Half a Century of Hawaiian Marine Natural Products

Kehau A. Hagiwara; Anthony D. Wright

doi:10.1055/s-0042-105876

Planta Medica, Table of Contents

Planta Med 2016; 82(09/10): 800-815
DOI: 10.1055/s-0042-105876

Reviews

Georg Thieme Verlag KG Stuttgart · New York

Half a Century of Hawaiian Marine Natural Products^[*]

Authors

Kehau A. Hagiwara

¹DKI-College of Pharmacy, University of Hawaii at Hilo, Hilo, Hawaii, USA
Anthony D. Wright

¹DKI-College of Pharmacy, University of Hawaii at Hilo, Hilo, Hawaii, USA

²Right Consulting, Hilo, Hawaii, USA

Abstract

The following review covers the primary literature concerning marine natural products isolated for the first time from organisms collected around the islands of Hawaii published in the 51-year period 1964 to July 2015. The review is divided into seven main sections based on major taxonomic groupings; algae, sponges, mollusks, miscellaneous invertebrates, cyanobacteria, bacteria, and fungi. The aim of the review is to discuss the compounds and information concerning their original biological activity and other potentially interesting properties. The majority of the 320 structures of isolated compounds are not shown directly in the review but are contained in the Supporting Information section in 22 figures, Figs. 1 S–22 S. The Supporting Information section also contains Table 1 S that has information relating to the taxonomic identification of the source organism of each compound, collection location of the source organism, a trivial or semi-systematic name for each compound, as well as its general structural class. The authors hope that this review will be the spawning ground for other reviews and the basis for a great deal more research into the marine life found in Hawaiian waters.

Key words

Hawaii - marine - natural products - algae - sponges - cyanobacteria - bacteria - fungi

Full Text

References

References
1 Moore RE, Pettus jr. JA, Doty MS. Dictyopterene A, an odoriferous constituent from algae of the genus Dictyopteris . Tetrahedron Lett 1968; 9: 4787-4790
2 Pettus jr. JA, Moore RE. Isolation and structure determination of an undeca-1,3,5,8-tetraene and dictyopterene B from algae of the genus Dictyopteris . Chem Commun 1970; 9: 1093-1094
3 Moore RE, Pettus jr. JA. The Isolation and structure determination of dictyopterenes C′ and D′ from Dictyopteris. Stereospecificity in the Cope rearrangement of dictyopterenes A and B. J Am Chem Soc 1971; 93: 3087-3088
4 Müller DG, Jaenicke L, Donike M, Akintobi T. Sex attractant in a brown alga: chemical structure. Science 1971; 171: 815-817
5 Roller P, Au K, Moore RE. Isolation of S-(3-oxoundecyl) thioacetate, bis-(3-oxoundecyl) disulphide, (−)-3-hexyl-4,5-dithiacycloheptanone, and S-(trans-3-oxoundec-4-enyl) thioacetate from Dictyopteris . Chem Commun 1971; 10: 503-504
6 Moore RE. Bis-(3-oxoundecyl) polysulphides in Dictyopteris . Chem Commun 1971; 10: 1168-1169
7 Moore RE, Mistysyn J, Pettus jr. JA. (−)-Bis-(3-acetoxyundec-5-enyl) disulphide and S-(−)-3-acetoxyundec-5-enyl thioacetate, possible precursors to undeca-1,3,5-trienes in Dictyopteris . Chem Commun 1972; 6: 326-327
8 Moore RE, Yost G. Dihydrotropones from Dictyopteris . J Chem Soc Chem Commun 1973; 24: 937-938
9 Moore RE, Pettus jr. JA, Mistysyn J. Odoriferous C₁₁ hydrocarbons from Hawaiian Dictyopteris . J Org Chem 1974; 39: 2201-2207
10 Sun HH, Waraszkiewicz SM, Erickson KL, Finer J, Clardy J. Dictyoxepin and dictyolene, two new diterpenes from the marine alga Dictyota acutiloba (Phaeophyta). J Am Chem Soc 1977; 99: 3516-3517
11 Hardt IH, Fenical W, Cronin G, Hay ME. Acutilols, potent herbivore feeding deterrents from the tropical brown alga, Dictyota acutiloba . Phytochemistry 1996; 43: 71-73
12 Finer J, Clardy J, Fenical W, Minale L, Riccio R, Battaile J, Kirkup M, Moore RE. Structures of dictyodial and dictyolactone, unusual marine diterpenoids. J Org Chem 1979; 44: 2044-2047
13 Kirkup MP, Moore RE. Identity of sanadaol with β-crenulal, a diterpene from the brown alga Dictyota crenulata . Phytochemistry 1983; 22: 2527-2529
14 Ishitsuka M, Kusumi T, Kakisawa H. Acetylsanadaol, a diterpene having a novel skeleton, from the brown alga, Pachydictyon coriaceum . Tetrahedron Lett 1982; 23: 3179-3180
15 Kirkup MP, Moore RE. Two minor diterpenes related to dictyodial A from the brown alga Dictyota crenulata . Phytochemistry 1983; 22: 2539-2541
16 Waraszkiewicz SM, Erickson KL. Halogenated sesquiterpenoids from the Hawaiian marine alga Laurencia nidifica: nidificene and nidifidiene. Tetrahedron Lett 1974; 23: 2003-2006
17 Waraszkiewicz SM, Erickson KL. Halogenated sesquiterpenoids from the Hawaiian marine alga Laurencia nidifica. II. Nidifidienol. Tetrahedron Lett 1975; 4: 281-284
18 Sun HH, Waraszkiewicz SM, Erickson KL. Sesquiterpenoid alcohols from the Hawaiian marine alga Laurencia nidifica. III. Tetrahedron Lett 1976; 8: 585-588
19 Waraszkiewicz SM, Erickson KL. Halogenated sesquiterpenoids from the Hawaiian marine alga Laurencia nidifica. IV. Nidifocene. Tetrahedron Lett 1976; 18: 1443-1444
20 Waraszkiewicz SM, Sun HH, Erickson KL. C₁₅-Halogenated compounds from the Hawaiian marine alga Laurencia nidifica. V. The Maneonenes. Tetrahedron Lett 1976; 35: 3021-3024
21 Sun HH, Waraszkiewicz SM, Erickson KL. C₁₅-Halogenated compounds from the Hawaiian marine alga Laurencia nidifica. VI. The Isomaneonenes. Tetrahedron Lett 1976; 47: 4227-4230
22 Sun HH, Erickson KL. Sesquiterpenoids from the Hawaiian marine alga Laurencia nidifica. 7. (+)-Selin-4,7(11)-diene. J Org Chem 1978; 43: 1613-1614
23 Waraszkiewicz SM, Sun HH, Erickson KL. C₁₅-Halogenated compounds from the Hawaiian marine alga Laurencia nidifica. Maneonenes and isomaneonenes. J Org Chem 1978; 43: 3194-3204
24 Cardellina JH, Moore RE. Sphingosine derivatives from red algae of the Ceramiales. Phytochemistry 1978; 17: 554-555
25 Kim IK, Brennan MR, Erickson KL. Lauroxolanes from the marine alga Laurencia majuscula . Tetrahedron Lett 1989; 30: 1757-1760
26 Brennan MR, Kim IK, Erickson KL. Kahukuenes, new diterpenoids from the marine alga Laurencia majuscula . J Nat Prod 1993; 56: 76-84
27 Juagdan EG, Kalidindi R, Scheuer P. Two new chamigranes from an Hawaiian red alga, Laurencia cartilaginea . Tetrahedron 1997; 53: 521-528
28 Burreson BJ, Moore RE, Roller P. Haloforms in the essential oil of the alga Asparagopsis taxiformis (Rhodophyta). Tetrahedron Lett 1975; 16: 473-476
29 Burreson BJ, Moore RE, Roller PP. Volatile halogen compounds in the alga Asparagopsis taxiformis (Rhodophyta). J Agric Food Chem 1976; 24: 858-861
30 Woolard FX, Moore RE, Roller PP. Halogenated acetamides, but-3-en-2-ols, and isopropanols from Asparagopsis taxiformis (Delile) Trev. Tetrahedron 1976; 32: 2843-2846
31 Woolard FX, Moore RE, Roller PP. Halogenated acetic and acrylic acids from the red alga Asparagopsis taxiformis . Phytochemistry 1979; 18: 617-620
32 Moore RE. Volatile compounds from marine algae. Acc Chem Res 1977; 10: 40-47
33 Kirkup MP, Moore RE. Indole alkaloids from the marine red alga Martensia fragilis . Tetrahedron Lett 1983; 24: 2087-2090
34 Nagai H, Yasumoto T, Hokama Y. Aplysiatoxin and debromoaplysiatoxin as the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii. Toxicon 1996; 37: 753-761
35 Nagai H, Yasumoto T, Hokama Y. Manauealides, some of the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii. J Nat Prod 1997; 60: 925-928
36 Kato Y, Scheuer PJ. Aplysiatoxin and debromoaplysiatoxin, constituents of the marine mollusk Stylocheilus longicauda (Quoy and Gaimard, 1824). J Am Chem Soc 1974; 96: 2245-2246
37 Nagai H, Kan Y, Fujita T, Sakamoto B, Hokama Y. Manauealide C and anhydrodebromoaplysiatoxin, toxic constituents of the Hawaiian red alga, Gracilaria coronopifolia . Biosci Biotechnol Biochem 1998; 62: 1011-1013
38 Kan Y, Fujita T, Nagai H, Sakamoto B, Hokama Y. Malyngamides M and N from the Hawaiian red alga, Gracilaria coronopifolia . J Nat Prod 1998; 61: 152-155
39 Wang X, Liu X, Kono S, Wang G. The ecological perspective of microbial communities in two pairs of competitive Hawaiian native and invasive macroalgae. Microb Ecol 2013; 65: 361-370
40 Woolard FX, Burreson BJ, Moore RE. Isolation of (3S)-cis-octa-1,5-dien-3-ol from Chondrococcus hornemanni (Rhodophyta). J Chem Soc Chem Commun 1975; 12: 486-487
41 Burreson BJ, Woolard FX, Moore RE. Chondrocole A and B, two halogenated dimethylhexahydrobenzenofurans from the red alga Chondrococcus hornemanni (Mertens) Schmitz. Tetrahedron Lett 1975; 26: 2155-2158
42 Woolard FX, Moore RE, Van Engen D, Clardy J. The structure and absolute configuration of chondrocolactone, a halogenated monoterpene from the red alga Chondrococcus hornemanni, and a revised structure for chondrochole A. Tetrahedron Lett 1978; 27: 2367-2370
43 Horgen FD, Sakamoto B, Scheuer PJ. New triterpenoid sulphates from the red alga Tricleocarpa fragilis . J Nat Prod 2000; 63: 210-216
44 Hamann MT, Scheuer PJ. Kahalalide F: a bioactive depsipeptide from the sacoglossan mollusk Elysia rufescens and the green alga Bryopsis sp. J Am Chem Soc 1993; 115: 5825-5826
45 Hamann MT, Otto CS, Scheuer PJ. Kahalalides: bioactive peptides from a marine mollusk Elysia rufescens and its algal diet Bryopsis sp. J Org Chem 1996; 61: 6594-6600
46 Kan Y, Fujita T, Sakamoto B, Hokama Y, Nagai H. Kahalalide K: a new cyclic depsipeptide from the Hawaiian green alga Bryopsis sp. J Nat Prod 1999; 62: 1169-1172
47 Horgen FD, delos Santos DB, Goetz G, Sakamoto B, Kan Y, Nagai H, Scheuer PJ. A new depsipeptide from the sacoglossan mollusk Elysia ornata and the green alga Bryopsis species. J Nat Prod 2000; 63: 152-154
48 Dmitrenok A, Iwashita T, Nakajima T, Sakamoto B, Namikoshi M, Nagai H. New cyclic depsipeptides from the green alga Bryopsis species; application of a carboxypeptidase hydrolysis reaction to the structure determination. Tetrahedron 2006; 62: 1301-1308
49 Gao J, Caballero-George C, Wang B, Rao KV, Shilabin AG, Hamann MT. 5-OHKF and NorKA, depsipeptides from a Hawaiian collection of Bryopsis pennata: binding properties for NorKA to the human neuropeptide Y Y₁ receptor. J Nat Prod 2009; 72: 2172-2176
50 Carlos AA, Baillie BK, Kawachi M, Maruyama T. Phylogenetic position of Symbiodinium (Dinophyceae) isolates from tridacnids (Bivalvia), cardiids (Bivalvia), a sponge (Porifera), a soft coral (Anthozoa), and a free-living strain. J Phycol 1999; 35: 1054-1062
51 Onodera K, Nakamura H, Oba Y, Ojika M. Zooxanthellamide A, a novel polyhydroxy metabolite from a marine dinoflagellate of Symbiodinium sp. Tetrahedron 2003; 59: 1067-1071
52 Onodera K, Nakamura H, Oba Y, Ojika M. Zooxanthellamide B, a novel large polyhydroxy metabolite from a marine dinoflagellate of Symbiodinium sp. Biosci Biotechnol Biochem 2004; 68: 955-958
53 Onodera K, Nakamura H, Oba Y, Ohizumi Y, Ojika M. Zooxanthellamide Cs: vasoconstrictive polyhydroxylated macrolides with the largest lactone ring size from a marine dinoflagellate of Symbiodinium sp. J Am Chem Soc 2005; 127: 10406-10411
54 Vijayavel K, Martinez JA. In vitro antioxidant and antimicrobial activities of two Hawaiian marine limu: Ulva fasciata (Chlorophyta) amd Gracilaria Salicornia (Rhodophyta). J Med Food 2010; 13: 1494-1499
55 Kelman D, Posner EK, McDermid KJ, Tabandera NK, Wright PR, Wright AD. Antioxidant activity of Hawaiian marine algae. Mar Drugs 2012; 10: 403-416
56 Hart GM, Ticktin T, Kelman D, Wright AD, Tabandera N. Contemporary gathering practice and antioxidant benefit of wild seaweeds in Hawaiʼi. Econ Bot 2014; 68: 30-43
57 Ravi BN, Perzanowski HP, Ross RA, Erdman TR, Scheuer PJ. Recent research in marine natural products: the puupehenones. Pure Appl Chem 1979; 51: 1893-1900
58 Luibrand RT, Erdman TR, Vollmer JJ, Scheuer PJ. Ilimaquinone, a sesquiterpenoid quinone from a marine sponge. Tetrahedron 1979; 35: 609-612
59 Hagiwara K, Garcia Hernandez JE, Harper MK, Carroll A, Motti CA, Awaya J, Nguyen HY, Wright AD. Puupehenol, a potent antioxidant antimicrobial meroterpenoid from a Hawaiian deep-water Dactylospongia sp. sponge. J Nat Prod 2015; 78: 325-329
60 Schulte G, Scheuer PJ, McConnell OJ. Upial, a sesquiterpenoid bicyclo[3.3.1]nonane aldehyde lactone from the marine sponge Dysidea fragilis . J Org Chem 1980; 45: 552-554
61 Schulte G, Scheuer PJ, McConnell OJ. Two furanosesquiterpene marine metabolites with antifeedant properties. Helv Chim Acta 1980; 63: 2159-2167
62 Nasu SS, Yeung BKS, Hamann MT, Scheuer PJ, Kelly-Borges M, Goins K. Puupehenone-related metabolites from two Hawaiian sponges, Hyrtios spp. J Org Chem 1995; 60: 7290-7292
63 Sata N, Galario MA, Sitachitta N, Scheuer PJ, Kelly M. Poipuol, a new metabolite from a Hawaiian sponge of the genus Hyrtios . J Nat Prod 2005; 68: 262-263
64 Hagiwara KA, Harper-Ireland MK, Anklin C, Elyasberg M, Clark B, Wright AD. The use of DOSY in the structure elucidation of a Hawaiian deep-water sponge metabolite. Planta Med 2014; 80: PB14
65 Kalidindi RS, Yoshida WY, Palermo JA, Scheuer PJ. Pokepola ester: a phosphate diester from a Maui sponge. Tetrahedron Lett 1994; 35: 5579-5582
66 Erdman TR, Scheuer PJ. 28-Isofucosterol: major sterol of a marine sponge. Lloydia 1975; 38: 359-360
67 Theobald N, Shoolery JN, Djerassi C, Erdman TR, Scheuer PJ. 24-Ethyl-Δ ^5,24(28),28-cholestatrien-3β-ol – a naturally occurring allenic marine sterol. J Am Chem Soc 1978; 100: 5574-5575
68 Corgiat JM, Scheuer PJ, Rios Steiner JL, Clardy J. Three pregnane-10,2-carbolactones from a sponge, Strongylophora sp. Tetrahedron 1993; 49: 1557-1562
69 Sata N, Abinsay H, Yoshida WY, Horgen FD, Sitachitta N, Kelly M, Scheuer PJ. Lehualides A–D, metabolites from a Hawaiian sponge of the genus Plakortis . J Nat Prod 2005; 68: 1400-1403
70 Carney JR, Yoshida WY, Scheuer PJ. Kiheisterones, new cytotoxic steroids from a Maui sponge. J Org Chem 1992; 57: 6637-6643
71 Carney JR, Scheuer PJ, Kelly-Borges M. Three unprecedented chloro steroids from the Maui sponge Strongylacidon sp.: Kiheisterones C, D, and E. J Org Chem 1993; 58: 3460-3462
72 Burreson BJ, Christopherson C, Scheuer PJ. Cooccurence of a terpenoid isocyanide-formamide pair in the marine sponge Halichondria sp. J Am Chem Soc 1975; 97: 201-202
73 Burreson BJ, Scheuer PJ. Isolation of a diterpenoid isonitrile from a marine sponge. J Chem Soc Chem Commun 1974; 24: 1035-1036
74 Burreson BJ, Christopherson C, Scheuer PJ. Cooccurence of two terpenoid isocyanide-formamide pairs in a marine sponge (Halichondria sp.). Tetrahedron 1975; 31: 2015-2018
75 Burreson BJ, Scheuer PJ, Finer J, Clardy J. 9-Isocyanopupukeanane, a marine invertebrate allomone with a new sesquiterpene skeleton. J Am Chem Soc 1975; 97: 4763-4764
76 Delseth C, Tolela L, Scheuer PJ, Wells RJ, Djerassi C. 5α-24-Norcholestan-3β-ol and (24Z)-stigmasta-5,7,24(28)-trien-3β-ol, two new marine sterols from the Pacific sponges Terpios zeteki and Dysidea herbacea . Helv Chim Acta 1979; 62: 101-109
77 Gulavita NK, de Silva ED, Hagadone MR, Karuso P, Scheuer PJ. Nitrogenous bisabolene sesquiterpenes from marine invertebrates. J Org Chem 1986; 51: 5136-5139
78 Karuso P, Poiner A, Scheuer PJ. Isocyanoneopupukeanane, a new tricyclic sesquiterpene from a sponge. J Org Chem 1989; 54: 2095-2097
79 Hamann MT, Scheuer PJ. Cyanopuupehenol, an antiviral metabolite of a sponge of the order Verongida. Tetrahedron Lett 1991; 32: 5671-5672
80 Hamann MT, Scheuer PJ, Kelly-Borges M. Biogenetically diverse, bioactive constituents of a sponge, order Verongida: bromotyramines and sesquiterpene-shikimate derived metabolites. J Org Chem 1993; 58: 6565-6569
81 Lacy C, Scheuer PJ. New Molokaʼiamine derivatives from an undescribed verongid sponge. J Nat Prod 2000; 63: 119-121
82 Ross SA, Weete JD, Schinazi RF, Wirtz SS, Tharnish P, Scheuer PJ, Hamann MT. Mololipids, a new series of anti-HIV bromotyramine-derived compounds from a sponge of the order Verongida. J Nat Prod 2000; 63: 501-503
83 Jurek J, Yoshida WY, Scheuer PJ. Three new bromotyrosine-derived metabolites of the sponge Psammaplysilla purpurea . J Nat Prod 1993; 56: 1609-1612
84 Kato Y. Toxic constituents of the marine mollusk Stylocheilus longicauda [dissertation]. Manoa: University of Hawaii; 1973
85 Rose AF, Scheuer PJ, Springer JP, Clardy J. Stylocheilamide, an unusual constituent of the sea hare Stylocheilus longicauda . J Am Chem Soc 1978; 100: 7665-7670
86 Gallimore WA, Galario DL, Lacy C, Zhu Y, Scheuer PJ. Two complex proline esters from the sea hare Stylocheilus longicauda . J Nat Prod 2000; 63: 1022-1026
87 Gallimore WA, Scheuer PJ. Malyngamides O and P from the sea hare Stylocheilus longicauda . J Nat Prod 2000; 63: 1422-1424
88 Schulte GR, Chung MCH, Scheuer PJ. Two bicyclic C₁₅ enynes from the sea hare Aplysia oculifera . J Org Chem 1981; 46: 3870-3873
89 Hagadone MR, Burreson BJ, Scheuer PJ, Finer JS, Clardy J. Defense allomones of the nudibranch Phyllidia varicosa Lamarck 1801. Helv Chim Acta 1979; 62: 2484-2494
90 Terem B, Scheuer PJ. Scalaradial derivatives from the nudibranch Chromodoris youngbleuthi and the sponge Spongia oceania . Tetrahedron 1986; 42: 4409-4412
91 Okuda RK, Scheuer PJ, Hochlowski JE, Walker RP, Faulkner DJ. Sesquiterpenoid constituents of eight porostome nudibranchs. J Org Chem 1983; 48: 1866-1869
92 Ireland CM, Biskupiak JE, Hite GJ, Rapposch M, Scheuer PJ, Ruble JR. Ilikonapyrone esters, likely defense allomones of the mollusk Onchidium verruculatum . J Org Chem 1984; 49: 559-561
93 Roesener JA, Scheuer PJ. Ulapualide A and B, extraordinary antitumor macrolides from nudibranch egg masses. J Am Chem Soc 1986; 108: 846-847
94 Guella G, Mancini I, Chiasera G, Pietra F. Sphinxolide, a 26-membered antitumoral macrolide isolated from an unidentified Pacific nudibranch. Helv Chim Acta 1989; 72: 237-246
95 Coval SJ, Scheuer PJ. An intriguing C₁₆-alkadienone-substituted 2-pyridine from a marine mollusk. J Org Chem 1985; 50: 3024-3025
96 Coval SJ, Schulte GR, Matsumoto GK, Roll DM, Scheuer PJ. Two polypropionate metabolites from the cephalaspidean mollusk Philinopsis speciosa . Tetrahedron Lett 1985; 26: 5359-5362
97 Reese MT, Gulavita NK, Nakao Y, Hamann MT, Yoshida WY, Coval SJ, Scheuer PJ. Kulolide: a cytotoxic depsipeptide from a cephalaspidean mollusk Philinopsis speciosa . J Am Chem Soc 1996; 118: 11081-11084
98 Nakao Y, Yoshida WY, Scheuer PJ. Pupukeamide, a linear tetrapeptide from a cephalaspidean mollusk Philinopsis speciosa . Tetrahedron Lett 1996; 37: 8993-8996
99 Nakao Y, Yoshida WY, Szabo CM, Baker BL, Scheuer PJ. More peptides and other diverse constituents of the marine mollusk Philinopsis speciosa . J Org Chem 1998; 63: 3272-3280
100 Kimura J, Takada Y, Inayoshi T, Nakao Y, Goetz G, Yoshida WY, Scheuer PJ. Kulokekakilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa . J Org Chem 2002; 67: 1760-1767
101 Nakao Y, Yoshida WY, Takada Y, Kimura J, Yang L, Mooberry SL, Scheuer PJ. Kulokekahilide-2, a cytotoxic depsipeptide from cephalaspidean mollusk Philinopsis speciosa . J Nat Prod 2004; 67: 1332-1340
102 Goetz G, Nakao Y, Scheuer PJ. Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens . J Nat Prod 1997; 60: 562-567
103 Rao KV, Na M, Cook JC, Peng J, Matsumoto R, Hamann MT. Kahalalides V–Y isolated from a Hawaiian collection of the sacoglossan mollusk Elysia rufescens . J Nat Prod 2008; 71: 772-778
104 Moore RE, Scheuer PJ. Palytoxin: a new marine toxin from a coelenterate. Science 1971; 172: 495-498
105 Moore RE, Bartolini G. Structure of palytoxin. J Am Chem Soc 1981; 103: 2491-2494
106 Moore RE, Bartolini G, Barchi J, Bothner-By AA, Dadok J, Ford J. Absolute stereochemistry of palytoxin. J Am Chem Soc 1982; 104: 3776-3779
107 Quinn RJ, Kashiwagi M, Moore RE, Norton TR. Anticancer activity of zoanthids and the associated toxin, palytoxin, against Ehrlich ascites tumor and P-388 lymphocytic leukemia in mice. J Pharm Sci 1974; 63: 257-260
108 Ciminiello P, DellʼAversano C, Dello Iacovo E, Forino M, Tartaglione L, Pelin M, Sosa S, Tubaro A, Chaloin O, Poli M, Bignami G. Stereoisomers of 42-hydroxy palytoxin from Hawaiian Palythoa toxica and P. tuberculosa: stereostructure elucidation, detection, and biological activities. J Nat Prod 2014; 77: 351-357
109 Missakian MG, Burreson BJ, Scheuer PJ. Pukalide, a furanocembranolide from the soft coral Sinularia abrupta . Tetrahedron 1975; 31: 2513-2515
110 Coll JC, Bowden BF, Heaton A, Scheuer PJ, Li MKW, Clardy J, Schukte GK, Finer-Moore J. Structures and possible functions of epoxypukalide and pukalide diterpenes associated with eggs of sinularian soft corals (Cnidaria, Anthozoa, Octocorallia, Alcyonacea, Alcyoniidae). J Chem Ecol 1989; 15: 1177-1191
111 Coval SJ, Scheuer PJ, Matsumoto GK, Clardy J. Two new xenicin diterpenoids from the octocoral Anthelia edmondsoni . Tetrahedron 1984; 40: 3823-3828
112 Baker BJ, Okuda RK, Yu PTK, Scheuer PJ. Punaglandins: halogenated antitumor eicosanoids from the octocoral Telesto riisei . J Am Chem Soc 1985; 107: 2977-2978
113 Schwartz RE, Yunker MB, Scheuer PJ, Ottersen T. Constituents of bathyal marine organisms: a new zoanthoxanthin from a coelenterate. Tetrahedron Lett 1978; 26: 2235-2238
114 Schwartz RE, Yunker MB, Scheuer PJ, Ottersen T. Pseudozoanthoxanthins from gold coral. Can J Chem 1979; 57: 1707-1711
115 Schwartz RE, Scheuer PJ, Zabel V, Watson WH. The coraxeniolides, constituents of pink coral, Corallium sp. Tetrahedron 1981; 37: 2725-2733
116 Bonini C, Kinnel RB, Li M, Scheuer PJ, Djerassi C. Minor and trace sterols in the marine invertebrates 38: isolation, structure elucidation and partial synthesis of papakusterol, a new biosynthetically unusual marine sterol with a cyclopropyl-containing side chain. Tetrahedron Lett 1983; 24: 277-280
117 Li MKW, Scheuer PJ. Halogenated blue pigments of a deep sea gorgonian. Tetrahedron Lett 1984; 25: 587-590
118 Anderson jr. AG, Nelson JA, Tazuma JJ. Azulene. III. Electrophilic substitution. J Am Chem Soc 1953; 75: 4980-4989
119 Li MKW, Scheuer PJ. N,N-Dimethylamino-3-guaiazulenylmethane from a deep sea gorgonian. Tetrahedron Lett 1984; 25: 4707-4708
120 Li MKW, Scheuer PJ. A guaianolide pigment from a deep sea gorgonian. Tetrahedron Lett 1984; 25: 2109-2110
121 Nagai H, Takuwa K, Nakao M, Sakamoto B, Crow GL, Nakajima T. Isolation and characterization of a novel protein toxin from the Hawaiian box jellyfish (sea wasp) Carybdea alata . Biochem Biophys Res Commun 2000; 275: 589-594
122 Chang CWJ, Moore RE, Scheuer PJ. The Structure of spinochrome M. J Am Chem Soc 1964; 86: 2959-2961
123 Moore RE, Singh H, Scheuer PJ. Isolation of eleven new spinochromes from echinoids of the genus Echinothrix . J Am Chem Soc 1966; 31: 3645-3650
124 Moore RE, Singh H, Scheuer PJ. A Pyranonaphthazarin pigment from the sea urchin Echinothrix diadema . Tetrahedron Lett 1968; 43: 4581-4583
125 Higa T, Scheuer PJ. Constituents of the marine annelid Thelepus setosus . Tetrahedron 1975; 31: 2379-2381
126 Higa T, Okuda RK, Severns M, Scheuer PJ, He CH, Changfu X, Clardy J. Unprecedented constituents of a new species of acorn worm. Tetrahedron 1987; 43: 1063-1070
127 Moikeha SN, Chu GW, Berger LR. Dermatitis-producing alga Lyngbya majuscula Gomont in Hawaii. I. Isolation and chemical characterization of the toxic factor. J Phycol 1971; 7: 8-13
128 Engene N, Rottacker EC, Kaštovský J, Byrum T, Choi H, Ellisman MH, Komárek J, Gerwick WH. Moorea producens gen. nov., sp. nov. and Moorea bouillonii comb. nov., tropical marine cyanobacteria rich in bioactive secondary metabolites. Int J Syst Evol Microbiol 2012; 62: 1171-1178
129 Cardellina II JH, Marner FJ, Moore RE. Seaweed dermatitis: structure of lyngbyatoxin A. Science 1979; 204: 193-195
130 Marner FJ, Moore RE, Hirotsu K, Clardy J. Majusculamides A and B, two epimeric lipodipeptides from Lyngbya majuscula Gormont. J Org Chem 1977; 42: 2815-2819
131 Marner FJ, Moore RE. (+)-α(S)-Butyramido-γ-butyrolactone from Lyngbya majuscula . Phytochemistry 1978; 17: 553-554
132 Cardellina II JH, Dalietos D, Marner FJ, Mynderse JS, Moore RE. (−)-Trans-7(S)-methoxytetradec-4-enoic acid and related amides from the marine cyanophyte Lyngbya majuscula . Phytochemistry 1978; 17: 2091-2095
133 Cardellina II JH, Marner FJ, Moore RE. Malyngamide A, a novel chlorinated metabolite of the marine cyanophyte Lyngbya majuscula . J Am Chem Soc 1979; 101: 240-242
134 Cardellina II JH, Moore RE, Arnold EV, Clardy J. Structure and absolute configuration of Malyngolide, an antibiotic from the marine blue-green alga Lyngbya majuscula Gormont. J Org Chem 1979; 44: 4039-4042
135 Simmons CJ, Marner FJ, Cardellina II JH, Moore RE, Seff K. Pukeleimide C, a novel pyrrolic compound from the marine cyanophyte Lyngbya majuscula . Tetrahedron Lett 1979; 22: 2003-2006
136 Cardellina II JH, Moore RE. The structures of pukeleimides A, B, D, E, F, and G. Tetrahedron Lett 1979; 22: 2007-2010
137 Aimi N, Odaka H, Sakai SI, Fujiki H, Suganuma M, Moore RE, Patterson GML. Lynbyatoxins B amd C, two new irritants from Lyngbya majuscula. J Nat Prod 1990; 53: 1593-1596
138 Kan Y, Sakamoto B, Fujita T, Nagai H. New malyngamides for the Hawaiian cyanobacterium Lyngbya majuscula . J Nat Prod 2000; 63: 1599-1602
139 Entzeroth M, Mead DJ, Patterson GML, Moore RE. A herbicidal fatty acid produced by Lyngbya aestuarii . Phytochemistry 1985; 24: 2875-2876
140 Horgen FD, Yoshida WY, Scheuer PJ. Malevamides A–C, new depsipeptides from the marine cyanobacterium Symploca laete-viridis . J Nat Prod 2000; 63: 461-467
141 Adams B, Porzgen P, Pittman E, Yoshida WY, Westenburg HE, Horgen FD. Isolation and structure determination of malevamide E, a dolastatin 14 analogue, from the marine cyanobacterium Symploca laete-viridis . J Nat Prod 2008; 71: 750-754
142 Horgen FD, Kazmierski EB, Westenburg HE, Yoshida WY, Scheuer PJ. Malevamide D: isolation and structure determination of an isodolastatin H analogue from the marine cyanobacterium Symploca hydnoides . J Nat Prod 2002; 65: 487-491
143 Luesch H, Yoshida WY, Moore RE, Paul VJ, Mooberry SL, Corbett TH. Symplostatin 3, a new dolastatin 10 analogue from the marine cyanobacterium Symploca sp. VP452. J Nat Prod 2002; 65: 16-20
144 Choi H, Engene N, Smith JE, Preskitt LB, Gerwick WH. Crossbyanols A–D, toxic brominated polyphenol ethers from the Hawaiʼian bloom-forming cyanobacterium Leptolyngbya crossbyana . J Nat Prod 2010; 73: 517-522
145 Choi H, Mascuch SJ, Villa FA, Byrum T, Teasdale ME, Smith JE, Preskitt LB, Rowley DC, Gerwick L, Gerwick WH. Honaucins A–C, potent inhibitors of inflammation and bacterial quorum sensing: synthetic derivatives and structure-activity relationships. Chem Biol 2012; 19: 589-598
146 Sitachitta N, Gadepalli M, Davidson BS. New α-pyrone-containing metabolites from a marine-derived actinomycete. Tetrahedron 1996; 52: 8073-8080
147 Ford PW, Gadepalli M, Davidson BS. Halawanones A–D, new polycyclic quinones from a marine-derived streptomycete. J Nat Prod 1998; 61: 1232-1236
148 Schumacher RW, Talmage SC, Miller SA, Sarris KE, Davidson BS, Goldberg A. Isolation and structure determination of an antimicrobial ester from a marine sediment-derived bacterium. J Nat Prod 2003; 66: 1291-1293
149 Schumacher RW, Harrigan BL, Davidson BS. Kahakamides A and B, new neosidomycin metabolites from a marine-derived actinomycete. Tetrahedron Lett 2001; 42: 5133-5135
150 Feher D, Barlow RS, Lorenzo PS, Hemscheidt TK. A 2-Substituted prodiginine, 2-(p-hydroxybenzyl)prodigiosin, from Pseudoalteromonas rubra . J Nat Prod 2008; 71: 1970-1972
151 Feher D, Barlow R, McAtee J, Hemscheidt TK. Highly brominated antimicrobial metabolites from a marine Pseudoalteromonas sp. J Nat Prod 2010; 73: 1963-1966
152 Homann VV, Sandy M, Tincu JA, Templeton AS, Tebo BM, Butler A. Loihichelins A–F, a suite of amphiphilic siderophores produced by the marine bacterium Halomonas LOB-5. J Nat Prod 2009; 72: 884-888
153 Poch GK, Gloer JB. Helicasolides A and B: new lactones from the marine fungus Helicascus kanaloanus . J Nat Prod 1989; 52: 257-260
154 Amagata T, Rath C, Rigot JF, Tarlov N, Tenney K, Valeriote FA, Crews P. Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria . J Med Chem 2003; 46: 4342-4350
155 Tan RX, Jensen PR, Williams PG, Fenical W. Isolation and structure assignments of rostratins A–D, cytotoxic disulphides produced by the marine-derived fungus Exserohilum rostratum . J Nat Prod 2004; 67: 1374-1382
156 Oh DC, Jensen PR, Fenical W. Zygosporamide, a cytotoxic cyclic depsipeptide from the marine-derived fungus Zygosporium masonii . Tetrahedron Lett 2006; 47: 8625-8628
157 Cueto M, MacMillan JB, Jensen PR, Fenical W. Tropolactones A–D, four meroterpenoids from a marine-derived fungus of the genus Aspergillus . Phytochemistry 2006; 67: 1826-1831
158 Wu QX, Crews MS, Draskovic M, Sohn J, Johnson TA, Tenney K, Valeriote FA, Yao XJ, Bjeldanes LF, Crews P. Azonazine, a novel dipeptide from a Hawaiian marine sediment-derived fungus, Aspergillus insucola . Org Lett 2010; 12: 4458-4461
159 Wu QX, Draskovic M, Crews MS, Tenney K, Valeriote FA, Yao XJ, Crews P. Unraveling the numerous biosynthetic products of the marine sediment-derived fungus, Aspergillus insucola . Phytochem Lett 2012; 5: 114-117
160 Watts KR, Loveridge ST, Tenney K, Media J, Valeriote FA, Crews P. Utilizing DART mass spectrometry to pinpoint halogenated metabolites from a marine invertebrate-derived fungus. J Org Chem 2011; 76: 6201-6208

Supplementary Material

Supporting Information (PDF) (opens in new window)

Half a Century of Hawaiian Marine Natural Products[*]

Authors

Half a Century of Hawaiian Marine Natural Products^[*]