Cembrane

Cembrane are secondary natural substances from the class of diterpenes . They consist of a 14-membered ring that is substituted with three methyl groups and one isopropyl group. Many membranes also have one or more ether, furan or lactone rings. Cembrane are the central intermediate stage in the biosynthesis of a large number of diterpene frameworks.

Cembran

Occurrence

Cembrane are found mainly in marine invertebrates as well as in some plants and insects. About 1,000 membranes are known.

Marine invertebrates

Approx. 900 membranes were isolated from soft corals.

Leather corals , e.g. B. from the genera Sarcophyton and Sinularia
Horn corals ( gorgonians ), e.g. B. from Pseudopterogorgia bipinnata

plants

Approx. 100 membranes are known from plants so far. They only occur in a few families that are not closely related and in these families too they are restricted to individual genera or species.

Euphorbiaceae : approx. 30 membranes, e.g. B. in the genera Croton
Burseraceae , approx. 20 Cembrane in the genus Boswellia (incense), e.g. B. Incensol
Solanaceae : approx. 30 Cembrane in the genus Nicotiana (tobacco)
Cleomaceae : approx. 10 membranes in the genus Cleome (spider flower)
Lamiaceae : approx. 20 membranes in the genus Anisomeles

insects

Approx. 10 membranes were found in the ant genus Crematogaster and in termites of the genus Nasutitermes .

bacteria

Simple membranes were found in Streptomyces after the corresponding cyclases were found using genetic methods.

properties

Lophotoxin

Many membranes are antimicrobially active or cytotoxic. Incensol from frankincense shows anti-inflammatory and anti-anxiety effects.

function

The function of the membrane for the organism is in most cases not explicitly clarified, however there are some examples in which it has been proven that they protect the organism from predators or competition. Lophotoxin from the horn coral genus Lophogorgia is very poisonous for fish. Flexibilid and Sarcophytoxid inhibit the growth of hard coral in symbiosis living zooxanthellae , thereby protecting the soft corals that produce these Cembrane, ahead of the competition of stony corals .

biosynthesis

Cembrane are formed by the cyclization of geranylgeraniol diphosphate. The biosynthesis in Ricinus and Streptomyces has been clarified at the enzymatic and genetic level. The cyclases catalyze the same cyclization reaction, but show no sequence homology . The gradual oxidation of the membrane only takes place after the cyclization. Starting from the membrane or Casban, which has a dimethylcyclopropane ring instead of the isopropenyl group, many other diterpene structures are synthesized by a wide variety of organisms, e.g. B.

Lathyrane, Jatrophane, Tiglane, Ingenane in Euphorbiaceae and Thymeleaceae, e.g. B. Ingenol mebutate
Taxanes in Taxus, e.g. B. Paclitaxel
Fusicoccane in mushrooms, e.g. B. fusicoccin
Briarane, Eunicellane and Dolabellane in soft corals, e.g. B. Eleutherobin
Trinervitans in termites

Individual evidence

↑ Bin Yang, Xue-Feng Zhou, Xiu-Ping Lin, Juan Liu, Yan Peng: Cembrane Diterpenes Chemistry and Biological Properties . In: Current Organic Chemistry . tape 16 , no. 12 , May 31, 2012, p. 1512–1539 , doi : 10.2174 / 138527212800672583 ( eurekaselect.com [accessed January 1, 2018]).
↑ Dictionary of Natural Products 26.2 , CRC Press, search for (Type of Compound = "Cembrane" and Type of Organism = plant family) , accessed January 2, 2018.
^ ^A ^b Ayuko Meguro, Takeo Tomita, Makoto Nishiyama, Tomohisa Kuzuyama: Identification and Characterization of Bacterial Diterpene Cyclases that Synthesize the Cembrane Skeleton . In: ChemBioChem . tape 14 , no. 3 , February 11, 2013, p. 316–321 , doi : 10.1002 / cbic.201200651 ( wiley.com [accessed January 2, 2018]).
↑ Federica Pollastro, Samantha Golin, Giuseppina Chianese, Masteria Yunovilsa Putra, Aniello Schiano Moriello: Neuroactive and Anti-inflammatory Frankincense Cembranes: A Structure – Activity Study . In: Journal of Natural Products . tape 79 , no. 7 , July 22, 2016, p. 1762–1768 , doi : 10.1021 / acs.jnatprod.6b00141 .
↑ Mebs, D .: Poisons in the reef: Toxicology and biochemistry of a habitat . Wissenschaftliche Verlagsgesellschaft, Stuttgart 1989, ISBN 3-8047-1053-0 .
↑ James Kirby, Minobu Nishimoto, J. Genevieve Park, Sydnor T. Withers, Farnaz Nowroozi: Cloning of casbene and neocembrene synthases from Euphorbiaceae plants and expression in Saccharomyces cerevisiae . In: Phytochemistry . tape 71 , no. 13 , p. 1466–1473 , doi : 10.1016 / j.phytochem.2010.06.001 ( elsevier.com [accessed January 2, 2018]).
↑ Breitmaier, Eberhard: Terpene aromas, fragrances, pharmaceuticals, pheromones . 2., completely revised u. exp. Edition. Wiley-VCH, Weinheim 2012, ISBN 978-3-527-66048-3 .

[1] Bin Yang, Xue-Feng Zhou, Xiu-Ping Lin, Juan Liu, Yan Peng: Cembrane Diterpenes Chemistry and Biological Properties . In: Current Organic Chemistry . tape 16 , no. 12 , May 31, 2012, p. 1512–1539 , doi : 10.2174 / 138527212800672583 ( eurekaselect.com [accessed January 1, 2018]).

[2] Dictionary of Natural Products 26.2 , CRC Press, search for (Type of Compound = "Cembrane" and Type of Organism = plant family) , accessed January 2, 2018.

[:0-3] A ^b Ayuko Meguro, Takeo Tomita, Makoto Nishiyama, Tomohisa Kuzuyama: Identification and Characterization of Bacterial Diterpene Cyclases that Synthesize the Cembrane Skeleton . In: ChemBioChem . tape 14 , no. 3 , February 11, 2013, p. 316–321 , doi : 10.1002 / cbic.201200651 ( wiley.com [accessed January 2, 2018]).

[4] Federica Pollastro, Samantha Golin, Giuseppina Chianese, Masteria Yunovilsa Putra, Aniello Schiano Moriello: Neuroactive and Anti-inflammatory Frankincense Cembranes: A Structure – Activity Study . In: Journal of Natural Products . tape 79 , no. 7 , July 22, 2016, p. 1762–1768 , doi : 10.1021 / acs.jnatprod.6b00141 .

[5] Mebs, D .: Poisons in the reef: Toxicology and biochemistry of a habitat . Wissenschaftliche Verlagsgesellschaft, Stuttgart 1989, ISBN 3-8047-1053-0 .

[6] James Kirby, Minobu Nishimoto, J. Genevieve Park, Sydnor T. Withers, Farnaz Nowroozi: Cloning of casbene and neocembrene synthases from Euphorbiaceae plants and expression in Saccharomyces cerevisiae . In: Phytochemistry . tape 71 , no. 13 , p. 1466–1473 , doi : 10.1016 / j.phytochem.2010.06.001 ( elsevier.com [accessed January 2, 2018]).

[7] Breitmaier, Eberhard: Terpene aromas, fragrances, pharmaceuticals, pheromones . 2., completely revised u. exp. Edition. Wiley-VCH, Weinheim 2012, ISBN 978-3-527-66048-3 .