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J Nat Prod. 2015 Nov 25;78(11):2572-9. doi: 10.1021/acs.jnatprod.5b00508. Epub 2015 Oct 30.

Spiroindole Alkaloids and Spiroditerpenoids from Aspergillus duricaulis and Their Potential Neuroprotective Effects.

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Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University , Seoul 02841, Republic of Korea.
Laboratory of Pharmacognosy, College of Pharmacy, Dankook University , Cheonan 31116, Republic of Korea.
College of Pharmacy, Ewha Womans University , Seoul 03760, Republic of Korea.
Tianjin Key Laboratory of Molecular Drug Research, College of Pharmacy, Nankai University , Tianjin 300071, People's Republic of China.
Korean Agricultural Culture Collection, National Academy of Agricultural Science , Wanju 55365, Republic of Korea.


Six new spiroindole alkaloids (1-6) and two new spiroditerpenoids (7 and 8) were isolated from an EtOAc extract of Aspergillus duricaulis culture media together with five known compounds. The structures of the isolated compounds were elucidated by analysis of NMR and MS data, and the absolute configurations of compounds 1-8 were confirmed by CD spectroscopic methods. All isolated compounds were evaluated for their inhibition of beta-amyloid (Aβ) aggregate-induced toxicity in PC12 cells and Aβ aggregation. Compounds 8-11 efficiently protected PC12 cells against Aβ aggregate-induced toxicity, but only compound 9 inhibited Aβ aggregation. On the other hand, compounds 4 and 5 exhibited moderate inhibitory effects on Aβ aggregation, but did not protect the cells from Aβ aggregate-induced toxicity. Preincubating Aβ monomers with compounds 4 and 5 rescued PC12 cells against Aβ aggregate-induced toxicity by reducing neurotoxic Aβ aggregates. Compound 9 inhibited both Aβ aggregate-induced toxicity and Aβ aggregation.

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