Histopathology of the Nasal Cavity in Laboratory Animals Exposed to Cigarette Smoke and Other Irritants
D. V. M. Gerd Reznik, Sherman F. Stinson in Nasal Tumors in Animals and Man, 2017
The Dutch group of Feron, Kruysse, and others included, in their research program on the biological effects of cigarette smoke components, the aldehydes acrolein and acetaldehyde and the unsaturated lactone butenolide. In different experiments, they exposed hamsters to acrolein,63 acetaldehyde,64 and butenolide65 at maximum concentrations and durations of 5 ppm for 13 weeks, 4560 ppm for 90 days and 130 ppm for 13 weeks, respectively (all 6 hr/day, 5 days/week). Both aldehydes, in maximum concentration, caused necrotizing rhinitis and keratinizing squamous metaplasia of respiratory, if not olfactory, epithelia. The effects of butenolide did not exceed focal cuboidal or squamous metaplasia. Damage by the aldehydes was more severe in the nasal cavity or upper conducting airways than lower in the respiratory tract, in accordance with their differential uptake in the dog. Changes attributed to butenolide were confined entirely to the nasal cavity. The dorsomedial part of the nasomaxillary region was specified as a site of injury for all three smoke constituents.
Biotransformation of Monoterpenoids by Microorganisms, Insects, and Mammals
K. Hüsnü Can Başer, Gerhard Buchbauer in Handbook of Essential Oils, 2020
Metabolic pathways of citronellol (258), citronellal (261), geraniol (271), nerol (272), citral [neral (275) and geranial (276)], and myrcene (302) are summarized in Figure 22.203 (Seubert and Fass, 1964a,b; Hayashi et al., 1968; Rama Devi and Bhattacharyya, 1977a,b). Geraniol (271) is formed from citronellol (258), nerol (272), linalool (206), and geranyl acetate (270) and metabolized through 10 pathways. That is, compound 271 is hydrogenated to give citronellol (258), which is metabolized to 2,8-dihydroxy-2,6-dimethyl octane (260) via 6,7-epoxycitronellol (268), isopulegol (267), limonene (68), 3,7-dimethyloctane-1,8-diol (266) via 3,7-dimethyl-6-octene-1,8-diol (265), 267, citronellal (261), dihydrocitronellol (259), and nerol (272). Citronellyl acetate (269) and isopulegyl acetate (301) are hydrolyzed to citronellol (258) and isopulegol (267), respectively. Compound 261 is metabolized via pulegol (263) and isopulegol (267) to menthol (137). Compound 271 and 272 are isomerized to each other. Compound 272 is metabolized to 271, 258, citronellic acid (262), nerol-6-,7-epoxide (273), and neral (275). Compound 272 is metabolized to neric acid (277). Compounds 275 and 276 are isomerized to each other. Compound 276 is completely decomposed to CO2 and water via geranic acid (278), 2,6-dimethyl-8-hydroxy-7-oxo-2-octene (279), 6-methyl-5-heptenoic acid (280), 7-methyl-3-oxo-6-octenoic acid (283), 6-methyl-5-heptenoic acid (284), 4-methyl-3-heptenoic acid (284), 4-methyl-3-pentenoic acid (285), and 3-methyl-2-butenoic acid (286). Furthermore, compound 271 is metabolized via 3-hydroxymethyl-2,6-octadiene-1-ol (287), 3-formyl-2,6-octadiene-1-ol (288), and 3-carboxy-2,6-octadiene-1-ol (289) to 3-(4-methyl-3-pentenyl)-3-butenolide (290). Geraniol (271) is also metabolized to 3,7-dimethyl-2,3-dihydroxy-6-octen-1-ol (292), 3,7-dimethyl-2-oxo-3-hydroxy-6-octen-1-ol (293), 2-methyl-6-oxo-2-heptene (294), 6-methyl-5-hepten-2-ol (298), 2-methyl-2-heptene-6-one-1-ol (295), and 2-methyl-γ-butyrolactone (296). Furthermore, 271 is metabolized to 7-methyl-3-oxo-6-octanoic acid (299), 7-hydroxymethyl-3-methyl-2,6-octadien-1-ol (291), 6,7-epoxygeraniol (274), 3,7-dimethyl-2,6-octadiene-1,8-diol (300), and 3,7-dimethyloctane-1,8-diol (266).
Anti-biofilm effect of a butenolide/polymer coating and metatranscriptomic analyses
Published in Biofouling, 2018
Wei Ding, Chunfeng Ma, Weipeng Zhang, Hoyin Chiang, Chunkit Tam, Ying Xu, Guangzhao Zhang, Pei-Yuan Qian
Butenolide was synthesized by Shanghai Medicilon Inc. (Shanghai, China). The structure is shown in Figure 1. DCOIT was obtained from The Dow Chemical Company (Midland, MI, USA). The molar masses and dispersity of the poly (ε-caprolactone)-based polyurethane used in the present study were 27,000 and 1.87, respectively. Poly (ε-caprolactone)-based polyurethane was prepared by polyaddition according to the steps described in a previous study (Ma et al. 2013), and a general experimental procedure was as follows: first, isophorone diisocyanate was allowed to react with poly (ε-caprolactone) diol at 70°C for 1 h in tetrahydrofuran under a nitrogen atmosphere, yielding a prepolymer. Subsequently, 1,4-butanediol and dibutyltin dilaurate (DBTDL) were added as the chain extender and catalyst, respectively, and the mixture was allowed to react at 80°C for 3 h. The product was precipitated into hexane twice, filtered, and dried under vacuum at 40°C for 24 h.
Marine natural products as antifouling molecules – a mini-review (2014–2020)
Published in Biofouling, 2020
Ling-Li Liu, Chuan-Hai Wu, Pei-Yuan Qian
The degradation kinetics of butenolide under diverse environmental conditions were determined in comparison with a positive control DCOIT to ascertain the environmental safety of butenolide. Similar half-lives under different temperatures were observed for butenolide (> 64 d at 4 °C, 30.5 d at 25 °C and 3.9 d at 40 °C) and DCOIT (> 64 d at 4 °C, 27.9 d at 25 °C and 4.5 d at 40 °C) and exposure to sunlight accelerated the degradation of butenolide and DCOIT. Biodegradation resulted in the fastest degradation rate for butenolide in natural seawater, with a half-life of 0.5 d, whilst no obvious degradation was detected for DCOIT after incubation for 4 d. The accelerated cell growth of the marine diatom Skeletonema costatum suggested that the toxicity of seawater decreased gradually without the formation of more toxic by-products. These results provided compelling evidence for supporting butenolide as a promising AF compound (Chen, Xu, et al. 2015).
Combining a bio-based polymer and a natural antifoulant into an eco-friendly antifouling coating
Published in Biofouling, 2020
Ho Yin Chiang, Jiansen Pan, Chunfeng Ma, Pei-Yuan Qian
Poly(L-lactide) diol (PLA, Mw = 2,000g mol−1) from Daigang Biomaterial (Jinan, China) and 1,4-butanediol (BDO) from Shanghai Aladdin Bio-Chem Technology Co., Ltd (Shanghai, China) were dried at 110°C under reduced pressure for 2h prior to use. Isophorone diisocyanate (IPDI) and dibutyltin dilaurate (DBTDL) from Shanghai Aladdin Bio-Chem Technology Co., Ltd (Shanghai, China) were used as received. Tetrahydrofuran (THF) from Innochem (Beijing) Technology Co., Ltd (Beijing, China) was refluxed over CaH2 and distilled prior to use. Rosin, a naturally occurring resin that mainly consists of abietic acid (C19H29COOH), was obtained from Wuzhou Sun Shine Forestry & Chemicals Co., Ltd (Guangxi, China). Synthesized 5-octylfuran-2(5H)-one (butenolide) with a purity exceeding 99% was purchased from ChemPartner Co., Ltd (Shanghai, China) and used as received. Artificial seawater (ASW) was prepared according to ASTM D1141-98 (2013b). Epoxy panels and polyvinyl chloride (PVC) panels were obtained from local hardware stores in Hong Kong.
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