Message Board

Respected readers, authors and reviewers, you can add comments to this page on any questions about the contribution, review, editing and publication of this journal. We will give you an answer as soon as possible. Thank you for your support!

Name
E-mail
Phone
Title
Content
Verification Code
Volume 15 Issue 6
Nov.  2024
Turn off MathJax
Article Contents

QIU Suiping, CHANG Wenjun, WANG Hao, DAI Haofu, ZENG Yanbo. Cembranoids with anti-inflammatory activity extracted from the soft coral Sarcophyton crassocaule collected off the Xisha Islands[J]. Journal of Tropical Biology, 2024, 15(6): 812-822. doi: 10.15886/j.cnki.rdswxb.20240103
Citation: QIU Suiping, CHANG Wenjun, WANG Hao, DAI Haofu, ZENG Yanbo. Cembranoids with anti-inflammatory activity extracted from the soft coral Sarcophyton crassocaule collected off the Xisha Islands[J]. Journal of Tropical Biology, 2024, 15(6): 812-822. doi: 10.15886/j.cnki.rdswxb.20240103

Cembranoids with anti-inflammatory activity extracted from the soft coral Sarcophyton crassocaule collected off the Xisha Islands

doi: 10.15886/j.cnki.rdswxb.20240103
  • Received Date: 2024-04-12
  • Rev Recd Date: 2024-08-09
  • An attempt was made to identify chemical constituents and their biological activities of Sarcophyton crassocaule, a soft coral, collected off the Xisha Islands in the South China Sea. Using silica gel column chromatography, thin-layer chromatography, Sephadex-20 gel column chromatography, and semi-preparative highperformance liquid chromatography(Semi-Prep HPLC), the ethyl acetate fraction of S. crassocaule was separated and purified, from which 11 compounds were yielded. The physical and chemical properties and spectroscopic data of these compounds were compared with those in the literature. The 11 compounds were identified assarsolilide A( 1 ); trochelioid A( 2 );(1R*,2R*,7R*,8R*,15R*,3E,11E)-7,8: 1,15-diepoxycembra-3,11-dien-16,2-olide( 3 );(+)-7α,8β-dihydroxy-deepoxy-sarcophine( 4 ); 1,15β-epoxy-deoxysarcophine( 5 );(-)-isosarcophine( 6 ); cherbonolide A( 7 );sarcomililatin A( 8 ); trocheliolide A( 9 ); lobophytin B( 10 );(+)-sarcophine( 11 ). Compounds 1~11 are diterpenoids.Compound 3 was identified in S. crassocaule for the first time. The anti-inflammatory activity test showed that sarcomililatin A( 8 ) could inhibit the production of NO in RAW264.7 cells induced by LPS, with the IC50 value of(35.60 ±3.10) μmol·L-1, while the other compounds did not exhibit significant anti-inflammatory activity.
  • [1] ROCHA J, PEIXE L, GOMES N C, et al. Cnidarians as a source of new marine bioactive compounds-An overview of the last decade and future steps for bioprospecting[J].Marine Drugs, 2011, 9(10):1860-1886.
    [2] TIUS M A. Synthesis of cembranes and cembranolides[J].Chemical Reviews, 1988, 88(5):719-732.
    [3] ELKHAWAS Y A, ELISSAWY A M, ELNAGGAR M S, et al. Chemical diversity in species belonging to soft coral genus Sacrophyton and its impact on biological activity:A review[J]. Marine Drugs, 2020, 18(1):41.
    [4] 周洋,杨超杰,王沛政,等.海南岛附近海域肉芝软珊瑚的鉴定[J].应用海洋学学报, 2019, 38(1):30-42.
    [5] KOH M, IWANAGA T, HATANAKA M, et al. Distribution of sarcophytol A in soft coral of the Sarcophyton genus[J].Bioscience, Biotechnology, and Biochemistry, 2000, 64(4):858-861.
    [6] BENAYAHU Y, LOYA Y. Competition for space among coral reef sessile organisms at Eilat, Red Sea[J]. Bulletin of Marine Science, 1981, 31:514-522.
    [7] ROS J, ROMERO J, BALLESTEROS E, et al. Diving in blue water. The benthos[J]. Western Mediterranean, 1985:233-295.
    [8] ARATAKE S, TOMURA T, SAITOH S, et al. Soft coral Sarcophyton (Cnidaria:Anthozoa:Octocorallia) species diversity and chemotypes[J]. PLoS One, 2012, 7(1):e30410.
    [9] SLATTERY M, MCCLINTOCK J B. Population structure and feeding deterrence in three shallow-water antarctic soft corals[J]. Marine Biology, 1995, 122:461-470.
    [10] BONNARD I, JHAUMEER-LAULLOO S B, BONTEMPS N, et al. New lobane and cembrane diterpenes from two Comorian soft corals[J]. Marine Drugs, 2010, 8:359-372.
    [11] IBRAHIM H A H, MOHAMED S Z, EL-REGAL M A, et al. Antibacterial activity of some Red Sea soft corals,Egypt[J]. Blue Biotechnology Journal, 2012, 1(4):497.
    [12] XI Z F, BIE W, CHEN W, et al. Sarcophyolides B-E, new cembranoids from the soft coral Sarcophyton elegans[J].Marine Drugs, 2013, 11(9):3186-3196.
    [13] LIU X, ZHANG J S, LIU Q, et al. Bioactive cembranoids from the South China Sea soft coral Sarcophyton elegans[J].Molecules, 2015, 20(7):13324-13335.
    [14] LAI K H, YOU W J, LIN C C, et al. Anti-inflammatory cembranoids from the soft coral Lobophytum crassum[J].Marine Drugs, 2017, 15(10):327.
    [15] MOHAMMED-GEBA K, ELSHAARAWY R S, ALIAN A, et al. Unraveling the Red Sea soft coral Sarcophyton convolutum potentials against oxidative and inflammatory stresses in zebrafish[J]. Fish&Shellfish Immunology,2024, 147:109442.
    [16] NE'EMAN I, FISHELSON L, KASHMAN Y. Sarcophinea new toxin from the soft coral Sarcophyton glaucum (Alcyonaria)[J]. Toxicon, 1974, 12(6):593-594.
    [17] 李金凤,姚励功,曾艳波,等.西沙乳白肉芝软珊瑚中的化学成分及其抗炎活性研究[J].药学学报, 2022,57(3):741-749.
    [18] 吴敏,周开兵,戴好富,等.乳白肉芝软珊瑚Sarcophyton glaucum的西松烷二萜及生物活性研究[J].中国中药杂志, 2023, 48(3):707-714.
    [19] 高亚欣,王昊,戴好富,等.西沙短指软珊瑚Sinularia flexibilis中具有肿瘤细胞毒活性的甾体化合物[J].热带海洋学报, 2023, 42(5):56-63.
    [20] PENG H Y, ZENG Y B, WANG H, et al. Six undescribed capnosane-type macrocyclic diterpenoids from South China Sea soft coral Sarcophyton crassocaule:Structural determination and biological evaluation[J]. Marine Drugs, 2023, 21(12):645.
    [21] LIU F Z, WANG H, LI W, et al. Filarones A and B, new anti-inflammatory dimeric 2-(2-phenethyl) chromones from agarwood of Aquilaria filaria[J]. Phytochemistry Letters, 2021, 46:11-14.
    [22] ZHANG M, LONG K H, HUANG S H, et al. A novel diterpenolide from the soft coral Sarcophyton solidun[J].Journal of Natural Products, 1992, 55(11):1672-1675.
    [23] HEGAZY M E F, MOHAMED T A, ABDEL-LATIF F F, et al. Trochelioid A and B, new cembranoid diterpenes from the Red Sea soft coral Sarcophyton trocheliophorum[J].Phytochemistry Letters, 2013, 6(3):383-386.
    [24] ZHAO M, CHENG S M, YUAN W P, et al, Cembranoids from a Chinese collection of the soft coral Lobophytum crassum[J]. Marine Drugs, 2016, 14(6):111.
    [25] GROTE D, SOLIMAN H S M, SHAKER K H, et al. Cembranoid diterpenes and a briarane diterpene from corals[J].Natural Product Research, 2006, 20(3):285-291.
    [26] CHAO C H, Li W L, HUANG C Y, et al. Isoprenoids from the soft coral Sarcophyton glaucum[J]. Marine Drugs, 2017, 15(7):202.
    [27] PENG C C, HUANG C Y, AHMED F A, et al. New cembranoids and a biscembranoid peroxide from the soft coral Sarcophyton cherbonnieri[J]. Marine Drugs, 2018, 16(8):276.
    [28] LI S W, YE F, ZHU Z Det al. Cembrane-type diterpenoids from the South China Sea soft coral Sarcophyton mililatensis[J]. Acta Pharmaceutica Sinica B, 2018, 8(6):944-955.
    [29] LIU K M, CHENG C H, CHEN W F, et al. Trocheliolide A, a hydroperoxycembranoidal diterpene from the octocoral Sarcophyton trocheliophorum[J]. Natural Product Communications, 2015, 10(7):1163-1165.
    [30] SHEN H J, LIU X W, JIANG M H, et al. Antiinflammatory cembrane-type diterpenoids and prostaglandins from soft coral Lobophytum sarcophytoides[J].Marine Drugs, 2019, 17(8):481.
    [31] YIN S W, SHI Y P, LI X M, et al. A novel hydroperoxylsubstituted cembranolide diterpene from marine soft coral Lobophytum crassum[J]. Chinese Chemical Letters,2005, 16(11):1489-1491.
    [32] ANJANEYULU A S R, KRISHNA MURTHY M V R,GOWRI P M, et al. A rare prostaglandin from the soft coral Sarcophyton crassocaule of the Indian Ocean[J].Journal of Natural Products, 2000, 63(10):1425-1426.
    [33] ANJANEYULU A S, KRISHNA MURTHY M V R,GOWRI P M. Novel epoxy steroids from the Indian ocean soft coral Sarcophyton crassocaule[J]. Journal of Natural Products, 2000, 63(1):112-118.
    [34] DUH C Y, WANG S K, CHUNG S G, et al. Cytotoxic cembrenolides and steroids from the Formosan soft coral Sarcophyton crassocaule[J]. Journal of Natural Products,2000, 63(12):1634-1637.
    [35] WANG G H, HUANG H C, SU J H, et al. Crassocolides N-P, three cembranoids from the Formosan soft coral Sarcophyton crassocaule[J]. Bioorganic&Medicinal Chemistry Letters, 2011, 21(23):7201-7204.
    [36] HUANG H C, CHAO C H, KUO Y H, et al. Crassocolides G-M, cembranoids from the Formosan soft coral Sarcophyton crassocaule[J]. Chemistry&Biodiversity,2009, 6(8):1232-1242.
    [37] LI L, WANG C Y, SHAO C L, et al. Two new metabolites from the Hainan soft coral Sarcophyton crassocaule[J].Journal of Asian Natural Products Research, 2009,11(10):851-855.
    [38] ZHANG C, LI J, SU J, et al. Cytotoxic diterpenoids from the soft coral Sarcophyton crassocaule[J]. Journal of Natural Products, 2006, 69(10):1476-1480.
    [39] ZHANG C X, YAN S J, ZHANG G W, et al. Isolation of new polyhydroxylated sterol from soft coral Sarcophyton crassocaule Mosre[J]. Chemical Journal of Chinese Universities, 2007, 28(4):686-688.
    [40] LIN W Y, LU Y, CHEN B W, et al. Sarcocrassocolides M-O, bioactive cembranoids from the Dongsha Atoll soft coral Sarcophyton crassocaule[J]. Marine Drugs, 2012,10(3):617-626.
    [41] LIN W Y, SU J H, LU Y, et al. Cytotoxic and antiinflammatory cembranoids from the Dongsha Atoll soft coral Sarcophyton crassocaule[J]. Bioorganic&Medicinal Chemistry, 2010, 18(5):1936-1941.
    [42] LIN W Y, CHEN W, HUANG C Y, et al. Bioactive cembranoids, sarcocrassocolides P-R, from the Dongsha Atoll soft coral Sarcophyton crassocaule[J]. Marine Drugs,2014, 12(2):840-850.
    [43] LIN W Y, LU Y, SU J H, et al. Bioactive cembranoids from the Dongsha atoll soft coral Sarcophyton crassocaule[J].Marine Drugs, 2011, 9(6):994-1006.
    [44] 徐效华,孔垂华,林长江,等.软珊瑚Sarcophyton crassocaule中Cembrane型二萜的分离与鉴定[J].高等学校化学学报, 2003, 24(6):1023-1025.
    [45] LIN W Y, LU Y, SU J S, et al. Bioactive cembranoids from the Dongsha Atoll soft coral Sarcophyton crassocaule[J].Marine Drugs, 2011, 9(6):994-1006.
    [46] HEGAZY M E F, ELDEEN A M, SHAHAT A A, et al.Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum[J]. Marine Drugs, 2012,10(1):209-222.
    [47] MOHAMED T A, ELSHAMY A I, ABEDL-TAEAB A M,et al. Oxygenated cembrene diterpenes from Sarcophyton convolutum:Cytotoxic sarcoconvolutum A-E[J]. Marine Drugs, 2021, 19(9):519.
  • 加载中
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

Article views(45) PDF downloads(0) Cited by()

Proportional views
Related

Cembranoids with anti-inflammatory activity extracted from the soft coral Sarcophyton crassocaule collected off the Xisha Islands

doi: 10.15886/j.cnki.rdswxb.20240103

Abstract: An attempt was made to identify chemical constituents and their biological activities of Sarcophyton crassocaule, a soft coral, collected off the Xisha Islands in the South China Sea. Using silica gel column chromatography, thin-layer chromatography, Sephadex-20 gel column chromatography, and semi-preparative highperformance liquid chromatography(Semi-Prep HPLC), the ethyl acetate fraction of S. crassocaule was separated and purified, from which 11 compounds were yielded. The physical and chemical properties and spectroscopic data of these compounds were compared with those in the literature. The 11 compounds were identified assarsolilide A( 1 ); trochelioid A( 2 );(1R*,2R*,7R*,8R*,15R*,3E,11E)-7,8: 1,15-diepoxycembra-3,11-dien-16,2-olide( 3 );(+)-7α,8β-dihydroxy-deepoxy-sarcophine( 4 ); 1,15β-epoxy-deoxysarcophine( 5 );(-)-isosarcophine( 6 ); cherbonolide A( 7 );sarcomililatin A( 8 ); trocheliolide A( 9 ); lobophytin B( 10 );(+)-sarcophine( 11 ). Compounds 1~11 are diterpenoids.Compound 3 was identified in S. crassocaule for the first time. The anti-inflammatory activity test showed that sarcomililatin A( 8 ) could inhibit the production of NO in RAW264.7 cells induced by LPS, with the IC50 value of(35.60 ±3.10) μmol·L-1, while the other compounds did not exhibit significant anti-inflammatory activity.

QIU Suiping, CHANG Wenjun, WANG Hao, DAI Haofu, ZENG Yanbo. Cembranoids with anti-inflammatory activity extracted from the soft coral Sarcophyton crassocaule collected off the Xisha Islands[J]. Journal of Tropical Biology, 2024, 15(6): 812-822. doi: 10.15886/j.cnki.rdswxb.20240103
Citation: QIU Suiping, CHANG Wenjun, WANG Hao, DAI Haofu, ZENG Yanbo. Cembranoids with anti-inflammatory activity extracted from the soft coral Sarcophyton crassocaule collected off the Xisha Islands[J]. Journal of Tropical Biology, 2024, 15(6): 812-822. doi: 10.15886/j.cnki.rdswxb.20240103
Reference (47)

Catalog

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return