Isopetrosynol, a New Protein Tyrosine Phosphatase 1B Inhibitor, from the Marine Sponge &lt;i&gt;Halichondria&lt;/i&gt; cf. &lt;i&gt;panicea&lt;/i&gt; Collected at Iriomote Island

Abdjul, Delfly B.; Yamazaki, Hiroyuki; Takahashi, Ohgi; Kirikoshi, Ryota; Ukai, Kazuyo; Namikoshi, Michio

doi:10.1248/cpb.c16-00061

Cited by 14 publications

(12 citation statements)

References 19 publications

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“…[396][397][398][399] Unusually, only one new polyacetylene 802 was reported in 2016, from Halichondria panicea. 400 Examination of the two-sponge association between Xestospongia deweerdtae and Plakortis halichondrioides, in addition to P. zyggompha, resulted in the isolation of 6-epi-7,8dihydroplakortide K 803, plakortide AA 804, and three chemically unstable plakinic acids N-P 805-807. A combination of both Mosher's acid analysis, as well as comparison of density functional theory (DFT) calculated and experimental ECD spectra were used to establish the absolute congurations of these compounds.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2018

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Covering: 2016. Previous review: Nat. Prod. Rep., 2017, 34, 235-294This review covers the literature published in 2016 for marine natural products (MNPs), with 757 citations (643 for the period January to December 2016) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1277 in 432 papers for 2016), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included.

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Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2018

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“…Compound 31 inhibited PTP1B activity with IC 50 values of 8.2 ± 0.3 μ m , while its stereoisomer 32 showed only 28.9 ± 4.5% inhibition at 21.6 μ m , indicating that the configurations of OH groups at C(14) and C(17) markedly affected this activity. Besides, compounds 33 and 34 inhibited PTP1B activity with IC 50 values of 7.8 ± 0.5 and 12.2 ± 0.5 μ m , respectively …”

Section: Spongesmentioning

confidence: 97%

Inhibitors of Protein Tyrosine Phosphatase 1B from Marine Natural Products

Zhou

Zhang

Liu

et al. 2017

Chemistry & Biodiversity

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The ocean is a capacious area with the most abundant biological resources on the earth. The particularity of the marine ecological environment (high pressure, high salt, and hypoxia) makes the marine species survival competition fiercely, forcing many marine organisms in the process of life to produce a great deal of secondary metabolites with special structures and biological activities. In this article, 118 natural products which were isolated from four kinds of marine organisms, sponges, algae, soft corals and fungus, showing PTP1B inhibitory activity were summarized from 2010 to 2016, which may become the leading compounds towards treating Diabetes mellitus (DM). What's more, we briefly summarized the structure-activity relationship of PTP1B inhibitors.

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“…2) Considering potent PTP1B inhibitory property previously reported for numerous prenylated flavonoids, 1) all the isolates were subjected to testing in vitro for their inhibitory effects against PTP1B with oleanolic acid as the positive control (IC 50 =2.74±0.20 µM), which has proved to be an excellent PTP1B inhibitor. 26,27) As shown in Table 2, all the compounds tested, except for 4, inhibited strongly PTP1B activity. In particular, compounds 5-7 exhibited more potent PTP1B inhibitory activity with IC 50 values of 2.58±0.52, 2.44±0.35, and 2.23±0.14 µM, respectively, than the positive control, oleanolic acid.…”

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confidence: 89%

Aglaiabbrevins A–D, New Prenylated Bibenzyls from the Leaves of <i>Aglaia abbreviata</i> with Potent PTP1B Inhibitory Activity

Sun

Jiang

Zhang

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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Four new prenylated bibenzyls, named aglaiabbrevins A-D (2, 4-6), were isolated from the leaves of Aglaia abbreviata, along with two known related analogues, 3,5-dihydroxy-2-[3,7-dimethyl-2(E),6-octadienyl] bibenzyl (7) and 3,5-dihydroxy-2-(3-methyl-2-butenyl)bibenzyl (8). The structures of the new compounds were elucidated on the basis of extensive spectroscopic experiments, mainly one and two dimensional (1D-and 2D)-NMR, and the absolute configuration of 5 was determined by the measurement of specific rotation. The isolated compounds were evaluated for their protein tyrosine phosphatase-1B (PTP1B) inhibitory activity. The results showed that compounds 5-7 exhibited more potent PTP1B inhibitory effects with IC 50 values of 2.58 0.52, 2.44 0.35, and 2.23 0.14 µM, respectively, than the positive control oleanolic acid (IC 50 2.74 0.20 µM). On the basis of the data obtained, these bibenzyls with the longer C-2 prenyl groups may be considered as potential lead compounds for the development of new anti-obesity and anti-diabetic agents. Also, the PTP1B inhibitory effects for prenylated bibenzyls are being reported for the first time.Key words Aglaia abbreviata; prenylated bibenzyl; aglaiabbrevin; protein tyrosine phosphatase-1B inhibitor; potential lead compound Type 2 diabetes (T2D) is a chronic disorder characterized by hyperglycemia associated with a gradual decline in insulin sensitivity and/or insulin secretion, and has become one of the most serious health problems worldwide. On the other hand, obesity is one of the major risk factors for developing T2D due to insulin resistance. 1) Protein tyrosine phosphatases (PTPs) are responsible for the dephosphorylation of tyrosine residues and are considered negative regulators of insulin signaling.2) Among the various members of the PTP superfamily, PTP1B plays a critical role in metabolic signaling pathways, which places it in an ideal position as a therapeutic drug target for diabetes and obesity.3) Therefore, PTP1B is a promising drug target for the treatment of T2D and obesity and is also involved in cancer. Although there have been a number of reports on the design and development of PTP1B inhibitors, new types of such compounds with suitable pharmacological properties remain to be discovered.The plant Aglaia abbreviata C. Y. WU (Meliaceae), which is a wild evergreen shrub found on mountain slopes at up to ca. 500-1600 m altitude, is widely distributed throughout southwestern China. 4) Members of the genus Aglaia have been studied extensively, resulting in the isolation of many types of interesting secondary metabolites, particularly of various triterpenoids (e.g., cycloartanes, dammaranes, tirucallanes) and flavaglines (e.g., cyclopenta [b] [8][9][10] In an ongoing research for biologically active substances from various natural sources, 11-15) the plant A. abbreviata attracted our attention because the ethyl acetate (EtOAc) extract of the leaves of this plant showed inhibitory activity against PTP1B with an 65.2% inhibition at the concentration of 20 µg/mL. A...

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Isopetrosynol, a New Protein Tyrosine Phosphatase 1B Inhibitor, from the Marine Sponge <i>Halichondria</i> cf. <i>panicea</i> Collected at Iriomote Island

Cited by 14 publications

References 19 publications

Marine natural products

Marine natural products

Inhibitors of Protein Tyrosine Phosphatase 1B from Marine Natural Products

Aglaiabbrevins A–D, New Prenylated Bibenzyls from the Leaves of <i>Aglaia abbreviata</i> with Potent PTP1B Inhibitory Activity

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