2061-64-5Relevant articles and documents
A new 5α,8α-epidioxy sterol from the Okinawan marine sponge of the Axinyssa genus
Iguchi, Kazuo,Shimura, Hiromi,Yang, Zhi,Yamada, Yasuji
, p. 410 - 413 (1993)
A new sterol (axinysterol) was isolated from the Okinawan marine sponge of the genus Axinyssa.The structure of axinysterol was assigned as 5α,8α-epidioxyergosta-6,22,25-trien-3β-ol based on spectroscopic analysis and chemical transformation. (Steroids 58: 410-413, 1993). Keywords: 5α,8α-epidioxyergosta-6,22,25-trien-3β-ol; axinysterol; marine sponge; Axinyssa genus; sterol; structure
Synthesis and biological evaluation of novel steroidal 5α,8α-endoperoxide derivatives with aliphatic side-chain as potential anticancer agents
Bu, Ming,Cao, Tingting,Li, Hongxia,Guo, Mingzhou,Yang, Burton B.,Zhou, Yue,Zhang, Na,Zeng, Chengchu,Hu, Liming
, p. 46 - 53 (2017)
By inspiration of significant anti-cancer activity of our previously screened natural ergosterol peroxide (EP), a series of novel steroidal 5α,8α-endoperoxide derivatives 5a–d and 14a–f were designed, synthesized, and biologically evaluated for their in vitro anti-proliferative inhibitory and cytotoxic activity. The results revealed that most of these compounds showed moderate-to-excellent anti-proliferative effects against the tested cancer cell lines (i.e. HepG2, SK-Hep1, MDA-MB-231 and MCF-7). Among them, compound 5b and 14d exhibited preferable inhibitory activities (IC50 of 5b and 14d are 8.07 and 9.50?μM against HepG2, respectively). The structure-activity relationships indicated that incorporation the peroxidic bridge to the steroid scaffolds at C-5 and C-8 positions together with the aliphatic side-chain at the C-17 position would provide synergistic effect for the bioactivity.
Development of ergosterol peroxide probes for cellular localisation studies
Ling, Taotao,Lang, Walter H.,Martinez-Montemayor, Michelle M.,Rivas, Fatima
, p. 5223 - 5229 (2019)
Ergosterol peroxide selectively exhibits biological activity against a wide range of diseases; however, its mode of action remains unknown. Here, we present an efficient synthesis of ergosterol peroxide chemical probes for in vitro anticancer evaluation,
New biologically active marine sesquiterpenoid and steroid from the okinawan sponge of the genus Axinyssa
Iwashima, Makoto,Terada, Ikuo,Iguchi, Kazuo,Yamori, Takao
, p. 1286 - 1289 (2002)
A new bisabolane-type sesquiterpenoid, (E)-3-isocyanobisabolane-7,10-diene (1), and a new epidioxyergostane-type steroid, 9(11)-dehydroaxinysterol (2), were isolated from the Okinawan sponge of the genus Axinyssa. Their structures were elucidated based on
Minor and Trace Sterols in Marine Invertebrates. 26. Isolation and Structure Elucidation of Nine New 5α,8α-Epidioxy Sterols from Four Marine Organisms
Gunatilaka, Leslie A. A.,Gopichand, Yalamanchili,Schmitz, Francis J.,Djerassi, Carl
, p. 3860 - 3866 (1981)
Sixteen 5α,8α-epidioxy Δ6 and Δ6,9(11) sterols, of which nine are new, have been isolated from the marine organisms Ascidia nigra, Dendrogyra cylindrus, Thalysias juniperina, and Aplysia dactylomela by reverse-phase high-performance liquid chromatography and characterized by high-resolution mass spectrometry and 360-MHz proton NMR spectroscopy.Attention is drawn to some unusual concentration-dependent NMR shifts of methyl signals.The probable biological significance of these epidioxy sterols is discussed with special reference to sterol biosynthesis.
Biogenesis-Guided Synthesis and Structural Revision of Sarocladione Enabled by Ruthenium-Catalyzed Endoperoxide Fragmentation
Ning, Yuhan,Tian, Hailong,Gui, Jinghan
supporting information, p. 11222 - 11226 (2021/04/19)
Sarocladione is the first 5,10:8,9-diseco-steroid with a 14-membered macrocyclic diketone framework to have been isolated from a natural source. Herein we report a biomimetic synthesis of sarocladione in only two or seven steps from inexpensive, commercially available ergosterol. The key feature of this synthesis was a novel ruthenium-catalyzed endoperoxide fragmentation, which transformed various saturated endoperoxides into olefinic diketones by cleavage of two C?C bonds. This synthesis allowed us to unambiguously determine the structure of sarocladione and provided experimental support for its revised biosynthetic origin. This work also vividly demonstrates that consideration of the biogenesis is a powerful tool for elucidating the structures of natural products.
Antagonistic activity of hydroxycoumarin-based antioxidants as possible singlet oxygen precursor photosensitizers
Guerrero, Tomás,Vázquez-Ortega, Fernanda,Lagunes, Irene,Ortiz-Blanco, Erik,Sosa-Ortiz, Gabriela,Tovar-Miranda, Ricardo,Medina, Manuel E.,Trigos, ángel
, (2021/05/10)
Coumarins are phenolic-type compounds with efficient antioxidant activity due to their ability to scavenge reactive oxygen species. Nevertheless, their ability to behave as photosensitizers capable of generating reactive oxygen species, such as singlet oxygen, has been less studied. In this work, the photosensitizing ability of seven hydroxycoumarins was evaluated through the photooxidation of ergosterol by quantifying the conversion of ergosterol into ergosterol peroxide. In our experimental conditions, we found that almost every tested antioxidant coumarin promotes the peroxidation of ergosterol. The results suggest that the hydroxycoumarins exhibit potential photosensitizing activity by promoting singlet oxygen generation by a Type II photochemical mechanism. Density functional theory (DFT) calculations were also performed to obtain further insight into the chemical reactivity of tested compounds; the observed tendency in the group of antioxidant coumarins to promote the reaction was their hardness due to the principle of maximum hardness. To evaluate our conclusion, we performed the reaction using a highly polarizable coumarin as a photosensitizer, which resulted in an increased photosensitizing capacity supported with DFT calculations, which reinforces our analysis. Finally, we found that hydroxycoumarins can be potentially pro-oxidants since some of them can act as photosensitizers and generate singlet oxygen in the presence of UV–Vis light, a characteristic that must be considered when these compounds are used as antioxidants.
