5-Methoxy-2,2-dimethyl-6-[(2E)-2-methylbut-2-enoyl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one (calophyllolide)

Kalyanaraman, L.; Kumar, R.; Vishweshwar, Peddy; Pichai, R.; Narasimhan, S.

doi:10.1107/s1600536810013577

Cited by 3 publications

(3 citation statements)

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“…Ethanol extracts of the fruits were chromatographically separated multiple times on silica gel and Sephadex LH-20 columns to obtain pure calophyllolide (Figure 1). The structure of calophyllolide was confirmed using spectroscopic methods ( 1 H-NMR and MS), and by comparison with published data in the literature [19]. The purity of the calophyllolide was greater than 98%, according to the NMR spectra and HPLC profile.…”

Section: Resultsmentioning

confidence: 89%

Calophyllolide Content in Calophyllum inophyllum at Different Stages of Maturity and Its Osteogenic Activity

Liu¹,

Liu

Chen

et al. 2015

Molecules

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Calophyllum inophyllum is a coastal plant rich in natural substances. Its ingredients have been used for the development of an anti-human immunodeficiency virus (HIV) drug. In this study, we collected C. inophyllum fruit, and the ethanol extract of the fruit was chromatographically separated using silica gel and Sephadex LH-20 columns to obtain the major compound, calophyllolide. The fruits were harvested from September to December in 2011; a quantitative analysis of the calophyllolide content was conducted using HPLC to explore the differences between the different parts of the fruit during the growing season. The results showed that in fruits of C. inophyllum, calophyllolide exists only in the nuts, and dried nuts contain approximately 2 mg·g −1 of calophyllolide. The calophyllolide levels in the nuts decreased during maturity. In addition, calophyllolide dose-dependently OPEN ACCESSMolecules 2015, 20 12315 enhanced alkaline phosphatase (ALP) activity in murine osteoblastic MC3T3-E1 cells, without significant cytotoxicity. The expression of osteoblastic genes, ALP and osteocalcin (OCN), were increased by calophyllolide. Calophyllolide induced osteoblasts differentiation also evidenced by increasing mineralization and ALP staining.

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Section: Resultsmentioning

confidence: 89%

Calophyllolide Content in Calophyllum inophyllum at Different Stages of Maturity and Its Osteogenic Activity

Liu¹,

Liu

Chen

et al. 2015

Molecules

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“…The positive LC-HRESIMS shows molecular peak at 475 for 2 corresponding to the molecular formula C 28 H 29 NO 6 As the Ritter reaction is expected to add 59 amu to 1, this product is the expected Ritter reaction product. Hence, it is inferred that the structure for 2 contain the moiety -NHCOCH 3 in addition to 1.…”

Section: Characterization Ofmentioning

confidence: 96%

“…[2,5] Calophyllolide was isolated from Calophyllum inophyllum seed by Soxhlet extraction and the structure was confirmed by single crystal XRD studies. [6] Structural modification of calophyllolide [7,8] was attempted by Ritter reaction [9] with various nitriles.…”

Section: Introductionmentioning

confidence: 99%

An NMR and Lc-MS Based Mixture Analysis Approach for Structural Elucidation of Antimicrobial Derivatives of Calophyllolide

Kalyanaraman

Ganesh

Kumar³

et al. 2012

Journal of Liquid Chromatography & Related Technologies

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& This account details the structural modification of Calophyllolide 1, using Ritter reaction with various nitriles to study the antimicrobial properties. Ritter reaction of calophyllolide results in a 1:1 mixture of two structurally related compounds 2 and 3. A stereogenic center was generated in the reaction products resulting in a racemic mixture. NMR mixture analysis strategy was employed for the chemical structural analysis. 2D NMR experiments such as gDQCOSY, gHSQC, gHMBC at 500 MHz, and LC-MS analysis allowed the complete assignment of 1 H and 13 C NMR spectra of mixture components 2 and 3. These results suggested an unusual carbon-carbon bond cleavage in the reaction product 3. Our effort highlights the NMR mixture analysis approach for characterization of mixture of compounds. An efficient and operationally simple chiral method by HPLC was developed to evaluate the enantiomer compositions. Based on the aforementioned spectral data, the compounds 2 and 3 were characterized as (E)-N-(5-methoxy-2,2-dimethyl-6-(2-methylbut-2-enoyl)-8-oxo-10-phenyl-2,8-dihydropyrano[2,3-f]chromen-4-yl)acetamide and N-(5-methoxy-2,2-dimethyl-8-oxo-10-phenyl-2,8-dihydropyrano[2,3-f]chromen-4-yl)acetamide, respectively. The possible mechanisms for these compounds formation were also proposed.

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Indigenous Uses, Phytochemical Analysis, and Anti-Inflammatory Properties of Australian Tropical Medicinal Plants

Yeshi

Turpin

Jamtsho³

et al. 2022

Molecules

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Australian tropical plants have been a rich source of food (bush food) and medicine to the first Australians (Aboriginal people), who are believed to have lived for more than 50,000 years. Plants such as spreading sneezeweed (Centipeda minima), goat’s foot (Ipomoea pes-caprae), and hop bush (Dodonaea viscosa and D. polyandra) are a few popular Aboriginal medicinal plants. Thus far, more than 900 medicinal plants have been recorded in the tropical region alone, and many of them are associated with diverse ethnomedicinal uses that belong to the traditional owners of Aboriginal people. In our effort to find anti-inflammatory lead compounds in collaboration with Aboriginal communities from their medicinal plants, we reviewed 78 medicinal plants used against various inflammation and inflammatory-related conditions by Aboriginal people. Out of those 78 species, we have included only 45 species whose crude extracts or isolated pure compounds showed anti-inflammatory properties. Upon investigating compounds isolated from 40 species (for five species, only crude extracts were studied), 83 compounds were associated with various anti-inflammatory properties. Alphitolic acid, Betulinic acid, Malabaric acid, and Hispidulin reduced proinflammatory cytokines and cyclooxygenase enzymes (COX-1 and 2) with IC50 values ranging from 11.5 to 46.9 uM. Other promising anti-inflammatory compounds are Brevilin A (from Centipeda minima), Eupalestin, and 5′-methoxy nobiletin (from Ageratum conyzoides), Calophyllolide (from Calophyllum inophyllum), and Brusatol (from Brucea javanica). D. polyandra is one example of an Aboriginal medicinal plant from which a novel anti-inflammatory benzoyl ester clerodane diterpenoid compound was obtained (compound name not disclosed), and it is in the development of topical medicines for inflammatory skin diseases. Medicinal plants in the tropics and those associated with indigenous knowledge of Aboriginal people could be a potential alternative source of novel anti-inflammatory therapeutics.

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5-Methoxy-2,2-dimethyl-6-[(2E)-2-methylbut-2-enoyl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one (calophyllolide)

Cited by 3 publications

References 5 publications

Calophyllolide Content in Calophyllum inophyllum at Different Stages of Maturity and Its Osteogenic Activity

Calophyllolide Content in Calophyllum inophyllum at Different Stages of Maturity and Its Osteogenic Activity

An NMR and Lc-MS Based Mixture Analysis Approach for Structural Elucidation of Antimicrobial Derivatives of Calophyllolide

Indigenous Uses, Phytochemical Analysis, and Anti-Inflammatory Properties of Australian Tropical Medicinal Plants

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