Two new abietane-type diterpenoids, 15-hydroxy-12-O-methylsugiol (1) and 2a-hydroxy-12-O-methylsugiol (2) were isolated from the methanol extract of the bark of Cryptomeria japonica. Their structures were elucidated on the basis of spectroscopic analysis and comparison of NMR data with those of known analogues. Compounds 2 showed 13.5% inhibition towards xanthine oxidase enzyme at the concentration of 75 μM
GanWS. (1958) Manual of Medicine Plants in Taiwan, Vol 1, National Research Institute of Chinese Medicine, Taipei, 54.
2.
ShiehM, IizukaY, MatsubaraY. (1981) Monoterpenoid and sesquiterpenoid constituents of the essential oil of sugi (Cryptomeria japonica D. Don.). Agricultural and Biological Chemistry, 45, 1493–1495.
3.
NagahamaS, TazakiM. (1993) Terpenoids of wood oil of sugi (Cryptomeria japonica). Peculiarities of Obisugi variety. Mokuzai Gakkaishi, 39, 1077–1083.
4.
NagahamaS, TazakiM, SanetikaT, NishimuraK, TajimaM. (1996) Terpenoids of the wood oil of sugi (Cryptomeria japonica). 3. Components of Yakusugi. Mokuzai Gakkaishi, 42, 1121–1126.
5.
NagahamaS, TazakiM, NomuraH, NishimuraK, TajimaM, IwasitaY. (1996) Terpenoids of the wood oil of sugi (Cryptomeria japonica) IV. Components of form Yabukuguri. Mokuzai Gakkaishi, 42, 1127–1133.
6.
NagahamaS, TazakiM, SanetikaT, NishimuraK, TajimaM. (1998) Terpenoids of the wood oil of sugi (Cryptomeria japonica) V. Components of from Ayasugi. Mokuzai Gakkaishi, 44, 282–286.
7.
MoritaS, YatagaiM, FujitaS. (1995) Distributions of the extracts and sesquiterpenes in the trunk of Yakusugi (Cryptomeria japonica). Mokuzai Gakkaishi, 41, 938–944.
8.
NaritaH, YatagaiM, OhiraT. (2006) Chemical composition of the essential oils from bogwood of Cryptomeria japonica D. Don. Journal of Essential Oil Research, 18, 68–70.
9.
ShimizuM, TsujiH, ShogawaH, FukumuraH, TanaamiS, HayashiT, ArisawaM, MoritaN. (1988) Anti-inflammatory constituents of topically applied crude drugs. II. Constituents and anti-inflammatory effect of Cryptomeria japonica D. Don. Chemical & Pharmaceutical Bulletin, 36, 3967–3973.
10.
NagahamaS, TazakiM, KobayashiH, SumimotoM. (1993) Sesquiterpene alcohols from Cryptomeria japonica and C. Fortunei leaf oil. Phytochemistry, 33, 879–882.
11.
SuWC, FangJM, ChengYS. (1993) Hexacarbocyclic triterpenes from leaves of Cryptomeria japonica. Phytochemistry, 34, 779–782.
12.
SuWC, FangJM, ChengYS. (1994) Abietanes and kauranes from leaves of Cryptomeria japonica. Phytochemistry, 35, 1279–1284.
13.
SuWC, FangJM, ChengYS. (1994) Labdanes from leaves of Cryptomeria japonica. Phytochemistry, 37, 1109–1114.
14.
SuWC, FangJM, ChengYS. (1995) Sesquiterpenes from leaves of Cryptomeria japonica. Phytochemistry, 39, 603–607.
15.
SuWC, FangJM, ChengYS. (1996) Diterpenoids from leaves of Cryptomeria japonica. Phytochemistry, 41, 255–261.
16.
SuWC, FangJM, ChengYS. (1995) Synthesis and structure determination of cryptomanhydride, an uncommon natural terpenic anhydride. Tetrahedron Letters, 36, 5367–5370.
17.
ChenXH, KimCS, KashiwagiT, TebayashiSI, HoriikeM. (2001) Antifeedants against Acusta despesta from the Japanese cedar, Cryptomeria japonica II. Bioscience, Biotechnology, and Biochemistry, 65, 1434–1437.
18.
MorisawaJ, KimCS, KashiwagiT, TebayashiSI, HoriikeM. (2002) Repellents in the Japanese cedar, Cryptomeria japonica, against the pill-bug, Armadillidium vulgare. Bioscience, Biotechnology, and Biochemistry, 66, 2424–2428.
19.
AriharaS, UmeyamaA, BandoS, ImotoS, OnoM, TaniM.YoshikawaK.A new abietane and two dimeric abietane diterpenes from the black heartwood of Cryptomeria japonica. (2004) Chemical & Pharmaceutical Bulletin, 52, 354–358.
20.
ShibuyaT. (1992) Cryptoquinonemethides D and E, C 30-terpene quinone methides, from Cryptomeria japonica. Phytochemistry, 31, 4289–4294.
21.
YoshikawaK, TanakaT, UmeyamaA, AriharaS. (2006) Three abietane diterpenes and two diterpenes incorporated sesquiterpenes from the bark of Cryptomeria japonica. Chemical & Pharmaceutical Bulletin, 54, 315–319.
22.
YoshikawaK, SuzukiK, UmeyamaA, AriharaS. (2006) Abietane diterpenoids from the barks of Cryptomeria japonica. Chemical & Pharmaceutical Bulletin, 54, 574–578.
23.
KofujitaH, OtaM, TakahashiK, KawaiY, HayashiY. (2002) A diterpene quinone from the bark of Cryptomeria japonica. Phytochemistry, 61, 895–898.
24.
MoiteiroC, EstevesT, RamalhoL, RojasR, AlvarezS, ZacchinoS, BragançaH. (2013) Essential oil characterization of two Azorean Cryptomeria japonica populations and their biological evaluations. Natural Product Communications, 8, 1785-1790.
25.
KofujitaH, OtaM, TakahashiK, KawaiY, HayashiY. (2002) A diterpene quinone from the bark of Cryptomeria japonica, Phytochemistry, 61, 895–898.
26.
HoribaH, NakagawaT, ZhuQ, AshourA, WatanabeA, ShimizuK. (2016) Biological activities of extracts from different parts of Cryptomeria japonica. Natural Product Communications, 11, 1337-1342.
27.
ShyurLF, HuangCC, LoCP, ChiuCY, ChenYP, WangSY, ChangST. (2008) Hepatoprotective phytocompounds from Cryptomeria japonica are potent modulators of inflammatory mediators. Phytochemistry, 69, 1348–1358.
28.
WuB, KashiwagiT, KurodaI, ChenXH, TebayashiSI, KimCS. (2008) Antifeedants against Locusta migratoria from the Japanese Cedar, Cryptomeria japonica II. Bioscience, Biotechnology, and Biochemistry, 72, 611–614.
29.
MorisawaJ, KimCS, KashiwagiT, TebayashiS, HoriikeM, (2002) Repellents in the Japanese cedar, Cryptomeria japonica, against the pill-bug, Armadillidium vulgare. Bioscience, Biotechnology, and Biochemistry, 66, 2424–2428.
30.
ChenCC, WuJH, YangNS, ChangJY, KuoCC, WangS Y, KuoYH. (2010) Cytotoxic C35 terpenoid cryptotrione from the bark of Cryptomeria japonica. Organic Letters, 12, 2786–2789.
31.
ChangCI, ChenCC, WangSY, ChaoeC Y, ChaoLK, ChenJJ, KoHH, ChenCC, KuoYH. (2016) Three new abietane-type diterpenes from the bark of Cryptomeria japonica. Helvetica Chimica Acta, 99, 710–715.
32.
ChangCI, ChenCC, WangS Y, ChangHS, ChaoLK, ChenJJ, ChenCC, KuoYH. (2017) Three new abietane-type diterpenes from the bark of Cryptomeria japonica. Phytochemistry Letters, 19, 46–49.
33.
ChangCI, ChenCC, ChaoC Y, KoHH, ChangHS, WangSY, ChenJJ, ChenCC, KuoYH. (2017) Two new abietane-type diterpenes from the bark of Cryptomeria japonica. Natural Product Communications, 12, 1553–1555.
34.
ChangCI, WangSS, WuMD, ChengMJ, KoHH, ChangHS, ChenJJ, ChenCC, KuoYH. (2017) Two new sesquarterpenoids from the bark of Cryptomeria japonica. Phytochemistry Letters, 22, 56–60.
35.
KuoYH, YuMT. (1996) Dehydroabietane diterpenes from Juniperus formosana hay. var. concolor hay. Phytochemistry, 42, 779–781.
36.
GonzalezAG, HerreraJR, LuisJG, RaveloAG, FerroEA. (1988) Terpenes and flavones of Salvia cardiophylla. Phytochemistry, 27, 1540–1541.
37.
CosP, YingL, CalommeM, HuJP, CimangaK, VanPB, PietersL, VlietinckAJ, VandenBD. (1998) Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. Journal of Natural Products, 61, 71–76.
38.
LinCN, HuangAM, LinKW, HourTC, KoHH, YangSC, PuYS. (2010) Xanthine oxidase inhibitory terpenoids of Amentotaxus formosana protect cisplatin-induced cell death by reducing reactive oxygen species (ROS) in normal human urothelial and bladder cancer cells. Phytochemistry, 71, 2140–2146.
39.
ChenCH, ChanH-C, ChuYT, HoHY, ChenPY, LeeTH, LeeCK. (2009) Antioxidant activity of some plant extracts towards xanthine oxidase, lipoxygenase and tyrosinase. Molecules, 14, 2947–2958.
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