Ectocarpene Explained

Ectocarpene is the rearrangement product of pre-ectocarpene,^[1] the sexual attractant, or pheromone, found with several species of brown algae (Phaeophyceae). Ectocarpene has a fruity scent and can be sensed by humans when millions of algae gametes swarm the seawater and the females start emitting the substance's precursor to attract the male gametes.

All the double bonds are cis and the absolute configuration of the stereocenter is (S).^[2]

History

Ectocarpene was isolated from algae Ectocarpus (order Ectocarpales) by Müller and col. in 1971.^[3] It has been mistakened to be the active substance for gamete attraction until 1995, and pre-ectocarpene was discovered to be active. This confusion arises from the sigmatropic rearrangement (and thus deactivation) of pre-ectocarpene in minutes at room temperature:^[4] This is as to only have the phermon active in the proximity of the female gametes.

The presence of ectocarpene in Capsicum fruit was reported in 2010. Studies concluded that its "sweet and green" aroma surfaced through identification tests as well as sensory tests. Its relatively low but influential presence helps develop the Capsicum fruit’s profile.^[5]

Related Compounds

(E)-Ectocarpene is a product associated to a group referred to as Bryophytes, a family of liverworts, algae, and other species with medicinal and nutritional properties. It is suggested that (E)-ectocarpene may have an evolutionary relationship between families of liverworts and algae as its concentration of formation varies based on the species’ environmental conditions.^[6]

See also

• Dictyopterene

External links

• Evidence of ectocarpene and dictyopterenes A and C’ in the water of a freshwater lake’

Notes and References

1. Wilhelm Boland . 1995 . The Chemistry of Gamete Attraction: Chemical Structures, Biosynthesis, and (a)biotic Degradation of Algal Pheromones . Proceedings of the National Academy of Sciences of the United States of America . 92 . 1 . 37–43 . 1995PNAS...92...37B . 10.1073/pnas.92.1.37 . 2366495 . 42813 . 7816845 . free.
2. Wilhelm Boland . 1995 . The Chemistry of Gamete Attraction: Chemical Structures, Biosynthesis, and (a)biotic Degradation of Algal Pheromones . Proceedings of the National Academy of Sciences of the United States of America . 92 . 1 . 37–43 . 1995PNAS...92...37B . 10.1073/pnas.92.1.37 . 2366495 . 42813 . 7816845 . free.
3. Mueller, D. G. . Jaenickel, L. . Donike, M. . Akintobi, T. . Sex attractant in a brown alga: chemical structure . Science . 1971 . 171 . 3973 . 815–817 . 10.1126/science.171.3973.815 . 17812027. 1971Sci...171..815M . 41629286 .
4. Book: Clayden . Jonathan . Organic chemistry . Greeves . Nick . Warren . Stuart G. . 2012 . Oxford University Press . 978-0-19-927029-3 . 2nd . Oxford ; New YorK . 915.
5. Rodríguez-Burruezo. Adrián. Kollmannsberger. Hubert. González-Mas. M. Carmen. Nitz. Siegfried. Fernando. Nuez. 2010-04-14. HS-SPME Comparative Analysis of Genotypic Diversity in the Volatile Fraction and Aroma-Contributing Compounds of Capsicum Fruits from the annuum − chinense − frutescens Complex. Journal of Agricultural and Food Chemistry. en. 58. 7. 4388–4400. 10.1021/jf903931t. 20199081. 0021-8561.
6. Asakawa. Yoshinori. Ludwiczuk. Agnieszka. 2018-03-23. Chemical Constituents of Bryophytes: Structures and Biological Activity. Journal of Natural Products. en. 81. 3. 641–660. 10.1021/acs.jnatprod.6b01046. 29019405. 0163-3864.