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

Wu, Lin; Wang, Xiao-Bing; Li, Ruijun; Zhang, Ya-long; Yang, Ming‐Hua; Luo, Jun

doi:10.1016/j.phytochem.2016.08.014

Cited by 26 publications

(18 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 13 C NMR and HSQC spectra of 1 exhibited 25 carbon signals corresponding to nine methyls, two methylenes, seven methines (including two olefinic carbons at δ C 130.9 and 135.2), and seven quaternary carbons (including two carbonyls at δ C 198.6 and 213.4, two olefinic carbons at δ C 110.3 and 167.0, and one oxygenated carbon at δ C 76.2). The above-mentioned NMR data were similar to those of callistiviminene M [7], except for the presence of an additional methylene. The 1 H– 1 H COSY spectrum disclosed the presence of a single spin system.…”

Section: Resultssupporting

confidence: 66%

Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus

Qin

Shu

Qian

et al. 2017

Nat. Prod. Bioprospect.

View full text Add to dashboard Cite

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, 9.12 ± 0.3, and 16.33 ± 3.3 μM, respectively.Graphical AbstractCytotoxic Acylphloroglucinol Derivatives from Callistemon salignus Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-017-0138-6) contains supplementary material, which is available to authorized users.

show abstract

Section: Resultssupporting

confidence: 66%

Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus

Qin

Shu

Qian

et al. 2017

Nat. Prod. Bioprospect.

View full text Add to dashboard Cite

show abstract

“…The available literature concerning Myrtaceae also reports the existence of products that are not classifiable as acylphloroglucinol oligomers, and are hence not included in this review. Particularly, monomers of either acylphloroglucinol (e.g., callisalignene A–C [25], xanchryone A–D [55], operculatol A–B [56]) or syncarpic acid (e.g., myrtucommulone K [35,57], callistiviminene A–O [58]), and flavonoids conjugated to a syncarpic acid residue (e.g., kunzeanones A–C [59], myrtocummunines A–D [51]).…”

Section: Structures and Chemical Propertiesmentioning

confidence: 99%

Structures and Bioactive Properties of Myrtucommulones and Related Acylphloroglucinols from Myrtaceae

et al. 2018

View full text Add to dashboard Cite

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 acylphloroglucinol compounds have been characterized from several species that represent the basic active principles to be considered in view of possible drug development. Aspects concerning chemical and biological properties of these products are reviewed in the present paper.

show abstract

“…Analysis of the 13 C NMR data of 1 with the aid of the DEPT spectrum revealed the presence of 22 carbons, attributable to two keto-carbonyls, an olefinic bond, and 18 aliphatic carbons (including five methylenes and two oxygenated quaternary carbons). The aforementioned data suggested that 1 could be a triketone–monoterpene adduct …”

Section: Resultsmentioning

confidence: 99%

Myrcaulones A–C, Unusual Rearranged Triketone–Terpene Adducts from Myrciaria cauliflora

Chen

Wang

et al. 2020

J. Nat. Prod.

View full text Add to dashboard Cite

Three rearranged triketone−terpene adducts, myrcaulones A−C (1−3), were isolated from the leaves of Myrciaria cauliflora. Myrcaulones A (1) and B (2) feature a new carbon skeleton with an unprecedented spiro[bicyclo[3.1.1]heptane-2,2′cyclopenta[b]pyran] core. Myrcaulone C (3) possesses an unusual cyclobuta[6,7]cyclonona[1,2-b]cyclopenta[e]pyran backbone. Their structures with absolute configurations were elucidated by NMR spectroscopy, X-ray diffraction, and electronic circular dichroism calculations. A plausible biogenetic pathway for myrcaulones A−C involving the rearrangement of a triketone unit is also proposed. In addition, myrcaulones A (1) and B (2) exhibited inhibitory effects against tumor necrosis factor-α and nitric oxide generation induced by lipopolysaccharide in RAW 264.7 macrophages.

show abstract

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

Cited by 26 publications

References 15 publications

Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus

Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus

Structures and Bioactive Properties of Myrtucommulones and Related Acylphloroglucinols from Myrtaceae

Myrcaulones A–C, Unusual Rearranged Triketone–Terpene Adducts from Myrciaria cauliflora

Contact Info

Product

Resources

About