Lichexanthone

Lichexanthone

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Lichexanthone
Category Others
Catalog number BBF-04970
CAS 15222-53-4
Molecular Weight 286.28
Molecular Formula C16H14O5

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Description

Lichexanthone is separated from the bark of Cupania cinerea. It has a role as a plant metabolite.

Specification

IUPAC Name 1-hydroxy-3,6-dimethoxy-8-methylxanthen-9-one
Canonical SMILES CC1=CC(=CC2=C1C(=O)C3=C(C=C(C=C3O2)OC)O)OC
InChI InChI=1S/C16H14O5/c1-8-4-9(19-2)6-12-14(8)16(18)15-11(17)5-10(20-3)7-13(15)21-12/h4-7,17H,1-3H3
InChI Key QDLAGTHXVHQKRE-UHFFFAOYSA-N

Reference Reading

1. Lichens of Parmelioid Clade as Promising Multitarget Neuroprotective Agents
Víctor Sieteiglesias, Elena González-Burgos, Paloma Bermejo-Bescós, Pradeep K Divakar, María Pilar Gómez-Serranillos Chem Res Toxicol. 2019 Jun 17;32(6):1165-1177. doi: 10.1021/acs.chemrestox.9b00010. Epub 2019 Jun 7.
Neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease are multifactorial disorders which are increasing in incidence and prevalence over the world without existing effective therapies. The search for new multitarget compounds is the latter therapeutic strategy to address these pathological conditions. Lichens have an important and unknown therapeutic value attributed to their unique secondary metabolites. The aim of this study is to evaluate for the first time the in vitro neuroprotective activities and molecular mechanisms underlying methanol extracts of lichens of the parmelioid clade and to characterize major bioactive secondary metabolites responsible for their pharmacological actions. Of the 15 parmelioid lichen species, our results showed that Parmotrema perlatum and Hypotrachyna formosana methanol extracts exhibited high antioxidant activity as evidenced in ORAC, DPPH, and FRAP assays. Then, SH-SY5Y cells were pretreated with methanol extracts (24 h) followed by Fenton reagent exposure (2 h). Pretreatments with these two more antioxidant methanol lichen extracts increased cell viability, reduced intracellular ROS, prevented oxidative stress biomarkers accumulation, and upregulated antioxidant enzyme (CAT, SOD, GR, and GPx) activity compared to Fenton reagent cells. The neuroprotective activity was much higher for H. formosana than for P. perlatum, even equal to or higher than Trolox (reference compound). Moreover, H. formosana extracts inhibited both AChE and BuChE activities in a concentration dependent manner, and P. perlatum only showed concentration dependent activity against AChE. Finally, chemical composition analysis using TLC and HPLC methods revealed that physodic acid, lividic acid, and lichexanthone are major secondary metabolites in H. formosana and stictic acid and constictic acid are in P. perlatum. These results demonstrated that P. perlatum and, specially, H. formosana are promising multitargeted neuroprotective agents due to their antioxidant and AChE and BuChE inhibition activities.
2. New species and records of Pyxine (Caliciaceae) in China
Mei-Xia Yang, Xin-Yu Wang, Dong Liu, Yan-Yun Zhang, Li-Juan Li, An-Cheng Yin, Christoph Scheidegger, Li-Song Wang MycoKeys. 2019 Jan 29;(45):93-109. doi: 10.3897/mycokeys.45.29374. eCollection 2019.
In this study, the diversity of Pyxine Fr. in China was assessed based on morphological and chemical traits and molecular data are inferred from ITS and mtSSU sequences. Nineteen species were recognised, including three that are new to science (i.e. P.flavicans M. X. Yang & Li S. Wang, P.hengduanensis M. X. Yang & Li S. Wang and P.yunnanensis M. X. Yang & Li S. Wang) and three records new to China were found (i.e. P.cognata Stirt., P.himalayensis Awas. and P.minuta Vain.). Pyxineyunnanensis is diagnosed by the small size of the apothecia, a white medulla of the stipe and the presence of lichexanthone. Pyxineflavicans is characterised by broad lobes, a pale yellow medulla of the stipe and the presence of atranorin. Pyxinehengduanensis can be distinguished by its pale yellow medulla, marginal labriform soralia and the absence of atranorin. Detailed descriptions of each new species are presented, along with a key to the known species of Pyxine in China.
3. Rubescins I and J, further limonoid derivatives from the stem bark of Trichilia rubescens (Meliaceae)
Armelle Tontsa Tsamo, Raduis Melong, Pierre Mkounga, Augustin Ephrem Nkengfack Nat Prod Res. 2019 Jan;33(2):196-203. doi: 10.1080/14786419.2018.1443087. Epub 2018 Mar 3.
Two new tetranorterpenoid derivatives named rubescins I (1) and J (2), were isolated along with six known compounds including rubescin D (3), lichexanthone (4), scopoletin (5), scopoletin O-glycoside (6), β-sitosterol (7) and stigmasterol (8) from the stem bark of Trichilia rubescens (Meliaceae). The structures of the compounds were determined by means of MS, different NMR and by comparison with related data reported in the literature.

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