河北医科大学药学院 加强海洋环保 加强海洋环保 Anti-fouling Activity ·天然除垢剂仙（氰类） 白从1明5年目本F■setani所完小组从毒第Am 动 多个污损天然产物。化合物别 源于海洋无脊椎动物的抗污损天然产物 Marine Toxins and Sea Food Safety 记花表失性贝Amnesic Shellish Poiso 其它海洋争素cel山 us Marine Tovins) Ciguatera Fish Poisoning 4.促进有机化学发展 e2a 茶 天然药化教研室史清文教授 6 河北医科大学药学院 天然药化教研室史清文教授 6 • 自从1995年日本Fusetani 研究小组从海绵Acanthella cavernosa 首次分离获得具有抗藤壶幼虫附着的异氰基萜类 化合物开始，世界范围各课题组已从海绵、珊瑚等海洋无脊 椎动物中分离获得共90 多个抗污损天然产物。化合物类别主 要有异氰基萜类、甾体、二萜、溴代环肽以及吲哚生物碱。 • It is estimated that governments and industry spend over US $6.5 billion annually to prevent and control marine biofouling 加强海洋环保 Anti-fouling Activity 加强海洋环保 • 天然除垢剂 Isocyanoterpenoids (异氰基萜类） H H NHCHO O Cl Kalihinene X H H NHCHO H H NC H H NHCHO O O Cl Cl Kalihipyran O NHCHO 15-formamidoKalihinene HO NC 10b-formamidoKalihinol All of them, isolated from sponge, inhibited the larval settlement and metamorphosis at concentrations less than 0.1 µg/mL. Anti-fouling Activity 1991-1995 Fusetani Antifouling Project 源于海洋无脊椎动物的抗污损天然产物 H H NHCHO O Cl O O H O OAc H Cl O O OH H AcO AcO AcO AcO O C4H9OCO O O O O CO2CH3 N H HN NH O O HN NH2 NH Br HN Br CN Marine Toxins and Sea Food Safety 河豚毒素 (Puffer Fish Poisoning) 麻痹性贝毒素 (Paralytic Shellfish Poisoning) 腹泻性贝毒素 (Diarrheic Shellfish Poisoning) 肝脏毒贝毒素 (Hepatotoxic Shellfish Poisoning) 神经性贝毒素 (Neurotoxic Shellfish Poisoning) 记忆丧失性贝毒素 (Amnesic Shellfish Poisoning) 西加毒素 (Ciguatoxin) 其它海洋毒素 (Miscellaneous Marine Toxins) 结构：聚醚,生物碱(石房蛤毒素),肽类(芋螺毒素),氨基酸(软骨藻草酸) Ciguatera Fish Poisoning • The most commonly reported marine toxin disease in the world. – Associated with consumption of contaminated reef fish. • 50,000 people per year. – Debilitating neurologic symptoms, including profound weakness, temperature sensation changes, pain, and numbness in the extremities. • Onset: <6 hours • Symptoms: – Gastrointestinal: nausea, vomiting, diarrhea – Neurological: numbness and tingling around mouth, joint pain, muscle ache, headache, temperature sensory reversal – Cardiovascular: arrhythmia, bradycardia, tachycardia, reduced blood pressure O O O O O O O O O O O O O H H H H H HO H H H H OH H OH H H H H H H H H H H OH HO OH 4. 促进有机化学发展 NMR/MS Techniques The architecturally complex molecules provide the driving force for the development of new synthetic strategies/new reactions