Article: New Bicyclic Cembranoids from the South China Sea Soft Coral Sarcophyton trocheliophorum

Nine new bicyclic cembranoids, sarcophytrols M-U(1-9), were isolated from the South China Sea soft coral Sarcophyton trocheliophorum as minor components, along with one known related cembranoid 10. Their structures were elucidated by detailed spectroscopic analysis and chemical conversion. The chemical structures of these metabolites are characterized by the different patterns of the additional cyclization within the 14-member skeleton, which leading to the formation of furan, pyran, oxepane, and peroxyl rings, respectively. Among them, sarcophytrols R and S(6 and 7) share a rare decaryiol skeleton with an unusual C12/C15 cyclization. In addition, the absolute configurations of sarcophytrols M and T(1 and 8) were determined by the modified Mosher's method. The research of these new secondary metabolites provided a further understanding of the diversity of cyclized cembranoids from the title species.

Citing Articles

Cembranoid Diterpenes from South China Sea Soft Coral .

Peng H, Zeng Y, Zhang R, Yang L, Wu F, Gai C Mar Drugs. 2024; 22(12).

PMID: 39728111 PMC: 11676429. DOI: 10.3390/md22120536.

Structurally Diverse Diterpenes from the South China Sea Soft Coral .

Song Y, Yu D, Su M, Luo H, Cao J, Liang L Mar Drugs. 2023; 21(2).

PMID: 36827110 PMC: 9960596. DOI: 10.3390/md21020069.

Cembrane Diterpenes Possessing Nonaromatic Oxacycles from the Hainan Soft Coral .

Zhang L, Yang M, Chen Z, Ge Z, Li S, Yan X Int J Mol Sci. 2023; 24(3).

PMID: 36768306 PMC: 9915928. DOI: 10.3390/ijms24031979.

The Soft Coral : A Warehouse of Terpenoids with Structural and Pharmacological Diversity.

Yang Q, Wu Q, Chen J, Liang L Mar Drugs. 2023; 21(1).

PMID: 36662203 PMC: 9865811. DOI: 10.3390/md21010030.

Bioactive Cembranoids from the Coral of Ximao Island.

Zeng Z, Chen J, Wang H, Zhang H, Li J, Xu B ACS Omega. 2022; 7(45):41678-41686.

PMID: 36406568 PMC: 9670263. DOI: 10.1021/acsomega.2c05687.

References

1.

Liang L, Gao L, Li J, Taglialatela-Scafati O, Guo Y . Cembrane diterpenoids from the soft coral Sarcophyton trocheliophorum Marenzeller as a new class of PTP1B inhibitors. Bioorg Med Chem. 2013; 21(17):5076-80. DOI: 10.1016/j.bmc.2013.06.043. View

2.

Jiang C, Liang L, Guo Y . Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades. Acta Pharmacol Sin. 2012; 33(10):1217-45. PMC: 4002712. DOI: 10.1038/aps.2012.90. View

3.

Liang L, Kurtan T, Mandi A, Yao L, Li J, Zhang W . Unprecedented diterpenoids as a PTP1B inhibitor from the Hainan soft coral Sarcophyton trocheliophorum Marenzeller. Org Lett. 2013; 15(2):274-7. DOI: 10.1021/ol303110d. View

4.

Zhang C, He X, Zhang J, Guo Q, Lei L, Su J . New precursor of tetraterpenoids from the soft coral Sarcophyton glaucum. Nat Prod Res. 2012; 27(9):782-6. DOI: 10.1080/14786419.2012.701211. View

5.

Li Y, Pattenden G . Perspectives on the structural and biosynthetic interrelationships between oxygenated furanocembranoids and their polycyclic congeners found in corals. Nat Prod Rep. 2011; 28(7):1269-310. DOI: 10.1039/c1np00023c. View

6.

Chen W, Liang L, Li X, Xiao W, Guo Y . Further New Highly Oxidative Cembranoids from the Hainan Soft Coral Sarcophyton trocheliophorum. Nat Prod Bioprospect. 2016; 6(2):97-102. PMC: 4805653. DOI: 10.1007/s13659-016-0088-4. View

7.

Lu Y, Huang C, Lin Y, Wen Z, Su J, Kuo Y . Anti-inflammatory cembranoids from the soft corals Sinularia querciformis and Sinularia granosa. J Nat Prod. 2008; 71(10):1754-9. DOI: 10.1021/np8003563. View

8.

Cheng S, Wang S, Chiou S, Hsu C, Dai C, Chiang M . Cembranoids from the octocoral Sarcophyton ehrenbergi. J Nat Prod. 2010; 73(2):197-203. DOI: 10.1021/np900693r. View

9.

Liang L, Guo Y . Terpenes from the soft corals of the genus Sarcophyton: chemistry and biological activities. Chem Biodivers. 2013; 10(12):2161-96. DOI: 10.1002/cbdv.201200122. View

10.

Lai D, Geng Z, Deng Z, van Ofwegen L, Proksch P, Lin W . Cembranoids from the soft coral Sinularia rigida with antifouling activities. J Agric Food Chem. 2013; 61(19):4585-92. DOI: 10.1021/jf401303q. View

11.

Jia R, Guo Y, Mollo E, Gavagnin M, Cimino G . Sarcophytonolides E-H, cembranolides from the Hainan soft coral Sarcophyton latum. J Nat Prod. 2006; 69(5):819-22. DOI: 10.1021/np050477u. View

New Bicyclic Cembranoids from the South China Sea Soft Coral Sarcophyton Trocheliophorum