A new diphenyl ether glycoside, xylosmaloside (1), was isolated from the MeOH extract of Xylosma longifolium Clos. The structure of xylosmaloside (1) was elucidated using MS analyses, extensive 2D-homo and heteronuclear NMR data interpretation and the chemical conversions. Xylosmaloside (1) showed stronger antioxidant activity than ascorbic acid.
(a) UmeyamaA., MatsuokaN., MineR., NakataA., ArimotoE., MatsuiM., ShojiN., AriharaS., TakeiM., HashimotoT. (2010) Polyacetylene diols with antiproliferative and driving Th1 polarization effects from the marine sponge Callyspongia sp. Journal of Natural Medicines, 64, 93–97; (b) Umeyama A, Takahashi K, Grudniewska A, Shimizu M, Hayashi S, Kato M, Okamoto Y, Suenaga M, Ban S, Kumada T, Ishiyama A, Iwatsuki M, Otoguro K, Ōmura S, Hashimoto T. (2014) In vitro antitrypanosomal activity of the cyclodepsipeptides, cardinalisamides A-C, from the insect pathogenic fungus Cordyceps cardinalis NBRC 103832. The Journal of Antibiotics, 67, 163–167; (c) Umeyama A, Ohta C, Shino Y, Okada M, Nakamura Y, Hamagaki T, Imagawa H, Suenaga M, Tanaka M, Ishiyama A, Iwatsuki, K, Otoguro M, Ōmura S, Hashimoto T. (2014) Three lanostane triterpenoids with antitrypanosomal activity from the fruiting body of Hexagonia tenuis. Tetrahedron, 70, 8312–8315; (d) Kokudo N, Okazoe M, Takahashi J, Iseki K, Yoshikawa K, Imagawa H, Hashimoto T, Noji M, Umeyama A. (2016) Six new lanostane triterpenoids from fruiting body of Tyromyces sambuceus and antiproliferative activity. Natural Product Communications, 11, 169–173; (e) Ganaha M, Yoshii K, Otsuki Y, Iguchi M, Okamoto Y, Iseki K, Ban S, Ishiyama A, Hokari R, Iwatsuki M, Otoguro K, Omura S, Hashimoto T, Noji M, Umeyama A. (2016) In vitro antitrypanosomal activity of the secondary metabolites from the mutant strain IU-3 of the insect pathogenic fungus Ophiocordyceps coccidiicola NBRC 100683. Chemical and Pharmaceutical Bulletin, 64, 988–990; (f) Nishio A, Mikami H, Imagawa H, Hashimoto T, Tanaka M, Ito T, Iguchi M, Iseki K, Noji M, Umeyama A. (2016) Two novel diphenolic metabolites form the inedible mushroom Thelephora palmata. Natural Product Communications, 11, 1147–1149.
2.
ParveenM., GhalibR.M. (2012) Flavonoids and antimicrobial activity of leaves of Xylosma longifolium. Journal of Chilean Chemical Society, 57, 989–991.
3.
DeviW.R., SinghS.B., SinghC.B. (2013) Antioxidant and anti-dermatophytic properties leaf and stem bark of Xylosma longifolium clos. BMC Complementary and Alternative Medicine, 13, 155–163.
4.
BohlmannF., BohlmannR. (1980) Three guanianolides from Hypochoeris radicata. Phytochemistry, 19, 2045–2046.
5.
UluvelenA., TimmermannB.N., MabryT.J. (1980) Flavonoids from Brickellia chlorolepis and B. dentate. Phytochemistry, 19, 905–908.
6.
KumarM., RawatP., KhanM.F., TamarkarA.K., SrivastavaA.K., AryaK.R., MauryaR. (2010) Phenolic glycosides from Dodecadenia grandiflora and their glucose-6-phosphatase inhibitory activity. Fitoterapia, 81, 475–479.
7.
AdinarayanaD., GunasekarD., RamachandraiahP., SeligmannO., WagnerH. (1980) Tirumalin, a new prenylated dihydroflavonol from Rhynchosia cyanosperma. Phytochemistry, 19, 478–480.
OtsukaH., YaoM., KamadaK., TakedaY. (1995) Alangionosides G-M: Glycosides of megastigmane derivatives from the leaves of Alangium premnifolium. Chemical and Pharmaceutical Bulletin, 43, 754–759.
10.
TanakaT., NakashimaT., UedaT., TomiiK., KounoI. (2007) Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chemical and Pharmaceutical Bulletin, 55, 899–901.
11.
(a) ZhaoH., WangG.Q., TongX.P., ChenG.D., HuangY.F., CuiJ.Y., KongM.Z., GuoL.D., ZhengY.Z., YaoX.S., GaoH. (2014) Diphenyl ethers form Aspergillus sp. and their anti-Aβ42 aggregation activities. Fitoterapia, 98, 77–83; (b) Ly HD, Vo TN, Duong TH, Nguyen TD, Nguyen KPP. (2015) A new depside and two new diphenyl ether compounds from the lichen Ramalina farinacea (L.) Ach. Phytochemistry Letters, 11, 146–150; (c) Liu H, Lohith K, Rossario M, Pulliam TH, O'Connor RD, Bell LJ, Bewley CA. (2016) Polybrominated diphenyl ethers: Structure determination and trends in antibacterial activity. Journal of Natural Products, 79, 1872–1876.
12.
UkedaH., KawanaD., MaedaS., SawamuraM. (1999) Spectrophotometric assay for superoxide dismutase based on the reduction of highly water-soluble tetrazolium salts by xanthine-xanthine oxidase. Bioscience, Biotechnology, and Biochemistry, 63, 485–488.
