N,N-Diethyl thujamide (4d) was found to be a highly active repellent of the yellow fever mosquito (Aedes aegypti) as well as of other insect species.
TL;DR: In this paper, cell-free extracts prepared from Wedgwood iris (Iris hollandica Hoog) were used to extract terpene alcohols and acid-hydrolyzable terpenes.
Abstract: Excised shoots and cell-free extracts prepared from Wedgwood iris (Iris hollandica Hoog. "Wedgwood") shoots metabolized (14)C-labeled mevalonic acid (MVA). By using cell-free extracts, the (14)C from MVA-1-(14)C was recovered as (14)CO(2), while that from MVA-2-(14)C was recovered as neutral terpenes, acid-hydrolyzable terpenes, or (14)CO(2). Also, under optimal incubation conditions, 12.8 nanomoles R-MVA-2-(14)C was incorporated into neutral terpenes per milligram fresh weight per hour. In contrast, excised shoots incorporated only 0.58 nanomoles R-MVA-2-(14)C per mg fresh weight per hour. Labeled products identified from the cell-free system were squalene, farnesol, geranylgeraniol, and compounds that are converted to farnesol and geranylgeraniol after alkaline hydrolysis. Squalene and a 4,4-dimethylsterol were identified as products from excised shoots but not the terpene alcohols or the alkaline-hydrolyzable compounds.
Journal Article•
01 Jan 1973
01 Jan 1973
TL;DR: Labeled products identified from thecell-free system were squalene, farnesol, geranylgeraniol, and compounds that are converted to farnesols and geranylgersaniol afteralkalinehydrolysis, but not theterpenealcohoLs or the alkaline-Hydrolyzable compounds.
Abstract: Excisedshootsand cell-free extractspreparedfrom Wedgwoodiris(Iris hollandica Hoog."Wedgwood") shoots metabolized '4C-labeled mevalonicacid(MVA).Byusingcellfreeextracts, the"C fromMVA-1-`C was recovered as 'CO2, whilethatfromMVA-2V"C was recovered as neutralterpenes, acid-hydrolyzable terpenes, or "4CO2. Also, underoptimal incubationconditions, 12.8nanomolesR-MVA-2-"Cwas incorporated intoneutral terpenes permilligram freshweight per hour.In contrast, excisedshootsincorporated only0.58 nanomoles R-MVA-2-"C per mg freshweight per hour.Labeled products identified fromthecell-free systemwere squalene, farnesol, geranylgeraniol, andcompounds thatare converted to farnesol and geranylgeraniol afteralkalinehydrolysis. Squalene anda 4,4-dimethylsterol were identified as products fromexcised shootsbutnot theterpenealcohoLs or the alkaline-hydrolyzable compounds.