Biodiversity Literature Repository

Submit to community
Liberated Data
Published March 31, 2023 | Version v1
Journal article Restricted

Sarcoelegans A-H, eight undescribed cembranes with anti-inflammatory and anti-thrombotic activities from the South China Sea soft coral Sarcophyton elegans

Authors/Creators

  • 1. ** & * & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, China & ** & * & Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266003, China

Description

Wang, Cili, Zhang, Jiarui, Gan, Yu, Wang, Mengfei, Li, Xiaolei, Liu, Xuehuan, Shi, Xing, Mi, Yue, Liu, Kechun, Zhang, Yun, Li, Guoqiang, Li, Pinglin (2023): Sarcoelegans A-H, eight undescribed cembranes with anti-inflammatory and anti-thrombotic activities from the South China Sea soft coral Sarcophyton elegans. Phytochemistry (113578) 207: 1-10, DOI: 10.1016/j.phytochem.2022.113578, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113578

Files

Restricted

The record is publicly accessible, but files are restricted to users with access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:FFEAFF9E79481748FFFE6923AA4AFC48

Cites
Publication: 10.1021/acs.orglett.1c00847 (DOI)
Publication: 10.1016/S0300-483X(98)00124-3 (DOI)
Publication: 10.1039/B701534H (DOI)
Publication: 10.1016/j.ijbiomac.2022.09.210 (DOI)
Publication: 10.3390/md20050297 (DOI)
Publication: 10.1021/acs.orglett.1c01601 (DOI)
Publication: 10.1039/D1QO00034A (DOI)
Publication: 10.1248/cpb.56.988 (DOI)
Publication: 10.1021/acs.orglett.8b04019 (DOI)
Publication: 10.1016/0002-8703(84)90132-7 (DOI)
Publication: 10.1002/cjoc.202100564 (DOI)
Publication: 10.1021/acs.orglett.0c01155 (DOI)
Publication: 10.1021/ol403723b (DOI)
Publication: 10.1002/cjoc.202100597 (DOI)
Publication: 10.1021/ol901070e (DOI)
Publication: 10.3390/md19090519 (DOI)
Publication: 10.3390/md19050260 (DOI)
Publication: 10.1002/jat.3303 (DOI)
Publication: 10.1080/14786419.2021.1948041 (DOI)
Publication: 10.1021/acs.jctc.8b01026 (DOI)
Publication: 10.1021/ja105035r (DOI)
Publication: 10.1007/s00214-012-1209-8 (DOI)
Publication: 10.1074/jbc.M510798200 (DOI)
Publication: 10.3390/md20090574 (DOI)
Publication: 10.3390/md11114318 (DOI)
Publication: 10.3390/md11093186 (DOI)
Publication: 10.2174/138527212800672583 (DOI)
Publication: 10.1021/acs.joc.8b03020 (DOI)
Publication: 10.1021/acs.orglett.1c02772 (DOI)
Has part
Figure: 10.5281/zenodo.8290616 (DOI)
Figure: 10.5281/zenodo.8290618 (DOI)
Figure: 10.5281/zenodo.8290622 (DOI)
Figure: 10.5281/zenodo.8290624 (DOI)
Figure: 10.5281/zenodo.8290626 (DOI)
Figure: 10.5281/zenodo.8290628 (DOI)
Figure: 10.5281/zenodo.8290630 (DOI)

References

  • An, J.S., Shin, B., Kim, T.H., Hwang, S., Shin, Y.H., Cui, J., Du, Y.E., Yi, J., Nam, S.J., Hong, S., Shin, J., Jang, J., Yoon, Y.J., Oh, D.C., 2021. Dumulmycin, an antitubercular bicyclic macrolide from a riverine sediment-derived streptomyces sp. Org. Lett. 23, 3359-3363. https://doi.org/10.1021/acs.orglett.1c00847.
  • Badria, F.A., Guirguis, A.N., Perovic, S., Steffen, R., Muller, W.E.G., Schroder, H.C., 1998. Sarcophytolide: a new neuroprotective compound from the soft coral Sarcophyton glaucum. Toxicology 131, 133-143. https://doi.org/10.1016/S0300-483X(98) 00124-3.
  • Blunt, J.W., Copp, B.R., Hu, W.P., Munro, M.H., Northcote, P.T., Prinsep, M.R., 2008. Marine natural products. Nat. Prod. Rep. 25, 35-94. https://doi.org/10.1039/ B701534H.
  • Bu, Q., Yang, M., Yan, X.-Y., Yao, L.-G., Guo, Y.-W., Liang, L.-F., 2022. New flexible cembrane-type macrocyclic diterpenes as TNF-α inhibitors from the South China Sea soft coral Sarcophyton mililatensis. Int. J. Biol. Macromol. 222, 880-886. https:// doi.org/10.1016/j.ijbiomac.2022.09.210.
  • Chao, C.-H., Lin, K.-H., Huang, C.-Y., Hwang, T.-L., Dai, C.-F., Huang, H.-C., Sheu, J.-H., 2022. Computationally assisted structural elucidation of cembranoids from the soft coral Sarcophyton tortuosum. Mar. Drugs 20, 297. https://doi.org/10.3390/ md20050297.
  • Chen, Z.H., Li, W.S., Zhang, Z.Y., Luo, H., Wang, J.R., Zhang, H.Y., Zeng, Z.R., Chen, B., Li, X.W., Guo, Y.W., 2021. Sinusiaetone A, an anti-inflammatory norditerpenoid with a bicyclo[11.3.0]hexadecane nucleus from the hainan soft coral Sinularia siaesensis. Org. Lett. 23, 5621-5625. https://doi.org/10.1021/acs.orglett.1c01601.
  • Costa, F.L.P., de Albuquerque, A.C.F., Fiorot, R.G., Litao, L.M., Martorano, L.H., Mota, G. V.S., Valverde, A.L., Carneiro, J.W.M., dos Santos Junior, F.M., 2021. Structural characterisation of natural products by means of quantum chemical calculations of NMR parameters: new insights. Org. Chem. Front. 8, 2019-2058. https://doi.org/ 10.1039/D1QO00034A.
  • Cuong, N.X., Tuan, T.A., Kiem, P.V., Minh, C.V., Choi, E.M., Kim, Y.H., 2008. New cembranoid diterpenes from the Vietnamese soft coral Sarcophyton mililatensis stimulate osteoblastic differentiation in MC3T3-E1 cells. Chem. Pharm. Bull. 56, 988-992. https://doi.org/10.1248/cpb.56.988.
  • Dauben, W.G., Thiessen, W.E., Resnick, P.R., 1965. Cembrene, a fourteen-membered ring diterpene Hydrocarbon*,1,2. J. Org. Chem. 30, 1693-1698.
  • Gui, Y.H., Jiao, W.H., Zhou, M., Zhang, Y., Zeng, D.Q., Zhu, H.R., Liu, K.C., Sun, F., Chen, H.F., Lin, H.W., 2019. Septosones A-C, in vivo anti-inflammatory meroterpenoids with rearranged carbon skeletons from the marine sponge Dysidea septosa. Org. Lett. 21, 767-770. https://doi.org/10.1021/acs.orglett.8b04019.
  • Jouve, R., Rolland, P.H., Delboy, C., Mercier, C.J.A.H.J., 1984. Thromboxane B2, 6-keto- PGF1 alpha, PGE2, PGF2 alpha, and PGA1 plasma levels in arteriosclerosis obliterans: relationship to clinical manifestations, risk factors, and arterial pathoanatomy. Am. Heart J. 107, 45-52. https://doi.org/10.1016/0002-8703(84) 90132-7.
  • Li, J.-F., Zeng, Y.-B., Li, W.-S., Luo, H., Zhang, H.-Y., Guo, Y.-W., 2022. Xishaglaucumins A-J, new cembranoids with anti-inflammatory activities from the South China Sea Soft coral Sarcophyton glaucum. Chin. J. Chem. 40, 79-90. https://doi.org/ 10.1002/cjoc.202100564.
  • Li, S.-W., Cuadrado, C., Yao, L.-G., Daranas, A.H., Guo, Y.-W., 2020. Quantum mechanical-NMR-aided configuration and conformation of two unreported macrocycles isolated from the soft coral Lobophytum sp.: energy calculations versus coupling constants. Org. Lett. 22, 4093-4096. https://doi.org/10.1021/acs. orglett.0c01155.
  • Lin, K.H., Tseng, Y.J., Chen, B.W., Hwang, T.L., Chen, H.Y., Dai, C.F., Sheu, J.H., 2014. Tortuosenes A and B, new diterpenoid metabolites from the Formosan soft coral Sarcophyton tortuosum. Org. Lett. 16, 1314-1317. https://doi.org/10.1021/ ol403723b.
  • Lin, N., Li, H., Wang, J.-R., Tang, W., Zheng, M.-Y., Wang, H., Jiang, C.-S., Guo, Y.-W., 2022. New cembrane-type diterpenoids from the South China Sea Soft coral Sinularia nanolobata. Chin. J. Chem. 40, 28-38. https://doi.org/10.1002/cjoc.202100597.
  • Lin, S.-T., Wang, S.-K., Cheng, S.-Y., Duh, C.-Y., 2009a. Lobocrasol, a new diterpenoid from the soft coral Lobophytum crassum. Org. Lett. 11, 3012-3014. https://doi.org/ 10.1021/ol901070e.
  • Lin, S.T., Wang, S.K., Cheng, S.Y., Duh, C.Y., 2009b. Lobocrasol, a new diterpenoid from the soft coral Lobophytum crassum. Org. Lett. 11, 3012-3014. https://doi.org/ 10.1021/ol901070e.
  • Mohamed, T.A., Elshamy, A.I., Abdel-Tawab, A.M., AbdelMohsen, M.M., Ohta, S., Pare, P.W., Hegazy, M.F., 2021. Oxygenated cembrene diterpenes from Sarcophyton convolutum: Cytotoxic Sarcoconvolutum A-E. Mar. Drugs 19. https://doi.org/ 10.3390/md19090519.
  • Peng, C.C., Huang, T.Y., Huang, C.Y., Hwang, T.L., Sheu, J.H., 2021. Cherbonolides M and N from a formosan soft coral. Sarcophyton cherbonnieri. Mar. Drugs 19. https:// doi.org/10.3390/md19050260.
  • Pereira, T.C.B., Campos, M.M., Bogo, M.R., 2016. Copper toxicology, oxidative stress and inflammation using zebrafish as experimental model. J. Appl. Toxicol. 36, 876-885. https://doi.org/10.1002/jat.3303.
  • Ren, L., Leng, X., Li, T., Liu, J., Wang, W., Yan, X., Yan, X., He, S., 2021. Four new cembranoids from the South China Sea soft coral Sarcophyton trocheliophorum. Nat. Prod. Res. 1-8 https://doi.org/10.1080/14786419.2021.1948041.
  • Roos, K., Wu, C., Damm, W., Reboul, M., Stevenson, J.M., Lu, C., Dahlgren, M.K., Mondal, S., Chen, W., Wang, L., Abel, R., Friesner, R.A., Harder, E.D., 2019. OPLS3e: extending Force Field Coverage for Drug-Like Small Molecules. J. Chem. Theor.
  • Comput. 15, 1863-1874. https://doi.org/10.1021/acs.jctc.8b01026.
  • Smith, S.G., Goodman, J.M., 2010. Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 probability. J. Am. Chem. Soc. 132, 12946-12959. https://doi.org/10.1021/ja105035r.
  • Su, L.-H., Geng, C.-A., Li, T.-Z., Ma, Y.-B., Huang, X.-Y., Zhang, X.-M., Chen, J.-J., 2020. Artatrovirenols A and B: two cagelike sesquiterpenoids from artemisia atrovirens.
  • Suramitr, S., Piriyagagoon, A., Wolschann, P., Hannongbua, S., 2012. Theoretical study on the structures and electronic properties of oligo(p-phenylenevinylene) carboxylic acid and its derivatives: effects of spacer and anchor groups. Theor. Chem. Acc. 131, 1-15. https://doi.org/10.1007/s00214-012-1209-8.
  • Vetting, M.W., Yu, M., Rendle, P.M., Blanchard, J.S., 2006. The substrate-induced conformational change of Mycobacterium tuberculosis mycothiol synthase. J. Biol. Chem. 281, 2795-2802. https://doi.org/10.1074/jbc.M510798200.
  • Wang, C., Zhang, J., Shi, X., Li, K., Li, F., Tang, X., Li, G., Li, P., 2022. Sarcoeleganolides C-G, five new cembranes from the South China Sea Soft coral Sarcophyton elegans. Mar. Drugs 20, 574. https://doi.org/10.3390/md20090574.
  • Wang, S.K., Hsieh, M.K., Duh, C.Y., 2013. New diterpenoids from soft coral Sarcophyton ehrenbergi. Mar. Drugs 11, 4318-4327. https://doi.org/10.3390/md11114318.
  • Xi, Z., Bie, W., Chen, W., Liu, D., van Ofwegen, L., Proksch, P., Lin, Wenhan, 2013. Sarcophyolides B-E, new cembranoids from the soft coral Sarcophyton elegans. Mar. Drugs 11, 3186-3196. https://doi.org/10.3390/md11093186.
  • Yang, B., Zhou, X.-F., Lin, X.-P., Liu, J., Peng, Y., Yang, X.-W., Liu, Y., 2012. Cembrane diterpenes chemistry and biological properties. Curr. Org. Chem. 16, 1512-1539. https://doi.org/10.2174/138527212800672583.
  • Yang, M., Li, X.L., Wang, J.R., Lei, X., Tang, W., Li, X.W., Sun, H., Guo, Y.W., 2019. Sarcomililate A, an unusual diterpenoid with tricyclo[11.3.0.0(2,16)]hexadecane carbon skeleton, and its potential biogenetic precursors from the hainan soft coral Sarcophyton mililatensis. J. Org. Chem. 84, 2568-2576. https://doi.org/10.1021/ acs.joc.8b03020.
  • Zeng, Z.R., Li, W.S., Nay, B., Hu, P., Zhang, H.Y., Wang, H., Li, X.W., Guo, Y.W., 2021. Sinunanolobatone A, an anti-inflammatory diterpenoid with bicyclo[13.1.0] pentadecane carbon scaffold, and related casbanes from the sanya soft coral Sinularia nanolobata. Org. Lett. 23, 7575-7579. https://doi.org/10.1021/acs. orglett.1c02772.