Optically Active N-Acetyldopamine Dimer of the Crude Drug "Zentai", the Cast-off Shell of the Cicada, Cryptotympana sp.

Noda, Naoki; Kubota, Shinichi; Miyata, Yoko; Miyahara, Kazumoto

doi:10.1248/cpb.48.1749

Cited by 44 publications

(51 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These compounds were identified as (22E,24R)-ergosta-5,7,22-trien-3 -ol (2) (Adler et al, 1977;Smith, 1977), (22E,24R)-ergosta-7,22-dien-3 ,5 ,6 -triol (3) (Cafieri et al, 1985), (22E,24R)-5 ,8 -epidioxyergosta-6,22-dien-3 -ol (4) (Yue et al, 2001), asperamide A (5) (Zhang et al, 2007), asperamide B (6) (Zhang et al, 2007), chrysogine (7) (Hikino et al, 1973;Kettering et al, 2004), methyl 2-(N-(2-hydroxyphenyl)carbamoy)ace tate (8) (TimTec Compound Libraries, 2010), N-(2-hydroxypropanoyl)-2-aminobenzoic acid amide (9) (Dai et al, 1993), N-(2-hydroxyphenyl)acetamide (10) (Rahaim Jr et al, 2006), 4-hydroxybenzaldehyde (11) (Andersen et al, 1974), N-acetyldopamine (12) (Noda et al, 2000), methyl 2-([2-(1H-indol-3-yl)eth yl]carbamoyl)acetate (13) (Franzén et al, 2009), N2 -acetyltryptophan methyl ester (14) (AmirHeidari and Micklefield, 2007), and meleagrin (15) (Du et al, 2009). The chemical structures of compounds 1-15 are shown in Fig.2 and the peaks of the major compounds in the crude extract were assigned in the HPLC profile (Fig.3).…”

Section: Sd-118mentioning

confidence: 99%

Chemical profile of the secondary metabolites produced by a deep-sea sediment-derived fungus Penicillium commune SD-118

Shang

et al. 2012

Chin. J. Ocean. Limnol.

View full text Add to dashboard Cite

Section: Sd-118mentioning

confidence: 99%

Chemical profile of the secondary metabolites produced by a deep-sea sediment-derived fungus Penicillium commune SD-118

Shang

et al. 2012

Chin. J. Ocean. Limnol.

View full text Add to dashboard Cite

“…Noda et al [46] first isolated a mixture of saturated dehydro NADA dimers ( 35 ) as the principle component of the drug. Following this work, Tada et al [47] isolated the same compounds from a different species ( Cryptotympana tuslulata ) and showed that they possessed strong tyrosinase inhibitory activity and could be used as potential cosmetic skin whitening agents.…”

Section: Simple Dehydrodopa Derivatives: 12-dehydro-n-acetyldopammentioning

confidence: 99%

Bioactive Dehydrotyrosyl and Dehydrodopyl Compounds of Marine Origin

Sugumaran

Robinson

2010

Marine Drugs

View full text Add to dashboard Cite

The amino acid, tyrosine, and its hydroxylated product, 3,4-dihydroxyphenylalanine (dopa), plays an important role in the biogenesis of a number of potentially important bioactive molecules in marine organisms. Interestingly, several of these tyrosyl and dopa-containing compounds possess dehydro groups in their side chains. Examples span the range from simple dehydrotyrosine and dehydrodopamines to complex metabolic products, including peptides and polycyclic alkaloids. Based on structural information, these compounds can be subdivided into five categories: (a) Simple dehydrotyrosine and dehydrotyramine containing molecules; (b) simple dehydrodopa derivatives; (c) peptidyl dehydrotyrosine and dehydrodopa derivatives; (d) multiple dehydrodopa containing compounds; and (e) polycyclic condensed dehydrodopa derivatives. These molecules possess a wide range of biological activities that include (but are not limited to) antitumor activity, antibiotic activity, cytotoxicity, antioxidant activity, multidrug resistance reversal, cell division inhibition, immunomodulatory activity, HIV-integrase inhibition, anti-viral, and anti-feeding (or feeding deterrent) activity. This review summarizes the structure, distribution, possible biosynthetic origin, and biological activity, of the five categories of dehydrotyrosine and dehydrodopa containing compounds.

show abstract

“…Periostracum cicadae is known as chantui in traditional Chinese medicine and has been historically used in the treatment of sore throat, hoarseness, itching, spasms, and other symptoms. The crude extract of periostracum cicadae can be used as a sedative, hypothermic, anticonvulsive [19], antioxidant, anti-inflammatory [19][20], antipyretic, and antiallergic agent [21], as well as a sympathetic ganglionic blocker [22] when administered by various routes. To our knowledge, this is the first study that has investigated the molecular mechanism of periostracum cicadae in inflammation and fibrosis using an IgAN model.…”

Section: Introductionmentioning

confidence: 99%

Effects of Periostracum Cicadae on Cytokines and Apoptosis Regulatory Proteins in IgA Nephropathy Rat Model

Lu¹,

Wang²,

Nuerbiye³

et al. 2018

Preprint

View full text Add to dashboard Cite

Periostracum cicadae, the cast-off shell of the cicada Cryptotympana pustulata Fabricius, is used in traditional Chinese medicine for its diaphoretic, anticonvulsive, sedative, antipyretic, and antiallergic effects. However, the exact pathogenesis of immunoglobulin A nephropathy (IgAN) remains unclear, thereby hindering investigations to identify novel therapeutic agents. A rat IgAN model was established by administration of bovine serum albumin, lipopolysaccharide, and carbon tetrachloride, which simultaneously established blood stasis and a heat syndrome model. The animals were sacrificed to detect changes in protein levels in urine and blood. Immunofluorescence was performed to assess IgA deposition in the glomeruli. Tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), and interleukin 6 (IL-6) levels were measured in bronchoalveolar lavage fluid (BALF) by enzyme-linked immunosorbent assay. Hematology and eosin, periodic acid-Schiff, TUNEL, and immunohistochemical staining were performed to evaluate histopathological changes in kidney tissues. Additionally, target-related proteins were measured by western blotting. Periostracum cicadae resulted in a reduction in blood and urine protein levels. Serum TNF-α, IL-1β, and IL-6 levels significantly decreased in the periostracum cicadae-treated groups compared to the IgAN group. Furthermore, a reduction in MCP-1, TLR4, and IgA expression levels and a dose- dependent increase in caspace-3 expression were observed in response to periostracum cicadae treatment. TGF-β1 levels decreased, whereas that of Fas increased in the kidney tissues of the periostracum cicadae-treated groups. The findings of the present study indicate that periostracum cicadae induces apoptosis and improves kidney inflammation and fibrosis in IgA nephropathy rat models.

show abstract

Optically Active N-Acetyldopamine Dimer of the Crude Drug "Zentai", the Cast-off Shell of the Cicada, Cryptotympana sp.

Cited by 44 publications

References 1 publication

Chemical profile of the secondary metabolites produced by a deep-sea sediment-derived fungus Penicillium commune SD-118

Chemical profile of the secondary metabolites produced by a deep-sea sediment-derived fungus Penicillium commune SD-118

Bioactive Dehydrotyrosyl and Dehydrodopyl Compounds of Marine Origin

Effects of Periostracum Cicadae on Cytokines and Apoptosis Regulatory Proteins in IgA Nephropathy Rat Model

Contact Info

Product

Resources

About