Antibacterial hydroperoxysterols from Xanthosoma robustum

Kato, Takeshi; Frei, Barbara; Heinrich, Michael; Sticher, Otto

doi:10.1016/0031-9422(95)00765-2

Cited by 42 publications

(37 citation statements)

References 8 publications

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“…This sterol was recognized as a hydroperoxysterol by the presence of the characteristic signal for the hydroperoxy proton at d 7.76 ppm in the 1 H-NMR spectrum of 1 (Table 1). [5][6][7][8][9][10][11][12][13][14] An olefinic proton signal in the 1 H-NMR spectrum appeared at d C and DEPT spectra of 1 displayed the signals of twenty-seven carbons, including five methyls, ten methylenes, nine methines, and three quaternary carbons (Table 1). Two olefinic carbons (d 140.0, s, C-5; 121.6, d, CH-6), a hydroxy-bearing methine carbon (d 71.3, CH-3), and a hydroperoxy-bearing methine carbon (d 86.5, CH-7) were further identified.…”

Section: Resultsmentioning

confidence: 99%

“…Its 1 H-NMR spectrum showed a broad singlet at d 7.68 ppm which revealed the presence of a hydroperoxy group. [5][6][7][8][9][10][11][12][13][14] Based on detailed spectral data analysis (IR, 1 H-, and 13 C-NMR), it was found that the structure of 2 was similar to that of 1. Comparison of the 5) showed that the configuration of C-7 in 2 should be existed in a-oriented.…”

Section: Resultsmentioning

confidence: 99%

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Hydroperoxysterols from the Tunicate Eudistoma sp.

Sung

Lin

Chen

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Tunicates have been well-recognized as marine organisms containing large quantities of secondary metabolites that exhibit varying degrees of biological activities. 1,2) In connection with our continuing investigations of bioactive substances from marine organisms, a tunicate Eudistoma species (subphylum Urochordata, class Ascidiacea, order Enterogona, suborder Aplousobranchiata, family Polycitoridae) was selected for study, 3,4) as the EtOAc extract of this organism was found to exhibit cytotoxicity against MCF-7 (human breast cancer), NCI-H460 (human non-small cell lung cancer), and SF-268 (human CNS cancer) cells. In this paper, we report the isolation, structure elucidation, and biological activity of two hydroperoxysterols, 7b-hydroperoxycholesterol (1) and its stereoisomer 7a-hydroperoxycholesterol (2), from a Formosan tunicate identified as Eudistoma sp.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Hydroperoxysterols from the Tunicate Eudistoma sp.

Sung

Lin

Chen

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…1859±1871, 1998 # 1998 Elsevier Science Ltd. All rights reserved Printed in Great Britain 0277-9536/98/$ -see front matter PII: S0277-9536(98)00181-6 *Author for correspondence. of the active constituents are isolated and their structures elucidated (Farnsworth, 1990;Kato et al, 1996;Bork et al, 1997).…”

Section: Introductionmentioning

confidence: 99%

Medicinal plants in Mexico: healers' consensus and cultural importance

Heinrich

Ankli

Frei

et al. 1998

Social Science & Medicine

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“…The most plausible biosynthetic pathway for 1 and 2 in sponge involves the abstraction of an allylic proton by an activated oxygen, such as O 2 , along with migration of the carboncarbon double bond (Figure 2). Several naturally occurring hydroperoxy steroids have been isolated from tunicates (Sung et al, 2007), seaweeds (Teixeira et al, 2006), algae (Sheu et al, 1997a,b) and some plants (Kato et al, 1996), supporting the assumption that these compounds are not artifacts. We propose that the bioactive and unstable steroid can be biosynthesized in sponge under a special ecological environment to act as a defensive strategy against invaders.…”

Section: Resultsmentioning

confidence: 94%

Bioactivities of six sterols isolated from marine invertebrates

Zhou

Sun

et al. 2013

Pharmaceutical Biology

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Context: Epidioxy sterols and sterols with special side chains, such as hydroperoxyl sterols, usually obtained from marine natural products, are attractive for bioactivities. Objective: To isolate and screen bioactive and special sterols from China Sea invertebrates. Materials and methods: Two hydroperoxyl sterols (1 and 2) from the sponge Xestospongia testudinaria Lamarck (Petrosiidae), three epidioxy sterols (3-5) from the sea urchin Glyptocidaris crenularis A. Agassiz (Glyptocidaridae), sponge Mycale sp. (Mycalidae) and gorgonian Dichotella gemmacea Milne Edwards and Haime (Ellisellidae) and an unusual sterol with 25-acetoxy-19-oate (6) also from D. gemmacea were obtained and identified. Using high-throughput screening, their bioactivities were tested toward Forkhead box O 3a (Foxo3a), 3-hydroxy-3-methylglutaryl CoA reductase gene fluorescent protein (HMGCR-GFP), nuclear factor kappa B (NF-kB) luciferase, peroxisome proliferator-activated receptor-g co-activator 1a (PGC-1a), protein-tyrosine phosphatase 1B (PTP1B), mitochondrial membrane permeabilization (MMP) and adenosine monophosphate-activated protein kinase. Results: Their structures were determined by comparing their nuclear magnetic resonance data with those reported in the literature. Three epidioxy sterols (3-5) showed inhibitory activities toward Foxo3a, HMGCR-GFP and NF-kB-luciferase with the IC 50 values 4.9-6.8 mg/mL. The hydroperoxyl sterol 29-hydroperoxystigmasta-5,24(28)-dien-3-ol (2) had diverse inhibitory activities against Foxo3a, HMGCR-GFP, NF-kB-luciferase, PGC-1a, PTP1B and MMP, with IC 50 values of 3.8-19.1 mg/mL. Discussion and conclusion: The bioactivities of 3-5 showed that 5a,8a-epidioxy is the active group. Otherwise, the most plausible biosynthesis pathway for 1 and 2 in sponge involves the abstraction of an allylic proton by an activated oxygen, such as O 2 , along with migration of carbon-carbon double bond. Therefore, the bioactive and unstable steroid should be biosynthesized in sponge under a special ecological environment to act as a defensive strategy against invaders.

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Antibacterial hydroperoxysterols from Xanthosoma robustum

Cited by 42 publications

References 8 publications

Hydroperoxysterols from the Tunicate Eudistoma sp.

Hydroperoxysterols from the Tunicate Eudistoma sp.

Medicinal plants in Mexico: healers' consensus and cultural importance

Bioactivities of six sterols isolated from marine invertebrates

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