Pericolactines A–C, a New Class of Diterpenoid Alkaloids with Unusual Tetracyclic Skeleton

Abstract

Fusicoccane diterpenoids usually possess a fused 5-8-5 tricyclic ring system, which are biogenetically generated from geranylgeranyl diphosphate (GGDP). In our report, three novel diterpenoid alkaloids with fusicoccane skeleton, pericolactines A–C (1–3), were isolated from Periconia sp.. Their structures with absolute configurations were determined by spectroscopic analyses and quantum chemical ECD calculation. Pericolactines A–C (1–3) are a new class of diterpenoid alkaloids with an unusual fused 5-5-8-5 tetracyclic ring system, which derive from a geranylgeranyl diphosphate (GGDP) and serine conjugated biosynthesis. They belong to the atypical diterpenoid alkaloids.

Periconiastone A, an Antibacterial Ergosterol with a Pentacyclo[8.7.0.01,5.02,14.010,15]heptadecane System from Periconia sp. TJ403-rc01

“…TJ403-rc01, a fungus isolated from the leaves of Rosa chinensis Jacq., came into our sight. Previous chemical investigations on fungi of this genus demonstrated the presence of diterpenoids, sesquiterpenoids, diterpenoid alkaloids, meroterpenoids, cytochalasans, etc., with wide-ranging applications such as antibacterial, anti-inflammatory, antitumor, and anti-HIV agents. Inspired by the complex chemical architectures and promising bioactivities of secondary metabolites produced by species of Periconia fungi, we performed a systematic investigation on the secondary metabolites of the title fungus, which led to the isolation of periconiastone A ( 1 ), an architecturally intricate ergosterol with an unprecedented pentacyclo­[8.7.0.0 1,5 .0 2,14 .0 10,15 ]­heptadecane system.…”

Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

“…A new class of fusicoccane-type diterpenoid alkaloids with an unusual 5/5/8/5 tetracyclic system, i.e., pericolactines A–C 81 – 83 , have been isolated from Periconia sp. [ 108 ].…”

Natural Products Research in China From 2015 to 2016

“…Sibirolide A ( 566 ) was the first example of a 3/5/6/5 tetracyclic eudesmane sesquiterpene lactone formed at C-6 and C-7, and norxanthantolide B ( 567 ) was the first example of the naturally-occuring xanthane tetranorsesquiterpene, while norxanthantolides C–F ( 568 - 571 ) were the first xanthane trinorsesquiterpenes to date (Shi et al, 2015 ). Six novel Diels-Alder adducts of a polymethylated phloroglucinol derivative with myrcene, calliviminones C–H ( 572 – 577 ), were produced by fruits of Callistemon viminalis (Guangdong, China) (Wu et al, 2015f ). A pair of coumarin enantiomers ((±)- 578 ) with a rare polycyclic pyrano[3-2c] skeleton were isolated from the whole plants of Ainsliaea fragrans (Shiyany, Hubei, China) (Xue et al, 2015 ).…”