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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

γ-Hydroxybutenolide Containing Marine Natural Products and Their Synthesis: A Review

Author(s): Supriya Tilvi*, Safia Khan and Mahesh S. Majik

Volume 23, Issue 22, 2019

Page: [2436 - 2468] Pages: 33

DOI: 10.2174/1385272823666191021122810

Price: $65


γ-Hydroxybutenolides (γ-HB) is an important structural core found in many bioactive marine natural products (MNPS). The γ-HB core containing NPS served as an inspiration to medicinal chemists to undertake designing of the new synthetic strategies to construct γ-HB core. Subsequently, it further results in the development of novel physiological and therapeutic agents. The most notable example includes manoalides, cacospongionolides, petrosaspongioide M and dysidiolide from marine sponges possessing anti-inflammatory properties. γ-HB containing MNPS were known to possess various pharmacological properties such as antimicrobial (acantholide B), cytotoxic (acantholide A-E, spongianolide A), inhibitors of secretory phospholipase A2 (cladocorans A and B), BACE inhibitors (ianthellidone G), etc. Moreover, the γ-HB moiety was explored as antifouling agents as well. Owing to their numerous biological activities and attractive molecular structures, there are lots of advances in the synthetic methodology of these compounds. This review gives the account on isolation and biological studies of MNPS with γ-HB skeleton as a core unit. Furthermore, the synthesis of selective γ-HB containing bioactive MNPS like manoalide, secomanoalide, cacospongionolides, luffarielloide and dysidiolide were highlighted in the article.

Keywords: Anti-inflammatory, biological activities, γ-hydroxybutenolide, marine natural products, synthesis, luffarielloide.

Graphical Abstract
Glaser, K.B.; Jacobs, R.S. Molecular pharmacology of manoalide. Inactivation of bee venom phospholipase A2. Biochem. Pharmacol., 1986, 35(3), 449-453.
[] [PMID: 3947381]
Gunasekera, S.P.; McCarthy, P.J.; Kelly-Borges, M.; Lobkovsky, E.; Clardy, J. Dysidiolide: A novel protein phosphatase inhibitor from the Caribbean sponge Dysidea etheria de Laubenfels. J. Am. Chem. Soc., 1996, 118, 8759-8760.
Pettit, G.R.; Tan, R.; Cichacz, Z.A. Antineoplastic agents. 542. Isolation and structure of sesterstatin 6 from the Indian ocean sponge Hyrtios erecta. J. Nat. Prod., 2005, 68(8), 1253-1255.
[] [PMID: 16124771]
De Rosa, S.; Mitova, M. Bioactive Marine Sesterterpenoids Studies In: Natural Products Chemistry, Ed. Atta-ur-Rahman, Ed;; Elsevier Science: Amsterdam, 2005; 32, p. 109-168.
Peng, J.; Franzblau, S.G.; Zhang, F.; Hamann, M.T. Novel sesquiterpenes and a lactone from the Jamaican sponge Myrmekioderma styx. Tetrahedron Lett., 2002, 43, 9699-9702.
Layne, T.H.; Tinto, W.F. A butenolide from the marine sponge Callyspongia vaginalis. Heterocycles, 2006, 68, 2161-2164.
Lee, J.; Wang, W.; Hong, J.; Lee, C-O.; Shin, S. Im, K.S.; Jung, J.H. A new 2,3-dimethyl butenolide from the brittle star Ophiomastix mixta. Chem. Pharm. Bull. (Tokyo), 2007, 55(3), 459-461.
[] [PMID: 17329891]
Shi, H.; Yu, S.; Liu, D.; van Ofwegen, L.; Proksch, P.; Lin, W. Sinularones A-I, new cyclopentenone and butenolide derivatives from a marine soft coral Sinularia sp. and their antifouling activity. Mar. Drugs, 2012, 10(6), 1331-1344.
[] [PMID: 22822376]
Cartè, B.; Mong, S.; Poehland, B.; Sarau, H.; Westley, J.W. 15-acetylthioxy-furodysinin lactone, a potent LTB4 receptor partial agonist from a marine sponge of the genus Dysidea. Tetrahedron Lett., 1989, 30, 2725-2726.
Sera, Y.; Adachi, K.; Nishida, F.; Shizuri, Y. A new sesquiterpene as an antifouling substance from a palauan marine sponge, dysidea herbacea. J. Nat. Prod., 1999, 62(2), 395-396.
[] [PMID: 10075800]
Reddy, N.S.; Venkatesham, U.; Rao, T.P.; Venkateswarlu, Y. New sesquiterpenes from the marine sponge Dysidea fragilis. Indian J. Chem., 2000, 39, 393-395.
Ravikumar, K.; Selvanayagam, S.; Goud, T.V.; Krishnaiah, P.; Venkateswarlu, Y. A furodysinin lactone derivative from the marine sponge Dysidea fragilis. Acta Crystallogr., 2004, 60, 139-141.
Montagnac, A.; Martin, M.T.; Debitus, C.; Pais, M. Drimane sesquiterpenes from the sponge Dysidea fusca. J. Nat. Prod., 1996, 59, 866-868.
Sakio, Y.; Hirano, Y.J.; Hayashi, M.; Komiyama, K.; Ishibashi, M. Dendocarbins A--N, new drimane sesquiterpenes from the nudibranch Dendrodoris carbunculosa. J. Nat. Prod., 2001, 64(6), 726-731.
[] [PMID: 11421732]
Huang, X-C.; Li, J.; Li, Z-Y.; Shi, L.; Guo, Y-W. Sesquiterpenes from the Hainan sponge Dysidea septosa. J. Nat. Prod., 2008, 71(8), 1399-1403.
[] [PMID: 18627201]
Dumdei, E.J.; Kubanek, J.; Coleman, J.E.; Pika, J.; Andersen, R.J.; Steiner, J.R.; Clardy, J. New terpenoid metabolites from the skin extracts, an egg mass, and dietary sponges of the northeastern pacific dorid nudibranch Cadlina luteomarginata. Can. J. Chem., 1997, 75, 773-789.
Giannini, C.; Debitus, C.; Posadas, I.; Payá, M.; D’Auria, M.V. Dysidotronic acid, a new and selective human phospholipase A2 inhibitor from the sponge Dysidea sp. Tetrahedron Lett., 2000, 41, 3257-3260.
Posadas, I.; Terencio, M.C.; Giannini, C.; D’Auria, M.V.; Payá, M. Dysidotronic acid, a new sesquiterpenoid, inhibits cytokine production and the expression of nitric oxide synthase. Eur. J. Pharmacol., 2001, 415(2-3), 285-292.
[] [PMID: 11275011]
Li, L.; Wang, C-Y.; Huang, H.; Mollo, E.; Cimino, G.; Guo, Y-W. Further highly oxygenated guaiane lactones from the South China sea Gorgonian Menella sp. Helv. Chim. Acta, 2008, 91, 111-117.
Kao, S-Y.; Chang, Y-C.; Su, J-H.; Lu, M-C.; Chen, Y-H.; Sheu, J-H.; Wen, Z-H.; Wang, W-H.; Kuo, Y-H.; Hwang, T-L.; Sung, P-J. (-)-Hydroxylindestrenolide, a new sesquiterpenoid from a gorgonian coral Menella sp. (Plexauridae). Chem. Pharm. Bull. (Tokyo), 2011, 59(8), 1048-1050.
[] [PMID: 21804253]
Kao, S-Y.; Su, J-H.; Hwang, T-L.; Sheu, J-H.; Wen, Z-H.; Wu, Y-C.; Sung, P-J. Menelloides C and D, new sesquiterpenoids from the Gorgonian coral Menella sp. Mar. Drugs, 2011, 9(9), 1534-1542.
[] [PMID: 22131956]
Lee, C-H.; Kao, C-Y.; Kao, S-Y.; Chang, C-H.; Su, J-H.; Hwang, T-L.; Kuo, Y-H.; Wen, Z-H.; Sung, P-J. Terpenoids from the octocorals Menella sp. (Plexauridae) and Lobophytum crassum (Alcyonacea). Mar. Drugs, 2012, 10(2), 427-438.
[] [PMID: 22412810]
Wang, L-H.; Sheu, J-H.; Kao, S-Y.; Su, J-H.; Chen, Y-H.; Chen, Y-H.; Su, Y-D.; Chang, Y-C.; Fang, L-S.; Wang, W-H.; Wu, Y-C.; Sung, P-J. Natural product chemistry of gorgonian corals of the family Plexauridae distributed in the Indo-Pacific ocean. Mar. Drugs, 2012, 10(11), 2415-2434.
[] [PMID: 23203268]
Wei, W-C.; Sung, P-J.; Duh, C-Y.; Chen, B-W.; Sheu, J-H.; Yang, N-S. Anti-inflammatory activities of natural products isolated from soft corals of Taiwan between 2008 and 2012. Mar. Drugs, 2013, 11(10), 4083-4126.
[] [PMID: 24152566]
Lyakhova, E.G.; Diep, C.N.; Berdyshev, D.V.; Kolesnikova, S.A.; Kalinovsky, A.I.; Dmitrenok, P.S.; Tu, V.A.; Cuong, N.X.; Thanh, N.V.; Nam, N.H.; Kiem, P.V.; Stonik, V.A.; Minh, C.V. Nat. Prod. Commun., 2016, 11(7), 913-916.
Mitchell, S.S.; Harper, M.K.; Faulkner, D.J. Spongiabutenolides A-D: minor γ-hydroxybutenolide diterpenoids from a Philippines Spongia sp. Tetrahedron, 1999, 55, 10887-10892.
Hyosu, M.; Kimura, J. Two new spongian diterpenes from Coscinoderma mathewsi. J. Nat. Prod., 2000, 63(3), 422-423.
[] [PMID: 10757738]
Yu, S.; Deng, Z.; Proksch, P.; Lin, W. Oculatol, oculatolide, and A-nor sterols from the sponge Haliclona oculata. J. Nat. Prod., 2006, 69(9), 1330-1334.
[] [PMID: 16989529]
Shen, Y-C.; Wu, Y-R.; Lin, J-J.; Lo, K-L.; Kuo, Y-C.; Khalil, A.T. Eight new diterpenoids from soft coral Cespitularia hypotentaculata. Tetrahedron, 2007, 63, 10914-10920.
Shen, Y-C.; Lo, K-L.; Kuo, Y-H.; Kuo, Y-C.; Chen, C-H.; Khalil, A.T. Cespihypotins Q-V, verticillene diterpenoids from Cespitularia hypotentaculata. J. Nat. Prod., 2008, 71(12), 1993-1997.
[] [PMID: 19061391]
Duh, C-Y.; El-Gamal, A.A.; Wang, S-K.; Dai, C-F. Novel terpenoids from the formosan soft coral Cespitularia hypotentaculata. J. Nat. Prod., 2002, 65(10), 1429-1433.
[] [PMID: 12398538]
(a)Lin, Y-C.; El-Razek, M.H.; Shen, Y-C. Erratum: verticillane‐type diterpenoids and an eudesmanolide‐type sesquiterpene from the Formosan soft coral Cespitularia hypotentaculata. Helv. Chim. Acta, 2010, 93, 1238-1239.
(b)Lin, Y-C.; Fazary, A.E.; Shen, Y-C. Cespitulins A-D, novel diterpenoids from Taiwanese Cespitularia taeniata. Tetrahedron Lett., 2010, 51, 6654-6657.
Chang, J.Y.; Fazary, A.E.; Lin, Y.C.; Hwang, T.L.; Shen, Y.C. New verticillane diterpenoids from Cespitularia taeniata. Chem. Biodivers., 2012, 9(3), 654-661.
[] [PMID: 22422532]
Rodríguez, A.D.; Ramírez, C.; Rodríguez, I.I. Sandresolides A and B: novel nor-diterpenes from the sea whip Pseudopterogorgia elisabethae (Bayer). Tetrahedron Lett., 1999, 40, 7627-7631.
Wei, X.; Rodríguez, I.I.; Rodríguez, A.D.; Barnes, C.L. Caribenols A and B, sea whip derived norditerpenes with novel tricarbocyclic skeletons. J. Org. Chem., 2007, 72(19), 7386-7389.
[] [PMID: 17715964]
Shimbo, K.; Tsuda, M.; Fukushi, E.; Kawabata, J.; Kobayashi, J. Dytesinins A and B, new clerodane-type diterpenes with a cyclopropane ring from the tunicate Cystodytes sp. Tetrahedron, 2000, 56, 7923-7926.
Bourguet-Kondracki, M-L.; Guyot, M. A new sesquiterpene tetronic acid derivative from the marine sponge Smenospongia sp. Tetrahedron Lett., 1999, 40, 3149-3150.
Chung, H-M.; Hu, L-C.; Yen, W-H.; Su, J-H.; Lu, M-C.; Hwang, T-L.; Wang, W-H.; Sung, P-J. Echinohalimane A, a bioactive halimane-type diterpenoid from a Formosan gorgonian Echinomuricea sp. (Plexauridae). Mar. Drugs, 2012, 10(10), 2246-2253.
[] [PMID: 23170081]
Cheng, C.H.; Chung, H-M.; Hwang, T-L.; Lu, M-C.; Wen, Z-H.; Kuo, Y-H.; Wang, W-H.; Sung, P-J.; Echinoclerodane, A. A new bioactive clerodane-type diterpenoid from a gorgonian coral Echinomuricea sp. Molecules, 2012, 17(8), 9443-9450.
[] [PMID: 22871646]
Hong, P-H.; Su, Y-D.; Su, J-H.; Chen, Y-H.; Hwang, T-L.; Weng, C-F.; Lee, C-H.; Wen, Z-H.; Sheu, J-H.; Lin, N-C.; Kuo, Y-H.; Sung, P-J. Briarenolides F and G, new briarane diterpenoids from a Briareum sp. octocoral. Mar. Drugs, 2012, 10(5), 1156-1168.
[] [PMID: 22822363]
Xu, L.; Patrick, B.O.; Roberge, M.; Allen, T.; Ofwegen, L.V.; Andersen, R.J. New diterpenoids from the octocoral Pachyclavularia violacea collected in Papua New Guinea. Tetrahedron, 2000, 56, 9031-9037.
Sheu, J.H.; Wang, G-H.; Duh, C.Y.; Soong, K. Pachyclavulariolides M-R, six novel diterpenoids from a Taiwanese soft coral Pachyclavularia violacea. J. Nat. Prod., 2003, 66(5), 662-666.
[] [PMID: 12762802]
Sheu, J-H.; Wang, G-H.; Sung, P-J.; Duh, C-Y.; Chiang, M.Y. Pachyclavulariolides G-L and secopachyclavulariaenone A, seven novel diterpenoids from the soft coral Pachyclavularia violacea. Tetrahedron, 2001, 57, 7639-7648.
Liu, Y.; Mansoor, T.A.; Hong, J.; Lee, C-O.; Sim, C.J. Im, K.S.; Kim, N.D.; Jung, J.H. New cytotoxic sesterterpenoids and norsesterterpenoids from two sponges of the genus Sarcotragus. J. Nat. Prod., 2003, 66(11), 1451-1456.
[] [PMID: 14640517]
Khushi, S.; Nahar, L.; Salim, A.A.; Capon, R.J. Cacolides: Sesterterpene butenolides from a southern Australian marine sponge, Cacospongia sp. Mar. Drugs, 2018, 16(11), 1-17.
[] [PMID: 30463335]
Miyaoka, H.; Nishijima, S.; Mitome, H.; Yamada, Y. Three new scalarane sesterterpenoids from the Okinawan sponge Hyrtios erectus. J. Nat. Prod., 2000, 63(10), 1369-1372.
[] [PMID: 11076554]
Qiu, Y.; Deng, Z.; Pei, Y.; Fu, H.; Li, J.; Proksch, P.; Lin, W. Sesterterpenoids from the marine sponge Hyrtios erectus. J. Nat. Prod., 2004, 67(5), 921-924.
[] [PMID: 15165168]
Tsukamoto, S.; Miura, S.; van Soest, R.W.M.; Ohta, T. Three new cytotoxic sesterterpenes from a marine sponge Spongia sp. J. Nat. Prod., 2003, 66(3), 438-440.
[] [PMID: 12662110]
Lu, Q.; Faulkner, D.J. Two new sesterterpenoids and a new 9,11-secosterol from Spongia matamata. J. Nat. Prod., 1997, 60(2), 195-198.
[] [PMID: 9051917]
Bergquist, P.R.; Cambie, R.C.; Kernan, M.R. Scalarane sesterterpenes from Collospongia auris, a new thorectid sponge. Biochem. Syst. Ecol., 1990, 18, 349-357.
Mahidol, C.; Prawat, H.; Sangpetsiripan, S.; Ruchirawat, S. Bioactive scalaranes from the Thai sponge Hyrtios gumminae. J. Nat. Prod., 2009, 72(10), 1870-1874.
[] [PMID: 19788270]
Chang, L.C.; Otero-Quintero, S.; Nicholas, G.M.; Bewley, C.A. Phyllolactones A-E: new bishomoscalarane sesterterpenes from the marine sponge Phyllospongia lamellosa. Tetrahedron, 2001, 57, 5731-5738.
Fu, X.; Zeng, L.M.; Su, J.Y.; Pais, M.; Potier, P. Scalarane-type bishomosester terpenes from the sponge Phyllospongia foliascens. J. Nat. Prod., 1992, 55(11), 1607-1613.
[] [PMID: 1479378]
Wan, Y.; Li, Q.; Zeng, L.; Su, J. Secondary metabolites of the marine sponge, Phyllospongia foliascens. Acta Sci. Natur., 1998, 37, 81-84.
Lan, W-J.; Li, H-J. New sesterterpenoids from the marine sponge Pyllospongia papyracea. Helv. Chim. Acta, 2007, 90, 1218-1222.
Fu, X.; Zeng, L.; Su, J.; Pais, M.; Potier, P. Two new sesterterpenes from a south China sea sponge. J. Nat. Prod., 1993, 56, 1985-1988.
Zeng, L.; Fu, X.; Su, J.; Wang, Q. Phyllactones F and G, further bis-homoscalarane sesterterpenes from the sponge Phyllospongia foliascens. Chem. Res. Chin. Univ., 1993, 9, 161-164.
Williams, D.E.; Hollander, I.; Feldberg, L.; Frommer, E.; Mallon, R.; Tahir, A.; van Soest, R.; Andersen, R.J. Scalarane-based sesterterpenoid RCE-protease inhibitors isolated from the Indonesian marine sponge Carteriospongia foliascens. J. Nat. Prod., 2009, 72(6), 1106-1109.
[] [PMID: 19485329]
Li, H-J.; Amagata, T.; Tenney, K.; Crews, P. Additional scalarane sesterterpenes from the sponge Phyllospongia papyracea. J. Nat. Prod., 2007, 70(5), 802-807.
[] [PMID: 17455979]
De Marino, S.; Iorizzi, M.; Zollo, F.; Debitus, C.; Menou, J-L.; Ospina, L.F.; Alcaraz, M.J.; Payá, M. New pyridinium alkaloids from a marine sponge of the genus Spongia with a human phospholipase A(2) inhibitor profile. J. Nat. Prod., 2000, 63(3), 322-326.
[] [PMID: 10757711]
(a)De Rosa, S.; de Stefano, S.; Zavodnik, N. Cacospongionolide: a new antitumoral sesterterpene, from the marine sponge Cacospongia mollior. J. Org. Chem., 1988, 53, 5020-5023.
(b)De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Pronzato, R.; Zavodnik, N. Cacospongionolide B, a new sesterterpene from the sponge Fasciospongia cavernosa. J. Nat. Prod., 1995, 58(11), 1776-1780.
[] [PMID: 8594155]
García Pastor, P.; De Rosa, S.; De Giulio, A.; Payá, M.; Alcaraz, M.J. Modulation of acute and chronic inflammatory processes by cacospongionolide B, a novel inhibitor of human synovial phospholipase A2. Br. J. Pharmacol., 1999, 126(1), 301-311.
[] [PMID: 10051149]
Posadas, I.; De Rosa, S.; Terencio, M.C.; Payá, M.; Alcaraz, M.J. Cacospongionolide B suppresses the expression of inflammatory enzymes and tumour necrosis factor-α by inhibiting nuclear factor-κ B activation. Br. J. Pharmacol., 2003, 138(8), 1571-1579.
[] [PMID: 12721113]
Alcaraz, M.J.; Ferrandiz, M.L.; Garcia, P.; Payá, M.; Terencio, M.C.; Ubeda, A.; De Rosa, S.; De Giulio, A.; Crispino, A. Mediterranean marine organisms as source of new potential drugs; Pat. Application Spain, 1996, p. 9600884.
De Rosa, S.; Puliti, R.; Crispino, A.; de Giulio, A.; de Sena, C.; Iodice, C.; Mattia, C.A. 25-deoxycacospongionolide B and cacospongionolide C, two new terpenoids from the sponge Fasciospongia cavernosa. Tetrahedron, 1995, 51, 10731-10736.
De Rosa, S.; de Giulio, A.; Crispino, A.; Iodice, C.; Tommonaro, G. Further bioactive sesterterpenes from the Tyrrhenian sponge Fasciospongia cavernosa. Nat. Prod. Res., 1997, 10, 267-274.
De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Benrezzouk, R.; Terencio, M.C.; Ferrándiz, M.L.; Alcaraz, M.J.; Payá, M. A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides. J. Nat. Prod., 1998, 61(7), 931-935.
[] [PMID: 9677277]
De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Amodeo, P.; Tancredi, T. A new cacospongionolide derivative from the sponge Fasciospongia cavernosa. J. Nat. Prod., 1999, 62(9), 1316-1318.
[] [PMID: 10514323]
De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Tommonaro, G.; Pronzato, R.; Sidri, M. A novel C21 terpene lactone from the sponge Fasciospongia cavernosa. Tetrahedron, 1999, 55, 13805-13808.
De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Tommonaro, G. Cavernosolide, a new sesterterpene from a Tyrrhenian sponge. J. Nat. Prod., 1997, 60, 844-846.
Conte, M.R.; Fattorusso, E.; Lanzotti, V.; Magno, S.; Mayol, L. Lintenolides, new pentacyclic bioactive sesterterpenes from the Caribbean sponge Cacospongia cf. Linteiformis. Tetrahedron, 1994, 50, 849-856.
De Silva, E.D.; Scheuer, P.J. Manoalide, an antibiotic sesterterpenoid from the marine sponge Luffariella variabilis (Polejaeff). Tetrahedron Lett., 1980, 21, 1611-1614.
De Silva, E.D.; Scheuer, P.J. Three new sesterterpenoid antibiotics from the marine sponge Luffariella variabilis (Polejaeff). Tetrahedron Lett., 1981, 22, 3147-3150.
Kobayashi, J.; Zeng, C-M.; Ishibashi, M.; Sasaki, T. Luffariolides F and G, new manoalide derivatives from the Okinawan marine sponge Luffariella sp. J. Nat. Prod., 1993, 56(3), 436-439.
[] [PMID: 8482949]
Tsuda, M.; Shigemori, H.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. Luffariolides A-E, new cytotoxic sesterterpenes from the Okinawan marine sponge Luffariella sp. J. Org. Chem., 1992, 57, 3503-3507.
König, G.M.; Wright, A.D.; Sticher, O. Four new antibacterial sesterterpenes from a marine sponge of the genus Luffariella. J. Nat. Prod., 1992, 55(2), 174-178.
[] [PMID: 1624940]
Jacobs, R.S.; Culver, P.; Langdon, R.; O’Brien, T.; White, S. Some pharmacological observations on marine natural products. Tetrahedron, 1985, 41, 981-984.
Glaser, K.B.; Jacobs, R.S.; Clark, M.A.; Kruse, L.J.; Crooke, S.T. Inactivation of bee venom phospholipase A2 by manoalide. A model based on the reactivity of manoalide with amino acids and peptide sequences. Biochem. Pharmacol., 1987, 36(13), 2079-2086.
[] [PMID: 3111475]
Glaser, K.B.; de Carvalho, M.S.; Jacobs, R.S.; Kernan, M.R.; Faulkner, D.J. Manoalide: structure-activity studies and definition of the pharmacophore for phospholipase A2 inactivation. Mol. Pharmacol., 1989, 36(5), 782-788.
[PMID: 2586492]
Lombardo, D.; Dennis, E.A. Cobra venom phospholipase A2 inhibition by manoalide. A novel type of phospholipase inhibitor. J. Biol. Chem., 1985, 260(12), 7234-7240.
[PMID: 3997864]
Gross, H.; König, G.M. Terpenoids from marine organisms: unique structures and their pharmacological potential. Phytochem. Rev., 2006, 5, 115-141.
Kernan, M.R.; Faulkner, D.J.; Jacobs, R.S. The luffariellins, novel anti-inflammatory sesterterpenes of chemotaxonomic importance from the marine sponge Luffariella variabilis. J. Org. Chem., 1987, 52, 3081-3083.
Potts, B.C.M.; Capon, R.J.; Faulkner, D.J. Luffalactone and (4E,6E)-dehydromanoalide from the sponge Luffariella variabilis. J. Org. Chem., 1992, 57, 2965-2957.
Majik, M.S.; Shirodkar, D.; Rodrigues, C.; D’Souza, L.; Tilvi, S. Evaluation of single and joint effect of metabolites isolated from marine sponges, Fasciospongia cavernosa and Axinella donnani on antimicrobial properties. Bioorg. Med. Chem. Lett., 2014, 24(13), 2863-2866.
[] [PMID: 24825299]
Tsuda, M.; Endo, T.; Mikami, Y.; Fromont, J.; Kobayashi, J. Luffariolides H and J, new sesterterpenes from a marine sponge Luffariella species. J. Nat. Prod., 2002, 65(10), 1507-1508.
[] [PMID: 12398555]
Zhou, G-X.; Molinski, T.F. Manoalide derivatives from a sponge, Luffariella sp. J. Asian Nat. Prod. Res., 2006, 8(1-2), 15-20.
[] [PMID: 16753777]
Albizati, K.F.; Holman, T.; Faulkner, D.J.; Glaser, K.B.; Jacobs, R.S. Luffariellolide, an anti-inflammatory sesterterpene from the marine sponge Luffariella sp. Experientia, 1987, 43, 949-950.
Potts, B.C.M.; Faulkner, D.J.; De Carvalho, M.S.; Jacobs, R.S. Chemical mechanism of inactivation of bee venom phospholipase A2 by the marine natural products manoalide, luffariellolide, and scalaradial. J. Am. Chem. Soc., 1992, 114, 5093-5100.
Cao, S.; Foster, C.; Lazo, J.S.; Kingston, D.G.I. Sesterterpenoids and an alkaloid from a Thorectandra sp. as inhibitors of the phosphatase Cdc25B. Bioorg. Med. Chem., 2005, 13(17), 5094-5098.
[] [PMID: 15927472]
Ueoka, R.; Nakao, Y.; Fujii, S.; van Soest, R.W.M.; Matsunaga, S. Aplysinoplides A-C, cytotoxic sesterterpenes from the marine sponge Aplysinopsis digitata. J. Nat. Prod., 2008, 71(6), 1089-1091.
[] [PMID: 18461996]
Elkhayat, E.; Edrada, R.; Ebel, R.; Wray, V.; van Soest, R.; Wiryowidagdo, S.; Mohamed, M.H.; Müller, W.E.G.; Proksch, P. New luffariellolide derivatives from the Indonesian sponge Acanthodendrilla sp. J. Nat. Prod., 2004, 67(11), 1809-1817.
[] [PMID: 15568767]
Sullivan, B.; Faulkner, D.J. An antimicrobial sesterterpene from a Palauan sponge. Tetrahedron Lett., 1982, 23, 907-910.
Schmidt, E.W.; Faulkner, D.J. Palauolol, a new anti-inflammatory sesterterpene from the sponge Fascaplysinopsis sp. from Palau. Tetrahedron Lett., 1996, 37, 3951-3954.
Charan, R.D.; McKee, T.C.; Boyd, M.R.; Thorectandols, C.; Thorectandrols, C. D, and E, new sesterterpenes from the marine sponge Thorectandra sp. J. Nat. Prod., 2002, 65(4), 492-495.
[] [PMID: 11975486]
Potts, B.C.M.; Faulkner, D.J.; Jacobs, R.S. Phospholipase A2 inhibitors from marine organisms. J. Nat. Prod., 1992, 55(12), 1701-1717.
[] [PMID: 1294693]
Ebada, S.S.; Lin, W.H.; Proksch, P. Bioactive sesterterpenes and triterpenes from marine sponges: occurrence and pharmacological significance. Mar. Drugs, 2010, 8, 313-346.
Li, J.; Du, L.; Kelly, M.; Zhou, Y-D.; Nagle, D.G. Structures and potential antitumor activity of sesterterpenes from the marine sponge Hyrtios communis. J. Nat. Prod., 2013, 76(8), 1492-1497.
[] [PMID: 23944963]
Butler, M.S.; Capon, R.J. The luffarins (A-Z), novel terpenes from an Australian marine sponge, Luffariella geometrica. Aust. J. Chem., 1992, 45, 1705-1743.
Takahashi, M.; Dodo, K.; Sugimoto, Y.; Aoyagi, Y.; Yamada, Y.; Hashimoto, Y.; Shirai, R. Synthesis of the novel analogues of dysidiolide and their structure-activity relationship. Bioorg. Med. Chem. Lett., 2000, 10(22), 2571-2574.
[] [PMID: 11086732]
Magnuson, S.R.; Sepp-Lorenzino, L.; Rosen, N.; Danishefsky, S.J. A concise total synthesis of dysidiolide through application of a dioxolenium-mediated Diels-Alder reaction. J. Am. Chem. Soc., 1998, 120, 1615-1616.
Fontana, A.; Ciavatta, M.L.; Cimino, G. Cladocoran A and B: two novel γ-hydroxybutenolide sesterterpenes from the Mediterranean coral Cladocora cespitosa. J. Org. Chem., 1998, 63, 2845-2849.
Randazzo, A.; Debitus, C.; Minale, L.; García Pastor, P.; Alcaraz, M.J.; Payá, M.; Gomez-Paloma, L. Petrosaspongiolides M-R: new potent and selective phospholipase A2 inhibitors from the New Caledonian marine sponge Petrosaspongia nigra. J. Nat. Prod., 1998, 61(5), 571-575.
[] [PMID: 9599251]
Balsinde, J.; Balboa, M.A.; Insel, P.A.; Dennis, E.A. Regulation and inhibition of phospholipase A2. Annu. Rev. Pharmacol. Toxicol., 1999, 39, 175-189.
[] [PMID: 10331081]
Dennis, E.A.; Cao, J.; Hsu, Y-H.; Magrioti, V. Kokotos. G. Phospholipase A2 enzymes: physical structure, biological function, disease implication, chemical inhibition, and therapeutic intervention. Chem. Rev., 2011, 111(10), 6130-6185.
He, H.; Kulanthaivel, P.; Baker, J.B. New cytotoxic sesterterpenes from the marine sponge Spongia sp. Tetrahedron Lett., 1994, 35, 7189-7192.
Hata, T.; Tanaka, K.; Katsumura, S. First synthesis of (-)-spongianolide A and determination of its absolute structure. Tetrahedron Lett., 1999, 40, 1731-1734.
Herńandez-Guerrero, C.J.; Zubía, E.; Ortega, M.J.; Carballo, J.L. Sesterterpene metabolites from the sponge Hyatella intestinalis. Tetrahedron, 2006, 62, 5392-5400.
Zhang, H.; Dong, M.; Wang, H.; Crews, P. Secondary metabolites from the marine sponge genus Phyllospongia. Mar. Drugs, 2017, 15, 12.
Hahn, D.; Won, D.H.; Mun, B.; Kim, H.; Han, C.; Wang, W.; Chun, T.; Park, S.; Yoon, D.; Choi, H.; Nam, S-J.; Ekins, M.; Chin, J.; Kang, H. Cytotoxic scalarane sesterterpenes from a Korean marine sponge Psammocinia sp. Bioorg. Med. Chem. Lett., 2013, 23(8), 2336-2339.
[] [PMID: 23489626]
Harinantenaina, L.; Brodie, P.J.; Maharavo, J.; Bakary, G.; TenDyke, K.; Shen, Y.; Kingston, D.G.I. Antiproliferative homoscalarane sesterterpenes from two Madagascan sponges. Bioorg. Med. Chem., 2013, 21(11), 2912-2917.
[] [PMID: 23623678]
Shady, N.H.; El-Hossary, E.M.; Fouad, M.A.; Gulder, T.A.M.; Kamel, M.S.; Abdelmohsen, U.R. Bioactive natural products of marine sponges from the genus Hyrtios. Molecules, 2017, 22, 781.
Elhady, S.S.; Al-Abd, A.M.; El-Halawany, A.M.; Alahdal, A.M.; Hassanean, H.A.; Ahmed, S.A. Antiproliferative scalarane-based metabolites from the Red Sea Sponge Hyrtios erectus. Mar. Drugs, 2016, 14(7), 130.
[] [PMID: 27399730]
Katsumura, S.; Fujiwara, S.; Isoe, S. Total synthesis of manoalide and secomanoalide. Tetrahedron Lett., 1985, 26, 5827-5830.
Katsumura, S.; Fujiwara, S.; Isoe, S. Highly efficient total synthesis of manoalide and secomanoalide via Pd(0) catalyzed coupling of allyl halide with CO and 2-silyl-4-stannylfuran. Tetrahedron Lett., 1988, 29, 1173-1176.
Stille, J.K. Palladium catalyzed coupling of organotin reagents with organic electrophiles. Pure Appl. Chem., 1985, 57, 1771-1780.
Garst, M.E.; Tallman, E.A.; Bonfiglio, J.N.; Harcourt, D.; Ljungwe, E.G.; Tran, A. Total synthesis of manoalide. Tetrahedron Lett., 1986, 27, 4533-4536.
Wang, L.; Sun, M.; Ding, M-W. Catalytic intramolecular Wittig reaction based on a phosphine/phosphine oxide catalytic cycle for the synthesis of heterocycles. Eur. J. Org. Chem., 2017, 2568-2578.
Wang, L.; Guan, Z-R.; Ding, M-W. One-pot synthesis of 1H-isochromenes and 1,2-dihydroisoquinolines by a sequential isocyanide-based multicomponent/Wittig reaction. Org. Biomol. Chem., 2016, 14(8), 2413-2420.
[] [PMID: 26810599]
Tanis, S.P.; Head, D.B. Furans in synthesis 4. Silyl furans as butenolide equivalents. Tetrahedron Lett., 1984, 25, 4451-4454.
Pommier, A.; Kociénski, P.J. Synthesis of manoalide using a 1,2-metallate rearrangement. Chem. Commun. (Camb.), 1997, 1139-1140.
McDonald, F.E.; Schultz, C.C.; Chatterjee, A.K. Novel synthesis of α-stannyl vinyl ethers from catalytic and stoichiometric Fischer carbene anions. Organometallics, 1995, 14, 3628-3629.
Schoenberg, A.; Bartoletti, I.; Heck, R.F. Palladium-catalyzed carboalkoxylation of aryl, benzyl and vinylic halides. J. Org. Chem., 1974, 39, 3318-3326.
Pommier, A.; Stepanenko, V.; Jarowicki, K.; Kocienski, P.J. Synthesis of (+)-manoalide via a copper(I)-mediated 1,2-metalate rearrangement. J. Org. Chem., 2003, 68(10), 4008-4013.
[] [PMID: 12737584]
Laube, T.; Schröder, J.; Stehle, R.; Seifert, K. Total synthesis of yahazunol, zonarone and isozonarone. Tetrahedron, 2002, 58, 4299-4309.
Negishi, E.; King, A.O.; Klima, W.L. Conversion of methyl ketones into terminal acetylenes and (E)-trisubstituted olefins of terpenoid origin. J. Org. Chem., 1980, 45, 2526-2528.
Wipf, P.; Lim, S. Angew. Rapid carboalumination of alkynes in the presence of water. Chem. Int. Ed. Engl., 1993, 32, 1068-1071.
Lee, G.C.M.; Holmes, J.M.; Harcourt, D.A.; Garst, M.E. A General Approach to 5-substitution of 3-furaldehydes. J. Org. Chem., 1992, 57, 3126-3131.
Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. Preparation of optically active 2-furylcarbinols by kinetic resolution using the sharpless reagent and their application in organic synthesis. J. Org. Chem., 1989, 54, 2085-2091.
Keck, G.E.; Krishnamurthy, D.; Chen, X. Asymmetric synthesis of homopropargylic alcohols from aldehydes and allenyl tri-n-butylstannane. Tetrahedron Lett., 1994, 35, 8323-8324.
Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Baek, K.J. A total synthesis of gelsemine: synthesis of a key tetracyclic intermediate. Chem. Soc. Chem. Commun., 1997, (6), 763-764.
Coombs, J.; Lattmann, E.; Hoffmann, H.M.R. Total synthesis of manoalide. Synthesis, 1998, 9, 1367-1371.
Lattmann, E.; Hoffmann, H.M.R. From tetronic acid and furfural to C(4)halogenated, vinylated and formylated furan2(5H)-ones and their 5 alkoxy derivatives. Synthesis, 1996, 01, 155-163.
Bury, P.; Hareau, G.; Kocienski, P.J.; Dhanak, D. Two syntheses of manoalide via heteroatom-assisted alkyne carbometallation. Tetrahedron, 1994, 50, 8793-8808.
Cheung, A.K.; Snapper, M.L. Total syntheses of (+)- and (-)-cacospongionolide B: new insight into structural requirements for phospholipase A(2) inhibition. J. Am. Chem. Soc., 2002, 124(39), 11584-11585.
[] [PMID: 12296709]
Rocherla, U.S.; Liao, Y.; Brown, H.C. Chiral synthesis via organoboranes. 36. Exceptionally enantioselective allylborations of representative heterocyclic aldehydes at -100°C under salt-free conditions. J. Org. Chem., 1992, 57, 6614-6617.
Piscopio, A.D.; Minowa, N.; Chakraborty, K.K.; Bertinato, P.; Nicolaou, K.C. A highly convergent strategy towards rapamycin. Stereoselective construction of the C8-C18 fragment. J. Am. Chem. Soc. Chem. Commun., 1993, (7), 617-618>.
Scholl, M.; Ding, S.; Lee, C.W.; Grubbs, R.H. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Org. Lett., 1999, 1(6), 953-956.
[] [PMID: 10823227]
Cheung, A.K.; Murelli, R.; Snapper, M.L. Total syntheses of (+)- and (-)-cacospongionolide B, cacospongionolide E, and related analogues. Preliminary study of structural features required for phospholipase A2 inhibition. J. Org. Chem., 2004, 69(17), 5712-5719.
[] [PMID: 15307744]
Otha, T.; Ikegami, H.; Miyake, T. Takaya. H. BINAP-Ru(II) and BINAP-Rh(I)-catalyzed asymmetric hydrogenation of olefins without heteroatom-functionalities. J. Organomet. Chem., 1995, 502, 169-176.
Oshida, M.; Ono, M.; Nakazaki, A.; Kobayashi, S. Total synthesis of (+)-cacospongionolide B. Heterocycles, 2010, 80, 313-328.
Smiatacz, Z.; Myszka, H.; Ciunik, Z. Configuration and conformation of the products of reaction of 3,4-di-O-acetyl-2-deoxy-2-nitroso-β-D-arabino-pyranosyl chloride with pyrazole. Carbohydr. Res., 1988, 172, 171-182.
(a)Šrogl, J.; Janda, M.; Stibor, I. Experiments in the furan series. XII. Preparation of 3-furyl ketones. Collect. Czech. Chem. Commun., 1970, 35, 3478-3480.
(b)Politis, J.K.; Nemes, J.C.; Curtis, M.D. Synthesis and characterization of regiorandom and regioregular poly(3-octylfuran). J. Am. Chem. Soc., 2001, 123(11), 2537-2547.
Hagiwara, H.; Uda, H. Optically pure (4aS)-(+)- or (4aR)-(-)-1,4a-Dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione and its use in the synthesis of an inhibitor of steroid biosynthesis. J. Org. Chem., 1988, 53, 2308-2311.
Hayakawa, I.; Ueda, M.; Yamaura, M.; Ikeda, Y.; Suzuki, Y.; Yoshizato, K.; Kigoshi, H. Second-generation total synthesis of haterumalide NA using B-alkyl Suzuki-Miyaura coupling. Org. Lett., 2008, 10(9), 1859-1862.
[] [PMID: 18396895]
Murelli, R.P.; Cheung, A.K.; Snapper, M.L. Conformationally restricted (+)-cacospongionolide B analogues. Influence on secretory phospholipase A2 inhibition. J. Org. Chem., 2007, 72(5), 1545-1552.
[] [PMID: 17315974]
Renaud, J.; Ouellet, S.G. Novel synthesis of cyclic alkenylboronates via ring-closing metathesis. J. Am. Chem. Soc., 1998, 120, 7995-7996.
Crabtree, S.R.; Mander, L.N.; Sethi, S.P. Synthesis of β-keto esters by C-acylation of preformed enolates with methyl cyanoformate: Preparation of methyl (1α,4aβ,8aα)-2-oxodecahydro-1-naphthoate. Org. Synth., 1992, 70, 256-264.
Liu, M-G.; Liu, N.; Xu, W-H.; Wang, L. Tandem reaction strategy of the Passerini/Wittig reaction based on the in situ capture of isocyanides: One-pot synthesis of heterocycles. Tetrahedron, 2019, 75, 2748-2754.
Liu, N.; Chao, F.; Liu, M-G.; Huang, N-Y.; Zou, K.; Wang, L. Odorless isocyanide chemistry: One-pot synthesis of heterocycles via the passerini and postmodification tandem reaction based on the in situ capture of isocyanides. J. Org. Chem., 2019, 84(4), 2366-2371.
[] [PMID: 30676019]
Kerr, W.J.; McLaughlin, M.; Morrison, A.J.; Pauson, P.L. Formal total synthesis of (+/-)-α- and β-cedrene by preparation of cedrone. Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation. Org. Lett., 2001, 3(19), 2945-2948.
[] [PMID: 11554814]
Ohira, S. Methanolysis of dimethyl (1-diazo-2-oxopropyl) phosphonate: Generation of dimethyl (diazomethyl) phosphonate and reaction with carbonyl compounds. Synth. Commun., 1989, 19, 561-564.
Boukouvalas, J.; Robichaud, J.; Maltais, F. A unified strategy for the regiospecific assembly of homoallyl-substituted butenolides and γ-hydroxybutenolides: first synthesis of luffariellolide. Synlett, 2006, 15, 2480-2482.
Boukouvalas, J.; Lachance, N. A mild, efficient and general method for the synthesis of trialkylsilyl (Z)-4-oxo-2-alkenoates and γ-hydroxybutenolides. Synlett, 1998, 1998(1), 31-32.
(a)Torii, S.; Uneyama, K.; Ishihara, M. Alicyclic terpenoids from cyclocitral phenyl sulfides I. Acid-catalyzed cyclization of geranyl phenyl sulfides to cyclocitral derivatives. A Synthesis of α- and β-Ionones. Chem. Lett., 1975, 4(5), 479-482.
(b)Jeong, Y.C.; Ji, M.; Lee, J.S.; Yang, J-D.; Jin, J.; Baik, W.; Koo, S. General and systematic synthetic entry to carotenoid natural products. Tetrahedron, 2004, 60, 10181-10185.
Dauben, W.G.; Saugier, R.K.; Fleishhauer, I. Synthetic studies directed toward cembranolides. Synthesis of the basic nucleus of crassin acetate. J. Org. Chem., 1985, 50, 3767-3774.
Sato, K.; Inoue, S.; Onishi, A.; Uchida, N.; Minowa, N. Stereoselective synthesis of solanesol and all-trans-decaprenol. J. Chem. Soc., Perkin Trans. 1, 1981, 761-769.
Corey, E.J.; Roberts, B.E. Total synthesis of dysidiolide. J. Am. Chem. Soc., 1997, 119, 12425-12431.
Demeke, D.; Forsyth, C.J. Total synthesis of (±)-dysidiolide. Tetrahedron, 2002, 58, 6531-6544.

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