Inocalophyllins A, B and Their Methyl Esters from the Seeds of Calophyllum inophyllum

Abstract

Fractionation of the ethanolic extract of the seeds of Calophyllum inophyllum L. has resulted in the isolation of four novel pyranocoumarin derivatives, designated as inocalophyllins A (1), B (2) and their methyl esters (3, 4) in addition to the known calophyllolide. The structures of these compounds have been determined on the basis of spectroscopic analysis including MS, heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and two dimensional incredible natural abundance double quantum transfer experiment (2D-INADEQUATE). Two new methylated products, 5 and 6 were also prepared by methylation of compounds 1 and 2, respectively.

Caseinate-Stabilized Emulsions of Black Cumin and Tamanu Oils: Preparation, Characterization and Antibacterial Activity

“…Calophyllic acid and a lactone with antibiotic properties are the two main bioactive substances in the tamanu oil [9]. Calophyllum inophyllum is also known as a rich source of secondary metabolites (coumarins, xanthones, flavonoids, and triterpenes) [10], with some of them having anti-inflammatory, antibacterial, and antiviral properties [11,12]. Additionally, coumarin derivatives (calaustralin, calophyllolide, inophyllum, inophyllum E) that were obtained from a crude extract of the nuts were reported to have activity against Staphylococcus aureus [1] and antioxidant properties [13].…”

<b>PHLOROGLUCINOL DERIVATIVES AND FLAVONES FROM <i>HELICHRYSUM PARONYCHIOIDES</i></b>

“…Although compound 1 is herewith reported for the first time as a natural product, it is a principle building block of Calophyllum metabolites [25][26][27][28][29][30] and thus a precursor towards the total synthesis of an anti-HIV-1 compound, (±)-calanolide A [31]. The absolute configuration of 1, (2R,3R)-5,7-dihydroxy-2,3-dimethyl-4-chromanone, was inferred from the already established configuration of papuanic acid isolated from Calophyllum papuanum [28,32].…”

Coumarins and a Naphthyl Labdanoate Diarabinoside from the Fruits of Peucedanum grande C. B. Clarke

“…The HMBC spectrum of 1 showed interactions of C-6 with H 2 -11, H 2 -12, H-7, and H-8. The coumarins containing a 6-isoprenyl chain reported earlier are toddaculin from Toddalia asiatica stem bark (Vazquez et al, 2012), 6-(4-acetoxy-3-methyl-2-butenyl)-7-hydroxycoumarin and 6-(2-hydroxy-3-hydroxymethyl-3-butenyl)-7-hydroxycoumarin from Aegle marmelos green fruits (Chakthong et al, 2012), inocalophyllins from Calophyllum inophyllum seeds (Shen et al, 2003), fatouains from Fatoua pilosa plant (Chiang et al, 2010), isophellodenol C from Heracleum candicans roots (Nakamori et al, 2008), balsamiferone from Amyris balsamifera aerial parts (Burke and Parkins, 1979), and gravelliferon from Ruta graveolens (Reisch et al, 1968). On the basis of the foregoing discussion, the structure of 1 was elucidated as 5-hydroxy-6-isopranyl coumarin (Fig.…”