Filamentous Fungi-Derived Orsellinic Acid-Sesquiterpene Meroterpenoids: Fungal Sources, Chemical Structures, Bioactivities, and Biosynthesis

Hua Gao; Luning Zhou; Peng Zhang; Ying Wang; Xuan Qian; Yujia Liu; Guangwei Wu

doi:10.1055/a-2099-4932

Planta Medica, Table of Contents

Planta Med 2023; 89(12): 1110-1124
DOI: 10.1055/a-2099-4932

Biological and Pharmacological Activity

Reviews

Filamentous Fungi-Derived Orsellinic Acid-Sesquiterpene Meroterpenoids: Fungal Sources, Chemical Structures, Bioactivities, and Biosynthesis

Authors

Hua Gao‡

¹College of Chemical Engineering, Nanjing Forestry University, Nanjing, Peopleʼs Republic of China
Luning Zhou‡

²Key Laboratory of Marine Drugs, Chinese Ministry of Education; School of Medicine and Pharmacy, Ocean University of China, Qingdao, Shandong, Peopleʼs Republic of China
Peng Zhang

³Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah, United States
Ying Wang

¹College of Chemical Engineering, Nanjing Forestry University, Nanjing, Peopleʼs Republic of China
Xuan Qian

¹College of Chemical Engineering, Nanjing Forestry University, Nanjing, Peopleʼs Republic of China
Yujia Liu

¹College of Chemical Engineering, Nanjing Forestry University, Nanjing, Peopleʼs Republic of China
Guangwei Wu

¹College of Chemical Engineering, Nanjing Forestry University, Nanjing, Peopleʼs Republic of China

Abstract

Fungi-derived polyketide-terpenoid hybrids are important meroterpenoid natural products that possess diverse structure scaffolds with a broad spectrum of bioactivities. Herein, we focus on an ever-increasing group of meroterpenoids, orsellinic acid-sesquiterpene hybrids comprised of biosynthetic start unit orsellinic acid coupling to a farnesyl group or/and its modified cyclic products. The review entails the search of China National Knowledge Infrastructure (CNKI), Web of Science, Science Direct, Google Scholar, and PubMed databases up to June 2022. The key terms include “orsellinic acid”, “sesquiterpene”, “ascochlorin”, “ascofuranone”, and “Ascochyta viciae”, which are combined with the structures of “ascochlorin” and “ascofuranone” drawn by the Reaxys and Scifinder databases. In our search, these orsellinic acid-sesquiterpene hybrids are mainly produced by filamentous fungi. Ascochlorin was the first compound reported in 1968 and isolated from filamentous fungus Ascochyta viciae (synonym: Acremonium egyptiacum; Acremonium sclerotigenum); to date, 71 molecules are discovered from various filamentous fungi inhabiting in a variety of ecological niches. As typical representatives of the hybrid molecules, the biosynthetic pathway of ascofuranone and ascochlorin are discussed. The group of meroterpenoid hybrids exhibits a broad arrange of bioactivities, as highlighted by targeting hDHODH (human dihydroorotate dehydrogenase) inhibition, antitrypanosomal, and antimicrobial activities. This review summarizes the findings related to the structures, fungal sources, bioactivities, and their biosynthesis from 1968 to June 2022.

Key words

filamentous fungi - orsellinic acid - ascochlorin - antitumor - hDHODH - biosynthesis

Full Text

References

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