Gastrolatathioneine, an unusual ergothioneine derivative from an aqueous extract of “tian ma”: A natural product co-produced by plant and symbiotic fungus

Guo, Qing‐Lan; Lin, Sheng; Wang, Yanan; Zhu, Cheng‐Gang; Chen, Xu; Shi, Jian‐Gong

doi:10.1016/j.cclet.2016.06.040

Cited by 21 publications

(13 citation statements)

References 35 publications

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“…Other organisms acquire ERG through transportermediated uptake. Thus higher plants contain it but do not biosynthesise it (74) ; instead they and other organisms (68,75) take it up from fungal production in the soil (76)(77)(78)(79) , and possibly via actinobacterial (80) or fungal (80,81) symbionts. Animals are also considered not to biosynthesise it (82,83) , and accumulate it using a particular transporter, detailed below, via the plants and animals that they eat.…”

Section: Biosynthesis and Phylogenetic Distributionmentioning

confidence: 99%

The biology of ergothioneine, an antioxidant nutraceutical

et al. 2020

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Ergothioneine (ERG) is an unusual thio-histidine betaine amino acid that has potent antioxidant activities. It is synthesised by a variety of microbes, especially fungi (including in mushroom fruiting bodies) and actinobacteria, but is not synthesised by plants and animals who acquire it via the soil and their diet, respectively. Animals have evolved a highly selective transporter for it, known as solute carrier family 22, member 4 (SLC22A4) in humans, signifying its importance, and ERG may even have the status of a vitamin. ERG accumulates differentially in various tissues, according to their expression of SLC22A4, favouring those such as erythrocytes that may be subject to oxidative stress. Mushroom or ERG consumption seems to provide significant prevention against oxidative stress in a large variety of systems. ERG seems to have strong cytoprotective status, and its concentration is lowered in a number of chronic inflammatory diseases. It has been passed as safe by regulatory agencies, and may have value as a nutraceutical and antioxidant more generally.

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Section: Biosynthesis and Phylogenetic Distributionmentioning

confidence: 99%

The biology of ergothioneine, an antioxidant nutraceutical

et al. 2020

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“…The extraction procedures also differ from a classic protocol of utilization by decocting the medicines with water. Therefore, as part of our program to systematically study the chemical diversity of traditional Chinese medicines and their biological effects 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , an aqueous decoction of the raw lateral roots of A. carmichaelii was investigated. In previous papers, we reported four new hetisan-type, three new napeline-type, a new arcutine-type, and a novel type C 20 -diterpenoid alkaloids, twenty-six new aconitane-type C 19 -diterpenoid alkaloids including four unique glycosidic neoline derivatives with isomeric arabinosyls, two new 2-(quinonylcarboxamino)benzoates, and seven new aromatic acid derivatives, as well as solvent-/base-/acid-dependent transformation and equilibration between alcohol iminium and aza acetal forms of the napeline-type C 20 -diterpenoid alkaloids 43 , 44 , 45 , 46 , 47 , 48 , 49 .…”

Section: Introductionmentioning

confidence: 99%

C19-Diterpenoid alkaloid arabinosides from an aqueous extract of the lateral root of Aconitum carmichaelii and their analgesic activities

Guo

Xia

Meng

et al. 2018

Acta Pharmaceutica Sinica B

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Eight new C19-diterpenoid alkaloid arabinosides, named aconicarmichosides E–L (1–8), were isolated from an aqueous extract of the lateral roots of Aconitum carmichaelii (Fu Zi). Their structures were determined by spectroscopic and chemical methods including 2D NMR experiments and acid hydrolysis. Compounds 1–8, together with the previously reported four neoline 14-O-arabinosides from the same plant, represent the only examples of glycosidic diterpenoid alkaloids so far. At a dose of 1.0 mg/kg (i.p.), as compared with the black control, compounds 1, 2, and 4–6 exhibited analgesic effects with >65.6% inhibitions against acetic acid-induced writhing of mice. Structure–activity relationship was also discussed.

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“…A plausible biosynthetic pathway of 1 is proposed on the basis of a metabolic post-modification of the parent structure (Figure 3). Then the plant supposed to undergo alkylation may be with alkyl halides [26]. The quaternary amine in the aliphatic side chain was subjected to demethylation with SAM ( S -adenosylmethionine).…”

Section: Discussionmentioning

confidence: 99%

Persicaline, A New Antioxidant Sulphur-Containing Imidazoline Alkaloid from Salvadora persica Roots

et al. 2018

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Salvadora persica L. is a popular chewing stick commonly known as “miswak”. During our ongoing research activities on the chemical constituents of Salvadora persica roots, which is a new sulphur-containing imidazoline alkaloid 1,3-Dibenzyl-4-(1,2,3,4-tetrahydroxy-butyl)-1,3-dihydro-imidazole-2-thione, persicaline, (1) along with five known compounds (2–6) are identified. Compounds (2, 3) were reported for the first time from the family Salvadoraeceae. The structure of the new compound was established by extensive spectroscopic data and HR-MS. The antioxidant activities of the fractions and isolates were evaluated using different in vitro methods, such as DPPH, superoxide anion and nitric oxide radicals scavenging assays. Compound (1) showed a promising antioxidant activity with IC50 0.1, 0.08, and 0.09 µM in the three assays, respectively, comparable to ascorbic acid.

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Gastrolatathioneine, an unusual ergothioneine derivative from an aqueous extract of “tian ma”: A natural product co-produced by plant and symbiotic fungus

Cited by 21 publications

References 35 publications

The biology of ergothioneine, an antioxidant nutraceutical

The biology of ergothioneine, an antioxidant nutraceutical

C19-Diterpenoid alkaloid arabinosides from an aqueous extract of the lateral root of Aconitum carmichaelii and their analgesic activities

Persicaline, A New Antioxidant Sulphur-Containing Imidazoline Alkaloid from Salvadora persica Roots

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