Total Synthesis of Isohericerinol A and Its Analogues to Access Their Potential Neurotrophic Effects

  • Vishwanath, Manjunatha; 
  • Chaudhary, Chhabi Lal; 
  • Park, Yunjeong; 
  • Viji, Mayavan; 
  • Jung, Chanhyun; 
  • ... Kim, Sun Yeou; 
  • 외 9명
Citations

WEB OF SCIENCE

3
Citations

SCOPUS

3

초록

The secondary metabolites from Hericium erinaceus are well-known to have neurotrophic and neuroprotective effects. Isohericerinol A (1), isolated by our colleagues from its fruiting parts has a strong ability to increase the nerve growth factor secretion in C6 glioma cells. The current work describes the total synthesis of 1 and its regioisomer 5 in a few steps. We present two different approaches to 1 and a regiodivergent approach for both 1 and 5 by utilizing easily accessible feedstocks. Interestingly, the natural product 1, regioisomer 5, and their intermediates exhibited potent neurotrophic activity in in vitro experimental systems. Thus, these synthetic strategies provide access to a systematic structure-activity relationship study of natural product 1.

키워드

LIONS MANE MUSHROOM; HERICIUM-ERINACEUS; FRUITING BODIES; MEDICINAL MUSHROOMS; AROMATIC-COMPOUNDS; NERVE GROWTH; C-H; HERICENONES; MYCELIA; METABOLITES
제목
Total Synthesis of Isohericerinol A and Its Analogues to Access Their Potential Neurotrophic Effects
저자
Vishwanath, Manjunatha; Chaudhary, Chhabi Lal; Park, Yunjeong; Viji, Mayavan; Jung, Chanhyun; Lee, Kwanghee; Sim, Jaeuk; Hong, Seong Min; Yoon, Da Hye; Lee, Dae Hee; Lee, Jae Kang; Lee, Heesoon; Lee, Mi Kyeong; Kim, Sun Yeou; Jung, Jae-Kyung
DOI
10.1021/acs.joc.2c01096
발행일
2022-08
유형
Article
저널명
The Journal of Organic Chemistry
권
87
호
16
페이지
10836 ~ 10847