Xylorumphiins A−D, Mexicanolide Limonoids from the Seed Kernels of Xylocarpus rumphii

Abstract

Four new mexicanolide limonoids, named xylorumphiins A-D (1-4), were isolated from the seed kernels of Xylocarpus rumphii, together with three known limonoids. Their structures and configurations were established on the basis of spectroscopic data.

Quantitative 1H NMR. Development and Potential of an Analytical Method: An Update

“…From the perspective of the NPs researcher, NMR has recently experienced major gains in sensitivity due to the development of micro-cryoprobe technology. Martin and co-workers 35,36 (and references therein) are among the leaders in this field and have demonstrated the feasibility of acquiring a 2D gHSQC spectrum of 540 ng of strychnine ( 6 ) at 600 MHz utilizing a weekend of spectrometer time. Along the lines of low-level/high-sensitivity qHNMR, Weljie et al described a method for the detection and quantitation of low-intensity unknown peaks (LIUPs) in spiked urine samples.…”

Suppression of Inducible Nitric Oxide Synthase Pathway by 7-Deacetylgedunin, a Limonoid from Xylocarpus sp.

“…Compounds 1, 3, 5, and 24-29 were isolated from seed kernels of X. granatum [23], whereas 8-10 were obtained from X. moluccensis [24], both of which were collected in Samutsongkram province. Compounds 7,[11][12][15][16], and 23 were isolated from X. moluccensis collected in Phuket [26], and compounds 17-22 were isolated from X. rumphii from Rayong province [25]. Compounds 2, 4, 6, and 31 were obtained from X. granatum, while 13-14 and 30 were isolated from X. moluccensis, both of which were from Suratthani province (Supporting Information).…”

“…Additionally, the bark pressings of both Xylocarpus granatum and Xylocarpus moluccensis are utilized to treat cholera and fever, including that caused by malaria. Recently we reported the isolation and identification of a number of limonoids from the seeds of three Thai mangroves in this genus, X. granatum, X. moluccensis, and X. rumphii [23][24][25][26]. As part of an ongoing program to search for anti-inflammatory agents from Thai natural products and based on the activity of the extracts of the Xylocarpus plants, the present study was undertaken to evaluate the effects of isolated limonoids on inflammatory responses and to investigate the molecular mechanism of action of selected limonoids.…”

Xylomexicanins C and D, New Mexicanolide-Type Limonoids from Xylocarpus granatum

“…(Table 2) indicated that 7 units of these 13 unsaturations came from three carbon-carbon double bonds and four ester carbonyls, the other 6 units of unsaturations coming from six rings. In addition, a quaternary carbon at C 107.41 was assignable to C-1, a hemiacetal group related to that found in xylocessin F 14) and xylorumphiin C, 15) (Fig. 3).…”

“…12,14,15) Significant NOESY correlations from H-3 to Me-29 ( H 0.79, s), but not from H-3 to H-5, nor from H-3 to H-30 implied that H-3 was -oriented. The correlations of H-9 ( H 2.14, o)/Me-18 ( glioma (U251-SP), and breast (MCF-7) cancer cell lines (IC 50 >100 mM).…”