A Chemotaxonomic survey for biologically active compounds from Malaysian Calophyllum species led to the findings of the four new benzoylcoumarins 1a, 2, 3, and 4a (including the unusual prenylated 6-benzoylcoumann 1a), two uncommon coumarins 5 and 6a with a pyran-4-one moiety fused at C(6) and C(7), and compounds 7a, 9, and 10, all isolated from the bark of C. teysmannii var. inophylloide. Their structures were determined by spectroscopic analysis and chemical transformations. X-Ray crystal-structure determination of 2 provided information on the conformational preferences of substituents in this class of coumarins. The syntheses of the cytotoxic calanone (7a) and of some related coumarins are described.

Minor Coumarins from Calophyllum teysmannii var. inophylloide and Synthesis of Cytotoxic Calanone Derivatives

0009-3130/11/4606-0976 2011 Springer Science+Business Media, Inc. 1) Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, P. R. China, fax: 0086 898 65889422, e-mail:hchr116@hainnu.edu.cn; 2) Institute of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, P. R. China; 3) College of Chemistry and Life Science, China Three Gorges University, Yichang 443002, P. R. China. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 830–831, November–December, 2010. Original article submitted July 7, 2009. Chemistry of Natural Compounds, Vol. 46, No. 6, 2011

Xanthones from the roots of Calophyllum membranaceum

Incrassamarin A–D: Four new 4-substituted coumarins from Calophyllum incrassatum and their biological activities

The chemical composition of the leaf, bark and root oils of Goniothalamus malayanus Hook. f. and Thoms. was examined by capillary GC and GC–MS. The leaf oil was made up mainly of sesquiterpenoids, of which β-selinene (33.6%) was the dominant component. The other major compounds present were viridiflorol (13.1%), epi-globulol (7.7%), (E)-nerolidol (4.4%) and globulol (3.8%). The bark and root oils, which were qualitatively similar but with some variation in levels of the individual constituents, were also rich in sesquiterpenoids (97% and 95%, respectively), with eudesmols as the most abundant compounds. The bark oil contained a higher amount of β-eudesmol (32.2%), γ-eudesmol (21.8%) and α-eudesmol (6.6%) than the root oil. Copyright © 2002 John Wiley & Sons, Ltd.

Chemical constituents of the essential oils of Goniothalamus malayanus Hook. f. and Thoms

From a phytochemical screening of Calophyllum teysmannii var. inophylloide a new coumarin, isocalanone (1a), was isolated together with the known calanone (2). The structures of both compounds were confirmed by spec-troscopic data and single crystal X-ray crystallography.

Isocalanone, a New Pyranocoumarin from cAlophyllum teysmannii (Guttiferae)

A new, highly prenylated xanthone, gracilixanthone (1), was isolated from Calophyllum gracilipes together with three other known xanthones, pyranojacareubin (2), caloxanthone C (3) and trapezifolixanthone (4).

T.-B. Lim

Papers

A Highly Prenylated Xanthone from the Bark of Calophyllum Gracilipes (Guttiferae)