從兩種海綿Rhabdastrella sp.及Hippospongia sp.中分離純化出六個海綿天然物，包含了兩個從海綿Rhabdastrella sp.分離出的兩個isomalabaricane類新化合物rhabdastin H (1) 及 rhabdastin I (2)，另外從Hippospongia sp.海綿分離出4個已知的二倍半萜scalarane類化合物分別為，12-epi-scalaradial (3)、12-deacetyl-12-epi-scalaradial (4)、 scalarafuran (5)以及scalarolide acetate (6)，這些化合物結構是透過IR、MS、NMR技術和比對相關已知化合物資料來進行光譜數據分析以確定化合物1–6化學結構，其中化合物1和2在結構中有一個呋喃環(furan)，在海洋所分離出的isomalabaricane類的天然化合物當中是首次發現。
在生物活性測試方面，將化合物3–6進行五種癌細胞 (Molt-4、K562、SUP-T1、U937和KATO III)毒殺試驗，結果顯示化合物3–6針對以上癌細胞具細胞活性，然而更發現化合物3的細胞毒殺活性最為顯著 (IC50 : 0.1、1.29、4.42、0.07、2.09 μM)。

Studied on two marine sponges Rhabdastrella sp. and Hippospongia sp., we isolated six metabolites 1–6, including two new isomalabaricane-type compounds rhabdastin H (1) and rhabdastin I (2) from spong Rhabdastrella sp. From the other spongs Hippospong sp. we isolated four previously reported known scalarane sesterterpenoids, 12-epi-scalaradial (3), 12-deacetyl-12-epi-scalaradial (4), scalarafuran (5) and scalarolide acetate (6). The structure of compunds 1–6 were elucidated by means of IR, MS, and NMR techniques and by comparison of spectral data analysis with those of the related known compounds. Among these metabolites, compounds 1 and 2 are the first report of isomalabaricane –type with a furan ring in marine natural products.
In bioactive test, we tested the cytotoxicity of compounds 3–6 against five cancer cell lines Molt-4, K562, SUP-T1, U937 and KATO III. The results showed that natural products 3–6 were found to exhibit cytotoxicity against all or part of the above carcinoma cell lines, while compound 3 (IC50 values 0.1, 1.29, 4.42, 0.07, 2.09 μM against the five carcinoma cell lines Molt-4, K562, SUP-T1, U937 and KATO III, respectively) was the most potent.

第一章、緒論 1
第二章、文獻回顧 5
第一節、海綿 Rhabdastrella屬所含天然物及活性文獻回顧 5
第二節、isomalabaricane類化合物及活性文獻回顧 20
第三節、海綿 Hippospongia屬所含天然物及活性文獻回顧 26
第三章、生物材料及研究方法 35
第一節、生物材料的採集與分類 35
第二節、生物材料之萃取及分離 38
第四章、實驗材料與器材 41
第一節、儀器設備 41
第二節、藥品試劑 41
第三節、層析材料 42
第五章、化合物之結構證明 43
第一節、海綿 Rhabdastrella sp.之分離化合物結構解析 43
(一)、Rhabdastin H化合物之結構解析 45
(二)、Rhabdastin I化合物之結構解析 57
第二節、海綿 Hippospongia sp.之分離化合物結構解析 69
(一)、12-epi-Scalaradial 之結構解析 71
(二)、12-deacetyl-12-epi-Scalaradial之結構解析 75
(三)、Scalarafuran之結構解析 79
(四)、Scalarolide acetate之結構解析 83
第三節、新化合物實驗數據整理 86
第六章、生物活性試驗 87
第一節、細胞毒殺試驗 87
(一)、細胞毒殺活性試驗 (MTT assay) 87
(二)、細胞毒殺活性試驗結果 (MTT assay) 87
第七章、結論 89
第八章、參考文獻 91

1.Martins, A. Marketed Marine Natural Products in the Pharmaceutical and Cosmeceutical Industries: Tips for Success. Mar. Drugs. 2014. 1066－1101.
2.Zhang, G. Advanced tools in marine natural drug discovery. Curr. Opin. Biotechnol. 2016. 42, 13－23.
3.Anjum, K. Marine Sponges as a Drug Treasure. Biomol. Ther (Seoul). 2016. 24. 347–62.
4.Tasdemir, D. Bioactive isomalabaricane triterpenes from the marine sponge Rhabdastrella globostellata. J. Nat. Prod. 2002. 65, 210－4.
5.Clement, J.A. Bioactive isomalabaricane triterpenoids from Rhabdastrella globostellata that stabilize the binding of DNA polymerase beta to DNA. J. Nat. Prod. 2006. 373－6.
6.Fouad, M. Cytotoxic isomalabaricane triterpenes from the marine sponge Rhabdastrella globostellata. J. Nat. Prod. 2006. 69. 211－8.
7.Fouad, M., et al., Cytotoxic isomalabaricane triterpenes from the marine sponge Rhabdastrella globostellata. J. Nat. Prod. 2006. 211－8.Li, J. Globostelletins A–I, cytotoxic isomalabaricane derivatives from the marine sponge Rhabdastrella globostellata. Bioorg. Med. Chem. 2010. 18. 4639－47.
9.Li, J. Globostelletins J–S, isomalabaricanes with unusual cyclopentane sidechains from the marine sponge Rhabdastrella globostellata. Tetrahedron. 2012. 68. 559－565.
10.Lv, F. Isomalabaricane-type compounds from the marine sponge Rhabdastrella aff. distincta. J. Nat. Prod. 2004. 67. 2033－6.
11.Bourguet-Kondracki. New cytotoxic isomalabaricane-type sesterterpenes from the New Caledonian marine sponge Rhabdastrella globostellata. Tetrahedron. Lett. 2000. 41. 3087－3090.
12.Kiem, P.V. New isomalabaricane analogues from the sponge Rhabdastrella providentiae and their cytotoxic activities. Phytochemistry. Lett. 2018. 26. 199－204.
13.Aoki, S. Novel isomarabarican triterpenes, exhibiting selective anti-proliferative activity against vascular endothelial cells, from marine sponge Rhabdastrella globostellata. Bioorg. Med. Chem. 2007. 15. 4818－28.
14.Rao, Z. Rhabdastrellic Acid-A, a Novel Triterpenoid from the Marine Sponge Rhabdastrella globostellata. J. Nat. Prod. 1997. 60. 1163－1164.
15.Lv, F. Rhabdastrellins A-F, isomalabaricane triterpenes from the marine sponge Rhabdastrella aff. distincta. J. Nat. Prod. 2008. 71. 1738－41. 
16.Tanaka, N. Stelliferins J–N, isomalabaricane-type triterpenoids from Okinawan marine sponge Rhabdastrella cf. globostellata. Tetrahedron. 2011. 6689－6696.
17.Jin. D.-J. Jaspiferins C–F, four new isomalabaricane-type triterpenoids from the South China Sea sponge Jaspisstellifera. J. Asian. Nat Prod Res. 2014. 427－433.
18.Li, Y. Three new cytotoxic isomalabaricane triterpenes from the marine sponge Stelletta tenuis. Fitoterapia. 2015. 226－230.
19.Meragelman. K.M. New Cytotoxic Isomalabaricane Triterpenes from the Sponge Jaspis Species. J. Nat. Prod. 2001. 389－392.
20.Oku. N., New Isomalabaricane Triterpenes from the Marine Sponge Stelletta globostellata That Induce Morphological Changes in Rat Fibroblasts. J. Nat. Prod. 2000. 205－209.
21.Tang, S. Jaspolides A—F, Six New Isomalabricane-Type Terpenoids from the Sponge Jaspis sp. Chem. Pharm. Bull. 2006. 4－8.
22.Xu. W-G. Jaspiferin G, a new isomalabaricane-type triterpenoid from the sponge Jaspis stellifera. J. Biosci. 2015. 111－114.
23.Xue. D.-Q. Isomalabaricane triterpenes with potent protein-tyrosine phosphatase 1B (PTP1B) inhibition from the Hainan sponge Stelletta sp. Biochem Syst Ecol. 2013. 101－106.
24.Zampella, A. New Isomalabaricane Derivatives from a New Species of Jaspis sp. Collected at the Vanuatu Islands. J. Nat. Prod. 2000. 943－946.
25.Zhang. W-H. Isomalabaricane-Type Nortriterpenoids and Other Constituents of the Marine Sponge Geodia japonica. J. Nat. Prod. 2001. 1489－1492.
26.Chang, Y.C. Cytotoxic sesterterpenoids from a sponge Hippospongia sp. Mar. Drugs. 2012. 10. 987－97.
27.Nakamura, H. Dictyoceratin-A and -B, Novel Antimicrobial Terpenoids from the Okinawan Marine Sponge Hipposponqia sp. Tetrahedron. 1986. 42. 4197－4201.
28.Piao, S. Hippolides A–H, Acyclic Manoalide Derivatives from the Marine Sponge Hippospongia lachne. J. Nat. Prod. 2011. 74. 1248－1254.
29.Piao, S.-J. Hippolides A–H, Acyclic Manoalide Derivatives from the Marine Sponge Hippospongia lachne. J. Nat. Prod. 2011. 74. 1248－1254.
30.Rochfort, S.J. Hippospongins A-F:  New Furanoterpenes from a Southern Australian Marine Sponge Hippospongia sp. J. Nat. Prod. 1996. 59. 1024－1028.
31.Guo, Y.-W. Hurghamides A–D, new N-acyl-2-methylene-beta-alanine methyl esters from red sea Hippospongia sp. J. Asian. Nat. Prod. Res. 1997. 281－288.
32.Piao, S.J. New hippolide derivatives with protein tyrosine phosphatase 1B inhibitory activity from the marine sponge Hippospongia lachne. Mar. Drugs. 2014. 12. 4096－109.
33.Guo, Y.-W.；E. Trivellone. New Hurghamids from a Red Sea Sponge of the Genus Hippospongia. J. Asian. Nat. Prod. Res. 2000. 2. 251－256.
34.Madaio, A.New Polyhydrozysterols fron the Di tyoceratid Sponges Hippospongia Communis, Spongia officinalis, Ircinia Variabilis, and Spongionella gracilis. J. Nat. Prod. 1989. 52. 952－961.
35.Shen, Y.-C.；P.-W. Hsieh. New Sesquiterpene Hydroquinones from a Taiwanese Marine Sponge Polyfibrospongia australis. J. Nat. Prod. 1997. 60. 93－97.
36.Walker, R.P.；J.E. Thompson；D.J. Faulkner. Sesterterpenes from Spongia idia. J. Org. Chem. 1980. 45. 4976－4979.
37.R. Bergquist；R.C. Cambie；M.R. Kernan. Scalarane sesterterpenes from Collospongia auris, a new thorectid sponge. Biochem. Syst. Ecol. 1990. 349－357.