Callistiviminenes A-O: Diverse adducts of β-triketone and sesqui- or monoterpene from the fruits of Callistemon viminalis

Published on Nov 1, 2016in Phytochemistry3.044
· DOI :10.1016/J.PHYTOCHEM.2016.08.014
Lin Wu8
Estimated H-index: 8
(CPU: China Pharmaceutical University),
Xiao-Bing Wang31
Estimated H-index: 31
(CPU: China Pharmaceutical University)
+ 4 AuthorsLing-Yi Kong58
Estimated H-index: 58
(CPU: China Pharmaceutical University)
Sources
Abstract
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 single-crystal X-ray diffraction experiment. A plausible biosynthetic pathway to these compounds involves a hetero-Diels–Alder reaction. Callistiviminenes C and D exhibited inhibition against lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages with IC 50 value of 20.3  μ M and 32.5  μ M, respectively.
📖 Papers frequently viewed together
393 Citations
31 Citations
7 Authors (Jia-Qing Cao, ..., Wen-Cai Ye)
46 Citations
References17
Newest
#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
#1Hisashi Nishiwaki (Ehime University)H-Index: 18
#2Satomi FujiwaraH-Index: 1
Last. Yoshihiro ShutoH-Index: 12
view all 9 authors...
Ficifolidione (1), a moderately active insecticidal compound from two species of Myrtaceae, and its derivatives were synthesized to evaluate their insecticidal activity. X-ray crystallographic analyses and specific rotation values of ficifolidione and its C-4 (2) demonstrated that the structure of ficifolidione differs from the reported absolute structure; that is, the C-4 configuration of ficifolidione should have an S configuration. The reported insecticidal activity of ficifolidione (1) and i...
9 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
#1Duc N. Tran (EPFL: École Polytechnique Fédérale de Lausanne)H-Index: 13
#2Nicolai Cramer (EPFL: École Polytechnique Fédérale de Lausanne)H-Index: 58
(+)-Bicyclogermacrene is a strained bicyclic and common sesquiterpene found in several essential oils. A short and good yielding synthesis of bicyclogermacrene proceeding in seven steps is reported. This terpene is used as key platform intermediate for a biomimetic access to several aromadendrene sesquiterpenoids, such as ledene, viridiflorol, palestrol, and spathulenol. Furthermore, bicyclogermacrene is shown to be the terpene component in the synthesis of the meroterpenoids psiguadial A, C, an...
36 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
#1Filippo Cottiglia (University of Cagliari)H-Index: 23
#2Laura CasuH-Index: 19
Last. Giuseppina SannaH-Index: 19
view all 9 authors...
Bioactivity-guided fractionation of a dichloromethane extract of the leaves of Myrtus communis led to the isolation of phloroglucinol derivatives. The structures of the new myrtucommulones J, K, and L (1–3) and the previously known myrtucommulone A (4) were elucidated on the basis of extensive 1D and 2D NMR experiments as well as high-resolutionmass spectrometry. Myrtucommulone J was obtained as a tautomeric pair (1/1a). The compounds were tested in vitro for their cytotoxic and antibacterial ac...
45 CitationsSource
#1Meng Shao (JNU: Jinan University)H-Index: 3
#2Ying Wang (CPU: China Pharmaceutical University)H-Index: 3
Last. Wen-Cai YeH-Index: 46
view all 11 authors...
Psiguadials A (1) and B (2), two novel sesquiterpenoid-diphenylmethane meroterpenoids with unusual skeletons, along with a pair of known epimers, psidial A (3) and guajadial (4), were isolated from the leaves of Psidium guajava. Their structures with absolute configurations were elucidated by means of NMR, X-ray diffraction, and quantum chemical CD calculation. Compounds 1, 2, and 4 exhibited potent inhibitory effects on the growth of human hepatoma cells.
76 CitationsSource
#1Gilles LavernyH-Index: 15
#2Giuseppe Penna (NU: Northeastern University)H-Index: 3
Last. Luciano AdoriniH-Index: 83
view all 12 authors...
la,25(OH) 2 -16-ene-20-cyclopropyl-vitamin D 3 (13) is several fold more potent than the natural hormone 1α,25-dihydroxyvitamin D 3 (1) as an anti-inflammatory agent. Here, we have further analyzed the anti-inflammatory properties of 13, confirming it as the most potent analogue tested within this family. We then determined the structures of all the natural metabolites of 13, including the 24-oxo metabolite 14, and carried out its synthesis. A comparison of 13 with 14 showed a similar induction ...
28 CitationsSource
#1Noel M. O'Boyle (University of Cambridge)H-Index: 23
#2Adam L. Tenderholt (Stanford University)H-Index: 10
Last. Karol M. Langner (Wrocław University of Technology)H-Index: 11
view all 3 authors...
There are now a wide variety of packages for electronic structure calculations, each of which differs in the algorithms implemented and the output format. Many computational chemistry algorithms are only available to users of a particular package despite being generally applicable to the results of calculations by any package. Here we present cclib, a platform for the development of package-independent computational chemistry algorithms. Files from several versions of multiple electronic structu...
3,145 CitationsSource
#1Sheng Yin (CAS: Chinese Academy of Sciences)H-Index: 20
#2Jun-Juan XueH-Index: 3
Last. Jian-Min YueH-Index: 50
view all 6 authors...
Eucalyptals A−C (1−3) with a new skeleton of 3,5-diformyl-isopentyl phloroglucinol-coupled cadinane were isolated from the fruits of Eucalyptus globulus. Their structures were elucidated by spectroscopic analysis, and that of 1 was confirmed by single-crystal X-ray diffraction. The biosynthetic pathway of 1−3 was also postulated. Compounds 1−3 exhibited selective cytotoxicity against the HL-60 cell line.
29 CitationsSource
Cited By16
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
#1Odeta CelajH-Index: 2
Last. Brigida D’Abrosca (Stazione Zoologica Anton Dohrn)H-Index: 1
view all 7 authors...
Myrtaceae Juss. is a very large family of flowering plants, that are a valuable source of bioactive compounds. From the phytochemical point of view, apart from ubiquitous tannins, flavonoid derivatives and volatile oils, Myrtaceae plants are very rich in phloroglucinol derivatives, divided in two principal subclasses: oligomeric acylphloroglucinols and phloroglucinol-terpene adducts. Despite this large structural variability, many studies on phloroglucinols from the Myrtaceae have focused on uni...
7 CitationsSource
#1Lin Wu (CPU: China Pharmaceutical University)H-Index: 8
#2Xin Xie (CPU: China Pharmaceutical University)H-Index: 2
Last. Ling-Yi Kong (CPU: China Pharmaceutical University)H-Index: 58
view all 6 authors...
Abstract Leumelaleucols A-L (1-12), twelve new 5-methoxy-4-methyl-benzyl phloroglucinol-terpenoid hybrids were isolated from the fruits of Melaleuca leucadendron L. The structures were elucidated by analyses of spectral data, and the absolute configurations were determined by the circular dichroism (CD) exciton chirality method. The neuroprotective effects of the isolated compounds were assessed.
2 CitationsSource
#1Xin Deng (Anhui Medical University)
#2Xiu-rong Wang (Anhui Medical University)
Last. Lin Wu (Anhui Medical University)
view all 3 authors...
Eight new meroterpenoids (1-8) featuring beta-triketone-conjugated terpenoids, rtomentones A-H, were isolated from the leaves of Rhodomyrtus tomentosa. Structures of the isolates were unambiguously established by a combination of NMR and ECD spectroscopy and X-ray diffraction analysis. Rtomentone C (3) was the first example of aromadendrane-based meroterpenoid containing an oxa-spiro[5.6] ring. Rtomentone D (4) was obtained as a racemic mixture confirmed by chiral HPLC analysis. The cytotoxicity...
1 CitationsSource
#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
#1Jia-Qing Cao (JNU: Jinan University)H-Index: 5
#2Hai-Yan Tian (JNU: Jinan University)H-Index: 16
Last. Wen-Cai Ye (JNU: Jinan University)H-Index: 46
view all 7 authors...
Callisretones A (1) and B (2), two rearranged phloroglucinol-monoterpenoid adducts featuring an unprecedented isopropylcyclopenta[b]benzofuran backbone, together with their postulated biosynthetic precursors (3–9), were isolated from Callistemon rigidus. The previously assigned absolute configurations of viminalins H (7), L (8), and N (9) were revised and unequivocally established by X-ray diffraction data. A putative biosynthetic pathway toward callisretones A and B involving the rearrangement ...
12 CitationsSource
#1Ji-Qin Hou (CPU: China Pharmaceutical University)H-Index: 5
#2Cui Guo (CPU: China Pharmaceutical University)H-Index: 4
Last. Wang Hao (CPU: China Pharmaceutical University)H-Index: 7
view all 9 authors...
Frutescones H–R (1–11), new sesqui- or monoterpene-based meroterpenoids, were isolated from the aerial parts of Baeckea frutescens. Their structures and absolute configurations were established by means of spectroscopic analyses (HRESIMS, 1D and 2D NMR, and ECD), as well as single-crystal X-ray crystallography of 1, (−)-7, and 9. The anti-inflammatory activities of all isolates were evaluated by measuring their inhibitory effects on NO production in LPS-stimulated RAW 264.7 macrophages, and the ...
22 CitationsSource
#1Xu-Jie Qin (CAS: Chinese Academy of Sciences)H-Index: 19
#2Tong Shu (CAS: Chinese Academy of Sciences)H-Index: 4
Last. Hai-Yang Liu (CAS: Chinese Academy of Sciences)H-Index: 23
view all 10 authors...
Callisalignenes G-I (1-3), three new meroterpenoids of β-triketone and monoterpene, along with two known analogues (4 and 5), were isolated from Callistemon salignus. Their structures and absolute configurations were unambiguously established by a combination of NMR and MS analysis and electronic circular dichroism (ECD) evidence. Callisalignenes H (2) and I (3) have a rare sec-butyl moiety at C-7. Meroterpenoids 1-3 exhibited cytotoxicity against HCT116 cells with IC50 values of 8.51 ± 1.8, 9.1...
6 CitationsSource
#1Lin Wu (CPU: China Pharmaceutical University)H-Index: 8
#2Ya-Long Zhang (CPU: China Pharmaceutical University)H-Index: 9
Last. Jun Luo (CPU: China Pharmaceutical University)H-Index: 22
view all 7 authors...
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...
4 CitationsSource