The biosynthesis of annuloline, a unique oxazole alkaloid

O'Donovan, D. G.; Horan, H.

doi:10.1039/j39710000331

Cited by 16 publications

(7 citation statements)

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“…UV, Xma, (MeOH): 209 nm (e 1400). NMR shifts ( ) from Me4Si, assignments based on assessing the number of attached protons and the COSY data in Table I [[atom number], l3C 's at 75 MHz, 7.2, S's at 300 MHz, (Zs (hertz) at 300 MHz)]: (MeOH-d4) [1] 19.9, 1.13 (d, J = 6.6, Me); [2] 67.7, 3.90 (dq, J = 6.6, 3.6); [3] 78.8, 3.16 (dd, J = 6.6, 3.3); [4] 71.7, 3.65 (ddd, J = 6.6, 6.0, 2.4); [5] 40.4, 2.22 (ddd, J = 14.1, 7.2, 2.7), 1.88 (ddd = 14.1, 10.1, 6.0); [6] 66.2, 4.88 (dd, J = 10.1, 7.2); [7] 145.6; [8] 138.0, 7.84 (s); [9] 159.6; [10] 62. 8, 7.10 (s); [11] 147.6; [12] 127.5, 7.30 (s); Preparation of Dioxolane 9.…”

Section: Methodsmentioning

confidence: 99%

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Unusual anthelminthic oxazoles from a marine sponge

Adamczeski¹,

Quiñoá²,

Crews³

1988

J. Am. Chem. Soc.

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Section: Methodsmentioning

confidence: 99%

“…[2] 74.6, 3.88 (dq, J = 8.4, 6.0); [3] 82.6, 3.72 (dd, J = 8.4, 4.5); [4] 76.6, 4.54 (ddd, J = 8.7, 4.5, 2.4); [5] 31.6, 2.62 (ddd, J = 15.3, 8.7, 2.4), 2.31 (ddd, J = 15. 3, 8.7, 8.4); [6] 67.0, 4.63 (dd, J = 8.7, 8.4); [7] 177.2; [8] 109.6; [9] 27.3, 1.40 (s); [10] 26.9, 1.30 (s). C10H16O5 LREIMS m/z (rel intens): 216 [M+ (7)].…”

Section: Methodsmentioning

confidence: 99%

Unusual anthelminthic oxazoles from a marine sponge

Adamczeski¹,

Quiñoá²,

Crews³

1988

J. Am. Chem. Soc.

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“…Regarding C. dactylon and L. multiflorum , four cinnamic acids were described [caffeic acid ( 80 ), cinnamic acid ( 81 ), p -coumaric acid ( 82 ) and ferulic acid ( 84 )] ( Table S1 ). In the first species, these were retrieved from the 80% aqueous ethanol and methanol extracts, [ 58 , 64 , 82 , 83 ], while in the second from the cell walls [ 84 , 85 ]. In the case of I. cylindrica [ 86 , 87 , 88 ], caffeic acid ( 80 ), p -coumaric acid ( 82 ), 1- O - p -coumaroylglycerol ( 83 ) and ferulic acid ( 84 ) were isolated from 70% aqueous ethanol extract.…”

Section: Phytoconstituents Of Halophytic Grassesmentioning

confidence: 99%

Halophytic Grasses, a New Source of Nutraceuticals? A Review on Their Secondary Metabolites and Biological Activities

Faustino

Pinto

2019

IJMS

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The Poaceae family, known as grasses, is distributed worldwide and is considered the most important group of monocotyledonous crops. Salt stress is multifactorial, therefore to survive, halophytes evolved a variety of adaptations, which include the biosynthesis of different primary and secondary metabolites. This trait enhances the accumulation of important families of compounds crucial to the prevention of a variety of chronic diseases. Besides, if proven edible, these species could cope with the increased soil salinity responsible for the decline of arable land due to their high nutritional/nutraceutical value. Herein, the phytochemical investigations performed in halophytes from the Poaceae family as well as their biological properties were explored. Among the 65 genera and 148 species of known halophytic grasses, only 14% of the taxa were studied phytochemically and 10% were subjected to biological evaluation. Notably, in the studied species, a variety of compound families, as well as bioactivities, were demonstrated, highlighting the potential of halophytic grasses.

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“…[3] Naturally occurring oxazoles are usually found with a 2,4-substitution pattern, [4] a consequence of their biosynthetic assembly from serine residues, although 2,5-substituted oxazole natural products are known. [5] Synthesis and study of biological activities of compounds having both benzimiadazole and oxazole moieties have attracted our attention because both these moieties exhibit considerable biological activity independently, and when present together they may have synergistic affects leading to more potent molecules.…”

Section: Introductionmentioning

confidence: 99%