河北医科大学：《天然药物化学》课程教学资源（课件讲稿）第十章 海洋天然产物化学（海洋药物 Purpose and Aim，2020版）概述

天然药物化学 这些天然产物的共同特点？天然产物有哪些类型？ MeO OH e OH OH 4 Borneol I Quinine HO 2 Tanshinoe IlA 3 Galantamine OH OH 6 Sucrose 5 Menthol AcO 7 Parthenolide Ph NH Glc-O H OH OH HO H Glc HO OBz OAc 8 Ginsenoside Rg3 10 Taxol 9 Digitoxigenin HO HO H CHa HO H3C〈 o-o 14 Esculetin 0> H CH CH3 HO OH O 11 Camptothecin 12 Morphine 13 Daidzein 15 Artemisinin

这些天然产物的共同特点？ 天然产物有哪些类型？ O O O O H CH3 H CH3 O H H3C 15 Artemisinin O N MeO Me HO H 3 Galantamine HO AcO OBz H OAc OH O O O OH Ph NH O O HO O HO N H CH3 N N H H HO H3CO H 1 Quinine 12 Morphine 10 Taxol N N O O O 11 Camptothecin O O OH HO 13 Daidzein HO O O HO 14 Esculetin HO OH H O O 9 Digitoxigenin H Glc-O H H H 8 Ginsenoside Rg3 H OH OH Glc O O O 2 Tanshinoe IIA O O OH OH OH OH OHOH OH O 6 Sucrose OH 4 Borneol OH 5 Menthol 7 Parthenolide O O O OH

Life Originated from the Ocean 地球？ 水球？ 地：土也 Marine Biodiversity? A treasure troveof biochemical compounds?

Life Originated from the Ocean A treasure troveof biochemical compounds? Marine Biodiversity？ 地球？ 地：土 也 水球？

Marine Natural Medicine MINM What are they? Why do we care MNM? What/How do we study?

What in Sea?Will next anti-cancer drug come from Ocean? High Biodiversity High Chemical Diversity

High Biodiversity = High Chemical Diversity What in Sea? Will next anti-cancer drug come from Ocean?

海洋中天然产物的类型？特点？活性？ OAc Ac0、IH CO2H 0 H'H H HO HO OAC OH HH H HO OH OH ONa ONa 0=S=00H HO H H HOH OH O、 OH OH H H 9 OH H H H HO OH HO OH HO OH

O Br Cl Br HO O O O O O O O O O O O O O O OH O O O OH O O O O HO OH O OH S O O ONa HO OH OH OHOH OH O S O ONa HO OH O H H H H H H H HO H H H H H H H H O OH H H H H H H OH H OH HO OH H H OH H H OH OH H H HO H H H H H O O O O O O O H OH H H H H H H H H HO H A O O O O HO OH H H H H H H O O O HO OH H H O O Br H H O H OH OH H H HO H OH O O HO OH OH CO2H O H H HO N O H N O N O N O HN O S N H O H H H Br H OAc AcO OAc OH H H O I

海洋药物 Purpose and Aim 1了解开展海洋药物研究的现状和意义； 2知道海洋药物研究的主要对象；主要化合物类型； 3掌握大环内酯类的结构特点、分类，了解其生物活性； 4掌握聚醚类化合物的结构特点、分类，了解其生物活性； 5了解肽类的结构特点、分类和生物活性； 6 掌握前列腺素类化合物结构特点；了解其生物活性； 7 了解C15乙酸原类化合物的结构特点；

1 了解开展海洋药物研究的现状和意义； 2 知道海洋药物研究的主要对象; 主要化合物类型； 3 掌握大环内酯类的结构特点、分类，了解其生物活性； 4 掌握聚醚类化合物的结构特点、分类，了解其生物活性； 5 了解肽类的结构特点、分类和生物活性； 6 掌握前列腺素类化合物结构特点；了解其生物活性； 7 了解C15乙酸原类化合物的结构特点；

海洋药物 海洋天然产物化学研究的历史和现状 1.概述 海洋天然产物化学研究的对像 学科发展史？ 研究海洋天然产物化学的意义 大环内酯类化合物 开发的海洋药物？ 聚醚类化合物 肽类化合物 探索生命科学的工具？ 2.海洋天然产物主要的结构类型 前列腺素类化合物 C15乙酸原类化合物 生物碱类化合物 生物碱及其它类化合物 甾体类化合物 萜类化合物 3.海洋天然产物主要的生物活性 抗癌、海洋毒素

研究海洋天然产物化学的意义 1. 概述 海洋天然产物化学研究的历史和现状 2. 海洋天然产物主要的结构类型 大环内酯类化合物 聚醚类化合物 肽类化合物 前列腺素类化合物 C15乙酸原类化合物 生物碱及其它类化合物 海洋天然产物化学研究的对象 萜类化合物 生物碱类化合物 甾体类化合物 3. 海洋天然产物主要的生物活性 抗癌、海洋毒素

Marine Drugs Approved by the FDA or EMEA Anti-cancer Brentuximab vedotin As H2N rabine Eribul Me ylate HO C-K-G-K OH Q A-G D.Y K K03S0 0% 0S03K NH2 G-S-C OH KGS-R arrageenan HO H OH Neuropathic pain C-S-R-L-M Ziconotide Antivirus OH H Cytarabine mega-3-acidthyer Hyerrigyceride

Marine Drugs Approved by the FDA or EMEA

D.John Faulkner.Highlights of Marine Natural Products Chemistry (1972-1999).Nat.Prod.Rep.,2000,17,1-6. MILLENNIUM REVIEW Highlights of marine natural products chemistry (1972-1999) D.John Faulkner Scripps Institution of Oceanography.University of Califormia at San Diego,La Jolla,CA 92093-0212.USA Received(in Cambridge)12th November 1999 in structural elucidation.-10 Unfortunately,the tremendous Covering:1972-1999 impact of the palytoxin and maitotoxin studies had the effect of making studies of smaller toxic molecules seem less challeng- ing.which is far from the truth.The increasing frequency of 1 Highlights of marine natural products chemistry toxic algal blooms and the associated shellfish contamination (1972-1999) ensures that studies of marine toxins will continue to be of Marine Natural Products Chemistry is essentially a child of the importance well into the next century and probably for as long 1970's that developed rapidly during the 1980's and matured in as human consumption of seafood continues the last decade.With a few notable exceptions,it is difficult to Research on bioactive compounds from marine organisms select individual papers that significantly impacted the field. has provided the bread and butter support of marine natural However,marine natural products chemistry has often influ- products research throughout the past quarter century.Although enced other fields and that aspect is the focus of this review.It none of the discoveries has yet led to a pharmaceutical product. is clear that the early directions taken by marine natural there is hope that one or more of the many marine natural products chemists drew as much from the examples provided by products currently under investigation will eventually do so.11 insect chemical ecology as from the longer history of phy- Since the current status of marine biomedical research has been tochemistry.By 1975 there were already three parallel tracks in a popular subject for many recent reviews,12 just a few marine natural products chemistry:marine toxins,marine examples will be highlighted here.Among the anticancer comnounde mrentltt nnder investination hitoctatin 1 5 cenes

D. John Faulkner. Highlights of Marine Natural Products Chemistry (1972–1999). Nat. Prod. Rep., 2000, 17, 1-6

1216 J.Nat.Prod..2004,67,1216-1238 Marine Natural Products and Related Compounds in Clinical and Advanced Preclinical Trials' Chief at Natural Products Branch,National Cancer Institute David J.Newman*and Gordon M.Cragg Natural Products Branch.Developmental Therapeutics Program.NCI-Frederick,P.O.Box B.Frederick,Maryland 21702 Received February 10.2004 The marine environment has proven to be a very rich source of extremely pote demonstrated significant activities in antitumor,antiinflammatory,analgesia.im and anti-viral assays.Although the case can and has been made that the nucle Ara-C are derived from knowledge gained from investigations of bioactive mar directly from marine sources (whether isolated or by total synthesis)has yet m sector in any disease.However,as shown in this review,there are now sign interesting molecules that have come from marine sources,or have been sy knowledge gained from a prototypical compound,that are either in or approac trials in cancer,analgesia,allergy,and cognitive diseases.A substantial number are following in their wake in preclinical trials in these and in other diseases Newman D.J. H2N

Newman D. J. Chief at Natural Products Branch, National Cancer Institute