Vinigrol, a novel antihypertensive and platelet aggregation inhibitory agent produced by a fungus, Virgaria nigra. I. Taxonomy, fermentation, isolation, physicochemical and biological properties.

  title={Vinigrol, a novel antihypertensive and platelet aggregation inhibitory agent produced by a fungus, Virgaria nigra. I. Taxonomy, fermentation, isolation, physicochemical and biological properties.},
  author={T Ando and Yasuhisa Tsurumi and Nobutaka Ohata and Itsuo Uchida and K. Yoshida and Masakuni Okuhara},
  journal={The Journal of antibiotics},
  volume={41 1},
Vinigrol, produced by a fungal strain identified as Virgaria nigra, was extracted from the cultured mycelium, purified by solvent extraction followed by chromatography on silica gel and then isolated as crystals (C20H34O3, mp 108 degrees C). Vinigrol decreased arterial blood pressure of anesthetized normotensive rats dose-dependently when administered intravenously. Vinigrol inhibited platelet activating factor and epinephrine induced platelet aggregation. 
FK409, a novel vasodilator isolated from the acid-treated fermentation broth of Streptomyces griseosporeus. I. Taxonomy, fermentation, isolation, and physico-chemical and biological characteristics.
In vitro, FK409 showed a potent relaxation activity on noradrenaline induced contraction of rat aorta, and this compound also showed potent anti-aggregation activities towards rabbit platelets. Expand
Cardiovascular effects of the fungal extract of basidiomycetes sp. YL8006.
Vasodilating activity in the crude ethanol extract of the dried mycelia of Basidiomycetes sp. Expand
Elastase inhibitory activity of secondary metabolites from the fungus Virgaria nigra CF-231658.
Three known compounds were isolated from Virgaria nigra using Amberlite XAD-16 solid-phase extraction during the cultivation step and their structures were elucidated on the basis of 1D and 2D NMR as well as HRMS spectroscopic analyses. Expand
Cinatrins D and E, and virgaricin B, three novel compounds produced by a fungus, Virgaria boninensis FKI-4958
Two new hydroxycitric acid lactone derivatives named cinatrins D (1) and E (2), and a new γ-lactam, virgaricin B (3), along with a known similar compound, virgaricin (4), were isolated from aExpand
Effect of pathogenic yeasts on human platelet aggregation.
Somatic components of these yeasts, but not their metabolic products, exert an antagonistic effect on the aggregation of human platelets, possibly aiding the fungi in their evasion of the microbicidal defense system during vascular dissemination. Expand
A concise approach to vinigrol.
In 1987 Hashimoto and co-workers isolated the unusual diterpene vinigrol from the fungal strain Virgaria nigra F5408, providing a particularly difficult challenge, as it is the only natural product to contain the decahydro-1,5-butanonaphthalene carbon skeleton. Expand
Detection of novel secondary metabolites.
This review focuses on the genesis and development of the gamut of methodologies that have led to the successful detection of the wide variety of novel secondary metabolites that include antibacterial, antigungal, antiviral and antitumour antibiotics, enzyme inhibitors, pharmacologically and immunologically active agents, products useful in agriculture and animal husbandry, microbial regulators, and other compounds for which no bioactive role has yet been found. Expand
Synthetic studies inspired by vinigrol.
Barriault's synthesis of the vinigrol core is described, in addition to the elegant strategies disclosed by Njardarson and Hanna, which showcases the fundamental role that natural products play in spawning innovations in synthetic chemistry. Expand
Total synthesis of vinigrol.
Vinigrol has been evaluated in numerous biological assays and shown to impact platelet aggregation and act as a tumor necrosis factor (TNF) antagonist,3 as well as displaying other interesting properties. Expand
Scalable Total Synthesis of (-)-Vinigrol.
A new and efficient synthetic route has been developed to complete the asymmetric synthesis of (-)-vinigrol and provide over 600 mg of material, manifesting the power of macrocyclic stereocontrol and transannular Diels-Alder reaction. Expand


Studies on WF-5239, a new potent platelet aggregation inhibitor.
WF-5239 has inhibitory activity against rabbit platelet aggregation induced by arachidonic acid and collagen, with IC50 values of 1.25 and 5.0 micrograms/ml, respectively. Expand
Studies on new vasodilators, WS-1228 A and B. I. Discovery, taxonomy, isolation and characterization.
New vasodilators, designated WS-1228 A and B have been discovered in the culture filtrate of a strain of Streptomyces aureofaciens, obtained as pale yellow crystals and their molecular formulae were both C11H17N3O. Expand
Amauromine, a new vasodilator. Taxonomy, isolation and characterization.
Amauromine is a new alkaloid with vasodilating activity obtained from the culture broth of Amauroascus sp. No. 6237. Its molecular formula was determined to be C32H36N4O2 on the basis of elementaryExpand
Characterization of α2-Adrenoceptors on Blood Platelets from Various Species Using 3H-Yohimbine
Platelets from various mammalian species differ in the response to adrenaline mediated by activation of α2-adrenoceptors. In contrast to platelets from rabbit, dog and man, adrenaline did n
Effects of α2‐adrenoceptor agonists and of related compounds on aggregation of, and on adenylate cyclase activity in, human platelets
The data are not consistent with a model in which a single x2‐adrenoceptor mediates both the aggregatory response and inhibition of adenylate cyclase and hence support a models in which unique x2-adrenOceptors mediate these two responses. Expand
Epinephrine-induced aggregation of rabbit platelets refractory to ADP.
Epinephrine-induced aggregation of platelets refractory to ADP does not involve further detectable increase in the amount of 45Ca2+ associated with the platelets, suggesting that these effects are mediated by the alpha-adrenergic receptor. Expand
Alpha adrenoceptors in rat brain: Direct identification with prazosin
Labeled prazosin may be a useful tool to characterize α1 adrenoceptors in rat brain membranes and in contrast to the binding of the labeled agonist clonidine, Sodium ions and divalent cations as well as guanyl nucleotides have little or no effect on the bindingof the labeled antagonist. Expand
Effects of the calcium channel facilitator, CGP 28,392, on different modes of contraction in smooth muscle of rabbit and rat aortae and guinea‐pig taenia caeci
The results suggest that the Ca2+ channel facilitator, CGP 28,392, has a relatively selective activating effect on voltage‐dependent Ca2- channels in rabbit aorta, however, it also activates receptor‐linked Ca2+. Expand