377. The chemistry of fungi. Part XVII. Dehydroeburicoic acid

Gascoigne, R. M.; Robertson, Alexander; Simes, J. J. H.

doi:10.1039/jr9530001830

Cited by 14 publications

(5 citation statements)

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“…(7)(8)(9)(10), Lentinus spp. (9,10), Daedalea spp. (4,11), to our knowledge this is the first example of the isolation of a C31 lanostane from a dicotyledonous plant, and also the first report of a C31 lanostane possessing anti-HIV activity.…”

Section: And Discussionmentioning

confidence: 99%

Anti-AIDS Agents, 9. Suberosol, a New C₃₁ Lanostane-Type Triterpene and Anti-HIV Principle from Polyalthia suberosa

Li¹,

Sun²,

Kashiwada³

et al. 1993

J. Nat. Prod.

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A new C31 lanostane-type triterpene, assigned the trivial name suberosol [1], has been isolated from Polyalthia suberosa as an anti-HIV principle. The structure has been characterized as 24-methylenelanost-7,9(11)-diene-3 beta, 15 alpha-diol (suberosol) [1], based on spectroscopic evidence. Compound 1 was found to show anti-HIV replication activity in H9 lymphocyte cells with an EC50 of 3 micrograms/ml.

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Section: And Discussionmentioning

confidence: 99%

Anti-AIDS Agents, 9. Suberosol, a New C₃₁ Lanostane-Type Triterpene and Anti-HIV Principle from Polyalthia suberosa

Li¹,

Sun²,

Kashiwada³

et al. 1993

J. Nat. Prod.

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“…In the past decade our group has focused on studying the cytotoxic effect of triterpenoids isolated from medicinal mushrooms. − Among the compounds identified, dehydroeburicoic acid was the most potent. It is a lanostanoid derivative that was isolated from Antrodia cinnamomea and P. cocos . Dehydroeburicoic acid exhibited potent antileukemic effects in both in vitro and in vivo assays, and this study was the first report on the in vivo antitumor activity of a lanostanoid derivative.…”

mentioning

confidence: 82%

Cytotoxic Lanostanoids from Poria cocos

Lai

et al. 2016

J. Nat. Prod.

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Six new and 16 known lanostanoids were isolated from the sclerotia of Poria cocos. The structures of the new isolates were elucidated to be 16α-hydroxy-3-oxo-24-methyllanosta-5,7,9(11),24(31)-tetraen-21-oic acid (1), 3β,16α,29-trihydroxy-24-methyllanosta-7,9(11),24(31)-trien-21-oic acid (2), 3β,16α,30-trihydroxy-24-methyllanosta-7,9(11),24(31)-trien-21-oic acid (3), 3β-acetoxy-16α,24β-dihydroxylanosta-7,9(11),25-trien-21-oic acid (4), 3β,16α-dihydroxy-7-oxo-24-methyllanosta-8,24(31)-dien-21-oic acid (5), and 3α,16α-dihydroxy-7-oxo-24-methyllanosta-8,24(31)-dien-21-oic acid (6), based on extensive spectroscopic analyses. The absolute configuration of 4 was determined using Mosher's method. The antiproliferative activity of the isolated compounds (except 3 and 4) was evaluated against four leukemic cell lines (Molt 4, CCRF-CEM, HL 60, and K562). Dehydropachymic acid (9), dehydroeburicoic acid (12), pachymic acid (14), and lanosta-7,9(11),24-trien-21-oic acid (20) exhibited an antiproliferative effect on the CCRF-CEM cancer cell line with IC values of 2.7, 6.3, 4.9, and 13.1 μM, respectively. Both dehydropachymic acid (9) and dehydroeburicoic acid (12) showed antiproliferative effects against Molt 4 (IC 13.8 and 14.3 μM) and HL 60 (IC 7.3 and 6.0 μM) leukemic cell lines. Primary computational analysis using a chemical global positioning system for natural products (ChemGPS-NP) on the active lanostanoids from P. cocos suggested that targets other than topoisomerases may be involved in the antiproliferative activity.

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“…where the meanings of F 0 , F and [Q] are the same as for Equation (1). The double-logarithm plots for fluorescence quenching of the DeEA-HSA system at different temperatures were presented in Figure 4.…”

Section: Binding Constant and Binding Sitementioning

confidence: 99%

“…Dehydroeburicoic acid (DeEA) is a triterpene purified from medicinal fungi such as Taiwanofungus camphoratus, Fomitopsis officinalis, Fomitopsis pinicola and Wolfiporia cocos [1] [2]. The molecular structure of DeEA was presented in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Spectroscopy and Molecular Docking Approach to Probe the Interaction between Dehydroeburicoic Acid and Human Serum Albumin

Zheng¹,

Yang²,

Cheng³

et al. 2019

AiM

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The interaction between dehydroeburicoic acid (DeEA), a triterpene purified from medicinal fungi and the major transport protein, human serum albumin (HSA), were systematically studied by fluorescence spectroscopy, synchronous fluorescence spectroscopy, three-dimensional fluorescence spectroscopy and molecular docking approach under simulated physiological conditions. The intrinsic fluorescence of HSA was quenched through the combination of static and dynamic quenching mechanism. DeEA cannot be stored and carried by HSA in the body at higher temperature. The hydrogen bonding, hydrophobic force and van der Waals force were major acting forces. The site II was the major binding site. The energy transfer could occur with high probability and the binding distance was 3.29 nm. The binding process slightly changed the conformation and microenvironment of HSA. The DeEA molecule entered the hydrophobic cleft of HSA and formed the hydrogen bonding with Glu-492 and Lys-545.

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377. The chemistry of fungi. Part XVII. Dehydroeburicoic acid

Cited by 14 publications

References 0 publications

Anti-AIDS Agents, 9. Suberosol, a New C₃₁ Lanostane-Type Triterpene and Anti-HIV Principle from Polyalthia suberosa

Anti-AIDS Agents, 9. Suberosol, a New C₃₁ Lanostane-Type Triterpene and Anti-HIV Principle from Polyalthia suberosa

Cytotoxic Lanostanoids from Poria cocos

Fluorescence Spectroscopy and Molecular Docking Approach to Probe the Interaction between Dehydroeburicoic Acid and Human Serum Albumin

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377. The chemistry of fungi. Part XVII. Dehydroeburicoic acid

Cited by 14 publications

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Anti-AIDS Agents, 9. Suberosol, a New C31 Lanostane-Type Triterpene and Anti-HIV Principle from Polyalthia suberosa

Anti-AIDS Agents, 9. Suberosol, a New C31 Lanostane-Type Triterpene and Anti-HIV Principle from Polyalthia suberosa

Cytotoxic Lanostanoids from Poria cocos

Fluorescence Spectroscopy and Molecular Docking Approach to Probe the Interaction between Dehydroeburicoic Acid and Human Serum Albumin

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Product

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Anti-AIDS Agents, 9. Suberosol, a New C₃₁ Lanostane-Type Triterpene and Anti-HIV Principle from Polyalthia suberosa

Anti-AIDS Agents, 9. Suberosol, a New C₃₁ Lanostane-Type Triterpene and Anti-HIV Principle from Polyalthia suberosa