Cinnzeylanine, a new pentacyclic diterpene acetate from <i>Cinnamonum zeylanicum</i>

Isogai, Akira; Suzuki, Akira; Tamura, Shintaro; Ohashi, Y.; Sasada, Y.

doi:10.1107/s0567740877004324

Cited by 8 publications

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“…Such a fragmentation pattern aligns well with previous published data on cinnzeylanine, where fragments at m/z 347 and 329 were observed under negative ionization [33]. Cinnzeylanine as a diterpene acetate has been identified from different cinnamon species including C. verum, C. loureiroi, and C. cassia [33,34].…”

Section: Identification Of Cinnamon Metabolites Among Different Speciessupporting

confidence: 90%

Metabolomic profiling and comparison of major cinnamon species using UHPLC–HRMS

2020

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The metabolomic profiles of four major species of cinnamon (Cinnamomum verum, C. burmannii, C. loureiroi, and C. cassia) were investigated by ultra-high-performance liquid chromatographyhigh-resolution mass spectrometry (UHPLC-HRMS). Thirty-six metabolites were tentatively characterized, belonging to various compound groups such as phenolic glycosides, flavan-3-ols, phenolic acids, terpenes, alkaloids, and aldehydes. Principal component analysis (PCA) and partial least squares -discriminant analysis (PLS-DA) on the HRMS data matrix resulted in a clear separation of the four cinnamon species. Coumarin, cinnamaldehyde, methoxycinnamaldehyde, cinnamoyl-methoxyphenyl acetate, proanthocyanidins, and other components varied among the four species. Such variations were used to develop a step-by-step strategy for differentiating the four cinnamon species based on their levels of pre-selected components. This study suggests a significant variation in the phytochemical compositions of different cinnamon species, which have a direct influence on cinnamon's health benefit potentials.

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Section: Identification Of Cinnamon Metabolites Among Different Speciessupporting

confidence: 90%

Metabolomic profiling and comparison of major cinnamon species using UHPLC–HRMS

2020

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“…From the fraction eluted with 60% benzene, was obtained cinnzeylanine (1) as crystals (120 mg). The mother liquor was applied to preparative silicic acid TLC (benzene-ethyl acetate, 1: 3) to afford cinnzeylanine (I) (25 mg) and cinnzeylanol (2) (20 mg).…”

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“…(Table IV), and the larvae of fall webworm, Hyphantria cunea Drury died before pupation (Table V). The larvae of mulberry pyralid, Glyphodes pyroalis Isolation of cinnzeylanine (1) and cillllzeylanol (2) Four hundred grams of ceylon cinnamon, powdered barks of Cinnamonum zeylanicum Nees, were extracted with 8 liters of 80 % acetone, and the extract wa!> filtered and concentrated in vacuo. The residual aqueous solution was acidified to pH 2, and the resulting precipitates were removed by filtration with the aid of celite 545.…”

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Chemistry and Biological Activities of Cinnzeylanine and Cinnzeylanol, New Insecticidal Substances fromCinnamonum zeylanicumNees

Isogai

Murakoshi

Suzuki

et al. 1977

Agricultural and Biological Chemistry

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Pesticidal compounds from higher plants

Benner¹

1993

Pestic. Sci.

105

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Higher plants offer an excellent source of biologically active natural products. Over the centuries numerous plants have been exploited as sources of insecticides, but nowadays traditional botanical insecticides play only a minor role in world agriculture. Nevertheless, plant natural products still have enormous potential to inspire and influence modern agrochemical research.Few plant natural products will ever reach the market as products per se, but others will provide lead structures for programmes of synthetic chemistry and hopefully follow the success story of the synthetic pyrethroids. Structurally complex compounds, which are not amenable to synthetic chemistry programmes, may also have a role to play by validating new modes of action for pesticides.Examples are presented of compounds exhibiting insecticidal, fungicidal and herbicidal effects. Consideration is also given to the development of screening programmes to detect new compounds with interesting biological properties. Careful experimental design and thorough recording of procedures and data are crucial to success. Badly designed programmes afford only weakly active compounds or show effects which cannot be reproduced at a later date.Natural product chemistry, whether based on higher plants, micro-organisms or other sources, is a very difficult science, but there is little doubt that dedicated research will eventually be rewarded with exciting new lead structures for industrial application.

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Cinnzeylanine, a new pentacyclic diterpene acetate from Cinnamonum zeylanicum

Cited by 8 publications

References 0 publications

Metabolomic profiling and comparison of major cinnamon species using UHPLC–HRMS

Metabolomic profiling and comparison of major cinnamon species using UHPLC–HRMS

Chemistry and Biological Activities of Cinnzeylanine and Cinnzeylanol, New Insecticidal Substances fromCinnamonum zeylanicumNees

Pesticidal compounds from higher plants

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