Discovery of New Bohemamines and Synthesis of Methylene-Bridged Chimeric Derivatives through Natural Product Chimera Strategy

被引：5
|
作者：
Zhang, Rongxin [1 ]
Yan, Xiaotang [1 ]
Yin, Shupeng [1 ]
Wang, Weihong [1 ]
Zhu, Weiming [1 ,2 ]
Fu, Peng [1 ,2 ]
机构：
[1] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Minist Educ China, Qingdao 266003, Shandong, Peoples R China
[2] Pilot Natl Lab Marine Sci & Technol Qingdao, Lab Marine Drugs & Bioprod, Qingdao 266237, Shandong, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2022年 / 40卷 / 12期
基金：
中国国家自然科学基金;
关键词：
Natural products; Structure elucidation; Dimerization; Pyrrolizidine alkaloids; Biological activity; PYRROLIZIDINE ALKALOIDS; STREPTOMYCES SP; JENAMIDINE-A; PHENYLACETALDEHYDE; ACTIVATION; ASSAY;
D O I：
10.1002/cjoc.202200034
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Comprehensive Summary Five new pyrrolizidine alkaloids, bohemamines J-N (1-5), were isolated from Streptomyces sp. CPCC 200497. Their structures were assigned based on detailed spectroscopic analysis and semisynthesis. Bohemamine J (1) possesses a new chimeric skeleton derived from bohemamine A (6) and phenylacetaldehyde. Inspired by the nonenzymatic formation mechanism of the methylene-bridged dimers isolated from this strain, we synthesized a series of chimeric derivatives (8, 9, and 12-23) through natural product chimera strategy. Compounds 13, 15, 19, and 21 showed significant antioxidant activity.
引用
收藏
页码：1413 / 1421
页数：9
相关论文
共 35 条
  • [21] NEW STRATEGY FOR SYNTHESIS OF THE DISACCHARIDE MOIETY OF THE HIGHLY POTENT ANTICANCER NATURAL PRODUCT OSW-1
    Kongkathip, Boonsong
    Kongkathip, Ngampong
    Rujirawanich, Janjira
    SYNTHETIC COMMUNICATIONS, 2014, 44 (15) : 2248 - 2255
  • [22] Synthesis of New Monoarylidenes Derivatives of Limona-ketone: Natural Product Isolated from Cedrus atlantica Oil
    Lahcen Intissar, Ait
    Saadia, Oubaassine
    Brahim, Boualy
    Soufiane, El Houssame
    Larbi, El Firdoussi
    Abdallah, Karim
    LETTERS IN ORGANIC CHEMISTRY, 2018, 15 (08) : 698 - 704
  • [23] SYNTHESIS OF BIOACTIVE COMPOUNDS FROM ABUNDANT NATURAL PRODUCT .13. THE SYNTHESIS AND ANALGESIC PROPERTIES OF NEW SPIROISOCHROMANYL ACID-DERIVATIVES SYNTHESIZED FROM NATURAL SAFROLE
    CABRAL, LM
    BARREIRO, EJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (03) : 959 - 962
  • [24] New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium
    Feng Jun-Tao
    Wang De-Long
    Wu Yong-Ling
    Yan He
    Zhang Xing
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (15) : 4393 - 4397
  • [25] Solid-phase parallel synthesis of natural product-like diaza-bridged heterocycles through Pictet-Spengler intramolecular cyclization
    Lee, SC
    Park, SB
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (01): : 50 - 57
  • [26] Diversity-Oriented Synthesis of Natural-Product-like Libraries Containing a 3-Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors
    He, Xingrui
    Chen, Xia
    Lin, Songbo
    Mo, Xiaochang
    Zhou, Pengyong
    Zhang, Zhihao
    Lu, Yaoyao
    Yang, Yu
    Gu, Haining
    Shang, Zhicai
    Lou, Yonggen
    Wu, Jun
    CHEMISTRYOPEN, 2017, 6 (01): : 102 - 111
  • [27] Studies on Synthesis and Structure-Activity Relationship (SAR) of Derivatives of a New Natural Product from Marine Fungi as Inhibitors of Influenza Virus Neuraminidase
    Li, Jing
    Zhang, Dingmei
    Zhu, Xun
    He, Zhenjian
    Liu, Shu
    Li, Mengfeng
    Pang, Jiyan
    Lin, Yongcheng
    MARINE DRUGS, 2011, 9 (10): : 1887 - 1901
  • [28] New Tricks for an Old Natural Product: Discovery of Highly Potent Evodiamine Derivatives as Novel Antitumor Agents by Systemic Structure-Activity Relationship Analysis and Biological Evaluations
    Dong, Guoqiang
    Wang, Shengzheng
    Miao, Zhenyuan
    Yao, Jianzhong
    Zhang, Yongqiang
    Guo, Zizhao
    Zhang, Wannian
    Sheng, Chunquan
    JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (17) : 7593 - 7613
  • [29] Diverted organic synthesis (DOS): accessing a new, natural product inspired, neurotrophically active scaffold through an intramolecular Pauson-Khand reaction
    Mehta, Goverdhan
    Samineni, Ramesh
    Srihari, Pabbaraja
    Reddy, R. Gajendra
    Chakravarty, Sumana
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (34) : 6830 - 6833
  • [30] A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates:: Total synthesis of a highly potent antitumor natural product OSW-1
    Yu, WS
    Jin, ZD
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (14) : 3369 - 3370
1234