Racemosin C, a novel minor bisindole alkaloid with protein tyrosine phosphatase-1B inhibitory activity from the green alga <i>Caulerpa racemosa</i>

Yang, Hui; Liu, Dingquan; Liang, Tong-Jun; Li, Jia; Liu, Aihong; Yang, Peng; Lin, Kun; Yu, Xiaoqing; Guo, Yue‐Wei; Mao, Shui-Chun; Wang, Bin

doi:10.1080/10286020.2014.965162

Cited by 36 publications

(14 citation statements)

References 22 publications

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“…The analysis of C. peltata and C. racemosa ethanolic extracts showed caulerpin as one of the main products [96,97]. Other indolic alkaloids of the genus Caulerpa found in algae and already identified are racemosin A (38) [98], B (39) [99], and C (40), and caulersin (41) [100]. The first alkaloid showed protective activity on SH-SY5Y cell viability, the second one can give rise to alkylamide derivatives capable of inducing cell death in the breast cancer cell line MDA-MB-231, and the last two showed inhibitory activity on PTP1B; however, anti-inflammatory activity of these compounds has not been registered to date.…”

Section: Anti-inflammatory Alkaloids In Marine Algaementioning

confidence: 99%

“…Many alkaloids have already been identified in seaweed species, and algae of the genus Caulerpa are known sources of alkaloids with already described biological activities [98][99][100]102,116]. However, while numerous studies elucidate the anti-inflammatory activity of other seaweed compounds such as phenols and polyphenols, carotenoids, proteins and peptides, and sulfated polysaccharides, very few studies have addressed the anti-inflammatory activity of seaweed alkaloids.…”

Section: Bioprospecting Of Marine Anti-inflammatory Alkaloids and Futmentioning

confidence: 99%

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Marine Alkaloids with Anti-Inflammatory Activity: Current Knowledge and Future Perspectives

2020

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Alkaloids are nitrogenous compounds with various biological activities. Alkaloids with anti-inflammatory activity are commonly found in terrestrial plants, but there are few records of the identification and characterization of the activity of these compounds in marine organisms such as fungi, bacteria, sponges, ascidians, and cnidarians. Seaweed are a source of several already elucidated bioactive compounds, but few studies have described and characterized the activity of seaweed alkaloids with anti-inflammatory properties. In this review, we have gathered the current knowledge about marine alkaloids with anti-inflammatory activity and suggest future perspectives for the study and bioprospecting of these compounds.

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Section: Anti-inflammatory Alkaloids In Marine Algaementioning

confidence: 99%

Section: Bioprospecting Of Marine Anti-inflammatory Alkaloids and Futmentioning

confidence: 99%

Marine Alkaloids with Anti-Inflammatory Activity: Current Knowledge and Future Perspectives

2020

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“…Subfraction B3 (1.2 g) PTP1B Inhibitory Activity Bioassay The PTP1B inhibitory activity bioassay of compounds 2 and 4-8 was carried out as described in our previous paper. 28) Oleanolic acid was used as the positive control. interest.…”

Section: Methodsmentioning

confidence: 99%

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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“…The investigation of the Chinese marine green alga Caulerpa racemosa resulted in the discovery of a new minor bisindole alkaloid, racemosin C ( 74 ), and one known related metabolite, caulersin ( 75 ), which were characterized by a naturally unprecedented 8‐hydroxy‐2,4,6‐cyclooctatrienone ring fused with two indole systems. They both exhibited significant PTP1B inhibitory activity with IC 50 values of 5.86 ± 0.57 and 7.14 ± 1.00 μ m , respectively …”

Section: Algaementioning

confidence: 99%

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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Racemosin C, a novel minor bisindole alkaloid with protein tyrosine phosphatase-1B inhibitory activity from the green alga Caulerpa racemosa

Cited by 36 publications

References 22 publications

Marine Alkaloids with Anti-Inflammatory Activity: Current Knowledge and Future Perspectives

Marine Alkaloids with Anti-Inflammatory Activity: Current Knowledge and Future Perspectives

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

Inhibitors of Protein Tyrosine Phosphatase 1B from Marine Natural Products

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