Rhodomyrtials A and B, Two Meroterpenoids with a Triketone-Sesquiterpene-Triketone Skeleton from Rhodomyrtus tomentosa: Structural Elucidation and Biomimetic Synthesis

2016 ◽  
Vol 18 (16) ◽  
pp. 4068-4071 ◽  
Author(s):  
Ya-Long Zhang ◽  
Chen Chen ◽  
Xiao-Bing Wang ◽  
Lin Wu ◽  
Ming-Hua Yang ◽  
...  
Keyword(s):  
Structural Elucidation ◽  
Biomimetic Synthesis ◽  
Rhodomyrtus Tomentosa

A Biomimetic Synthesis-Enabled Stereochemical Assignment of Rhodotomentones A and B, Two Unusual Caryophyllene-Derived Meroterpenoids from Rhodomyrtus tomentosa

2021 ◽  
Author(s):  
Lu-Ming Deng ◽  
Li-Jun Hu ◽  
Wei Tang ◽  
Jia-Xin Liu ◽  
Xiao-Jun Huang ◽  
...  
Keyword(s):  
Ring System ◽  
Biomimetic Synthesis ◽  
Stereochemical Assignment ◽  
Rhodomyrtus Tomentosa

Rhodotomentones A and B (1 and 2), two unusual caryophyllene-derived meroterpenoids (CDMTs) featuring a rare 6/6/9/4/6/6 hexacyclic ring system, along with their biogenetically-related CDMTs 7 and 12–15, were isolated from...

Leptosperols A and B, Two Cinnamoylphloroglucinol–Sesquiterpenoid Hybrids from Leptospermum scoparium: Structural Elucidation and Biomimetic Synthesis

2020 ◽  
Vol 22 (5) ◽  
pp. 1796-1800 ◽  
Author(s):  
Ji-Hong Gu ◽  
Wen-Jing Wang ◽  
Jun-Zi Chen ◽  
Jun-Shan Liu ◽  
Ni-Ping Li ◽  
...  
Keyword(s):  
Structural Elucidation ◽  
Biomimetic Synthesis ◽  
Leptospermum Scoparium

Rhodomentosones A and B: Two Pairs of Enantiomeric Phloroglucinol Trimers from Rhodomyrtus tomentosa and Their Asymmetric Biomimetic Synthesis

2021 ◽  
Author(s):  
Lu-Ming Deng ◽  
Li-Jun Hu ◽  
Yang-Ting-Zhi Bai ◽  
Jie Wang ◽  
Guan-Qiu Qin ◽  
...  
Keyword(s):  
Biomimetic Synthesis ◽  
Rhodomyrtus Tomentosa

Structural Elucidation and Biomimetic Synthesis of (±)-Cochlactone A with Anti-Inflammatory Activity

2018 ◽  
Vol 83 (10) ◽  
pp. 5516-5522 ◽  
Author(s):  
Xing-Rong Peng ◽  
Shuang-Yang Lu ◽  
Li-Dong Shao ◽  
Lin Zhou ◽  
Ming-Hua Qiu
Keyword(s):  
Structural Elucidation ◽  
Biomimetic Synthesis ◽  
Inflammatory Activity ◽  
Anti Inflammatory

Isolation and structural elucidation of novel natural compounds from twigs of Pinus banksiana

Planta Medica ◽  
2013 ◽  
Vol 79 (13) ◽  
Author(s):  
C Si ◽  
X Ren ◽  
S Liu ◽  
G Xu ◽  
J Jiang
Keyword(s):  
Pinus Banksiana ◽  
Natural Compounds ◽  
Structural Elucidation

Isolation and structural elucidation of secondary metabolites obtained from the soft coral Sinularia candidula present in the Egyptian Red Sea

Planta Medica ◽  
2015 ◽  
Vol 81 (16) ◽  
Author(s):  
RF Abou El Ezz ◽  
M Afifi ◽  
A Kamal ◽  
E Sannad ◽  
M Radwan ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Red Sea ◽  
Soft Coral ◽  
Structural Elucidation

Synthesis and Reactivity of Precolibactin 886

2019 ◽  
Author(s):  
Seth Herzon ◽  
Alan R. Healy ◽  
kevin wernke ◽  
Chung Sub Kim ◽  
Nicholas Lees ◽  
...  
Keyword(s):  
Colorectal Cancer ◽  
Gene Cluster ◽  
Amino Alcohol ◽  
Biomimetic Synthesis ◽  
Cross Linking ◽  
E Coli ◽  
Hplc Purification ◽  
Structural Assignment ◽  
Biosynthetic Precursor ◽  
Double Oxidation

<div>The clb gene cluster encodes the biosynthesis of metabolites known as precolibactins and colibactins. The clb pathway is found in gut commensal E. coli, and clb metabolites are thought to initiate colorectal cancer via DNA cross-linking. Precolibactin 886 (1) is one of the most complex isolated clb metabolites; it contains a 15-atom macrocycle and an unusual 5-hydroxy-3-oxazoline ring. Here we report confirmation of the structural assignment via a biomimetic synthesis of precolibactin 886 (1) proceeding through the amino alcohol 9. Double oxidation of 9 afforded the unstable α-ketoimine 2 which underwent macrocyclization to precolibactin 886 (1) upon HPLC purification (3% from 9). Studies of the putative precolibactin 886 (1) biosynthetic precursor 2, the model α-ketoimine 25, and the α-dicarbonyl 26 revealed that these compounds are susceptible to nucleophilic rupture of the C36–C37 bond. Moreover, cleavage of 2 produces other known clb metabolites or biosynthetic intermediates. This unexpected reactivity explains the difficulties in isolating full clb metabolites and accounts for the structure of a recently identified colibactin–adenine adduct. The colibactin peptidase ClbP deacylates synthetic precolibactin 886 (1) to form a non-genotoxic pyridone, suggesting precolibactin 886 (1) lies off-path of the major biosynthetic route.</div>

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