A lanostane triterpenoid from Poria cocos

Shingu, Tetsuro; Tai, Takaaki; Akahori, Akira

doi:10.1016/0031-9422(92)83325-s

Cited by 37 publications

(14 citation statements)

References 2 publications

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“…The 13 C‐NMR and DEPT spectra displayed 33 carbon resonances ( Table 2) categorized into eight methyl groups, ten methylene groups (one olefinic at δ (C) 107.2 C(31)), five methine groups (one oxygenated at δ (C) 81.1 C(3) and one olefinic at δ (C) 125.5 C(16)), and ten non‐protonated carbons (four olefinic ones at δ (C) 134.0 C(8), 134.8 C(9), 148.0 C(17), and 155.2 C(24)), a carboxylic carbon at δ (C) 179.8 C(21), and an ester carbonyl group at δ (C) 171.3). The above information coupled with the 1 H, 1 H‐COSY correlations ( Figure 4) of H−C(5)/CH 2 (6)/CH 2 (7) and CH 2 (11)/CH 2 (12) indicated that 3 was a lanosta‐8‐ene‐type triterpenoid and its structure was similar to that of pachymic acid ( 8 ) [16] . Compared to 8 , however, the 13 C‐NMR data of 3 lacked signals of the C(15) oxymethine and C(16) aliphatic methine but displayed resonances for one trisubstituted double bond at δ (C) 125.5 C(16) and 148.0 C(17), suggesting that 3 was dehydration derivative of 8 .…”

Section: Resultsmentioning

confidence: 80%

Tetranorlanostane and Lanostane Triterpenoids with Cytotoxic Activity from the Epidermis of Poria cocos

Jiang

Ding

Nie

et al. 2021

Chemistry & Biodiversity

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Two unprecedented tetranorlanostane triterpenoids, poricolides A (1) and B (2), and two new lanostane triterpenoids, 3β‐acetoxy‐24‐methyllanosta‐8,16,24(31)‐trien‐21‐oic acid (3) and 3β‐acetoxylanosta‐7,9(11),16,23‐tetraen‐21‐oic acid (4), were isolated from the epidermis of Poria cocos. The structures of 1–4 were determined via analysis of 1H‐, 13C‐, and 2D‐NMR, and HR‐ESI‐MS data, and the absolute configurations of 1 and 3 were established by single‐crystal X‐ray diffraction analysis. Compounds 1 and 2 were the first report of tetranorlanostane triterpenoid having a δ‐lactone ring at C(17). Compounds 3 and 4 were rare lanostane triterpenoids having a double bond between C(16) and C(17). Compounds 1–4 exhibited potent antiproliferative effects against A549, SMMC‐7721, MCF‐7, and SW480 cancer cell lines with IC50 values from 16.19±0.38 to 27.74±1.12 μM.

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Section: Resultsmentioning

confidence: 80%

Tetranorlanostane and Lanostane Triterpenoids with Cytotoxic Activity from the Epidermis of Poria cocos

Jiang

Ding

Nie

et al. 2021

Chemistry & Biodiversity

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“…1B ), the shape of the mean exhibits a clear similarity and the presence of informative features of the spectra is mainly found in the wavelengths of 208, 235, 242 and 252 nm, which could be explained by the existence of some triterpenoids in the epidermis of W. cocos 24 , 25 . Especially, the strongest absorption appears at about 242 nm, probably indicating the presence of a heteroannular diene moiety of dehydropachymic acid 26 . In addition, it also shows obvious difference in the absorbance and the cultivated epidermis samples have lower peak heights than those of wild ones apart from the cultivated samples obtained from Lincang region, and the epidermis of W. cocos from different geographical regions display the changes of UV absorption intensities.…”

Section: Resultsmentioning

confidence: 99%

“…The VIP scores are presented in Table S2 and there is a close agreement between the spectral discussion and the variables with greater importance. As can be seen in this table, the variables formatted in bold present distinguishable peaks of the samples, specifically the most obvious characteristic (242 nm) of the UV spectra and the main distinction of FTIR spectral features of the epidermis (474–410 cm −1 ), indicating the presence of some triterpenes and polysaccharides 26 , 31 . It could be inferred from the results that the differentiation of the wild and cultivated epidermis of W. cocos may be related to the diversity of triterpenes and polysaccharides.…”

Section: Resultsmentioning

confidence: 99%

Differentiation and comparison of Wolfiporia cocos raw materials based on multi-spectral information fusion and chemometric methods

Wang

2018

Sci Rep

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In order to achieve the target of deeper insight into the differentiation and comparison of Wolfiporia cocos, a total of 350 samples including distinct growth patterns, various collection regions and different medicinal parts were investigated using multi-spectral information fusion based on ultraviolet (UV) and Fourier transform infrared (FT-IR) spectroscopies coupled with chemometrics. From the results, the discrimination of samples was obtained successfully and good classification performances were shown according to partial least squares discriminant analysis (PLS-DA) models. Comparatively, the distinctness of chemical information in the two medicinal parts of W. cocos were much more than that in the same part with different growth patterns and collection areas. Meanwhile, an interesting finding suggested that growth patterns rather than geographical origins could be the dominant factor to effect the chemical properties of the same part samples, especially for the epidermis. Compared with the epidermis samples, there were better quality consistency for the inner part of W. cocos. Totally, this study demonstrated that the developed method proved to be reliable to perform comparative analysis of W. cocos. Moreover, it could provide more comprehensive chemical evidence for the critical supplement of quality assessment on the raw materials of W. cocos.

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“…Compounds 3 -8 were identified as dehydropachymic acid [16], dehydrotumulosic acid [15], 29-hydroxypolyporenic acid C [8], polyporenic acid C [17], tumulosic acid, and pachymic acid [16], respectively, by spectral analysis and comparison with spectroscopic data reported in the literature.…”

Section: Results Andmentioning

confidence: 99%

Triterpenes from the Fungus Poria cocos and Their Inhibitory Activity on Nitric Oxide Production in Mouse Macrophages via Blockade of Activating Protein‐1 Pathway

Cai¹,

Cai

2011

Chemistry & Biodiversity

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Two new triterpenes, 29-hydroxydehydrotumulosic acid (1) and 29-hydroxydehydropachymic acid (2), together with six known compounds, dehydropachymic acid (3), dehydrotumulosic acid (4), 29-hydroxypolyporenic acid C (5), polyporenic acid C (6), tumulosic acid (7), and pachymic acid (8), were isolated from the dried sclerotia of Poria cocos. In the in vitro bioassays, these isolated compounds reduced, in a dose-dependent manner, nitric oxide (NO) production from lipopolysaccharide (LPS)-induced RAW 264.7 cells, with compounds 5 and 6, the IC(50) values of which were 16.8±2.7 and 18.2±3.3 μM, respectively, exhibiting the greatest inhibition activity. Further Western blot analysis conducted on cells pre-treated with compounds 5 and 6, and luciferase assays on activator protein 1-dependent gene expression revealed that the inhibited NO release was attributed to the reduced expression of iNOs (=inducible NO synthase) enzymes, which might be regulated via the blockade of activator protein-1 signaling pathway.

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A lanostane triterpenoid from Poria cocos

Cited by 37 publications

References 2 publications

Tetranorlanostane and Lanostane Triterpenoids with Cytotoxic Activity from the Epidermis of Poria cocos

Tetranorlanostane and Lanostane Triterpenoids with Cytotoxic Activity from the Epidermis of Poria cocos

Differentiation and comparison of Wolfiporia cocos raw materials based on multi-spectral information fusion and chemometric methods

Triterpenes from the Fungus Poria cocos and Their Inhibitory Activity on Nitric Oxide Production in Mouse Macrophages via Blockade of Activating Protein‐1 Pathway

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