Tolypothrix

The tjipanazoles (18, 19a-d, 20a-b) a group of A-glycosides of indolo-[2,3-a]carbazole, have been isolated from the moderately antifungal extract of the blue-green alga Tolypothrix tjipanasensis. These alkaloids do not exhibit antitumor or protein kinase C (PKC) inhibitory activity, which is in contrast with the... 

The unusual tolyporphin was isolated from the Pacific cyanophyte Tolypothrix nodosa and it has been shown that tolyporphin eliminates the multidrug resistance (MDR) in certain carcinoma sublines thus potentiating the cytotoxicity of anticancer drugs in these cell lines.2... 

Phycochrome a, extracted from Tolypothrix distorta, Phormidium luridum, Nostoc muscorum and Anacystis nidulans, has one form absorbing maximally at about 590 nm, formed in red light, and another one absorbing at 570 nm, formed in yellow-green and blue-green light. 

Phycochrome b, also found in Tolypothrix, occurs in two forms absorbing maximally at 510 and 570 nm respectively, and produced in yellow-green and blue-green light respectively. 

Phycochrome c, occurring in Nostoc and probably also in Tolypothrix, has one form absorbing at around 650nm and another, absorbing weakly in the green, produced in green and red light respectively. 

Phycochrome d, extracted also from Tolypothrix, shows an absorbance increase at 650nm after irradiation with 650 nm, as well as an absorbance decrease at the same wavelength after irradiation with 610nm light. 

Fig. 8. Difference spectrum (green irradiated minus red irradiated) of phycochrome c (solid line), action spectrum for induction of filamentous growth of Nostoc muscorum (dotted line), and action spectrum for inhibition of C-phycoerythrin synthesis in Tolypothrix tenuis (dashed-dotted line). Abscissa wavelength in nm Ordinates relative absorbance change und relative action (after Bjorn and Bjorn 5))...

Suppressed pigment biosynthesis in Aulosira fertissima and Tolypothrix tenuis, reduced growth in Anabaena oryzae and Nostoc muscorum, and reduced carbohydrate content in Nostoc and Tolypothrix (Shabana 1987)... 

Shabana, E.F. 1987. Use of batch assays to assess the toxicity of atrazine to some selected cyanobacteria. 1. Influence of atrazine on the growth, pigmentation and carbohydrate contents of Aulosira fertilissima, Anabaena oryzae, Nostoc muscorum and Tolypothrix tenuis. Jour. Basic Microbiol. 2 113-119. 

Hyella caespitosa Bron et Flah Tedania ignis Nostoc sphaericum Tolypothrix tjipanasensis New Zealand Ascidian Australian Ascidian Didemnum sp. 

Scytonemin-containing cyanobacterial sheaths are estimated to attenuate more than 88% of incident UVA radiation (at 370 nm).194 Several studies have demonstrated the ability of scytonemin to prevent UV-induced damage in cells, and these results have generally demonstrated that the presence of scytonemin does increase the UV tolerance of cyanobacteria. Dose response experiments with strains of the terrestrial/freshwater cyanobacterium Tolypothrix, with and without scytonemin in the filament sheaths, show that a nonpigmented sheath results in greater UV... 

Adhikary, S. P. and Sahu, J. K., UV protecting pigment of the terrestrial cyanobacterium Tolypothrix... 

Scheme 6. Synthesis of the Tolypothrix pentamethyl ether 33 according to Bruckner et al. a) 2 equiv LDA, I equiv MePh2SiCl, -78"C-rt b) 35, -78 C-rt c) Rh/C/H d) MeLi, -78X e) H.O,. PPTS ...

Tolyporphyrin A from the microalga Tolypothrix nodosa reverses multidrug resistance in a Vinblastine-resistant population of human ovarian adenocarcinoma cells. In a synthesis of Tolyporphin A, four 0-benzyl groups were cleaved from the C-glycoside rings of 150.1 [Scheme 4.150] using zinc chloride and ethane-... 

Subjection of this material to a formylation protocol involving a Rh catalyst, a bulky phosphite and DABCO (l,4-diazabicyclo[2.2.2]octane) in the presence of H2/CO gas mixture, gives a high yield of the desired aldehyde. Iteration of these steps leads to the synthesis of Tolypothrix pentaether. 

Tolypodiol (13) is a meroditerpene that was isolated from a cultured sample of Tolypothrix nodosa originally collected in a soil sample from Nan Madol, Pohnpei. Its structure was determined by a combination of mass spectral analysis and NMR of the parent compound as well as its acetylated analogue. Tolypodiol was found to possess anti-inflammatory activity in the mouse ear edema assay with an ED50 = 30 pg per ear, which rivals that of the standard, hydrocortisone (20 pg per ear). ... 

Another intriguing sugar-based metabolite from a cyanobacterium is cyclodextrin 33, isolated from a Hawaiian Tolypothrix byssoidea strain. A range of related metabolites were produced these proved inseparable and were analyzed as a mixture. However, acetylation of the mixture yielded peracetate derivatives that could be separated by HPLC and analysis of both the purified peracetate and the unmodified mixture was used in the elucidation of the major component 33. MS and extensive NMR analysis led to the structure shown. 2D NMR analysis was crucial in the determination of the individual sugar units, while their sequence was solved by difference nuclear overhauser effect (NOE) experiments. The configurations of all sugar units were presumed to be D on the basis of comparison with related cyclodextrins. The Tolypothrix cyclodextrins were found to block the activity of some of the other toxic metabolites produced by this cyanobacterium. " ... 

An example of a compound displaying both cytotoxic and antifungal activity is given by scytophycin A (68). The scytophycins were initially isolated from the terrestrial cyanobacterium Scytonema pseudohofmanni in 1986 by Ishibashi et ul whereas tolytoxin (69) was initially isolated in 1977 from Tolypothrix conglutinate, but due to... 

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