Two new tetracyclic diterpenoids trivially named as limbatenolide D (1) and limbatenolide E (2) have been isolated from Otostegia limbata. The structure elucidation of the compounds was based primarily on two-dimensional (2D) NMR techniques and on comparison with the literature data.
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http://dx.doi.org/10.1248/cpb.55.471 | DOI Listing |
Nat Commun
December 2024
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi, 712100, China.
Marine cyclopianes are a family of diterpenoid with novel carbon skeleton and diverse biological activities. Herein, we report our synthetic and chemical proteomics studies of cyclopiane diterpenes which culminate in the asymmetric total synthesis of conidiogenones C, K and 12β-hydroxy conidiogenone C, and identification of Immunity-related GTPase family M protein 1 (IRGM1) as a cellular target. Our asymmetric synthesis commences from Wieland-Miescher ketone and features a sequential intramolecular Pauson-Khand reaction and gold-catalyzed Nazarov cyclization to rapidly construct the 6-5-5-5 tetracyclic skeleton.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Euphorbialoid A () belongs to the rare diterpenoid family of premyrsinanes and exhibits potent anti-inflammatory effects. The 5/7/6/3-membered carbocycle (ABCD-ring) of contains 11 contiguous stereocenters and seven oxygen-containing functional groups. Moreover, four of the six hydroxy groups of are concentrated in the southern sector and flanked by four structurally different acyl groups.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, Gansu Province, 730000, China.
Kalmanol (1) is the first isolated kalmane-type grayanoid featuring a highly oxidized 5/8/5/5 tetracyclic carbon skeleton and 9 contiguous stereocenters. We have accomplished the efficient and asymmetric total synthesis of 1 in 16 steps from known compounds (20 steps from commercially available starting materials) by a modular synthetic strategy. A tetracyclic intermediate was prepared in a convergent manner through a Grignard reaction and a subsequent ring-closing metathesis reaction of two enantiomerically enriched fragments.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, China.
A three-stage chemoenzymatic synthesis of the cyclopiane family and related diterpenes is reported. Deoxyconidiogenol with a 6/5/5/5-fused tetracyclic cyclopiane skeleton was first produced by an engineered E. coli host harboring the corresponding terpene cyclase PchDS.
View Article and Find Full Text PDFPlant Physiol Biochem
November 2024
Institute of Medicinal Plant Physiology and Ecology, School of Pharmaceutical Science, Guangzhou University of Chinese Medicine, Guangzhou, 510006, China. Electronic address:
Pogostemon cablin (Blanco) Benth (Patchouli) is an aromatic herb extensively used in pharmaceutical and cosmetic industries. Sesquiterpenes are the characteristic constitutes in patchouli which are synthesized in the glandular trichomes on leaves and stems. Gibberellic acid (GA), a tetracyclic diterpenoid, plays a crucial role in the formation of glandular trichome.
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