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TitleBioactive Marine Natural Products - D. Bhakuni, D. Rawat (Springer, 2005) WW
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LanguageEnglish
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Page 2

Bioactive Marine
Natural Products

Page 198

Bioactive Marine Toxins 183

which affect the pseudo cyclic conformation formed by interaction between
C1 carboxylic acid and C24 hydroxyl group also reduced the potency.

5.4 Pectenotoxins
Pectenotoxin-l (PTX1, 91)

248–254 was isolated as one of the diarrheic shellfish
toxins from the digestive glands of the scallop, Patinopecten yessoensis
found Northeastern Japan.242 The toxins were isolated by repeated
chromatography on silicic acid and gel permeation through Sephadex LH-
20. DTX1, DTX2 and DTX3 which had bulky fatty acid moiety were separated
by this procedure, HPLC on reversed phase column and HPLC on a silicic

85

87

88

89

82, R = Bz
90, R = H

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184 Bioactive Marine Natural Products

acid column were used to separate PTX1 from PTX3 and PTX2 from PTX4.
200 kg of digestive glands of scallop yielded pectenotoxin-l (PTX1) (20 mg)
m.p. 208-209°C; [α]D +17.1° (c, 0.41 MeOH); pectenotoxin-2 (PTX2)
(40 mg) as white amorphous solid, [α]D +16.2° (c, 0.015 MeOH); pectenotoxin-
3 (PTX3)10 mg; pectenotoxin-4 (PTX4) (7 mg); and pectenotoxin-5 (PTX5)
(0.5 mg) as colorless solids.

Minimum lethal dose of PTX1 to mouse was 250 µg/kg (ip); PTX2
60 µg/kg (ip). Structure (91) for pectenotoxin-l (PTX1) was assigned by
X-ray crystallographic analysis.242 The structures of four pectenotoxin
homolog have been elucidated so far.255 They all have essentially the same
structure except at C43 where various stages of oxidation from methyl to
carboxylic acid are found (PTX2, CH3; PTX1, CH2OH; PTX3, CHO, and
PTX6, CO2H). PTX1 was also found in dinoflagellate Dinophysis fortii along
with dinophysistoxin-l.233

Histopathological investigations have shown that PTX1 is hepatotoxic
and induces rapid necrosis of hepatocytes. The pathological action of PTX1
resembles that of phalloidin.256 PTXs are substantially different from other
dinoflagellate toxins, especially in a longer carbon backbone (C40), a C33
lactones ring rather than an acyclo structure, and a novel dioxabicyclo moiety.
The large oxygen-rich internal cavity is grossly similar to cavities found in
the polyether ionophores from terrestrial microorganisms.

5.5 Yessotoxin
Yessotoxin (92), a novel polyether toxin, had been isolated from scallops
Patinopecten yessoensis implicated in diarrheic shellfish poisoning.242,257–261

Digestive glands of scallops (84 kg) collected at Mutsu Bay, Japan, yielded
60 mg yessotoxin (92) as an amorphous solid. The toxin was isolated from
the toxin fractions by initial chromatography on an alumina column, and
subsequently by successive chromatography on Fujgel (DDS-Q3), Develosil
and Toyopearl. It had [α]D + 3.01 (c, 0.45, MeOH); UV λmax (MeOH) 230
nm (ε10,600), IR (KBr), 3400, 1240, 1220 cm–1 ; FABMs (negative), m/z
1163 (M+-Na).

91

Page 396

Subject Index 381

Taraxerol, 6
Tawicyclamide A, B, 294
Tedania, 48
Tedania digitata, 45, 50, 219, 221
Tedania ignis, 43, 47
Tedanolide, 47
Tedania ignis, 47
Teleocidin A-I, 195
Telesto riisei, 335, 343, 344
Terebralia palustris, 116
Terpios hoshinota, 52
Terpios zeteki, 348, 349
Tethya aurantia, 45, 141
Tethys fimbria, 348, 349
Tetrodotoxin, 18, 35, 74, 104, 130, 151,

164, 165, 166, 167, 168, 172
Tetrosia, 48
Thalassia hemprichii, 107
Thalassiolins A, 100
Thalassiolins A-C, 100
Thelenata ananas, 115
Theonella spp., 118
Theonella swinhoei, 47
Theonella, 283, 284, 286, 287, 291
Theophylline, 225, 227
Therapeutic index, 83
Thioacetamide, 89
Thymidine, 213
Tobacco mosaic virus, 111
Topical activity, 284
Topoisomerase I, 253
Topoisomerase II, 235, 250, 254, 267
Toxadocia zumi, 37
Toxopneustes pileolus, 51
Toyocomycin, 222
Trebouxia, 132
Trichoderma virens, 313
Trichodermamides, 314
Trichodermamides A and B, 313, 314
Trichodesmium erythraeum, 106
Trichophyton asteroids, 30, 114
Tridacna, 145
Tridacna maxima, 144, 224, 228
Trididemnum solidum, 118, 266, 305
Trididemnum sp., 51, 245, 292
Trochus spp., 117
Trychophyton, 15
Tubercidin, 222
Tumor promoting activity, 281, 286
Tunicates, 51, 53
Tunichlorin, 266

Tunichromes, 261
Turbinaria decurrens, 109
Turbo intercostalis, 114
TZT-1027, 303

Ubiquitin-isopeptidase activity, 345
Udotea, 16
Udotea indica, 109
Ulcer therapy, 10
Ulicyclamide, 51
Ulithiacyclamide, 51, 292, 294
Ulongapeptin, 310
Ulva, 1
Ulva faciata, 106, 111, 112
Ulva lactua, 111, 133
Ulva reticulata, 109
Urchin egg assay, 47, 260
Uronic acid, 11

V. cauliformis, 33
Vaccinia, 111
Vaccinia virus, 107, 111
Valoniopsis pachynema, 109
Valoniopsis spp., 109
Varacin, 239
Varamine-A, 239, 240, 252
Varamine-B, 239, 240, 252
Varicella zoster virus (VZV), 210, 212, 213,

228
Veiutamine, 267
Yellow fever virus, 292
Yessotoxin, 184, 185
Verapamil, 175
Verongia cauliformis, 33
Verongia thiona, 33, 135
Vidarabine, 212
Viscosin, 315
Vitilevuamide, 52

W-7, 259
Wakayin, 250, 254

Xestospongia carbonaria, 242
Xestospongia cf. carbonaria, 252
Xestospongia exigua, 47
Xestospongin A, B, C and D, 47, 53
Xestosterol, 139

Yanucamides, 311, 312

Z-PNG4, 345, 346

Page 397

382 Subject Index

Zeatin, 72
Zeatin riboside, 72
Zidovudine, 213
Zoanthamide, 264
Zoanthaminone, 264

Zoanthenamine, 264
Zoanthus, 264
Zoanthus spp., 116
Zonarol, 39
Zosimus aeneus, 36

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