Caloforines A–G, coumarins from the bark of Calophyllum scriblitifolium

Ogasawara, Ai; Noguchi, Ryo; Shigi, Takuya; Nugroho, Alfarius Eko; Hirasawa, Yusuke; Kaneda, Toshio; Tougan, Takahiro; Horii, Toshihiro; Hadi, A. Hamid A.; Morita, Hiroshi

doi:10.1007/s11418-022-01613-6

Cited by 9 publications

(3 citation statements)

References 24 publications

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“…The plants belonging to Meliaceae have been reported to produce limonoids [ 1 ]. In our search for new bioactive compounds from medicinal plants, we have reported the isolation of new limonoids from plants of this genus [ 2 – 15 ], and alkaloids [ 16 – 23 ] and coumarins [ 24 ] showing antimalarial activity or inhibiting acetylcholinesterase. Ceramicine B, in particular, has been reported to show a strong lipid droplets accumulation (LDA) inhibitory activity on mouse pre-adipocyte cell line (MC3T3-G2/PA6) [ 6 – 8 ] and also anti-melanin deposition activity [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

Antimalarial ceramicines Q-T from Chisocheton ceramicus

et al. 2023

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Ceramicines are a series of limonoids that were isolated from the bark of Malaysian Chisocheton ceramicus (Meliaceae) and were known to show various biological activity. Four new limonoids, ceramicines Q–T ( 1 – 4 ) were isolated from the barks of C. ceramicus , and their structures were determined on the basis of the 1D and 2D NMR analyses in combination with calculated 13 C chemical shift data. Ceramicines Q–T ( 1–4 ) were established to be new limonoids with a cyclopentanone[α]phenanthren ring system with a β-furyl ring at C-17, and without a tetrahydrofuran ring like ceramicine B, which is characteristic of known ceramicines. Ceramicine R ( 2 ) exhibited potent antimalarial activity against Plasmodium falciparum 3D7 strain with IC 50 value of 2.8 µM. Graphical abstract Supplementary Information The online version contains supplementary material available at 10.1007/s11418-023-01706-w.

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Section: Introductionmentioning

confidence: 99%

Antimalarial ceramicines Q-T from Chisocheton ceramicus

et al. 2023

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“…10 C. scriblitifolium was collected in Mersing, Malaysia, from which we also isolated and recently reported some new coumarines, caloforines A−G. 4 Some polyphenolic compounds, including chromanones, that exist in a wide variety of plants are considered to have cardiovascular system protection. During the past few years, a number of polyphenols such as xanthones, coumarins,and chromanones have been identified from the Calophylleae tribe and the Clusiaceae family.…”

Section: ■ Introductionmentioning

confidence: 99%

“…So far, we have reported many novel compounds from tropical plants by our exploratory research on bioactive substances. − Some of these compounds, most of which were indole alkaloids and isoquinoline alkaloid derivatives, have a vasorelaxant effect and may be useful as an antihypertensive. − In the course of such research activities, we isolated six chromanones, calofolic acids A–F, from Calophyllum scriblitifolium bark that have vasorelaxation activity …”

Section: Introductionmentioning

confidence: 99%

Calofolic Acid-A from Calophyllum scriblitifolium Bark Has Vasorelaxant Activity via Indirect PKA Activation Caused by PI-3 Kinase Inhibition in Rat Vascular Smooth Muscle Cells

et al. 2022

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Previously, we isolated 2R,3S,15R-calofolic acids (CAs) from Calophyllum scriblitifolium bark, which showed vasorelaxant activity on phenylephrine (PE)-precontracted rat aortic rings. Although the effect was suggested to be induced via an extracellular Ca2+-independent manner and mainly acts on vascular smooth muscle, the exact mechanism of action of CAs remained unclear. Thus, this study investigated the detailed mechanism of calofolic acid-A (CA-A) induced vasorelaxation in an aortic ring specimen using rat vascular smooth muscle cells (VSMCs). The levels of PE-induced phosphorylation on MLC Ser19 decreased in VSMCs pretreated with CA-A. CA-A also decreased the phosphorylation of MYPT1 Thr696 and MYPT1 Thr853. On the other hand, CA-A increased the PE-induced phosphorylation of MYPT1 Ser695 and MYPT1 Ser668, which are reported to be phosphorylated by a cAMP-dependent protein kinase (PKA). CA-A slightly increased PKA substrate phosphorylation in a concentration-dependent manner. Furthermore, CA-A enhanced isoproterenol (ISO)-induced cAMP accumulation and PKA substrate phosphorylation. Treatment with PI-3 kinase (PI3K) inhibitor, LY294002, enhanced ISO-induced cAMP accumulation and PKA substrate phosphorylation in the same manner as CA-A treatment. Furthermore, CA-A was found to directly inhibit PI3K enzyme activity in a dose-dependent manner. Taken together, the present study indicated that CA-A induces vasorelaxation through an indirectly activated PKA-MYPT1 pathway caused by inhibition of PI3K activity.

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Exploring the Recent Pioneering Developments of Small Molecules in Antimalarial Drug Armamentarium: A Chemistry Prospective Appraisal

Bagratee,

Prawlall,

Ndlovu

et al. 2024

Chemistry & Biodiversity

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Malaria is a very destructive and lethal parasitic disease that causes significant mortality worldwide, resulting in the loss of millions of lives annually. The uncontrolled intake of antimalarial drugs often employed in clinical settings has resulted in the emergence of numerous strains of plasmodium that are resistant to these drugs, including multidrug‐resistant strains. Hence, there is an urgent need for developing unique classes of antimalarial drugs that function with distinct mechanisms of action. In this context, the design and development of hybrid compounds that combine pharmacophoric properties from different lead molecules into a single unit gives a unique perspective towards further development of malaria drugs in the next generation. In light of this, we have reviewed the progress of hybrid antimalarial agents from 2021 up to the present. This manuscript presents a comprehensive overview of the latest advancements in the medicinal chemistry pertaining to small molecules, with a specific focus on their potential as antimalarial agents. This review explores a variety of physiologically active compounds that have been described in the literature in order to lay a strong foundation for the logical design and eventual identification of antimalarial drugs based on lead frameworks.

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Caloforines A–G, coumarins from the bark of Calophyllum scriblitifolium

Cited by 9 publications

References 24 publications

Antimalarial ceramicines Q-T from Chisocheton ceramicus

Antimalarial ceramicines Q-T from Chisocheton ceramicus

Calofolic Acid-A from Calophyllum scriblitifolium Bark Has Vasorelaxant Activity via Indirect PKA Activation Caused by PI-3 Kinase Inhibition in Rat Vascular Smooth Muscle Cells

Exploring the Recent Pioneering Developments of Small Molecules in Antimalarial Drug Armamentarium: A Chemistry Prospective Appraisal

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