デブロモアプリシアトキシン
| デブロモアプリシアトキシン | |
|---|---|
 | |
| (1S,3R,4S,5S,9R,13S,14R) -13-Hydroxy-9-[(1R)-1-hydroxyethyl] -3-[(2S,5S)-5-(3-hydroxyphenyl)-5-methoxypentan-2-yl] -4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]octadecane-7,11-dione | |
| Identification information | |
| CAS registration number | 52,423-28-6 |
| PubChem | 5352033 |
| ChemSpider | 4509004 |
| KEGG | C05148 |
| Beilstein | 4624539 |
| |
| |
| Characteristic | |
| Chemical formula | C32H48O10 |
| Molar mass | 592.72 g mol-1 |
| The appearance | White powder |
| Density | 1.2+-0.1 g/cm3 |
| Solubility to water | 0.00911 mg/mL |
| log POW | 4.2 |
| Vapor pressure | 0.0+-2.7 mmHg |
| Acid dissociation constant pKa | 9.36 |
| Base dissociation constant pKb | -3 |
| The risk | |
| The main risk | Cancerous, dermitis, oral and gastrointestinal inflammations |
| Ignition point | 239.0+-26.4 degrees Celsius |
| I can put a case, the data without the special mention for normal temperature (25 degrees Celsius), the ordinary pressure (100 kPa). | |
デブロモアプリシアトキシン (debromoaplysiatoxin) is the cyanotoxin which kind Moorea producens of the cyanobacterium produces. This oceanic climate cyanobacterium causes seaweed dermatitis (seaweed dermatitis). デブロモアプリシアトキシン is a carcinogenetic promoter. In addition, I have antiincrease activity for the cancer cell strain of various mice.
Table of contents
History
Seaweed dermatitis was reported for the first time in Hawaiian Oahu in 1958. Approximately 125 people who swam in the sea were troubled by an itch, a burn, a bladder, a rash, the symptom such as the desquamation. The causative agent of this seaweed dermatitis was not known until it was suffered from the same symptom in the case of Hawaii in 1968 people of Okinawa of Japan. After researchers took a sample out of Lyngbya majuscula (is classified as Moorea producens where is different from the Lyngbya genus now) in 1973, they made clear that デブロモアプリシアトキシン was a causative agent of this dermatitis [1]; [2].
In 1980, great outbreak of seaweed dermatitis happened in Hawaiian Oahu. L. From a sample of majuscula, this cyanobacterium was found to include application Shea toxin, デブロモアプリシアトキシン, a mixture of ring beer toxin A. These three materials are like the causative agent of seaweed dermatitis [2].
In later 1994, Hawaii Island, Maui Island, inhabitants of Oahu suffered from food poisoning. The inhabitants of these islands often eat various types of algae including red algae Gracilaria coronopifolia. After having taken the sample of these red algae, I understood that they contained application Shea toxin and two kinds of toxins of デブロモアプリシアトキシン. Furthermore, it was observed that a cyanobacterium was parasitic on the surface of G. coronopifolia. Therefore, the true cause of this food poisoning case may be a cyanobacterium [3].
Synthetic
For the three-dimensional complexity and specific molecular structure, デブロモアプリシアトキシン becomes the target of the total synthesis. The total synthesis by the group of Yoshito Kishi of Harvard University is reported in 1987 [4].
Action mechanism
Activation of protein kinase C (PKC) seems to be necessary for the antiincrease activity of application Shea toxin related compounds and cancer-causing promotion activity. The carcinogenetic promoter such as phorbol ester and the application Shea toxin is strongly connected in C1 domain of the PKC.
Toxic
デブロモアプリシアトキシン shows antiincrease activity for a P-388 mouse lymph-related leukaemic cell. In addition, I cause dermatitis. I show activity with quantity of the 0.005 nmol for the ear of the mouse. デブロモアプリシアトキシン was isolated from a gut for the first time in Aplysia Stylocheilus longicauda [5].
アンヒドロデブロモアプリシアトキシン which I spin-dried is mildly-toxic.
Footnote
- ^ Hashimoto, Y.; Kamiya, H.; Yamazato, K.; Nozawa (1975). "Occurrence of a toxic blue-green alga inducing skin dermatitis in okinawa." Toxicon 13 (2): 95,96.
- ^ a b Fujiki, H.; Ikegami, K.; Hakii, H.; Suganuma, M.; Yamaizumi, Z.; Yamazato, K.; Moore, R.E.; Sugimara, T. (1985). "A blue-green alga from Okinawa contains aplysiatoxins, the third class of tumor promoters.." Japanese journal of Cancer Research 76 (4): 257–259.
- ^ Nagai, H.; Yasumoto, T.; Hokama, Y. (July 1996). "Aplysiatoxin and debromoaplysiatoxin as the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii." Toxicon 34 (7): 753–761.
- ^ Pyeong Uk Park, Chris A. Broka, Bruce F. Johnson, Yoshito Kishi (1987). "Total synthesis of debromoaplysiatoxin and aplysiatoxin." J. Am. Chem. Soc. 109 (20): 6205–6207. doi: 10.1021/ja00254a062.
- ^ Kato Y, Scheuer PJ (1974). "Aplysiatoxin and debromoaplysiatoxin, constituents of the marine mollusk Stylocheilus longicauda" (Quoy and Gaimard, 1824). J. Am. Chem. Soc. 96 (7): 2245-2246. PMID 4833645.
This article is taken from the Japanese Wikipedia デブロモアプリシアトキシン
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