在針對養殖型八放珊瑚Briareum excavatum所含化學成分的研究中分離出三十二個briarane型式的雙萜化合物1‒32，其中化合物1‒18為新化合物，化合物19‒32為已知化合物。所有化合物的化學構造均由光譜數據分析而確定，而化合物briaexcavatins I (1)、U (13)、W (15)以及已知化合物excavatolides C (19)、E (20)的結構更進一步以X-ray單晶繞射實驗確認。化合物13與20的絕對立體構型則分別藉由X-ray單晶繞射實驗以及Mosher酯化反應修飾而確定。化合物briaexcavatin Y (17)是在briarane型態骨架的化合物中，第一個在C-8/9具有epoxy官能基的化合物。在此次研究也討論在C-11,12具有epoxy官能基的briarane化合物在13C NMR化學位移與結構立體位向的關係。在細胞毒殺活性試驗方面，briaexcavatin S (11)和已知化合物excavatolide C (19)、Z (24)對於人類淋巴瘤細胞CCRF-CEM具有微弱的細胞毒殺活性，另外化合物
briaexcavatin J (2) 和已知化合物excavatolide C (19)對於直腸腫瘤細胞DLD-1也顯示有微弱的細胞毒殺活性；在抗發炎活性試驗方面，excavatolide Z (24)和briaexcavatolides
O (26)、P (27)對於超氧自由基的產生顯示有中等的抑制活性；而在抑制彈性蛋白酶產生的試驗中briaexcavatin V (14) 、excavatolide Z (24)、briaexcavatolide O (26)、
11-hydroxybrianthein U (30)顯示具有中等的抑制效果；另外briaexcavatin Z (18)卻發現有中等的促進彈性蛋白酶的產生情形。

In the continuing search for novel substances from marine invertebrates originally distributed in Taiwan waters. The octocoral Briareum excavatum was transplanted to the culturing tanks located in the NMMBA for its interesting chemical constituents. This study had led to the isolation of 32 briarane derivatives 1–32, including 18 new compounds,
briaexcavatins I–Z (1–18) from the cultured B. excavatum. The structures of compounds
1–32 were determined by spectroscopic methods and the structures of briaexcavatins I (1), U (13), W (15) and the known compound excavatolides C (19) and E (20) were confirmed by X-ray data analysis. The absolute configurations of briaranes 13 and 20 were determined by X-ray diffraction analysis and modified Mosher’s method, respectively. It is noteworthy
to mention that briaexcavatin Y (17) represents the first example of a briarane possessing a C-8/9 epoxy group. The relationships between 13C NMR chemical shifts and the conformations of the briaranes possessing an 11,12-epoxy group are described.
In biological activity experiments, briaranes 11, 19, and 24 exhibited weak cytotoxicity toward CCRF-CEM tumor cells and compounds 2 and 19 showed weak
cytotoxicity toward DLD-1 tumor cells, respectively. Moreover some of these briaranes such as compounds 24, 26, and 27 have displayed mild inhibitory effects on superoxide anion generation by human neutrophils. Compounds 14, 24, 26, and 30 showed mild inhibitory effects on human neutrophil elastase release. Compound 18 exhibited mild
activity to enhance human neutrophil elastase release.

中文摘要 XVII

英文摘要 XVIII

壹、緒論 1
第一節、前言 1
第二節、研究動機 2
第三節、Briareum屬軟珊瑚文獻回顧 5
貳、生物材料與研究方法 35
第一節、生物材料的採集與分類 35
第二節、生物樣品的萃取與分離流程 37
第三節、Mosher’s 酯化反應 40
參、實驗器材與有機溶劑 41
第一節、儀器 41
第二節、有機溶劑 42
肆、生物活性試驗 44
第一節、細胞毒殺活性測試 44
第二節、抗發炎活性測試 45
伍、結果與討論 49
第一節、軟珊瑚Briareum excavatumn所含成分之研究 49
(一)、Briaexcavatin I (1)之結構解析 49
(二)、Briaexcavatin J (2)之結構解析 61
(三)、Briaexcavatin K (3)之結構解析 71
(四)、Briaexcavatin L (4)之結構解析 81
(五)、Briaexcavatin M (5)之結構解析 91
(六)、Briaexcavatin N (6)之結構解析 103
(七)、Briaexcavatin O (7)之結構解析 115
(八)、Briaexcavatin P (8)之結構解析 127
(九)、Briaexcavatin Q (9)之結構解析 137
(十)、Briaexcavatin R (10)之結構解析 149
(十一)、Briaexcavatin S (11)之結構解析 159
(十二)、Briaexcavatin T (12)之結構解析 169
(十三)、Briaexcavatin U (13)之結構解析 181
(十四)、Briaexcavatin V (14)之結構解析 193
(十五)、Briaexcavatin W (15)之結構解析 205
(十六)、Briaexcavatin X (16)之結構解析 217
(十七)、Briaexcavatin Y (17)之結構解析 227
(十八)、Briaexcavatin Z (18)之結構解析 237
(十九) Excavatolide C (19)之結構解析 247
(二十) Excavatolide E (20)之結構解析 249
(二十一) Excavatolide D (21)之結構解析 255
(二十二) Excavatolide F (22)之結構解析 259
(二十三) Excavatolide M (23)之結構解析 263
(二十四) Excavatolide Z (24)之結構解析 267
(二十五) Briaexcavatolide L (25)之結構解析 271
(二十六) Briaexcavatolide O (26)之結構解析 275
(二十七) Briaexcavatolide P (27)之結構解析 279
(二十八) Briaexcavatolide W (28)之結構解析 283
(二十九) Briaexcavatolide U (29)之結構解析 287
(三十) 11-Hydroxybrianthein U (30)之結構解析 291
(三十一) Pachyclavulide A (31)之結構解析 295
(三十二) Briareolide B (32)之結構解析 299
第二節、化合物實驗數據整理 303
第三節、化合物生物活性試驗結果 307
陸、結論 311
柒、參考文獻 315
捌、附錄 321
附錄一、X-ray解析資料 321

1. 戴昌鳳，洪聖雯“台灣珊瑚圖鑑”家庭傳媒城邦分公司，2009，pp 12–24。
2. 戴昌鳳“墾丁國家公園 珊瑚之美”墾丁國家公園管理處員工消費合作社，1987，pp 9–16。
3. 方力行“珊瑚學”教育部大學聯合出版委員會，1989，pp 1–30。
4. 許實波“海洋生物製藥”化學工業出版社，2002，pp 48–64。
5. Blunt, J. W.; Copp, B. R.; Hu, W.-P.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. “Marine Natural Products” Nat. Prod. Rep. 2008, 25, 35–94.
6. William Fenical “New pharmaceuticals from marine organisms” Mar. Biotech. 1997, 15, 339–341.
7. M. J. Garson, in Sponges in Time and Space (Proceedings of the 4th International Porifera Congress, Amsterdam), Balkema, Rotterdam, 1994, 427–440.
8. Simmons, T. L.；Andrianasolo, E.；McPhail, K.；Flatt, P.；Gerwick, H. W. “Marine natural products as anticancer drugs” Mol Cancer Ther, 2005, 4, 333–342.
9. Harvey, A. L. “Natural products in drug discovery” DDT. 2008, 13, 894–901.
10. Sung, P. J.; Sheu, J. H.; Xu, J. P. “Survey of briarane-type diterpenoids of marine origin” Heterocycles, 2002, 57, 535–579.
11. Ciereszko, L. S.; Sifford, D. H.; Weinheimer, A. J. “Chemistry of coelenterates. I. occurrence of terpenoid compound in gorgonians” Ann. N. Y. Acad. Sci. 1960, 90, 917–919.
12. Burks, J. E.; Helm, D. V. D.; Chang, C. Y.; Ciereszko, L. S. “The crystal and molecular structure of briarein A, a diterpenoid from the gorgonian Briareum asbestinum” Acta Cryst, 1977, 33B, 704–709.
13. Stierle, D. B.; Carté, B.; Faulkner, D. J.; Tagle, B.; Clardy, J. “The asbestinins, a novel class of diterpenes from the gorgonian Briareum asbestinum” J. Am. Chem. Soc. 1980, 102, 5088–5092.
14. Selover, S. J.; Crews, P.; Tagle, B.; Clardy, J. New “Diterpenes from the Common Caribbean Gorgonian Briareum asbestinum (Pallus)” J. Org. Chem., 1981, 46, 964–970.
15. Rodríguez, A. D.; Ramírez, C.; Cóbar, O. M. “Briareins C-L, 10 new briarane diterpenoids from the common caribbean gorgonian Briareum asbestinum” J. Nat. Prod. 1996, 59, 15–22.
16. Coval, S. J.; Cross, S.; Bernardinelli, G.; Jefford, C. W. “Brianthein V, a new cytotoxic and antiviral diterpene isolated from Briareum asbestinum” J. Nat. Prod. 1988, 51, 981–984.
17. Maharaj, D.; Mootoo, B. S.; Longh, A. L.; Mclean, S.; Reynolds, W. F.; Tinto, W. F. “Methyl brtareolate, the frist briarein diterpene containing a C-19 methyl ester” Tetrahedron Lett. 1992, 33, 7761–7764.
18. Dookran, R, Maharaj, D.; Mootoo, B. S.; Ramsewak, R.; Mclean, S.; Reynolds, W. F.; Tinto, W. F. “Briarane and asbestinane diterpenes from Briareum asbestinum” Tetrahedron, 1994, 50, 1983–1992.
19. Mootoo, B. S.; Ramsewak, R.; Sharma, R.; Tinto, W. F. Lough, A. J.; Mclean, S.; Reynolds, W. F.; Yang, J. P.; Yu, M. “Further briareolate esters and briareolides from the caribbean gorgonian octocoral Briareum asbestinum” Tetrahedron, 1996, 52, 9953–9962.
20. González, N.; Rodríguez, J.; Kerr, R. G.; Jiménez, C. “Cyclobutenbriarein A, the first diterpene with a tricyclo[8.4.0.03,6] tetradec-4-ene ring system isolated from the gorgonian Briareum asbestinum” J. Org. Chem. 2002, 67, 5117–5123.
21. Schmitz, F. J.; Schulz, M. M.; Siripitayananon, J.; Hossain, M. B.; Helm, D. V. D. “New diterpenes from the gorgonian Solenopodium excavatum” J. Nat. Prod. 1993, 56, 1339–1349.
22. Sheu, J. -H.; Sung, P. -J.; Cheng, M. -C.; Liu, H. -Y.; Fang, L. -S.; Duh, C. -Y.; Chiang, M. Y. “Novel cytotoxic diterpenes, excavatolidea A‒E, isolated from the formosan gorgonian Briareum excavatum” J. Nat. Prod. 1998, 61, 602–608.
23. Sung, P.-J.; Su, J.-H.; Wang, G.-H.; Lin, S.-F.; Duh, C.-Y.; Sheu, J. -H. “Excavatolides F−M, New Briarane Diterpenes from the Gorgonian Briareum excavatum” J. Nat. Prod. 1999, 62, 457–463.
24. Neve, J. E.; Mccool, B. J.; Bowden, B. F. “Excavatolides N‒T, new briaran diterpenes from the western australian gorgonian Briareum excavatum” Aust. J. Chem. 1999, 52, 359–366.
25. Sheu, J. H.; Sung, P. J.; Su, J. H.; Wang, G. H.; Duh, C. Y.; Shen, Y. C.; Chiang, M. Y.; Chen, I. T. “Excavatolides U−Z, New Briarane Diterpenes from the Gorgonian Briareum excavatum” J. Nat. Prod. 1999, 62, 1415–1420.
26. Sheu, J.-H.; Sung, P.-J.; Su, J.-H.; Liu, H.-Y.; Duh, C.-Y.; Chiang, M.-Y. “Briaexcavatolides A–J, New Diterpenes from the Gorgonian Briareum excavatum” Tetrahedron, 1999, 55, 14555–14564.
27. Sung, P.-J.; Su, J.-H.; Duh, C.-Y.; Chiang, M.-Y.; Sheu. J.-H. “Briaexcavatolides
K–N, New Briarane Diterpenes from the Gorgonian Briareum excavatum” J. Nat.
Prod. 2001, 64, 318–323.
28. Wu, S.-L.; Sung, P.-J.; Chaing, M.-Y.; Wu, J.-Y.; Sheu, J.-H. “New Polyoxygenated Briarane Diterpenoids, Briaexcavatolides O–R, from the Gorgonian Briareum excavatum” J. Nat. Prod. 2001, 64, 1415–1420.
29. S. Aoki, M. Okano, K. Matsui, T. Itoh, R. Satari, S. Akiyama, and M. Kobayashi.
“Brianthein A, a novel briarane-type diterpene reversing multidrug resistance in
human carcino- ma cell line, from the gorgonian Briareum excavatum” Tetrahedron, 2001, 57, 8951– 8957.
30. Wu, S.-L.; Sung, P.-J.; Su, J.-H.; Sheu, J.-H. “Briaexcavatolides S–V, four New Briaranes from a Formosan Gorgonian Briareum excavatum” J. Nat. Prod. 2003, 66, 1252–1256.
31. Wu, S.-L.; Sung, P.-J.; Su, J.-H.; Wang, G. -H.; Sheu, J.-H. “Briaexcavatolide W, a New Diterpenoid from Briareum excavatum” Heterocycles, 2004, 63, 895–898.
32. Sung, P.-J.; Hu, W.-P.; Wu, S.-L.; Su, J.-H.; Fang, L.-S.; Wang, J.-J.; Sheu, J.-H. “Briaexcavatolides X–Z, Three New Briarane-Related Derivatives from the Gorgonian Coral Briareum excavatum” Tetrahedron, 2004, 60, 8975–8979.
33. Sung, P.-J.; Chao, C.-H.; Chen, Y.-P.; Su, J.-H.; Hu, W.-P.; Sheu, J.-H. “Briaexcavatins A and B, Novel Briaranes from the Octocoral Briareum excavatum” Tetrahedron Lett. 2006, 47, 167–170.
34. Sung, P.-J.; Chen, Y.-P.; Hwang, T.-L.; Hu, W.-P.; Fang, L.-S.; Wu, Y.-C.; Li, J.-J.; Sheu, J.-H “Briaexcavatins C–F, Four New Briarane-Related Diterpenoids from the Formosan Octocoral Briareum excavatum (Briareidae)” Tetrahedron, 2006, 62, 5686–5691.
35. Chen, Y.-P.; Wu, S.-L.; Su, J.-H.; Lin, M.-R.; Hu, W.-P.; Hwang, T.-L.; Sheu, J.-H.; Fan, T.-Y.; Fang, L.-S.; Sung, P.-J. “Briaexcavatins G and H, Two New Briaranes from the Octocoral Briareum excavatum” Bull. Chem. Soc. Jpn. 2006, 79, 1900–1905.
36. Cardellina, J. H.; James, T. R. “Structure of brianthein W, from the soft coral Briareum polyanthes” J. Org. Chem. 1984, 49, 3398–3399.
37. Grode, S. H.; James, T. R.; Jr., Cardellina, J. H. “Molecular structures of the briantheins, new insecticidal diterpenes from Briareum polyanthes” J. Org. Chem. 1983, 48, 5203–5207.
38. Grode, S. H.; James, T. R.; Cardellina, J. H. “Brianthein Z, a new polyfunctional diterpene from the gorgonian Briareum polyanthes” Tetrahedron Lett. 1983, 24, 691–694.
39. Cardellina, J. H., II. “Marine Natural Products as Leads to New Pharmaceutical and Agrochemical Agents” Pure & Appl. Chem. 1986, 58, 365–374.
40. Linz, G. S.; Musmar, M. J.; Weinheimer, A. J.; Martin, G. E. “Two-dimensional NMR studies of marine natural products. III. reassignment of the 13C-NMR spectrum of brianthein-x using heteronuclear relayed coherence transfer” Spectroscopy Lett. 1986, 19, 545–557.
41. Barnekow, D. E.; Cdellina, J. H. “Determining the absolute configuration of hindered secondary alcohols – a modified horeau,s method” Tetrahedron, 1989, 30, 3629–3632.
42. Van Der Helm, D.; Loghry, R. A. “Crystal and molecular structure of brianthein X” J. Chem. Crystallogr. 1986, 16, 713–720.

43. Sheu, J. -H.; Sung, P. -J.; Huang, L. -H.; Lee, S. -F.; Wu, -T.; Chang, B. -Y.; Duh, C. -Y.; Fang, L. -S.; Soong, K.; Lee, T. -J. “New Cytotoxic Briaran Diterpenes from the Formosan Gorgonian Briareum sp.” J. Nat. Prod. 1996, 59, 935–938.
44. Ospina, C. A.; Rodríguez, A. D. “Bioactive Compounds from the Gorgonian Briareum polyanthes. Correction of the Structures of Four Asbestinane-Type Diterpenes” J. Nat. Prod. 2006, 69, 1721–1727.
45. Bowden, B. F.; Coll, J. C.; Patalinghug, W.; Skelton, B.W.; Vasilescu, I.; White, A. H. “Studies of australian soft corals. XLII* structure determination of new briaran derivtives from Briareum stechei (coelenterata, octocorallia, gorgonacea)” Aust. J. Chem. 1987, 40, 2085–2096.
46. Bloor, S. J.; Schmitz, F. J.; Hossain, M. B.; Helm, D. V. D. “Diterpenoids from the gorgonian Solenopodium stechei” J. Org. Chem. 1992, 57, 1205–1216.
47. Kawak, J. H.; Schmitz, F. J.; Williams, G. C. “Milolides, new briarane diterpenoids from the western pacific octocoral Briareum stechei” J. Nat. Prod. 2001, 64, 754–760.
48. Kwak, J. H.; Schmitz, F. J.; Willians, G. C. “Milolides G‒N, new briarane diterpenoids from the western pacific octocoral Briareum stechei” J. Nat. Prod. 2002, 65, 704–708.
49. Bowden, B. F.; Coll, J. C.; Vasilescu, I. M. “Studies of australian soft corals. XLVI* new diterpenes from a Briareum species (anthozoa, octocorallia, gorgonacea)” Aust. J. Chem. 1989, 42, 1705–1726.
50. Bowden, B. F.; Coll, J. C.; Vasilescu, I. M.; Alderslade, P. N. “Studies of australian soft corals. XLVII* new halogenated briaran diterpenes from a Briareum species (octocorallia, gorgonacea)” Aust. J. Chem. 1989, 42, 1727–1734.
51. Iwagawa, T.; Takenoshita, N.; Okamura, H.; Nakatani, M.; Doye, M.; Shibata, K.; Shiro, M. “New briarane diterpenes from a gorgonacean Briareum sp.” Heterocycles, 1998, 48, 123–128.
52. Groweiss, A.; Look, S. A.; Fenical, W. “Solenolides, new antiinflammatory and antiviral diterpenoids from a marine octocoral of the genus Solenopodium” J. Org. Chem. 1988, 53, 2401–2406.
53. Cheng, J. F.; Yamamura, S.; Terada, Y. “Stereochemistry of the brianolide avetate (=solenolide d) by the molecular mechanics calculations” Tetrahedron Lett. 1992, 33, 101–104.
54. Kobayashi, J.; Cheng, J. F.; Nakamura, H.; Ohizum, Y.; Tomotake, Y.; Matsuzaki, T.; Grace, K. J. S.; Jacobs, R. S.; Kato, Y.; Brinen, L. S.; Clardy, J. “Structure and stereochemistry of brianolide, a new antiinflammatory diterpenoid from the okinawan gorgonian Briareum sp.” Experientia, 1991, 47, 501–502.
55. Pordesimo, O. E.; Schmitz, F. J.; Ciereszko, L. S.; Hossain, M. B.; Van der Helm D. “New briarein diterpenes from the caribbean gorgonians Erythropodium caribaeorum and Briareum sp.” J. Org. Chem. 1991, 56, 2344–2357.
56. Rodríguez, J.; Nieto, R. M.; Jiménez, C. “New briarane stecholide diterpenes from the indonesian gorgonian Briareum sp.” J. Nat. Prod. 1998, 61, 313–317.
57. Iwagawa, T.; Takayama, K.; Okamura, H.; Nakatani, M.; Doye, M. “New Briarane Diterpenes from a Gorgonacean Briareum sp.” Heterocycles, 1999, 51, 1653–1659.
58. Iwagawa, T.; Takayama, K.; Okamura, H.; Nakatani, M.; Doye, M.; Takemura, K.; Shiro, M. “Cytotoxic Briarane Diterpenes from a Gorgonacean Briareum sp.” Heterocycles, 1999, 51, 2919–2625.
59. Iwagawa, T; Hirose, T.; Takayama, K.; Okamura, H.; Nakatani, M.; Doe, M.; Takemura, K. “Violides N‒P, new briarane diterpenes from a gorgonacean Briareum sp.” Heterocycles, 2000, 53, 1789–1792.
60. Iwagawa, T.; Nishitani, N.; Kurosaki, S.; Okamura, H.; Nakatani, M.; Doe, M.; Takemura, K. “Briarlides, briarane diterpenes from a gorgonian Briareum sp.” J. Nat. Prod. 2003, 66, 1412–1415.
61. Iwagawa, T.; Nishitani, N.; Nakatani, M.; Doe, M.; Morimoto, Y.; Takemura, K. “Briarlides I−R, Briarane Diterpenes from a Gorgonian Briareum sp.” J. Nat. Prod. 2005, 68, 31–35.
62. Iwagawa, T.; Nishitani, N.; Nakatani, M.; Doe, M.; Morimoto, Y.; Takemura, K. “Briarlides I−R, Briarane Diterpenes from a Gorgonian Briareum sp.” J. Nat. Prod. 2005, 68, 818.
63. Iwagawa, T.; Babazono, K.; Nakatani, M.; Doe, M.; Morimoto, Y.; Takemura, K. “Briarane Diterpenes from a Gorgonian Briareum sp.” Heterocycles, 2005, 65, 607–617.
64. Iwagawa, T.; Babazono, K.; Okamura, M. Nakatani, M.; Doe, M.; Morimoto, Y.; Shiro, M.; Takemura, K. “Briviolides, New Briarane Diterpenes from a Gorgonian Briareum sp.” Heterocycles, 2005, 65, 2083–2093.
65. Sung, P.-J.; Hu, W.-P.; Fang, L.-S.; Fan, T.-Y.; Wang, J.-J. “Briarenol A, a New Diterpenoid from a Gorgonian Briareum sp. (Briareidae).” Nat. Prod. Res. 2005, 19, 689–694.
66. Hoshino, A.; Mitome, H.; Tamai, S.; Takiyama, H.; Miyaoka, H. “8,17-Epoxybriarane Diterpenoids, Briaranolides A−J, from an Okinawan Gorgonian Briareum sp.” J. Nat. Prod. 2005, 68, 1328–1335.
67. Su, J.-H.; Sung, P.-J.; Kuo, Y.-H.; Hsu, C.-H.; Sheu, J.-H. “Briarenolides A–C, Briarane Diterpenoids from the Gorgonian Coral Briareum sp.” Tetrahedron, 2007, 63, 8282–8285.
68. James, A. –D.; Harry S. M. “Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters” J. Am. Chem. Soc., 1973, 95 (2), 512‒519.
69. Ikuko O.; Takenori K.; Yoel K.; Hiroshi K. “High-field FT NMR application of
Mosher's method.The absolute configurations of marine terpenoids” J. Am. Chem.
Soc., 1991, 113 (11), 4092‒4096.
70. Hwang, T.-L.; Leu, Y.-L.; Kao, S.-H.; Tang, M.-C.; Chang, H.-L. “Viscolin, a new
chalcone from Viscum coloratum, inhibits human neutrophil superoxide anion and
elastase release via a cAMP-dependent pathway” Free Radical Biol. Med. 2006,
41, 1443–1441.
71. Yeh, S.-H.; Chang, F.-R.; Wu, Y.-C.; Yang, Y.-L.; Zhuo, S.-K.; Hwang, T.-L. “An
anti-inflammatory ent-kaurane from the stems of Anmona squamosa that inhibits
various human neutrophil functions” Planta Med. 2005, 71, 904–909.
72. Iwasaki, J.; Ito, H.; Aoyagi, M.; Sato, Y.; Iguchi, K. “Briarane-type diterpenoids
from the okinawan soft coral Pachyclavularia violacea” J. Nat. Prod. 2006, 69,
2–6.
73. Wratten, S. J.; Faulkner, D. J.; Hirotsu, K.; Clardy, J. “Stylatulide, a sea pen toxin”
J. Am. Chem. Soc. 1977, 99, 2824–2825.
74. Wratten, S. J.; Faulkner, D. J. “Some diterpenes from the sea pen stylatula sp.”
Tetrahedron 1979, 35, 1907–1912.
75. Ksebati, M. B.; Schmitz, F. J. Bull. Soc. Chim. Belg. 1986, 95, 835–851.
76. Tanaka, C.; Yamamoto, Y.; Otsuka, M.; Tanaka, J.; Ichiba, T.; Marriott, G.;
Rachmat, R.; Higa, T. “Briarane diterpenes from two species of octocorals,
Ellisella sp. and Pteroeides sp.II” J. Nat. Prod. 2004, 67, 1368–1373.
77. Barsby, T.; Kubanek, J. “Isolation and structure elucidation of feeding deterrent
diterpenoids from the sea pansy, Renilla reniformis.” J. Nat. Prod. 2005, 68,
511–516.
78. Fu, X.; Schmitz, F. J.; Williams, G. C. “Malayenolides A‒D, novel diterpenes
from the indonesian sea pen Veretillum malayense” J. Nat. Prod. 1999, 62,
584–586.