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{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulfooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0^{3,25}.0^{5,22}.0^{7,20}.0^{9,18}.0^{11,16}.0^{31,48}.0^{33,46}.0^{35,44}.0^{37,42}]nonatetracontan-14-yl}oxidanesulfonic acid | 112514-54-2

中文名称
——
中文别名
——
英文名称
{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulfooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0^{3,25}.0^{5,22}.0^{7,20}.0^{9,18}.0^{11,16}.0^{31,48}.0^{33,46}.0^{35,44}.0^{37,42}]nonatetracontan-14-yl}oxidanesulfonic acid
英文别名
[34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-(2-sulfooxyethyl)-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.03,25.05,22.07,20.09,18.011,16.031,48.033,46.035,44.037,42]nonatetracontan-14-yl] hydrogen sulfate
{34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulfooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0^{3,25}.0^{5,22}.0^{7,20}.0^{9,18}.0^{11,16}.0^{31,48}.0^{33,46}.0^{35,44}.0^{37,42}]nonatetracontan-14-yl}oxidanesulfonic acid化学式
CAS
112514-54-2
化学式
C55H82O21S2
mdl
——
分子量
1143.4
InChiKey
HCYDZFJGUKMTQB-NTCAYCPXSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 密度:
    1.41±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.4
  • 重原子数:
    78
  • 可旋转键数:
    11
  • 环数:
    11.0
  • sp3杂化的碳原子比例:
    0.85
  • 拓扑面积:
    286
  • 氢给体数:
    4
  • 氢受体数:
    21

ADMET

代谢
四种毒素,分别是冈田酸(OA)、鳍藻毒素-1(DTX1)、扇贝毒素-6(PTX6)和亚苏毒素(YTX),它们都与腹泻性贝类中毒(DSP)有关,通过注射器给药给扇贝 Patinopecten yessoensis,并使用液相色谱-质谱分析技术分析了它们在肝胰腺、闭壳肌和混合其他组织(外套膜、鳃、生殖腺)中的分布。无论注射部位是闭壳肌还是肝胰腺,毒素都仅在肝胰腺中残留。当注射到肝胰腺时,OA、DTX1 和 YTX 分别被代谢为 7-O-棕榈酰OA、7-O-棕榈酰DTX1 和 45-羟基亚苏毒素(45OH-YTX)。当毒素注射到闭壳肌时,这种代谢变化不明显。每种毒素在肝胰腺中的残留率小于20%。经PTX6处理的扇贝死亡率低于其他毒素处理的扇贝。
Four toxins, okadaic acid (OA), dinophysistoxin-1 (DTX1), pectenotoxin-6 (PTX6), and yessotoxin (YTX), all associated with diarrhetic shellfish poisoning (DSP), were administered via syringe to Scallops Patinopecten yessoensis and their distribution in the hepatopancreas, adductor muscle, and combined other tissues (mantle, gill, gonad) was analyzed by liquid chromatography-mass spectrometry. Toxins exclusively remained in the hepatopancreas irrespective of the injection site, adductor muscle or hepatopancreas. When injected into hepatopancreas, OA, DTX1, and YTX were metabolized to 7-O-palmitoylOA, 7-O-palmitoylDTX1 and 45-hydroxyyessotoxin (45OH-YTX), respectively. Such metabolic changes were insignificant when toxins were injected into the adductor muscle. The residual ratio for each toxin in the hepatopancreas was less than 20%. Mortalities of scallops treated with PTX6 were lower than those treated with other toxins.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
潜在的有毒腹泻性贝类毒素(DSP)浮游生物甲藻... 包括浮游生物种类Dinophysis acuminata, D.caudata, D. fortii, D.hastata, D. mitra, D. rotundata, D. tripos以及底栖甲藻Prorocentrum lima, P. elegans, P. hoffmannianum和P.concavum... 这些物种无处不在,但它们的毒性是多变且不可预测的。浓密的藻华... 新西兰水域)有时可能完全没有毒性,但其他时候即使只有稀疏的甲藻种群存在,贝类也可能变得有毒。在新西兰,已经发生了两次小规模的DSP爆发。引起DSP毒素的是脂溶性聚醚化合物。第一种被化学特性表征的毒素是冈田酸(OA)... 随后的研究发现贝类中存在冈田酸衍生物,称为dino毒素(DTX),pectenotoxins(PTX,以扇贝属Pecten命名)和yessotoxins(YTX,以扇贝Patinopecten yessoensis命名)... 近年来,已经识别出大量新的DSP毒素,包括来自爱尔兰贻贝的DTX2和一种同分异构体,来自爱尔兰贻贝的新毒素KT3(现命名为螺旋酸),来自亚得里亚海D. fortii的pectenotoxin 2,来自Gonyaulax polyedra和Protoceratium reticulatum的yessotoxin和类似物。虽然yessotoxin具有很高的腹膜毒性,但其口服效力非常低,这种化合物可能需要被降级为DSP毒素... 腹泻效应仅对OA和DTX1和DTX3得到证实,而PTX1-4导致肝坏死,YTX在腹膜内注射到小鼠后损害心肌。一些腹泻毒素(OA和DTX1)是蛋白磷酸酶的强效抑制剂,这种作用方式可能与观察到的腹泻、小肠吸收上皮的退行性变化以及肿瘤促进有关。
Potentially toxic diarrhetic shellfish poisons (DSP) plankton dinoflagellates ... include the planktonic species Dinophysis acuminata, D.caudata, D. fortii, D.hastata , D. mitra, D. rotundata, D. tripos and the benthic dinoflagellates Prorocentrum lima, P. elegans, P. hoffmannianum and P.concavum ... . These species are omnipresent but their toxicity is variable and unpredictable. Dense blooms .... Zealand waters) can sometimes be completely non-toxic, but at other times shellfish can become toxic even when only sparse dinoflagellate populations are present. In New Zealand, there have been two small outbreaks of DSP. The causative DSP toxins are fat-soluble polyether compounds. The first toxin to be characterized chemically was okadaic acid (OA) ... Subsequent research revealed the presence in shellfish of okadaic acid derivatives, termed dinophysis toxins (DTX), pectenotoxins (PTX, after the scallop genus Pecten) and yessotoxins (YTX, after the scallop Patinopecten yessoensis) ... . In recent years, a large number of new DSP toxins have been recognised, including DTX2 and an isomer from Irish mussels, a new toxin KT3 (now named spiramino acid) from Irish mussels, pectenotoxin 2 from D. fortii in the Adriatic Sea, yessotoxin and analogues from Gonyaulax polyedra and Protoceratium reticulatum. While yessotoxin has a high intraperitoneal toxicity, its oral potency is very low, and this compound probably needs to be declassified as a DSP toxin ... .. Diarrhegenic effects have only been proven for OA and DTX1 and DTX3, whereas PTX1-4 causes liver necrosis and YTX damages cardiac muscle after intraperitoneal injection into mice. Some diarrhegenic toxins (OA and DTX1) are potent inhibitors of protein phosphatases and this mode of action may be linked to the observed diarrhea, degenerative changes in absorptive epithelium of the small intestine, and to tumor promotion.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
迹象和症状:在比利时的安特卫普,报告了403起在食用蓝色贻贝后发生的腹泻性贝类中毒案例。症状包括腹泻、呕吐、腹痛和恶心。对病人粪便标本的分析排除了细菌和病毒的病因。通过小鼠实验发现存在特定于甲藻的生物毒素,这些毒素通过液相色谱-质谱(LC-MS)被鉴定和量化。这些贻贝是从丹麦进口的,属于一批含有超过规定限量的高浓度软海绵酸。腹泻性贝类中毒(DSP)是由食用含有由浮游藻类(海洋甲藻)产生的生物毒素的贝类而引起的一种食源性疾病。它是一种没有神经症状的胃肠疾病。首次报告的病例出现在20世纪60年代的荷兰。自那时起,日本、欧洲、南美洲和远东地区都有爆发DSP的报道。DSP由一组聚醚类物质引起,包括软海绵酸(OA)、甲藻毒素(DTXs)、扇贝毒素(PTXs)和耶索毒素(YTXs)。在比利时和欧洲,DSP的记录案例很少,这可能是由于诊断不足和报告不足。这份报告描述了食用蓝色贻贝后发生的腹泻性贝类中毒爆发事件。调查是在几位全科医生(GPs)向传染病卫生检查部门(Gezondheidsinspectie)强制报告几例疑似食物中毒病例后开始的。
/SIGNS AND SYMPTOMS/ In Antwerp, Belgium, 403 cases of diarrheic shellfish poisoning were reported after consumption of blue mussels. Symptoms included diarrhea, vomiting, abdominal pain, and nausea. The analysis of fecal specimens from patients allowed diagnosis exclusions for bacteria and viruses. Mouse-assays revealed the presence of biotoxins specific of dinoflagellates, which were identified and quantified by LC-MS. The mussels were imported from Denmark, and were part of a batch presenting high concentrations of okadaic acid above the regulatory limits. Diarrheic shellfish poisoning (DSP) is a foodborne illness caused by the consumption of shellfish which contain biotoxins elaborated by planktonic algae (marine dinoflagellates). It is a gastrointestinal disease with no neurological symptoms. The first reported cases were in the Netherlands in the 1960s. Since then, outbreaks have been described in Japan, Europe, South America, and the Far East. DSP is caused by a group of polyethers, including okadaic acid (OA), dinophysis toxins (DTXs), pectenotoxins (PTXs), and yessotoxin (YTXs) . Well documented cases in Belgium and Europe are rare, and this may partly be due to underdiagnosis and underreporting. This report describes an outbreak of diarrhetic shellfish poisoning after the consumption of blue mussels. The investigation was begun after a mandatory notification of several cases of presumptive food poisoning by general practitioners (GPs) to the Health Inspections department of infectious diseases (Gezondheidsinspectie).
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
体征和症状/双壳类软体动物引起的腹泻型中毒,即腹泻型贝类中毒,是由于食用含有某些甲藻类生物毒素的贻贝所致。Yessotoxin(YTX)的毒性效应包括心脏和肝脏线粒体的形态改变...
/SIGNS AND SYMPTOMS/ The diarrhetic poisoning by bivalve molluscs, diarrhetic shellfish poisoning, is due to consumption of mussels containing biotoxins produced by some Dinoflagellate species. Toxic effects of yessotoxin (YTX) include morphological alterations of mitochondria from heart and liver ...
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
/替代性和体外测试/ 通过测量几种Yessotoxins(YTX)类似物在MCF-7乳腺癌细胞中引起E-cadherin 100 kDa分子量片段积累的能力,探讨了Yessotoxins(YTX)的结构-活性关系。在我们的实验条件下,YTX(参考化合物)的EC(50)为0.55 nM。在硫酸盐基团之一旁边引入一个亚甲基单位,如homoyessotoxin分子的情况,似乎并未显著影响类似物的活性,因为该化合物的测量EC(50)为0.62 nM。我们测量的45-羟基homoyessotoxin和carboxyyessotoxin的EC(50)值分别约为9.4和26 nM,而缺失大部分C(9)链的noroxoyessotoxin的EC(50)约为50 nM。因此,当结构变化涉及这些化合物的C(9)端链时,YTX类似物的活性显著不同,得出结论这一分子部分对YTX在MCF-7细胞中的活性至关重要。将我们的发现与关于YTX及其类似物在其他实验系统中的活性的现有信息进行比较,发现我们测量的不同化合物的EC(50)值低至200倍,且在更广泛的浓度范围内变化。/有人推测/ YTX的作用可能涉及两个独立的受体系统。
/ALTERNATIVE and IN VITRO TESTS/ The structure-activity relationship of yessotoxins (YTX) has been probed by measuring the potency of several YTX analogues to cause the accumulation of a 100 kDa MW fragment of E-cadherin in MCF-7 breast cancer cells. Under our experimental conditions, the EC(50) of YTX, the reference compound, was 0.55 nM. The introduction of a methylene unit adjacent to one of the sulfate groups, as is the case with the homoyessotoxin molecule, did not appear to greatly affect the potency of the analogue, as the measured EC(50) for this compound was 0.62 nM. The EC(50) values we measured for 45-hydroxyhomoyessotoxin and carboxyyessotoxin were about 9.4 and 26 nM, respectively, whereas the EC(50) of noroxoyessotoxin, lacking most of the C(9) chain, was about 50 nM. Thus, significant differences in the potencies of YTX analogues were found when structural changes involved the C(9) terminal chain of these compounds, leading to the conclusion that this portion of the molecule is essential for the activity of YTX in MCF-7 cells. A comparison of our findings with available information regarding the potency of YTX and its analogues in other experimental systems shows that the EC(50)'s we measured for the different compounds are up to 200-fold lower and vary in a wider concentration range. /It was speculated/ that YTX effects could involve two separate receptorial systems.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
替代和体外测试...将HeLa细胞中由yessotoxin (YTX)诱导的死亡反应与同一实验系统中由okadaic acid (OA)触发的死亡反应进行了比较。发现亚纳摩尔浓度的YTX在48-96小时孵化后能诱导HeLa细胞死亡。YTX导致HeLa细胞中完整的聚(ADP-核糖)聚合酶(PARP)丧失,并检测到85 kDa片段,这是由caspases蛋白酶攻击的标志。使用从YTX处理的细胞中提取的样本和caspase-3/7以及caspase-2亚型的底物来测量caspase活性,结果显示caspase-3/7底物的相对蛋白酶解活性是caspase-2的大约八倍,后者测得的水平是对照组细胞提取物的两倍。这些发现与使用HeLa细胞提取物对caspase-2、-3和-7进行西方印迹分析的结果相符,显示YTX处理对前caspase-2的水平没有太大影响,而前caspase-3和-7在YTX处理的细胞中被激活。总的来说,这些数据补充了之前使用OA获得的其他数据,并支持了OA和YTX诱导的细胞死亡中涉及的caspase亚型是细胞和毒素特异性的观点。
/ALTERNATIVE and IN VITRO TESTS/ .... the death response induced by yessotoxin (YTX) in cultured HeLa cells/was compared to/ that triggered by okadaic acid (OA) in the same experimental system. Sub-nanomolar concentrations of YTX were found to induce HeLa cell death after a 48-96-hr incubation. YTX caused loss of intact poly(ADP-ribose)-polymerase (PARP) in HeLa cells, and detection of the 85 kDa fragment, which is indicative of proteolytic attack by caspases. Measurements of caspase activities using extracts prepared from YTX-treated cells and substrates of the caspase-3/7 and caspase-2 isoforms, showed that the relative proteolysis of caspase-3/7 substrate was about eight-fold higher than that of caspase-2, the levels of which were about twice those measured with extracts from control cells. These findings were matched by Western blot analyses of caspase-2, -3 and -7 in HeLa cell extracts, which showed that the levels of pro-caspase-2 were not greatly affected by YTX treatment, whereas pro-caspase-3 and -7 were activated in YTX-treated cells. Taken together, these data complement others previously obtained with OA, and support the notion that caspase isoforms involved in cell death induced by OA and YTX are cell- and toxin-specific.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
四种毒素,分别是冈田酸(OA)、鳍藻毒素-1(DTX1)、扇贝毒素-6(PTX6)和亚苏毒素(YTX),它们都与腹泻性贝类中毒(DSP)有关,通过注射器给药给扇贝Patinopecten yessoensis,并使用液相色谱-质谱分析技术分析它们在肝胰腺、闭壳肌和混合其他组织(外套膜、鳃、性腺)中的分布。无论注射部位是闭壳肌还是肝胰腺,毒素都仅在肝胰腺中残留。当注射到肝胰腺时,OA、DTX1和YTX分别被代谢为7-O-棕榈酰OA、7-O-棕榈酰DTX1和45-羟基亚苏毒素(45OH-YTX)。当毒素注射到闭壳肌时,这种代谢变化不明显。每种毒素在肝胰腺中的残留比例不到20%。用PTX6处理的扇贝的死亡率低于用其他毒素处理的扇贝。
Four toxins, okadaic acid (OA), dinophysistoxin-1 (DTX1), pectenotoxin-6 (PTX6), and yessotoxin (YTX), all associated with diarrhetic shellfish poisoning (DSP), were administered via syringe to Scallops Patinopecten yessoensis and their distribution in the hepatopancreas, adductor muscle, and combined other tissues (mantle, gill, gonad) was analyzed by liquid chromatography-mass spectrometry. Toxins exclusively remained in the hepatopancreas irrespective of the injection site, adductor muscle or hepatopancreas. When injected into hepatopancreas, OA, DTX1, and YTX were metabolized to 7-O-palmitoylOA, 7-O-palmitoylDTX1 and 45-hydroxyyessotoxin (45OH-YTX), respectively. Such metabolic changes were insignificant when toxins were injected into the adductor muscle. The residual ratio for each toxin in the hepatopancreas was less than 20%. Mortalities of scallops treated with PTX6 were lower than those treated with other toxins.
来源:Hazardous Substances Data Bank (HSDB)

同类化合物

雪卡鱼毒素 同质毒素 1-甲基-5-(3-叠氮-2,3-二脱氧-2-氟-β-呋喃阿拉伯糖基)尿苷 (2R,2'R,3a'S,4a'R,5'S,6'S,6a'S,9'S,10'S,10a'R,11a'S,12a'R,13a'S,14a'R,15a'S,17'Z,19a'R,20a'S,22a'R,23a'S,24'R,24a'R,29a'S,30a'R,31a'S,32a'R,34a'S,35a'R,37'R,37a'S,38a'R)-26'-[(1E)-丁-1,3-二烯-1-基]-2',5',9',10',37a'-五甲基-1',3',3a',4,4a',5,5',6',6 Ciguatoxin-3 CTX3C Desulfo-yessotoxin Yessotoxin Ciguatoxin 3C (2S,3R,4aS,5aR,6aS,9aR,10aS,12aR,13aS,17aR,18aS,19aR,20aS,21aR,22aS,23aR)-2-(benzyloxy)-3-((benzyloxy)methyl)octacosahydro-1H-pyrano[2''',3''':5'',6'']pyrano[2'',3'':6',7']oxepino[2',3':5,6]pyrano[3,2-b]pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[2,3-g]oxocine Scaritoxin Gambiertoxin 4b (1S,3S,6R,8S,10R,12S,16S,18S,19R,20R,22S,25R,27R,29Z,32S,34R,36S,38S,40R,42S,43R,44S,45S,47S,48S,49S,50R,52S,54R,56R,58R,59R)-16-[(1Z)-buta-1,3-dienyl]-43,44,49,54,58-pentamethylspiro[2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxadodecacyclo[30.28.0.03,27.06,25.08,22.010,20.012,18.034,58.036,56.038,52.040,50.042,47]hexaconta-4,14,23,29-tetraene-45,2'-oxolane]-19,48,59-triol [(1R,3S,5R,6S,7S,8R,10S,11S,12S,13R,15S,17R,19R,21S,22R,24S)-6,7,12,17,21-pentamethyl-11-(naphthalen-2-ylmethoxy)-21-[(1R)-1-(naphthalen-2-ylmethoxy)but-3-enyl]spiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-22-yl]oxy-tri(propan-2-yl)silane [(1R,3S,5R,7S,9R,11S,13R,14R,16S,18R,22R,25S,27S,30S,31R,33R,34S,35R,37R,40S,42R,44S,46S,48R)-34-hydroxy-40-[(2S,3Z)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-(2-sulfooxyethyl)-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.03,25.05,22.07,20.09,18.011,16.031,48.033,46.035,44.037,42]nonatetracontan-14-yl] hydrogen sulfate [(1R,3S,4'S,5R,6S,7S,8R,10S,11S,12S,13R,15S,17R,19R,21S,22R,24S)-6,7,12,17,21-pentamethyl-4',11-bis(naphthalen-2-ylmethoxy)-21-[(1R)-1-(naphthalen-2-ylmethoxy)-3-phenylsulfanylpropyl]spiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-22-yl]oxy-tri(propan-2-yl)silane [(1R,3S,5R,7S,9R,11S,13R,14S,16R,18S,20R,22S,25R,27S,30S,31R,33S,34R,35R,37S,40S,42R,44S,46R,48S)-34-hydroxy-13-(2-hydroxyethyl)-40-[(2R,3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.03,25.05,22.07,20.09,18.011,16.031,48.033,46.035,44.037,42]nonatetracontan-14-yl] hydrogen sulfate [(1R,3S,5R,7S,9R,11S,13R,14S,16R,18S,20R,22S,25R,27S,30S,31R,33S,34R,35R,37S,40S,42R,44S,46R,48S)-34-hydroxy-40-[(2R,3E)-2-hydroxyhexa-3,5-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-(2-sulfooxyethyl)-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.03,25.05,22.07,20.09,18.011,16.031,48.033,46.035,44.037,42]nonatetracontan-14-yl] hydrogen sulfate (E,2R,5R)-5-hydroxy-5-[(1R,3S,5R,7S,9R,11S,13R,14S,16R,18S,20R,22S,25R,27S,30S,31R,33S,34R,35R,37S,40S,42R,44S,46R,48S)-34-hydroxy-13,25,27,30,35-pentamethyl-39-methylidene-14-sulfooxy-13-(2-sulfooxyethyl)-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.03,25.05,22.07,20.09,18.011,16.031,48.033,46.035,44.037,42]nonatetracontan-40-yl]-2-prop-2-enylhex-3-enoic acid [(1R,3S,4'S,5R,6S,7S,8R,10S,11S,12S,13R,15S,17R,19R,21S,22R,24S)-6,7,12,17,21-pentamethyl-4',11-bis(naphthalen-2-ylmethoxy)-22-tri(propan-2-yl)silyloxyspiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-21-yl]methanol (1R)-1-[(1R,3S,4'S,5R,6S,7S,8R,10S,11S,12S,13R,15S,17R,19R,21S,22R,24S)-6,7,12,17,21-pentamethyl-4',11-bis(naphthalen-2-ylmethoxy)-22-tri(propan-2-yl)silyloxyspiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-21-yl]but-3-en-1-ol tert-butyl-[[(1R,3S,4'S,5R,6S,7S,8R,10S,11S,12S,13R,15S,17R,19R,21S,22R,24S)-3-methoxy-6,7,12,17,21-pentamethyl-4',11-bis(naphthalen-2-ylmethoxy)-22-tri(propan-2-yl)silyloxyspiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-21-yl]methoxy]-diphenylsilane [(1R,3S,4'S,5R,6S,7S,8R,10S,11S,12S,13R,15S,17R,19R,21S,22R,24S)-6,7,12,17,21-pentamethyl-4',11-bis(naphthalen-2-ylmethoxy)-21-[(1R)-1-(naphthalen-2-ylmethoxy)but-3-enyl]spiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-22-yl]oxy-tri(propan-2-yl)silane [(3R)-3-[(1R,3S,4'S,5R,6S,7S,8R,10R,11S,12R,13R,15S,19R,21S,22R,24S)-4',22-dibenzoyloxy-6,7,12,21-tetramethyl-17-oxo-11-tri(propan-2-yl)silyloxyspiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-21-yl]-3-hydroxypropyl] benzoate (1R,3S,5R,6S,7S,8R,10S,11S,12S,13R,15S,17R,19R,21S,22R,24S)-21-[(1R)-1-hydroxybut-3-enyl]-6,7,12,17,21-pentamethyl-22-tri(propan-2-yl)silyloxyspiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-11-ol {34-hydroxy-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulfooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0^{3,25}.0^{5,22}.0^{7,20}.0^{9,18}.0^{11,16}.0^{31,48}.0^{33,46}.0^{35,44}.0^{37,42}]nonatetracontan-14-yl}oxidanesulfonic acid 45-Hydroxyyessotoxin Pacific Ciguatoxin 3 Pacific Ciguatoxin 4A [34-hydroxy-13-(2-hydroxyethyl)-40-[(3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.03,25.05,22.07,20.09,18.011,16.031,48.033,46.035,44.037,42]nonatetracontan-14-yl] hydrogen sulfate 3-De(2-(sulfooxy)ethyl)-3-(3-(sulfooxy)propyl)-Yessotoxin 3-Hydroxy-7-oxociguatoxin 54-Deoxy-50-hydroxyciguatoxin 52-Epiciguatoxin 4-Hydroxy-7-oxociguatoxin 7-Oxociguatoxin M-Secociguatoxin 4A (E)-5-hydroxy-5-[34-hydroxy-13,25,27,30,35-pentamethyl-39-methylidene-14-sulfooxy-13-(3-sulfooxypropyl)-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.03,25.05,22.07,20.09,18.011,16.031,48.033,46.035,44.037,42]nonatetracontan-40-yl]-2-prop-2-enylhex-3-enoic acid (1R,3S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,29Z,32S,34R,36S,38R,40S,42R,43S,44S,45S,47S,48S,49S,50R,52S,54R,56R,58S,59R)-16-[(1E)-buta-1,3-dienyl]-43,44,49,54,58-pentamethylspiro[2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxadodecacyclo[30.28.0.03,27.06,25.08,22.010,20.012,18.034,58.036,56.038,52.040,50.042,47]hexaconta-4,14,23,29-tetraene-45,2'-oxolane]-19,48,59-triol (1R,3S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,29E,32S,34R,36S,38R,40S,42R,43S,44S,45R,47S,48S,49S,50R,52S,54R,56R,58S,59R)-16-[(E,3S)-3,4-dihydroxybut-1-enyl]-43,44,49,54,58-pentamethylspiro[2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxadodecacyclo[30.28.0.03,27.06,25.08,22.010,20.012,18.034,58.036,56.038,52.040,50.042,47]hexaconta-4,14,23,29-tetraene-45,2'-oxolane]-19,48,59-triol (1R,3S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,29E,32S,34R,36S,38R,40S,42R,43S,44S,45S,47S,48S,49S,50R,52S,54R,56R,58S,59R)-16-[(E,3S)-3,4-dihydroxybut-1-enyl]-43,44,49,54,58-pentamethylspiro[2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxadodecacyclo[30.28.0.03,27.06,25.08,22.010,20.012,18.034,58.036,56.038,52.040,50.042,47]hexaconta-4,14,23,29-tetraene-45,2'-oxolane]-19,48,59-triol (1R,3S,5R,6S,7S,10S,11S,12S,13R,15S,17R,19R,21S,22R,24S)-21-ethenyl-6,7,12,17,21-pentamethyl-22-tri(propan-2-yl)silyloxyspiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-11-ol [(1R,3S,5R,7S,9R,11S,13R,14S,16R,18S,20R,22S,25R,27S,30S,31R,33S,35R,37S,40S,42R,44S,46R,48S)-40-[(2R,3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-(2-sulfonatooxyethyl)-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.03,25.05,22.07,20.09,18.011,16.031,48.033,46.035,44.037,42]nonatetracontan-14-yl] sulfate (1R,3S,3'S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,31R,33R,35S,37R,39S,41R,42S,43S,46S,47S,48S,49R,51S,53R,55R,57S,58R)-16-[(3S)-3,4-dihydroxybut-1-enyl]-42,43,48,53,57-pentamethylspiro[2,7,11,17,21,26,32,36,40,45,50,56-dodecaoxadodecacyclo[29.28.0.03,27.06,25.08,22.010,20.012,18.033,57.035,55.037,51.039,49.041,46]nonapentaconta-4,14,23,29-tetraene-44,5'-oxolane]-3',19,47,58-tetrol (1R,3S,3'S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,32S,34R,36S,38R,40S,42R,43S,44S,47S,49S,50R,52S,54R,56R,58S,59R)-16-[(3S)-3,4-dihydroxybut-1-enyl]-43,44,49,54,58-pentamethylspiro[2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxadodecacyclo[30.28.0.03,27.06,25.08,22.010,20.012,18.034,58.036,56.038,52.040,50.042,47]hexaconta-4,14,23,29-tetraene-45,5'-oxolane]-3',19,48,59-tetrol (3R)-3-[(1R,3S,5R,6S,7S,10S,11S,12S,13R,15S,17R,19R,21S,22R,24S)-6,7,11,12,17,21-hexamethyl-22-tri(propan-2-yl)silyloxyspiro[4,9,14,20,25-pentaoxapentacyclo[13.10.0.03,13.05,10.019,24]pentacosane-8,2'-oxolane]-21-yl]butanal (1R,3S,3'S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,32S,34R,36S,38R,40S,42R,43S,44S,47S,48S,49S,50R,52S,54R,56R,58S,59R)-16-[(3S)-3,4-dihydroxybut-1-enyl]-43,44,49,54,58-pentamethylspiro[2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxadodecacyclo[30.28.0.03,27.06,25.08,22.010,20.012,18.034,58.036,56.038,52.040,50.042,47]hexaconta-4,14,23,29-tetraene-45,5'-oxolane]-3',19,48,59-tetrol (1R,3S,3'S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,32S,34R,36S,38R,40S,42R,43S,44S,45R,47S,49S,50R,52S,54R,56R,58S,59R)-43,44,49,54,58-pentamethyl-16-[2-(2-naphthalen-2-yl-1,3-dioxolan-4-yl)ethenyl]spiro[2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxadodecacyclo[30.28.0.03,27.06,25.08,22.010,20.012,18.034,58.036,56.038,52.040,50.042,47]hexaconta-4,14,23,29-tetraene-45,5'-oxolane]-3',19,48,59-tetrol ciguatoxin (1R,3S,7R,9S,11R,13S,19R,20R,21S,23R,26S,28R,32S,34R,36S,38R,40S,42R,43S,44S,47S,48S,49S,50R,52S,54R,56R,58S,59R)-43,44,49,54,58-pentamethylspiro[2,8,12,18,22,27,33,37,41,46,51,57-dodecaoxadodecacyclo[30.28.0.03,28.07,26.09,23.011,21.013,19.034,58.036,56.038,52.040,50.042,47]hexaconta-4,15,24,30-tetraene-45,2'-oxolane]-20,48,59-triol