- STEROIDS FROM CALVATIA CYATHIFORMIS
-
Cyathisterone (ergosta-7,22-diene-3,6-dione) and cyanthisterol (8β-hydroxyergosta-4,6,22-trien-3-one), two new steroids, have been isolated from Calvatia cyanthiformis along with two known ergosterol derivatives, ergosta-4,7,22-triene-3,6-dione and ergosta-4,6,8(14),22-tetraen-3-one.Their molecular structures were defined by spectroscopic means and chemical correlations. - Key words: Calvatia cyathiformis; lycoperdaceae; sterois; cyanthisterone; ergosta-7,22-diene-3,6-dione; cyathisterol; 8β-hydroxyergosta-4,6,22-trien-3-one.
- Kawahara, Nobuo,Sekita, Setsuko,Satake, Motoyoshi
-
-
Read Online
- Reactive oxygen species altering the metabolite profile of the marine-derived fungus Dichotomomyces cejpii F31-1
-
To investigate the influence of reactive oxygen species (ROS) on the secondary metabolites of the marine-derived fungus Dichotomomyces cejpii F31-1, hydrogen peroxide (H2O2) was added to the GPY culture medium. The HPLC chromatogram of the EtOAc extract of the culture broth was distinct from that of the H2O2 free GPY medium. Further study of the metabolites in the GPY medium with H2O2 resulted in the discovery of eight known compounds. Among them, (22E)-5α, 8α-epidioxyergosta-6, 22-dien-3β-ol (2) and ergosta-4,6,8(14),22-tetraene-3-one (3) were present in the highest concentration, while ergosterol and diketopiperazines are abundant in the H2O2 free medium. Additionally, a new compound, dichocetide D (1) containing a chlorine element and a known ergosterol (10) were isolated from the H2O2 free medium. (22E)-5α, 8α-epidioxyergosta-6, 22-dien-3β-ol (2) exhibited moderate cytotoxic activity against human prostate cancer cell line LNCaP-C4-2B.
- Shaker, Sharpkate,Sun, Ting-Ting,Wang, Liang-Yue,Ma, Wen-Zhe,Wu, Dong-Lan,Guo, Yong-Wei,Dong, Jun,Chen, Yan-Xiu,Zhu, Long-Ping,Yang, De-Po,Li, Hou-Jin,Lan, Wen-Jian
-
-
Read Online
- Photochemical reaction of ergosta-4,6,8(14),22-tetraen-3-one
-
Chemical properties of ergosta-4,6,8(14),22-tetraen-3-one (1) were investigated. Though 1 is rather stable to acids of bases, it reacts easily with two molecules of oxygen on irradiation with UV light to give 6α,9α- epidioxy-14α-hydroperoxyergosta-4,7,22-dien-3-one (2), which is transformed successively to 6α,7α;8α,9α-diepozy-14α-hydroperxyergosta-4,22-dien-3- one (3) and 14α-hydroperoxy-9α-hydroxyergosta-4,7,22-triene-3,6-dione (4) under these reaction conditions.
- Tanaka, Nobutoshi,Hosoi, Ken-Ichi,Tanaka, Daizo,Takahashi, Mimei
-
-
Read Online
- An anti-aldosteronic diuretic component (drain dampness) in polyporus sclerotium
-
Polyporus Sclerotium, botanically from the Polyporus umbellatus (PERS.) FRIES, was traditionally used for the purpose of promoting diuresis. The present study investigated the diuretic effect of ergosta-4,6,8(14),22-tetraen-3-one (ergone) which is a maker component according to the chemical assay for its quality standardization. It resulted in a reversion to ordinary value of the urinary ratio of Na/K in deoxycoricosterone acetate (DOCA)-treated and adrenalectomized rats, although it had no this effect on the Na or K contents as well as Na/K value both in normal rats and in adrenalectomized rats without DOCA. These data indicate that ergone possesses an anti-aldosteronic diuretic effect. Moreover, it was identified in the blood and bile of rats after its administration to the gastrointestinal tract. The above results demonstrate that it is an active component of Polyporus Sclerotium.
- Yuan, Dan,Mori, Junna,Komatsu, Ken-Ich,Makino, Toshiaki,Kano, Yoshihiro
-
-
Read Online
- Synthesis of (22E,24R)-ergosta-4,7-22-triene-3,6-dione and its 14α-hydroxy-and 9α,14α-dihydroxy derivatives
-
Δ4,7-3,6-Diketosteroids have been synthesized from ergosterol (1).
- Kovganko,Sokolov
-
p. 320 - 323
(2007/10/03)
-
- Synthesis of fluorescent 4,6,8(14)-trien-3-one steroids via 3,5,7-trien- 3-ol ethers. Important probes for steroid-protein interactions
-
A general synthesis of fluorescent 4,6,8(14)-trien-3-one steroids with and without an aliphatic side chain is described via 3-alkoxy-3,5,7-trienes as intermediates. The advantages of this method are general applicability, good yields, limited number of reaction steps (up to four), and ready availability of starting materials (at low cost). a) Starting from ergosterol (1) or cholesta-5,7-dien-3-ol (2) and oxidizing them to ergosta-4,7,22-trien-3-one (3) or cholesta-4,7-dien-3-one (4) we synthesized the enol ethers (5) and (6). Subsequent treatment with DDQ gave the 4,6,8(14),22-tetraen-3-one (7) and the 4,6,8(14)-trien-3-one (8). b) Similarly 17β-(I-oxopropoxy)-androsta- 4,6,8(14)-trien-3-one (13) was obtained, but the required enol ether was synthesized via the 4,6-dien-3-one (11).
- Bohme,Kempfle
-
p. 265 - 269
(2007/10/02)
-
- Approaches towards the synthesis of a sulfur analog of ergosterol peroxide
-
In an analogous fashion to the preparation of ergosterol peroxide from singlet oxygen, the preparation of its sulfur analog was attempted via the Diels-Alder addition of diatomic sulfur to ergosterol.Two of the recently reported methods for generating and
- Tsantrizos, Youla S.,Folkins, Patricia L.,Britten, James F.,Harpp, David N.,Ogilvie, Kelvin K.
-
p. 158 - 164
(2007/10/02)
-
- Structure and Chemistry of ?-Allyl Palladium Complexes from Steroids
-
The synthesis and structures of ?-allyl palladium complexes prepared from vitamins D2 and D3 and from ergosterol, 7,8-didehydrocholesterol, and 3-epi-cholesterol are described.The mechanism of palladisation is descussed as well as the transformation of the complexes into conjugated trienes or allylic alcohols.
- Mahe, Christian,Patin, Henri,Hulle, Marie-Therese Van,Barton, Derek H.R.
-
p. 2504 - 2508
(2007/10/02)
-
- 4,6,8(14)-Triene steroids
-
There are provided novel 4,6,8(14)-triene-steroids as well as processes for preparing such compounds. The above compounds are useful as intermediates in the preparation of other steroids, which in turn, may be converted into valuable pharmaceutical agents.
- -
-
-