Record Information |
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Version | 2.0 |
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Created at | 2022-04-29 03:49:00 UTC |
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Updated at | 2022-04-29 03:49:00 UTC |
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NP-MRD ID | NP0082737 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (-)-Maelaxin A |
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Description | (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8R,8aR,9S,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. (-)-Maelaxin A is found in Maesa laxiflora. It was first documented in 2022 (PMID: 35490355). Based on a literature review a significant number of articles have been published on (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8R,8aR,9S,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid (PMID: 35490354) (PMID: 35490353) (PMID: 35490352) (PMID: 35490351) (PMID: 35490339) (PMID: 35490350). |
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Structure | C\C=C(\C)C(=O)O[C@H]1CC(C)(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)C(O)=O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)C[C@@H](O)[C@@]12CO InChI=1S/C65H104O29/c1-12-25(2)54(83)88-36-21-60(5,6)19-29-28-13-14-33-62(9)17-16-35(61(7,8)32(62)15-18-63(33,10)64(28,11)20-34(69)65(29,36)24-68)89-59-52(94-56-46(79)42(75)39(72)30(22-66)86-56)48(47(80)49(91-59)53(81)82)90-58-51(44(77)40(73)31(23-67)87-58)93-57-50(43(76)38(71)27(4)85-57)92-55-45(78)41(74)37(70)26(3)84-55/h12-13,26-27,29-52,55-59,66-80H,14-24H2,1-11H3,(H,81,82)/b25-12-/t26-,27-,29-,30+,31+,32-,33+,34+,35-,36-,37-,38-,39-,40-,41+,42-,43+,44-,45+,46+,47-,48-,49-,50+,51+,52+,55-,56-,57-,58-,59+,62-,63+,64+,65-/m0/s1 |
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Synonyms | Value | Source |
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(2S,3S,4S,5R,6R)-6-{[(3S,4ar,6ar,6BS,8R,8ar,9S,12as,14ar,14BR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate | Generator |
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Chemical Formula | C65H104O29 |
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Average Mass | 1349.5180 Da |
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Monoisotopic Mass | 1348.66633 Da |
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IUPAC Name | (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8R,8aR,9S,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid |
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Traditional Name | (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8R,8aR,9S,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | C\C=C(\C)C(=O)O[C@H]1CC(C)(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)C(O)=O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)C[C@@H](O)[C@@]12CO |
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InChI Identifier | InChI=1S/C65H104O29/c1-12-25(2)54(83)88-36-21-60(5,6)19-29-28-13-14-33-62(9)17-16-35(61(7,8)32(62)15-18-63(33,10)64(28,11)20-34(69)65(29,36)24-68)89-59-52(94-56-46(79)42(75)39(72)30(22-66)86-56)48(47(80)49(91-59)53(81)82)90-58-51(44(77)40(73)31(23-67)87-58)93-57-50(43(76)38(71)27(4)85-57)92-55-45(78)41(74)37(70)26(3)84-55/h12-13,26-27,29-52,55-59,66-80H,14-24H2,1-11H3,(H,81,82)/b25-12-/t26-,27-,29-,30+,31+,32-,33+,34+,35-,36-,37-,38-,39-,40-,41+,42-,43+,44-,45+,46+,47-,48-,49-,50+,51+,52+,55-,56-,57-,58-,59+,62-,63+,64+,65-/m0/s1 |
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InChI Key | UQBYDYIYFPALPT-LCZFIIHLSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Species Name | Source | Reference |
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Maesa laxiflora | Plant | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene glycosides |
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Direct Parent | Triterpene saponins |
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Alternative Parents | |
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Substituents | - Triterpene saponin
- Triterpenoid
- Oligosaccharide
- Fatty acyl glycoside
- O-glucuronide
- 1-o-glucuronide
- Glucuronic acid or derivatives
- O-glycosyl compound
- Glycosyl compound
- Fatty acid ester
- Beta-hydroxy acid
- Fatty acyl
- Pyran
- Oxane
- Hydroxy acid
- Dicarboxylic acid or derivatives
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Carboxylic acid
- Carboxylic acid derivative
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Baumbusch J, Blakey EP, Carapellotti AM, Dohmen M, Fick DM, Kagan SH, Melendez-Torres GJ, Morgan BE, Munsterman E, Resnick B, Young HM: Nurses and the decade of healthy ageing: An unprecedented opportunity. Int J Older People Nurs. 2022 May;17(3):e12469. doi: 10.1111/opn.12469. [PubMed:35490355 ]
- Hill NL, Bratlee-Whitaker E, Wion RK, Madrigal C, Bhargava S, Mogle J: Factors that influence the emotional impact of memory problems in older adults: A qualitative descriptive study. Int J Older People Nurs. 2022 May;17(3):e12439. doi: 10.1111/opn.12439. Epub 2021 Dec 8. [PubMed:35490354 ]
- Polastri M, Loforte A, Swol J: "Racing team" or "orchestra" approach? Two different perspectives on providing care in emergency and critical settings. Artif Organs. 2022 May 1. doi: 10.1111/aor.14274. [PubMed:35490353 ]
- Wei YF, Wang L, Xia ZY, Gou M, Sun ZY, Lv WF, Tang YQ: Microbial communities in crude oil phase and filter-graded aqueous phase from a Daqing oilfield after polymer flooding. J Appl Microbiol. 2022 May 1. doi: 10.1111/jam.15603. [PubMed:35490352 ]
- Authors unspecified: CORRIGENDUM. Transbound Emerg Dis. 2022 May 1. doi: 10.1111/tbed.14572. [PubMed:35490351 ]
- Cleland JGF, Bristow MR, Freemantle N, Olshansky B, Gras D, Saxon L, Tavazzi L, Boehmer J, Ghio S, Feldman AM, Daubert JC, de Mets D: The effect of cardiac resynchronization without a defibrillator on morbidity and mortality: an individual patient data meta-analysis of COMPANION and CARE-HF. Eur J Heart Fail. 2022 May 1. doi: 10.1002/ejhf.2524. [PubMed:35490339 ]
- Niu F, Zhang B, Du Y, Hu D, Ma S, Feng ZJ, Zhang Y, Pan W: Effect of microcrystalline cellulose under different hydrolysis durations on the stability of thyme oil emulsion. J Food Sci. 2022 Jun;87(6):2707-2717. doi: 10.1111/1750-3841.16154. Epub 2022 May 1. [PubMed:35490350 ]
- Arnold F, Wobser R, Kalbhenn J, Westermann L: Integration of sustained low-efficiency dialysis into extracorporeal membrane oxygenation circuit in critically ill COVID-19 patients-A feasibility study. Artif Organs. 2022 May 1. doi: 10.1111/aor.14277. [PubMed:35490349 ]
- Lavryk OA, Bandi B, Shawki SF, Floruta C, Xue J, Valente MA, Steele SR, Hull TL: Turnbull-Cutait abdominoperineal pull-through operation: The Cleveland Clinic experience in the 21st century. Colorectal Dis. 2022 May 1. doi: 10.1111/codi.16163. [PubMed:35490348 ]
- Cui N, Liu S, Zheng Z, Pi Z, Liu Z, Song F: The chemical profile of Fubai Chrysanthemum (Fubaiju) and its mechanism in preventing cataract based on ultrahigh-performance liquid chromatography coupled with mass spectrometry and network pharmacology. J Sep Sci. 2022 May 1. doi: 10.1002/jssc.202100832. [PubMed:35490347 ]
- Fletcher J, Drami I, Burns E, Mughal M, West MA, Corr A, Jenkins JT: Open sidewall excision for recurrent rectal cancer with gluteal flap reconstruction - a video vignette. Colorectal Dis. 2022 May 1. doi: 10.1111/codi.16162. [PubMed:35490346 ]
- Ramsden SC, Pergjika A, Janssen AC, Mudahar S, Fawcett A, Walkup JT, Hoffmann JA: A systematic review of the effectiveness and safety of droperidol for pediatric agitation in acute care settings. Acad Emerg Med. 2022 May 1. doi: 10.1111/acem.14515. [PubMed:35490341 ]
- Diskin CJ, Maldonado R, Leon J, Dansby LM, Carter TB, Radcliff L, Diskin CD: How effective is rescue therapeutic plasma exchange in treatment of SARS-Coronavirus-2? Ther Apher Dial. 2022 May 1. doi: 10.1111/1744-9987.13862. [PubMed:35490343 ]
- Long B, Gottlieb M: Mechanical thrombectomy for anterior circulation stroke beyond 6 h from stroke onset. Acad Emerg Med. 2022 Jun;29(6):801-803. doi: 10.1111/acem.14516. Epub 2022 May 22. [PubMed:35490342 ]
- Shine RJ, Glyn T, Frizelle F: Pelvic exenteration: a review of current issues/controversies. ANZ J Surg. 2022 Nov;92(11):2822-2828. doi: 10.1111/ans.17734. Epub 2022 May 1. [PubMed:35490337 ]
- Bini Viotti J, Natori Y, Loebe M: Infections in LVAD patients. J Card Surg. 2022 Jul;37(7):2090-2091. doi: 10.1111/jocs.16576. Epub 2022 May 1. [PubMed:35490345 ]
- Bianchi G, Memeo R, Ferraro V, Madaro A, Schena CA, De' Angelis N: Rectal adenocarcinoma with synchronous liver metastasis: Robotic liver and rectal resection with partial mesorectal excision: A Video Vignette. Colorectal Dis. 2022 Oct;24(10):1251-1252. doi: 10.1111/codi.16161. Epub 2022 May 24. [PubMed:35490344 ]
- Haile-Mariam T, Nakitende D, Wilder M, Omorogbe A, Haywood Y, Terry A, Powell NN, Blanchard J: Judge Ketanji Brown Jackson's victory is our own. Acad Emerg Med. 2022 Aug;29(8):1040-1041. doi: 10.1111/acem.14514. Epub 2022 May 16. [PubMed:35490340 ]
- Badhusha A, Nafeez Ahmed A, Suryakodi S, Abdul Wazith MJ, Mithra S, Kanimozhi K, Abdul Majeed S, Taju G, Sahul Hameed AS: First report on the occurrence of cyprinid herpesvirus 3 in koi carp (Cyprinus carpio koi) in India. J Fish Dis. 2022 Aug;45(8):1087-1098. doi: 10.1111/jfd.13631. Epub 2022 May 1. [PubMed:35490338 ]
- Dhillon K, Manji J, Tapia Cespedes M, Prasad J, Kleid S, Flatman S, Nguyen K, McLean T, Magarey M: Use of telemedicine consultations in head and neck cancer: patient perceptions, acceptability and accessibility. ANZ J Surg. 2022 Jun;92(6):1415-1422. doi: 10.1111/ans.17722. Epub 2022 May 1. [PubMed:35490336 ]
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