Structural Modifications and Biological Activities of Natural α- and β-Cembrenediol: A Comprehensive Review

Abstract

As one of the most characteristic ingredients of glandular trichome secretions from Nicotiana tabacum L. (tobacco), natural cembrenediols, namely, (1S,2E,4S,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (α-cembrenediol/α-CBD) and its C-4 epimer (β-cembrenediol/β-CBD), have attracted considerable attention for their potent antitumor, neuroprotective, antimicrobial, and other activities. Many researchers are committed to exploring the possibility of utilizing these two cembrenediols and their derivatives both in human medicine and in agricultural fungicides. To the best of our knowledge, this review is the first to provide a comprehensive summary of the chemical modifications and bioactivities of α- and β-CBD from their discovery to the present day; the review highlights their potential medicinal value for humans. The extensive references from 1962 to 2022 provided herein were systematically gathered from the SciFinder, Web of Science, and Google Scholar databases. We expect this review to assist in providing practical ideas for future drug development based on α- and β-CBD and in further facilitating the utilization of the tobacco cembrenediols.

Identification and Evaluation of Diterpenoids from Glandular Trichome Secretions of Air/Sun-Cured Tobacco Germplasm Resources

“…α-cembratriene-diol (α-CBT-diol), β-cembratriene-diol (β-CBT-diol), and cis-abienol are the main diterpenoids present in tobacco. The content of α-CBT-diol and β-CBT-diol can account for approximately 60% of the total glandular trichome secretions [2]. These diterpenoids are not only important precursors of the aromatic components of tobacco leaves but also exhibit useful biological effects, such as antibacterial, insecticidal, and anti-tumor activities [2][3][4].…”

“…The content of α-CBT-diol and β-CBT-diol can account for approximately 60% of the total glandular trichome secretions [2]. These diterpenoids are not only important precursors of the aromatic components of tobacco leaves but also exhibit useful biological effects, such as antibacterial, insecticidal, and anti-tumor activities [2][3][4]. During tobacco leaf curing, Cembratriene-diol (CBT-diol) is degraded to produce solanone, solanofuran, solandione, and other flavor components.…”

Uncommon Capnosane Diterpenes with Neuroprotective Potential from South China Sea Soft Coral Sarcophyton boettgeri

“…Moreover, from an ecological point of view, some representative cembranoids are regarded as chemical defense tools to protect soft corals against natural predators, servicing as feeding deterrents or acting by virtue of their toxicities [ 21 ]. Because cembranoids exhibit a huge potential for the development of various drug candidates with remarkable health and ecological benefits, numerous efforts toward the chemical modification and total synthesis of them were made [ 16 , 22 , 23 , 24 ].…”

Investigation of the growth performance, blood status, gut microbiome and metabolites of rabbit fed with low-nicotine tobacco

“…Moreover, tobacco is a rich source of different bioactive compounds with multiple biological activities, especially abundant in phenolic compounds, such as chlorogenic acid, kaempferol, caffeic acids, rutin, isoquercetin, and luteolin (Ru et al, 2012;Sifola et al, 2021). It can also synthesize a variety of beneficial components or drug precursors, such as cembrane diterpenes with antioxidant functions (Xu et al, 2022). The above features indicate that tobacco has great potential for further development and utilization.…”