Two new flavans, (2R, 4R)-4'-hydroxy-3',5'-methyl-6,7-methylenedioxy-4-O-2'-cycloflavan (1), and (2R, 4R)-4'-hydroxy-3'-methyl-6,7-methylenedioxy-4-O-2'-cycloflavan (2), along with six known compounds were isolated from the trunk and leaves of Horsfieldia glabra. Their structures were elucidated by means of extensive spectroscopic analysis. Compounds 1 and 2, together with 4-7 were assessed for their cytotoxicity against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that they had no activity.
Psychotria is a genus of ca. 1500 species in the family Rubiaceae. Up to now, 41 species of the Psychotria genus have been chemically investigated, and 159 compounds, including alkaloids of indole, quinoline and benzoquinolizidine type, terpenoids, steroids, phenolics and aliphatic compounds have been isolated. These compounds show potent bioactivities, such as antimicrobial, antiviral, and antiparasitic activities.
A new sesquiterpenoid (‒)-ethyl dihydrophaseate (1) was isolated from the stems and leaves of Polyalthia petelotii, together with two clerodane diterpenoids, 16α-hydroxycleroda-3,13(14)Z-dien-15,16-olide (2), 15-hydroxy-cis-ent-cleroda-3,13(E)-diene (3), a eudesmane sesquiterpenoid, eudesm-4(15)-ene-7α,11-diol (4), an aromatic aldehyde, vanillin (5), a bisisoquinolines alkaloid, spinosine (6) and an aporphine alkaloid, (‒)-oliveroline-β-N-oxide (7). Their structures were established by extensive spectroscopic analysis, including 2D-NMR techniques. Compounds 3, 4 and 6 were isolated from the genus Polyalthia for the first time and the others obtained originally from P. petelotii. The isolates were assessed for their cytotoxicity against five human tumour lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that only 2 displayed weak inhibitory activity.
The relative configuration of hedychenone, C 20 H 26 O 2 , which is a furanoid diterpene from Hedychium Yunnanense Gagnep, has been identified by single-crystal X-ray diffraction. CommentHedychium Yunnanense Gagnep is one species of Zingiberaceae occurring only in Yunnan Province of China. It is a natural perennial rhyzomatous herb growing at mountains. Several diterpenoids showing cytotoxity have been isolated from this plant (Zhao Qing et al., 1995). From its fresh rhyzomes, we isolated a furanoid diterpene, (I), which has been has been conformed to be Hedychenone by comparison its physical data including IR, UV, MS and NMR spectrum with those reported by Sharma et al. (1975). We report here its crystal structure.The chemical bond length and angle were listed in Table 1 and Table 2, respectively. The C10-C11, C14-C15, C16-C19 and C17-C18 bond length exist at 1.331 (3), 1.319 (3), 1.338 (3), and 1.337 (3) Å, respectively, showing doublebond character. The C9-O1 bond length is 1.233 (3), the C8-C9-O1 and C10-C9--O1 bond angles are 124.0 (2) and 120.5 (2)°, respresenting that C9 is sp 2 hybrid and C9-O1 is double bond. The C19-O2 and C18-O2 bond length are 1.366 (3) and 1.362 (3) Å, respectively, indicating that both of them are single C-O bonds. The other C-C bonds occur in the range 1.442 (3)-1.562 (3)Å exhibiting single-bond character. The torsion angles are listed in Table 3. From the torsion angles, we can see that C16, C17, C18, C19 and O2 of furane ring (ring C) in the molecular formed a slightly distorted planar. Ring A adopts distorted chair configuration. Ring B possesses a sofa conformation. C3 linked with a α-CH 3 (2) and a β-CH 3 (1). C7 linked with β-CH 3 (13). C8 and C12 linked with α-H. It means that the deca-ring adopted trans-form. The double-bond C14-C15 was linked with two trans-H atoms. ExperimentalThe title compounds was isolated from the methanol extracts of fresh rhyzomes of Hedychium Yunnannense Gagnep which were collected from Kunming, Yunnan Province of China in October 1997. RefinementAll H atoms were fixed at ideal positions with common isotropic displacement parameters (U iso = 0.08 Å 2 ). The absolute configuration is indeterminate from the diffraction experiment. The relative configuration agrees with that observed from two-dimensional NMR spectroscopy.
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