Synthesis and biological evaluation of bilobol and adipostatin A

  title={Synthesis and biological evaluation of bilobol and adipostatin A},
  author={Ayano Tanaka and Yasuhiro Arai and Su-Nam Kim and Jungyeob Ham and Toyonobu Usuki},
  journal={Journal of Asian Natural Products Research},
  pages={290 - 296}
Concise total synthesis of bilobol 5-pentadecenylresorcinol (1), isolated from Gingko biloba fruits, has been achieved in 10 steps with 51% overall yield from 3,5-dihydroxybenzoic acid (3). Adipostatin A (2), isolated from the fruits as well as from Streptomyces cyaneus 2299-SV1, has also been synthesized in two steps from methylated bilobol (10). The structure–activity relationship study of synthetic products was described by means of cytotoxic assay against human KB carcinoma cell lines. 
Isolation of a Novel Flavanonol and an Alkylresorcinol with Highly Potent Anti-Trypanosomal Activity from Libyan Propolis
It is concluded that a potent and highly selective new trypanocide may be present in the fraction, which revealed significant disturbances in trypanosomal phospholipid metabolism, especially the formation of cholineospholipids.
Bioactivity and Structural Properties of Novel Synthetic Analogues of the Protozoan Toxin Climacostol
The data collected demonstrate that the introduction of a methyl or a hydroxyl moiety to the aromatic ring of climacostol can effectively modulate its potency and its mechanism of action.
Polyhydroxybenzoic acid derivatives as potential new antimalarial agents
This work selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect and confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect.
Schistosomicidal Activity of Alkyl-phenols from the Cashew Anacardium occidentale against Schistosoma mansoni Adult Worms.
Results indicated that compound 7 presents promising in vitro schistosomicidal activity in worms incubated with compound 7.
Rethinking Ginkgo biloba L.: Medicinal uses and conservation
  • T. Isah
  • Biology
    Pharmacognosy reviews
  • 2015
The tree is slow growing, adapted to many ecological conditions and shows numerous adaptation in developmental patterns, especially the various parts of the tree that are used in orthodox or traditional medicine to treat diseases due to the many bioactive compounds.


Antitumor principles from Ginkgo biloba L.
Seven long-chain phenols were isolated from Ginkgo biloba L. Three of them, anacardic acid (Ib), bilobol (IIa), and cardanol (IIIa), showed antitumor activity against Sarcoma 180 ascites in mice. The
Tyrosinase inhibitors from Anacardium occidentale fruits.
Kinetic studies with the two principal active compounds have indicated that both of these phenolic compounds exhibit characteristic competitive inhibition of the oxidation of L-3,4-dihydroxyphenylalanine by mushroom tyrosinase.
Chemical studies of the Proteaceae. V. Synthesis of derivatives of 5-n-Alkylresorcinols and related compounds
A convenient reaction sequence in which the key step is a Stevens rearrangement, leading to dimethyl ethers of 5-n-alkylresorcinols has been developed and exemplified by the synthesis of the dimethyl
A cytotoxic constituent of Lysimachia japonica THUNB. (Primulaceae) and the structure-activity relationships of related compounds.
A cytotoxic alkylresorcinol was isolated from Lysimachia japonica THUNB and identified as grevillol and tested for cytotoxicity against KB, B-16, PC-13, L-5178Y, P-388, and HEp-2 cells in vitro.
Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies.
An enantioselective total synthesis of the proposed structure of mucoxin is described and it is reasoned that the spectral discrepancies are due to stereochemical misassignment of the natural product.
Adipostatins A and B, new inhibitors of glycerol-3-phosphate dehydrogenase.
Adipostatin A and adipostatin B inhibited glycerol-3-phosphate dehydrogenase at the IC50 values of 4.1 microM and 4.5 microM, respectively and prevented triglyceride accumulation in 3T3-L1 cells at a concentration of the microM level.
Chemistry and biology of terpene trilactones from Ginkgo biloba.
Ginkgo biloba, the ginkgo tree, is the oldest living tree, with a long history of use in traditional Chinese medicine, and several biological effects of the terpene trilactones have been discovered in recent years, making them attractive pharmacological tools that could provide insight into the effects of GinkGo biloba extracts.
Resorcinolic Lipids, the Natural Non-isoprenoid Phenolic Amphiphiles and Their Biological Activity.
The biogenetic pathway of these compounds, described in textbooks and recent reviews, is based on incomplete experimental data supplemented with chemical considerations, which suggests their less important role in cellular physiology and biochemistry.
Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil
Sixteen phenolic compounds isolated from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil exhibited potent antibacterial activity against only Gram-positive bacteria, among which Streptococcus mutans and Propionibacterium acnes were the most sensitive bacteria.