Chemistry

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(CNN) -- Chemists used to use balls and sticks to make models to help them understand how molecules worked.

(+)-Lingzhiol and (−)-lingzhiol, a pair of rotary door-shaped meroterpenoidal enantiomers, were isolated from Ganoderma lucidum. Their structures were identified by spectroscopic methods and X-ray diffraction crystallography. Lingzhiol bears an unusual 5/5/6/6 ring system characteristic of sharing a C-3′–C-7′ axis. Biological evaluation showed that (+)-lingzhiol or (−)-lingzhiol could selectively inhibit the phosphorylation of Smad3 in TGF-β1-induced rat renal proximal tubular cells and activate Nrf2/Keap1 in mesangial cells under diabetic conditions.

 

Yong-Ming Yan †‡, Jun Ai §, Li−Li Zhou §, Arthur C.K. Chung , Rong Li , Jing Nie §, Ping Fang †,Xin-Long Wang †, Jie Luo †, Qun Hu †, Fan-Fan Hou*§, and Yong-Xian Cheng

 

Org. Lett., Article ASAP

DOI: 10.1021/ol4026364

Via NatProdChem

STOCKHOLM—In recognition of his contributions to the field of making sixth-grade chemistry fun, Taft Middle School teacher Peter Ambler was awarded the Nobel Prize in Chemistry on Monday.

Fifteen meroterpenoids (1–15) with diverse ring systems including an unprecedented oxaspiro[5.5]nonane-fused cyclohexenone (1), hydrogenated benzofurans (2–5), hydrogenated chromans (6, 7), hydrogenated cyclopenta[b]chromans (8–11), and four monocyclic structures (12–15) were isolated from the sponge-associated fungus Alternariasp. JJY-32. The structures were elucidated by detailed spectroscopic analysis, including 2D NMR and electronic circular dichroism (ECD) calculations, and assisted by chemical derivatizations. On the basis of supplementation experiments with specific enzyme inhibitors and putative precursors, a shikimate–isoprenoid hybrid biosynthetic pathway is proposed. The NF-κB inhibitory activities of 1–15 were tested, and all of them, except 6 and7 (IC50 > 100 μM), showed activities with IC50 values ranging from 39 to 85 μM in RAW264.7 cells.

 

Guojian Zhang †, Guangwei Wu †, Tianjiao Zhu †,Tibor Kurtán ‡, Attila Mándi ‡, Jieying Jiao †, Jing Li †, Xin Qi †, Qianqun Gu †, and Dehai Li

 

J. Nat. Prod., Article ASAP

DOI: 10.1021/np4005757

Via NatProdChem

Akaeolide, a novel polycyclic polyketide, was isolated from the culture extract of a marine-derived actinomycete belonging to the genus Streptomyces. The planar structure of the new compound was elucidated by spectroscopic analysis including NMR and MS, and the absolute configuration was determined by X-ray crystallographic analysis of its chlorinated derivative. Akaeolide possesses a 15-membered carbocyclic framework, apparently derived from the malonate pathway, with a tetrahydrofuran ring and a β-keto-δ-lactone unit.

 

Yasuhiro Igarashi *†, Tao Zhou †, Seizo Sato ‡,Takashi Matsumoto §, Linkai Yu †, and Naoya Oku

 

Org. Lett., Article ASAP

DOI: 10.1021/ol402661r

 

 

Via NatProdChem