4955-03-7Relevant academic research and scientific papers
Alcohol absorption inhibitors from bay leaf (Laurus nobilis): Structure-requirements of sesquiterpenes for the activity
Yoshikawa, Masayuki,Shimoda, Hiroshi,Uemura, Toshiaki,Morikawa, Toshio,Kawahara, Yuzo,Matsuda, Hisashi
, p. 2071 - 2077 (2007/10/03)
Through a bioassay-guided separation using inhibitory activity on blood ethanol elevation in oral ethanol-loaded rat, various sesquiterpenes having an α-methylene-γ-butyrolactone moiety, costunolide (1), dehydrocostus lactone (2), zaluzanin D (3), reynosin (4), santamarine (5), 3α-acetoxyeudesma-1,4(15),11(13)-trien-12,6α-olide (6) and 3-oxoeudesma-1,4,11(13)-trien-12,6α-olide (7), were isolated as the active principle from the leaves of Laurus nobilis (bay leaf, laurel). In order to characterize the structure requirement for the activity, several reduction products (2a-2d) and amino acid adducts (2e, 2f) of the α-methylene-γ-butyrolactone moiety were synthesized from 2 and the inhibitory activities of these sesquiterpenes, together with α-methylene-γ-butyrolactone (12) and its related compounds (13-16), were examined. These results indicated that the γ-butyrolactone or γ-butyrolactol moiety having α-methylene or α-methyl group was essential for the inhibitory activity on ethanol absorption. Since 1, 2 and 12 showed no significant effect on glucose absorption, these sesquiterpenes appeared to selectively inhibit ethanol absorption. In addition, the acute toxicities of 1 and 2 in a single oral administration were found to be lower than that of 12. Copyright (C) 2000 Elsevier Science Ltd.
Microbial transformation of sesquiterpene lactones by the fungi Cunninghamella echinulata and Rhizopus oryzae
Barrero, Alejandro F.,Oltra, J. Enrique,Raslan, Delio S.,Saude, Denia A.
, p. 726 - 729 (2007/10/03)
Incubations of the fungi Cunninghamella echinulata and Rhizopus oryzae with the sesquiterpene lactones (+)-costunolide (1), (+)-cnicin (2), (+)- salonitenolide (3), (-)-dehydrocostuslactone (4), (-)-lychnopholide (5), and (-)-eremantholide C (6) were performed. Incubation of 1 with C. echinulata afforded Δ(11(13))-dihydrogenation and Δ(1(10))-epoxidation products (7- 10). C. echinulata also hydrolyzed the side chain of 2, and transformed 4 into (+)-11α,13-dihydrodehydrocostuslactone (12), a new natural product. R. oryzae converted 4 into both Δ(11(13))-dihydrogenation and Δ(10(14))- epoxidation products (16 and 17). Both fungi transformed 5 into (-)-16-(1- methyl-1-propenyl)eremantholanolide (13), providing experimental evidence for the biosynthesis of the eremantholide hemiketal unit. Compounds 3 and 6 were not metabolized by either fungus under the test conditions.
Developing new herbicide models from allelochemicals
Macias, Francisco A.,Galindo, Juan C. G.,Molinillo, Jose M. G.,Castellano, Diego,Velasco, Paul F.,Chinchilla, David
, p. 662 - 665 (2007/10/03)
Plants contain allelochemicals which are their own defence systems and can act as herbicides. Selected examples of guaianolides and heliannuols, which are sesquiterpenes, are discussed in the context of their potential use as natural herbicide templates.
Guaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokko lactone, eremanthin, and their derivatives
Yuuya, Saori,Hagiwara, Hisahiro,Suzuki, Toshio,Ando, Masayoshi,Yamada, Atsushi,Suda, Kouji,Kataoka, Takao,Nagai, Kazuo
, p. 22 - 30 (2007/10/03)
The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from l-α- santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an α-methylene γ- lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.
TOTAL SYNTHESES OF MOKKO LACTONE, DEHYDROCOSTUS LACTONE, AND EREMANTHIN
Ando, Masayoshi,Ono, Akio,Takase, Kahei
, p. 493 - 496 (2007/10/02)
A series of guaianolides such as mokko lactone, dehydrocostus lactone, and eremanthin which posses a common structural unit in A ring have been synthesized from 1-oxoeudesm-2-eno-13,6α-lactone in 7 steps.The key step involves solvolytic rearrangement of 1β-mesyloxyeudesm-4(14)-eno-13,6α-lactone.
