Acylphloroglucinols from the fruits of Callistemon viminalis

Published on Jun 1, 2017in Phytochemistry Letters1.459
· DOI :10.1016/J.PHYTOL.2017.04.014
Lin Wu8
Estimated H-index: 8
(CPU: China Pharmaceutical University),
Ya-Long Zhang9
Estimated H-index: 9
(CPU: China Pharmaceutical University)
+ 4 AuthorsJun Luo22
Estimated H-index: 22
(CPU: China Pharmaceutical University)
Sources
Abstract
Abstract Five new acylphloroglucinols, callistenones L-P ( 1–5 ), and three known compounds watsonianone A, callistenones F and H were isolated from the fruits of Callistemon viminalis . Callistenones L and M possessed a bisfuran fused-ring skeleton. Compounds 3–5 were acylphloroglucinol condensed with a β -triketone moiety via a pyrane. Their structures were established from analyses of NMR spectra, CD spectra and X-ray crystallography. Compound 8 showed antibacterial activity against S. aureus with MIC value of 20.3 μg/mL and E. coli with MIC value of 15.6 μg/mL.
📖 Papers frequently viewed together
20162.53Fitoterapia
7 Authors (Hongxin Liu, ..., Sheng-Xiang Qiu)
18 Citations
20172.23Tetrahedron
10 Authors (Xu-Jie Qin, ..., Hai-Yang Liu)
19 Citations
55 Citations
References20
Newest
#1Lin Wu (CPU: China Pharmaceutical University)H-Index: 8
#2Ya-Long Zhang (CPU: China Pharmaceutical University)H-Index: 9
Last. Ling-Yi Kong (CPU: China Pharmaceutical University)H-Index: 58
view all 7 authors...
Viminalins A-O (1–15), a series of new [3+2] hybrids of acylphloroglucinols and α-phellandrene featured a 2,3-dihydrobenzofuran core were isolated from the fruits of Callistemon viminalis. Their structures were established on the basis of extensive analysis of NMR spectra, circular dichroism, and X-ray crystallography. An oxidative [3+2] cycloaddition between acylphloroglucinol and monoterpene was speculated as the key step in the biosynthetic pathway. Bioactivities screen indicated that compoun...
6 CitationsSource
#1Lin Wu (CPU: China Pharmaceutical University)H-Index: 8
#2Xiao-Bing Wang (CPU: China Pharmaceutical University)H-Index: 31
Last. Ling-Yi Kong (CPU: China Pharmaceutical University)H-Index: 58
view all 7 authors...
Abstract Callistiviminenes A-O, fifteen adducts of β-triketone with sesqui- or monoterpene, along with a known compound, were isolated from the fruits of Callistemon viminalis . Callistiviminenes A and B are β-triketone-coupled (−)-bicyclosequiphellandrene contained an oxaspiro[5.5]undecene unit, and callistiviminenes C-E are rare adducts of β-triketone and bicyclogermacrene. Their structures and absolute configurations were elucidated by spectroscopic and computational methods, as well as by si...
16 CitationsSource
#1Hongxin Liu (CAS: Chinese Academy of Sciences)H-Index: 17
#2Yuchan Chen (CAS: Chinese Academy of Sciences)H-Index: 21
Last. Sheng-Xiang Qiu (CAS: Chinese Academy of Sciences)H-Index: 17
view all 7 authors...
A phytochemical study on the leaves of Callistemon viminalis, a widely distributed ornamental and medicinal plant of agricultural importance in China, resulted in the isolation of eleven acylphloroglucinols, including six new ones named callistenones F-K (1–6), as well as five known congeners. Their structures were fully characterized using spectral data interpretation for the new structures and compared to published data for the known ones. All the isolated compounds were evaluated for in vitro...
18 CitationsSource
#1Ya-Long Zhang (CPU: China Pharmaceutical University)H-Index: 9
#2Chen Chen (CPU: China Pharmaceutical University)H-Index: 6
Last. Ling-Yi Kong (CPU: China Pharmaceutical University)H-Index: 58
view all 10 authors...
Rhodomyrtials A and B (1 and 2), two unprecedented triketone-sesquiterpene-triketone adducts, along with five biogenetically related intermediates, rhodomentone A (3) and tomentodiones A–D (4–7), were isolated from the leaves of Rhodomyrtus tomentosa. Their structures and absolute configurations were determined by a combination of NMR spectroscopy, chemical conversion, and X-ray diffraction analysis. Compounds 1 and 2 were biomimetically synthesized via 5 and 4, respectively, rather than 3, reve...
36 CitationsSource
#1Lin Wu (CPU: China Pharmaceutical University)H-Index: 8
#2Jun Luo (CPU: China Pharmaceutical University)H-Index: 22
Last. Ling-Yi Kong (CPU: China Pharmaceutical University)H-Index: 58
view all 6 authors...
Calliviminones C–H (1–6), six novel Diels–Alder adducts of a polymethylated phloroglucinol derivative and acyclic monoterpene (myrcene), were isolated from the fruits of Callistemon viminalis. Their structures were elucidated on the basis of extensive analysis of NMR spectroscopic data and calculated electronic circular dichroism spectra. Compounds 1 and 2 were the first examples of a polymethylated phloroglucinol derivative connected with myrcene in a hetero-Diels–Alder manner and 3–6 were carb...
17 CitationsSource
#1Marcus Hans (Saarland University)H-Index: 2
#2Maël Charpentier (Saarland University)H-Index: 4
Last. Dietmar Quandt (University of Bonn)H-Index: 33
view all 7 authors...
Myrtucommulone A (MC A) (1), isolated from Myrtus communis (myrtle), shows the same pharmacological activity for inhibition of inflammation and induction of apoptosis as synthetic MC A, which consists of three stereoisomers, i.e., two enantiomers and one meso form. This led to the question of whether the natural MC A is a pure stereoisomer or a mixture of stereoisomers. The specific rotation and electronic circular dichroism (ECD) data of natural MC A (1) as well as of a pentacyclic derivative 4...
14 CitationsSource
#1Anais Gervais (BU: Boston University)H-Index: 1
#2Kiel E. Lazarski (BU: Boston University)H-Index: 8
Last. John A. Porco (BU: Boston University)H-Index: 68
view all 3 authors...
Herein, we report total syntheses of the tetramethyldihydroxanthene natural product rhodomyrtosone B and the related bis-furan β-triketone natural product rhodomyrtosone A. Nickel-(II)-catalyzed 1,4-conjugate addition of an α-alkylidene-β-dicarbonyl substrate was developed to access the congener rhodomyrtosone B, and oxygenation of the same monoalkylidene derivative followed by cyclization was employed to obtain the bis-furan natural product rhodomyrtosone A.
16 CitationsSource
#1Lin Wu (CPU: China Pharmaceutical University)H-Index: 8
#2Jun Luo (CPU: China Pharmaceutical University)H-Index: 22
Last. Ling-Yi Kong (CPU: China Pharmaceutical University)H-Index: 58
view all 14 authors...
(±)-Calliviminones A ( 1 ) and B ( 2 ), two Diels–Alder adducts of polymethylated phloroglucinol and myrcene with unprecedented spiro-[5.5] undecene skeleton, were isolated from the fruits of Callistemon viminalis . Structural elucidation was accomplished by NMR spectra studies, and the biomimetic synthesis of compounds 1 and 2 confirmed the pivotal role of Diels–Alder reaction in the plausible biosynthetic pathway. Compounds 1 and 2 were also the first example of Carbon Diels–Alder adducts betw...
26 CitationsSource
#1Suthida Rattanaburi (PSU: Prince of Songkla University)H-Index: 5
#2Wilawan Mahabusarakam (PSU: Prince of Songkla University)H-Index: 21
Last. Anthony Richard Carroll (Griffith University)H-Index: 41
view all 4 authors...
Five acylphloroglucinols, named callistenones A–E together with six known acylphloroglucinols, triterpenoids, and C-methylflavonoids were isolated from the leaves of Callistemon lanceolatus. Their structures were characterized by spectroscopic methods. Some of the compounds showed very strong antibacterial activity.
31 CitationsSource
#1Anthony Richard Carroll (Griffith University)H-Index: 41
#2Vicky M. Avery (Griffith University)H-Index: 46
Last. Gordon P. GuymerH-Index: 14
view all 5 authors...
Three new β-triketones, watsonianones A–C, and the known compound corymbone B were isolated from the flowers of the Australian eucalypt Corymbia watsoniana. Watsonianone A is the first naturally occurring methylene bridged bis-tetramethylcyclohexatrione, watsonianone B is only the fourth fused bisfurano β-triketone and watsonianone C is the first 4,4a,9,9a-tetrahydro-2H-xanthene-1,3,5,7(6H,8H)-tetraone to be reported in the literature. MS and NMR analysis established the structures of the new co...
17 CitationsSource
Cited By4
Newest
#1Ereny M. Abdelmalek (Assiut University)H-Index: 1
#2Mahmoud A. Ramadan (Assiut University)H-Index: 11
Last. Samir A. Ross (University of Mississippi)H-Index: 37
view all 6 authors...
Callistemon is an important genus in the family Myrtaceae which contains about 34 species. The members of this genus are known for their ornamental potentials, in addition to their outstanding value in conventional medicine in many parts of the world. Updated chemical analysis of the Callistemon genus has provided a variety of essential phytocompounds belonging to different chemical classes including terpenes, phenolic derivatives, flavonoids, anthocyanins, neolignans, phloroglucinol derivatives...
1 CitationsSource
#1Ereny M. Abdelmalek (University of Mississippi)H-Index: 1
#2Fazila Zulfiqar (University of Mississippi)H-Index: 4
Last. Samir A. Ross (University of Mississippi)H-Index: 37
view all 9 authors...
Abstract Phytochemical investigation of Callistemon citrinus (Curtis) Skeels (syn. Callistemon lanceolatus (Sm.) Sweet and Melaleuca citrina (Curtis) Dum.Cours.) leaves resulted in the isolation of five undescribed compounds, including one acylphloroglucinol derivative and four monoterpene galloylglucosides, in addition to 29 known diverse secondary metabolites. Interestingly, this study reports chemosystematically significant isolation of the monoterpene galloylglucosides from the genus for the...
Source
#1Yan Wu (JNU: Jinan University)H-Index: 1
#2Jiao‐Wen Liu (JNU: Jinan University)H-Index: 1
Last. Lei Wang (JNU: Jinan University)H-Index: 28
view all 7 authors...
Myrtucyclitones A-C ((+)- and (-)-1-3), three pairs of new triketone-phloroglucinol-triketone hybrids were isolated from the plant Myrtus communis. Their structures with absolute configurations were established by NMR analysis and chemical calculations. Myrtucyclitones B and C exhibited remarkable antibacterial effect.
Source
#1Rosario NicolettiH-Index: 18
#2Maria Michela Salvatore (University of Naples Federico II)H-Index: 9
Last. Anna Andolfi (University of Naples Federico II)H-Index: 39
view all 4 authors...
Myrtaceae are a group of plants that include a number of renowned species used in ethnomedicine in many areas worldwide. Their valuable therapeutic properties have stimulated a fruitful research activity addressed to the identification of the bioactive components of their extracts yielding a great diversity of terpenes; polyphenols; and other exclusive products. Among the latter, starting with the discovery of myrtucommulone A from myrtle (Myrtus communis), a series of structurally-related acylp...
4 CitationsSource