Chromanone Derivatives from the Pericarps of Calophyllum polyanthum

Abstract

Three new chromanone derivatives, calopolyanic acid (1), isocalopolyanic acid (2), and isorecedensic acid (3), were isolated from the pericarps of Calophyllum polyanthum Wall. ex Choisy, along with seven known compounds, apetalic acid, blancoic acid, chapelieric acid, methyl isoapetalate, isoapetalic acid, isocalolongic acid, and recedensic acid. All of these compounds were reported from C. polyanthum for the first time. The structures of 1 -3 were elucidated by spectroscopic methods.Introduction. . In previous studies of C. polyanthum, some chromanone derivatives such as calopolyanolides C and D have been isolated [6] [10]. We were interested in this type of constituents and conducted a phytochemical research on the pericarps of C. polyanthum, which led to the isolation of ten chromanone derivatives including three new ones, 1 -3. The structure elucidations of these new isolates are reported.

Chemical Constituents from the Root Bark of Calophyllum inophyllum

“…In addition, the in vitro cytotoxicity of these compounds against human tumor cell lines (KB and Hela S-3) was evaluated. [27]. This chain was suggested to be at C-9 (δ C 28.6) and confirmed by the HMBC correlations between H-9 [δ H 3.31 (1H, m)] and C-1′ (δ C 35.7) (Figure 1B).…”

“…The 1 H NMR spectrum showed a singlet signal of a chelated hydroxyl moiety (δ H 12.29) at C-5 (δ C 160.5), which was confirmed by HMBC correlations between the hydroxyl proton and C-4a (δ C 104.1), C-6 (110.3) and C-5 (160. and C-5″ (δ C 24.5), C-4″ (δ C 48.3); H-8″ [(δH 1.67 (3H, s)] and C-4″ (δ C 48.3), C-7″ (δ C 109.5) and C-6″ (δ C 146.6) supported the presence of a 3-isopropenyl-2,2-dimethylcyclobutylmethyl chain at C-6 (δ C 110.4) [26]. In addition, the signals at δ H 1.45 (2H, m, H-1′), 1.38 (2H, m, H-2′) and δ H 0.91 (3H, t, J = 7.2 Hz, H-3′) were assigned to the propyl chain in 1 [27]. This chain was suggested to be at C-9 (δ C 28.6) and confirmed by the HMBC correlations between H-9 [δ H 3.31 (1H, m)] and C-1′ (δ C 35.7) ( Figure 1B).…”

Pyranochromones with Anti-Inflammatory Activities in Arthritis from Calophyllum membranaceum

“…By the comparison of 1 H NMR spectra of 1 – 10 , 14 – 18 , together with several reported derivatives including pinetoric acid I, caloteysmannic acid, and calopolyanic acid, a noticeable convention of the 1 H NMR data for these pyranochromanones can be summarized. The C-2 proton shifts downfield and the methyl signals upfield on passing from the trans to the cis compounds, while C-3 signals are only slightly affected.…”

Propolis Components and Biological Activities from Stingless Bees Collected on South Sulawesi, Indonesia

“…for C 25 H 37 O 7 :449.2539 [M-H] -). To determine the relative configuration between C-2 and C-3 of 3, the proton coupling constant between these protons was compared with those of calopolyanic acid (cis-configured C-2 and C-3) and isocalopolyanic acid (trans-configured C-2 and C-3), which have the same 2,3-dimethylchroman-4-one skeleton as 3 (Wang et al 2010). Since the proton coupling constant between H-2 and H-3 in 3 (J = 11.2 Hz) was closer to that of isocalopolyanic acid (J = 11.6 Hz) than that of calopolyanic acid (J = 3.1 Hz), the relative configuration between C-2 and C-3 in 3 was determined to be a trans.…”

“…From the spectroscopic analysis and comparisons with literature data, the known compounds were identified to be isopapuanic acid (6) (Stout et al 1968), isocalopolyanic acid (7) (Wang et al 2010), glyasperin A (8) (Zeng et al 1992), broussoflavonol F (9) (Zheng et al 2008), (2S)-5,7-dihydroxy-4'methoxy-8-prenylflavanone (10) (Parsons et al 1993), isorhamnetin (11) (Lee et al 2008), (1'S)-2trans,4-trans-abscisic acid (12) (Ferreres et al 1996;Kikuzaki et al 2004), and (1'S)-2-cis,4-trans-abscisic acid ( 13) (Ferreres et al 1996;Kikuzaki et al 2004).…”