Chaetocochins A−C, Epipolythiodioxopiperazines from <i>Chaetomium cochliode</i>s

Li, Guo‐You; Li, Bogang; Yang, Tao; Yan, Jin; Liu, Guangye; Zhang, Guolin

doi:10.1021/np0602970

Cited by 83 publications

(72 citation statements)

References 10 publications

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“…The new saponins 1-4 were tested for their cytotoxic activities against five human cancer cell lines (HL-60, SMMC-7712, A-549, MCF-7, and SW480) in vitro. 8 and 20(R/S)-protopanaxtriol, 13 respectively, by comparison the spectroscopic and physical data with those previously reported values.…”

Section: Introductionmentioning

confidence: 53%

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Dammarane-type saponins from steamed leaves of Panax Notoginseng

Liu

et al. 2011

Nat. Prod. Bioprospect.

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Abstract:Four new dammarane-type triterpenoid saponins, namely notoginsenosides SFt 1 -SFt 4 (1-4) were isolated from the steamed leaves of Panax notoginseng (Burk.) F. H. Chen (Araliaceae), together with 17 known saponins. Their structures were established on the basis of detailed spectroscopic analyses and acidic hydrolysis. The known ginsenosides Rk 2 and Rh 3 were obtained from P. notoginseng for the first time. All of these new saponins showed no in vitro cytotoxicity against five human cancer cell lines (HL-60, SMMC-7712, A-549, MCF-7, and SW480). Keywords: Panax notoginseng, steamed leave, dammarane-type saponin, notoginsenoside IntroductionPanax notoginseng (Burk.) F. H. Chen (Araliaceae), a famous traditional Chinese medicinal (TCM) herb, is mainly cultivated in Yunnan and Guangxi province of China. Both roots and leaves have been used medicinally by the local people of its growing area for a long time. 1 Traditionally, the roots have been used in both raw and processed forms. The raw one has been mainly used for injuries from falls and removing blood stasis, while the processed one has been used as a tonic to promote blood circulation. 2 The leaves had the similar effects on hematological and cardiovascular systems as the roots. Dammarane-type triterpenoid saponins are known to be the main bioactive constituents in P. notoginseng. So far, more than 70 saponins have been isolated from different organs of this herbs. 3 Our previous study on the steamed roots of P. notoginseng resulted in the identification of five new and 23 known dammarane-type saponins, part of which are the minor constituents in non-processed roots. 4 As part of our continuing search for new saponins from Panax plants, a detailed chemical investigation on the steamed leaves of P. notoginseng was carried out, which led to the isolation of four new dammarane-type triterpenoid saponins (1-4), along with 17 known ones. Their structures were established based on the detailed spectroscopic analyses and acidic hydrolysis. The new saponins 1-4 were tested for their cytotoxic activities against five human cancer cell lines (HL-60, SMMC-7712, A-549, MCF-7, and SW480) in vitro.

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Section: Introductionmentioning

confidence: 53%

“…8 After steamed, a mass of low-pole triterpenoid saponins came forth. Being similar with the roots, the processed and the air-dried leaves must have different pharmacological activities and quality standard.…”

Section: Introductionmentioning

confidence: 99%

Dammarane-type saponins from steamed leaves of Panax Notoginseng

Liu

et al. 2011

Nat. Prod. Bioprospect.

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“…[8][9][10] Briey, Chaetomium cochliodes (C.3.198) was isolated from soil collected from Sichuan Province, PR China and identied at the Institute of Microbiology, the Chinese Academy of Sciences (CAS). The seed culture medium was comprised of dextrose (20 g …”

Section: Fermentation Extraction and Isolation Of Chetominmentioning

confidence: 99%

Enhanced antitumor activity and mechanism of biodegradable polymeric micelles-encapsulated chetomin in both transgenic zebrafish and mouse models

Deng

et al. 2014

Nanoscale

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Chetomin is a promising molecule with anti-tumor activities in the epipolythiodioxopiperazine family of fungal secondary metabolites; however, strong hydrophobicity has limited its further applications. In this work, chetomin was encapsulated into polymeric micelles to obtain an aqueous formulation, and the chetomin loaded micelles (Che-M) exhibited small particle size and high encapsulation efficiency. When the concentration of copolymer was higher than the critical gelation concentration, the Che-M could form a thermosensitive hydrogel (Che-H), which was free-flowing sol at ambient temperature and converted into a non-flowing gel at body temperature. The molecular modeling study has indicated that chetomin interacted with PCL as a core, which was embraced by PEG as a shell. Che-M showed equal cytotoxicity with free chetomin, but the apoptosis inducing effects of Che-M were more significant.Besides, Che-M could increase the GSSG level, decrease the GSH level, and increase the ROS in CT26 cells. Furthermore, stronger inhibitory effects of Che-M were observed on embryonic angiogenesis, tumor-induced angiogenesis and tumor growth in transgenic zebrafish models. In addition, Che-M was effective in inhibiting tumor growth and prolonging survival in a subcutaneous CT26 tumor model. In a colorectal peritoneal carcinomatosis model, both Che-M and Che-H showed excellent therapeutic effects, but Che-H was more effective. In conclusion, Che-M and Che-H may serve as candidates for cancer therapy.

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“…Sporidesmins are a diverse class of natural products containing molecules with one or two epidithiodioxopiperazine (ETP) rings that display a wide variety of biological activities (Waksman & Bugie, 1944;Saito et al, 1988;Fujimoto et al, 2004;Gardiner et al, 2005;Li et al, 2006). While toxic to mammalian cells, studies have suggested that certain sporidesmins, namely bis-ETPs chetomin (Waksman & Bugie, 1944) and chaetocin (Hauser et al, 1970), may possess anticancer activity due to their ability to suppress neovascularization (Waksman & Bugie, 1944;Hauser et al, 1970;McInnes et al, 1976;Brewer et al, 1978;Kung et al, 2004).…”

Section: Commentmentioning

confidence: 99%

Polymorphism and phase transition behavior of 6,6′-bis(chloromethyl)-1,1′,4,4′-tetramethyl-3,3′-(p-phenylenedimethylene)bis(piperazine-2,5-dione)

2009

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A crystallographic investigation of the title compound, C22H28Cl2N4O4, using crystals obtained under different crystallization conditions, revealed the presence of two distinct polymorphic forms. The molecular conformation in the two polymorphs is very different: one adopts a `C' shape, whereas the other adopts an `S' shape. In the latter, the molecule lies across a crystallographic twofold axis. The `S'‐shaped polymorph undergoes a reversible orthorhombic‐to‐monoclinic phase transition on cooling, whereas the structure of the `C'‐shaped polymorph is temperature insensitive.

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Chaetocochins A−C, Epipolythiodioxopiperazines from Chaetomium cochliodes

Cited by 83 publications

References 10 publications

Dammarane-type saponins from steamed leaves of Panax Notoginseng

Dammarane-type saponins from steamed leaves of Panax Notoginseng

Enhanced antitumor activity and mechanism of biodegradable polymeric micelles-encapsulated chetomin in both transgenic zebrafish and mouse models

Polymorphism and phase transition behavior of 6,6′-bis(chloromethyl)-1,1′,4,4′-tetramethyl-3,3′-(p-phenylenedimethylene)bis(piperazine-2,5-dione)

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