Isoprenyl Phenyl Ethers from Liverworts of the Genus Trichocolea:  Cytotoxic Activity, Structural Corrections, and Synthesis

Abstract

The main cytotoxic component in New Zealand collections of the liverwort Trichocolea mollissima was identified as methyl 4-[(5-oxogeranyl)oxy]-3-methoxybenzoate, a structure that has not been reported previously. Two double-bond isomers of this geranyl ether were present at lower levels. Reinvestigation of the benzoates from Japanese collections of Trichocolea tomentella led to the identification of four geranyl ethers (including two of the three compounds identified from T. mollissima), which had previously been assigned incorrect geranyl ester structures. One compound, previously reported as a 3,3-dimethylallyl ester, could not be reisolated from T. tomentella, but was found in a New Zealand collection of Trichocolea lanata. It was shown to be a 3,3-dimethylallyl ether by synthesis from methyl vanillate. Several of these compounds were active in cytotoxic and antifungal assays.

Cannabidiol Induces Cytotoxicity and Cell Death via Apoptotic Pathway in Cancer Cell Lines

“…Potential therapeutic applications of cannabis include analgesia, attenuation of the nausea, vomiting of cancer *Corresponding author Tel: +82-2-961-0278, Fax: +82-2-967-8401 E-mail: whchoi@khu.ac.kr chemotherapy, increase of stimulation, decrease of diarrhea, decrease of asthma by bronchial constriction, decrease of intraocular pressure by glaucoma, anti-rheumatic and anti-pyretic action, and treatment of convulsant disorders. These effects were reviewed by Asakawa et al, 1995 andPerry et al, 1996. The cannabinoid, cannabidiol compound, and the active constituents of Cannbis sativa L. have been known to affect many biological systems (Carrier et al, 2006;Esposito et al, 2006;Garcia-Arencibia et al, 2007;Giudice et al, 2007;Martin, 1986;Weiss et al, 2006).…”

Three New Furoquinoline Alkaloids from the Leaves of Boninia glabra

“…As a result, 2 exhibited the prominent cross peaks between 2Ј-H 2 /4Ј-H to establish Econfiguration of the 3Ј, 4Ј double bond. 9,10,12) This stereochemistry was also supported by the carbon chemical shift of C-10Ј (d 19.3) in 2.…”

“…Based on the evidence, the structure of compound 2 is proposed as shown in Fig. 1 9,10,12) These results, as well as the carbon chemical shift of C-10Ј (d 17.1), 9,10,12) indicated the E-configuration of the 2Ј, 3Ј double bond in 3. Based on the evidence, the structure of compound 3 is shown in Fig.…”

“…Since the 10Ј-methyl carbon signal of such 5Z-isomer is shifted upfield (d C Ͼ20 ppm) compared with that of the corresponding 5E-isomer (d C Ͻ20 ppm). 9,10,12) The unambiguous structure of the side-chain in 1 was established from HMBC experiments to indicate significant correlation peaks between 1Ј-H 2 /C-2Ј, C-3Ј, C-7, between 2Ј-H 2 /C-1Ј, C-3Ј, C-4Ј, C-10Ј, between 4Ј-H/C-2Ј, C-5Ј, C-10Ј, and between 6Ј-H/C-5Ј, C-8Ј, C-9Ј. The connection of the 5-oxogeranyl side-chain to C-7 on the furoquinoline ring was revealed by the HMBC correlation peak between 1Ј-H 2 /C-7 as well as NOE correlation peaks between 1Ј-H 2 /6-H and 1Ј-H 2 /8-H. On the basis of these results, the structure of compound 1 is shown in Fig.…”

Rearrangement Reactions for the Synthesis of Some Oxa- and Aza-tricyclic Rings Heterocyclic Compounds

“…A Claisen rearrangement of ether 9c yielded intermediate 10b which then underwent a homo [1,5] [14,15]. Several geranyl phenyl ethers were prepared and tested for inhibition of insect growth.…”