Xantholipin, a novel inhibitor of HSP47 gene expression produced by Streptomyces sp.

Terui, Yuichi; Chu, Yiwen; Li, Junying; Ando, Takuya; Yamamoto, Haruaki; Kawamura, Yoji; Tomishima, Yasumitsu; Uchida, Seiichi; Okazaki, Tetsuji; Munetomo, Eiji; Seki, Takayuki; Yamamoto, Kōji; Murakami, Shigeru; Kawashima, Akira

doi:10.1016/s0040-4039(03)01318-2

Cited by 37 publications

(48 citation statements)

References 19 publications

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“…Further to this, gHMBC correlations from the 6-OH to C-5, C-6, and C-7 positioned the phenol on the fully substituted ring D as indicated, and required placement of a coplanar C-8 carbonyl to achieve chelation-as indicated by the highly deshielded and sharp 1 H NMR resonance for 6-OH (d H = 14.23 ppm)-and thereby defined the regiochemistry of the ring E/F fusion. The upfield 13 C NMR chemical shift for the C-1 lactam carbonyl (d C = 156.36 ppm) was consistent with it being peri to a carbonyl/quinone (compare xantholipin) [2] as opposed to the sp 2 -hybridized carbon atom of a hydroquinone (compare actinoplanones and simaomicin). [3,4,5] The 13 C NMR shift for one of the remaining unassigned carbon atoms was indicative of a quinone (d C = 183.4 ppm), and was attributed to C-3-thereby defining ring B as a p-quinone.…”

Section: Resultsmentioning

confidence: 68%

“…Xantholipin from a Streptomyces sp. and simaomicin from Actinomadura madurea are related polyketides that are known to inhibit HSP47 gene expression [2] and bleomycin-induced G2 cell cycle arrest, [14] respectively. The anticancer kigamicins from an Amycolatopsis sp.…”

Section: Resultsmentioning

confidence: 99%

“…Ab [b] Af [c] Nt [d] xantholipins X [2,25] lysolipins X [26,27] [a] X indicates known "areas" of biological activity. Assays against each target "area" differ between structure classes, and as such comparisons should be viewed as indicative, not qualitative.…”

Section: Compound Classmentioning

confidence: 99%

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Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

Ratnayake

Lacey²,

Tennant³

et al. 2007

Chemistry A European J

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The kibdelones are a novel family of bioactive heterocyclic polyketides produced by a rare soil actinomycete, Kibdelosporangium sp. (MST-108465). Complete relative stereostructures were assigned to kibdelones A-C (1-3), kibdelone B rhamnoside (5), 13-oxokibdelone A (7), and 25-methoxy-24-oxokibdelone C (8) on the basis of detailed spectroscopic analysis and chemical interconversion, as well as mechanistic and biosynthetic considerations. Under mild conditions, kibdelones B (2) and C (3) undergo a facile equilibration to kibdelones A-C (1-3), while kibdelone B rhamnoside (5) equilibrates to a mixture of kibdelone A-C rhamnosides (4-6). A plausible mechanism for this equilibration is proposed and involves air oxidation, quinone/hydroquinone redox transformations, and a choreographed sequence of keto/enol tautomerizations that aromatize ring C via a quinone methide intermediate. Kibdelones exhibit potent and selective cytotoxicity against a panel of human tumor cell lines and display significant antibacterial and nematocidal activity.

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Section: Resultsmentioning

confidence: 68%

Section: Resultsmentioning

confidence: 99%

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Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

Ratnayake

Lacey²,

Tennant³

et al. 2007

Chemistry A European J

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“…Xanthofulvin and vinaxanthone were isolated from Penicillium species [49]. A polycyclic substance (xanthopterin) with the ability to inhibit the HSP47 (heat shock protein) gene expression was isolated from the culture broth of a Streptomyces species [50]. Xantholiptin is a potent inhibitor of collagen production induced by treatment with TGF-b in human dermal fibroblasts.…”

Section: Miscellaneousmentioning

confidence: 99%

Naturally Occurring Xanthones: Chemistry and Biology

Negi

Bisht

Singh

et al. 2013

Journal of Applied Chemistry

164

120

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Xanthones are one of the biggest classes of compounds in natural product chemistry. A number of xanthones have been isolated from natural sources of higher plants, fungi, ferns, and lichens. They have gradually risen to great importance because of their medicinal properties. This review focuses on the types, isolation, characterization, biological applications, and biosynthesis of naturally occurring xanthones isolated so far. Different physicochemical and instrumental methods such as liquid-solid and liquid-liquid extraction, TLC, flash chromatography, column chromatography, IR,1H NMR and13C NMR spectroscopy, GLC, HPLC, GC, and LCMS have been widely used for isolation and structural elucidation of xanthones. Hepatoprotective, anticarcinogenic, antileprosy, antimalarial, antioxidant, anticholinergic, mutagenicity, radioprotective, immunomodulatory, antibone resorption, antiparasitic, neuraminidase inhibitory, anticomplement, antibacterial, antifungal, algicidal, anti-HIV, cardioprotective, antitumoral, antidiabetes, antihyperlipidemic, antiatherogenic, anti-inflammatory, antiulcer, antidiabetic, hypolipidemic, analgesic, antiasthmatic, antihistaminic, antiamoebic, diuretic, antidiarrheal, larvicidal, and ovicidal activities have been reported for natural occurring xanthones. To a certain extent, this review provides necessary foundation for further research and development of new medicines.

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“…Few examples are xanthopterin [30], xantholiptin [31], and xanthofulvin (30) and vinaxanthone (31) [32].…”

Section: Miscellaneous Xanthonementioning

confidence: 99%

Synthesis and Biological Properties of Pharmaceutically Important Xanthones and Benzoxanthone Analogs: A Brief Review.

Bedi

Gupta

Pramanik

2018

Asian J Pharm Clin Res

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Xanthones are one of the biggest classes of compounds in natural product chemistry. A number of xanthones have been isolated from natural sources of higher plants such as fungi, ferns, and lichens. Synthetic analogs of xanthones have shown a large number of pharmacological properties such as antioxidant, anti-inflammatory, antidiabetics, antihistamine, antitumoral, antiulcer, and algicidal. Moreover, they also find usages in photodynamic therapy, laser technology, and dyes. This review lays stress on various solvents, catalyst and synthetic route for synthesis of xanthones, benzoxanthones analogs. The review has also focused on the classifications of xanthone as well as extensively studied biological properties of the xanthones and benzoxanthones analogs.

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Xantholipin, a novel inhibitor of HSP47 gene expression produced by Streptomyces sp.

Cited by 37 publications

References 19 publications

Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

Naturally Occurring Xanthones: Chemistry and Biology

Synthesis and Biological Properties of Pharmaceutically Important Xanthones and Benzoxanthone Analogs: A Brief Review.

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