Phytochemical analysis of Pinus thunbergii Parl. afforded eleven compounds, two of which were new. One was 8β,12ξ-dihydroxylabd-13(E)-en-19-oic acid and the other was a lignan acetate. The NMR data of all isolated compounds were recorded.
(a) HarmanA.L., KrusbergL.R., NickleW.R. (1986) Pinewood nematode, Bursaphelenchus xylophilus, associated with red pine, Pinus resinosa, in Western Maryland. Journal of Nematology, 96, 393–406; (b) Nakashima H, Eguchi N, Uesugi T, Yamashita N, Matsuda Y. (2016) Effect of ectomycorrhizal composition on survival and growth of Pinus thunbergii seedlings varying in resistance to the pine wilt nematode. Trees, 30, 475–481.
2.
(a) ZhouW., QueM., ZhaoX., YuanQ. (1981) Estimation and use of nutritive ingredients of tree needles of some conifer species. Linchan Huaxue Yu Gongye, 1, 31–39; (b) Yano S, Furuno T. (1994) Resin acids from extracts of pine cones of Kuromatsu (Pinus thunbergii). Mokuzai Gakkaishi, 40, 72–77; (c) Xu G, Su Z. (1994) Study on the terpenoids in Pinus thunbergii Parl. Infected with Bursaphelenchus xylophilus. Linchan Huaxue Yu Gongye, 14, 49–54; (d) Konishi T, Nishio T, Kiyosawa S. (1996) The constituents and analysis of Taxillus kaempferi and the host, Pinus thumbergii. Natural Medicines, 50, 28–33; (e) Liang J, Sun Z, Zhu X, Liang C. (2013) Extraction of chemical constituents of volatile oil from pinecone of Pinus thumbergii Parl. by CO2 supercritical fluid extraction and steam distillation. Yiyao Daobao, 32, 510–513; (f) Shpatov AV, Popov SA, Salnikova OI, Khokhrina EA, Schmidt EN, Um BH. (2013) Low-volatile lipophilic compounds in needles, defoliated twigs, and outer bark of Pinus thunbergii. Natural Product Communications, 8, 1759–1762; (g) Lee D,G, Ryu MJ, Cho S, Chung HS, Lee S. (2014) Identification of afzelin and quercitrin from Pinus koraiensis and their contents in genus Pinus using HPLC/UV analysis. Natural Product Sciences, 20, 206–210.
3.
WahlbergI., EklundA.M., NordforsK., VogtC., EnzellC., BergJ.E. (1988) Tobacco chemistry 69. Five new labdanic compounds from tobacco. Acta Chemica Scandinavica, Ser. B42, 708–716.
(a) PilkingtonL.I., BarkerD. (2012) Asymmetric synthesis and CD investigation of the 1,4-benzodioxane lignans eusiderins A, B, C, G, L, and M. The Journal of Organic Chemistry, 77, 8156–8166; (b) Kim TH, Ito H, Hayashi K, Hasegawa T, Machiguchi T, Yoshida T. (2005) Aromatic constituents from the heartwood of Santalum album L. Chemical and Pharmaceutical Bulletin, 53, 641–644; (c) Arnoldi A, Merlini L. (1985) Asymmetric synthesis of 3-methyl-2-phenyl-1,4-benzodioxanes. Absolute configuration of the neolignans eusiderin and eusiderin C and D. Journal of the Chemical Society-Perkin Transactions 1, 2555–2557.
6.
(a) D'AbroscaB., DellaGrecaM., FiorentinoA., MonacoP., PreviteraL., SimonetA.M., ZarrelliA. (2001) Potential allelochemicals from Sambucus nigra. Phytochemistry, 58, 1073–1081; (b) Popoff T, Theander O. (1975) Two glycosides of a new dilignol from Pinus silvestris. Phytochemsitry, 14, 2065–2066; (c) Van Dyck SMO, Lemiere GLF, Jonckers THM, Dommisse R, Pieters L, Buss V. (2001) Kinetic resolution of a dihydrobenzofuran-type neolignan by lipase-catalyzed acetylation. Tetrahedron: Asymmetry, 12, 785–789.
7.
HongS.S., JeongW., KimJ.K., KwonJ.G., LeeJ.Y., AhnE.K., OhJ., SeoD.W., OhJ.S. (2014) Neolignan inhibitors of antigen-induced degranulation inRBL-2H3 cells from the needles of Pinus thunbergii. Fitoterapia, 99, 347–351.
8.
FangJ.M., LeeC.K., ChengY.S. (1992) Lignans from leaves of Juniperus chinensis. Phytochemistry, 31, 3659–3661.
9.
(a) SunN.J., ChangC.J., CassadyJ.M. (1987) A cytotoxic tetralone derivative from Pararistlochia flos-avis. Phytochemistry, 26, 3051–3053; (b) Nishibe S, Tsukamoto H, Hisada S. (1984) Effects of O-methylation and O-glucosylation on carbon-13 nuclear magnetic resonance chemical shifts of matairesinol, (+)-pinoresinol and +)-epipinoresinol. Chemical and Pharmaceutical Bulletin, 32, 4653–4657; (c) Deyama T, Ikawa T, Kitagawa S, Nishibe S. (1987) The constituents of Eucommia ulmoides OLIV. V. Isolation of dihydroxydehydrodiconiferyl alcohol isomers and phenolic compounds. Chemical and Pharmaceutical Bulletin, 35, 1785–1789.
10.
(a) DeyamaT. (1983) The constituents of Eucommia ulmoides OLIV. I. Isolation of (+)-medioresinol di-O-β-D-glucopyranoside. Chemical and Pharmaceutical Bulletin, 31, 2993–2997; (b) Jong TT, Chau SW. (1998) Antioxidative activities of constituents isolated from Pandanus odoratissimus. Phytochemistry, 49, 2145–2148; (c) Macias F, Simonet AM, Galindo JCG, Castellano D. (1999) Bioactive phenolics and polar compounds from Melilotus messanensis. Phytochemistry, 50, 35–46.
11.
OhtsuH., TanakaR., MatsunagaS., TokudaH., NishinoH. (1999) Anti-tumor-promoting rearranged abietane diterpenes from the leaves of Larix kaempferi. Planta Medica, 65, 664–666.
12.
(a) SeidelV., BaileulF., WaltermanP.G. (2000) (Rel)-1β,2α-di-(2,4-dihydroxy-6-methoxybenzoyl)-3β,4α-di-(4-methoxyphenyl)-cyclobutane and other flavonoids from the aerial parts of Goniothalamus gardneri and Goniothalamus thwaitesii. Phytochemistry, 55, 439–446; (b) Tanaka R, Matsunaga S, Sasaki T. (1989) A new flavanone derivative from the leaves of Tsuga diversifolia. Planta Medica, 55, 570–571.