Flavonoid and Triterpenoid Compounds from the Heartwood of Dalbergia cochinchinensis
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    Abstract:

    To investigate the chemical constituents of Dalbergia cochinchinensi, five neoflavonoids and seven other compounds were isolated from its heartwood by various methods, such as organic solvent extraction, fractionation and chromatographic separation techniques. Based on physical and chemical properties and spectral data, their structures were identified as 7-hydroxy-2',3',4'-trimethoxyisoflavan (1), 6,4'-dihydroxy-7-methoxy-flavan (2), R-dalbergiphenol (3), R-4-methoxydalbergione (4), mimosifoliol (5), R-5-O-methyllatifolin (6), R-latifolin (7), maackiain (8), secundiflorol Ι (9), 3,9-dimethoxy-6H-benzofufo[3,2-c]chromen-6-one (10), muco-dianin C (11), lup-(20)29-ene-2α,3α-diol (12). Compounds 1, 5 and 8-12 were isolated from D. cochinchinensi for the first time.

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    [1] LIN G W. The kind of main wood that national standard mahogany included[J]. For Ecol, 2010(3):24. doi:10.13552/j.cnki.lyyst.2010. 03.016.林国网. 国标红木包括哪些主要木材[J]. 湖南林业, 2010(3):24. doi:10.13552/j.cnki.lyyst.2010.03.016.
    [2] WU P Y, ZHANG Y B, ZHANG J W. A new rosewood species:Dalbergia cochinchinensis[J]. Fujian Sci Technol Trop Crops, 2016, 41(4):51-54. doi:10.3969/j.issn.1006-2327.2016.04.016.吴培衍, 张荣标, 张金文. 红木树种新贵——交趾黄檀[J]. 福建热作科技, 2016, 41(4):51-54. doi:10.3969/j.issn.1006-2327.2016.04. 016
    [3] Palasuwan A, Soogarun S, Lertlum T, et al. Inhibition of heinz body induction in an in vitro model and total antioxidant activity of medicinal thai plants[J]. Asian Pac J Cancer Prev, 2005, 6(4):458-463.
    [4] DONNELLY D M X, NANGLE B J, PRENDERGAST J P, et al. Dalbergia species:V. Isolation of R-5-O-methyllatifolin from Dalbergia cochinchinensis Pierre.[J]. Phytochemistry, 1968, 7(4):647-649. doi:10.1016/S0031-9422(00)88241-2.
    [5] KUROYANAGI M, UENO A, HIRAYAMA Y, et al. Anti-androgen active constituents from Dalbergia cochinchinensis Pierre[J]. Nat Med (Tokyo, Jpn), 1996, 50(6):408-412.
    [6] PATHAK V, SHIROTA O, SEKITA S, et al. Antiandrogenic phenolic constituents from Dalbergia cochinchinensis[J]. Phytochemistry, 1997, 46(7):1219-1223. doi:10.1016/S0031-9422(97)80015-5.
    [7] SVASTI J, SRISOMSAP C, TECHASAKUL S, et al. Dalcochinin-8'-O-β-d-glucoside and its β-glucosidase enzyme from Dalbergia cochin-chinensis[J]. Phytochemistry, 1999, 50(5):739-743. doi:10.1016/S0031-9422(98)00552-4.
    [8] SHIROTA O, PATHAK V, SEKITA S, et al. Phenolic constituents from Dalbergia cochinchinensis[J]. J Nat Prod, 2003, 66(8):1128-1131. doi:10.1021/np0300683.
    [9] AREE T, TIP-PYANG S, SEESUKPHRONRARAK S, et al. 2-(5,7-Dihydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzoquinone iso-flavonequinone)[J]. Acta Crystallogr Sect E:Struct Rep Online, 2003, E59(3):o363-o365. doi:10.1107/S1600536803003684.
    [10] AREE T, TIP-PYANG S, PARAMAPOJN S, et al. 3,9-Dimethoxy-6a, 11a-dihydro-6H-benzo[4,5] furo[3,2-c]chromene-4,10-diol monohydrate[J]. Acta Crystallogr Sect E:Struct Rep Online, 2003, E59(3):o381-o383. doi:10.1107/S1600536803004227.
    [11] LIU R H, WEN X C, LI Y Y, et al. Chemical constituents from Dalbergia cochinchinensis[J]. J. Chin Med Mat, 2015, 38(9):1868-1871. doi:10.13863/j.issn1001-4454.2015.09.017.刘荣华, 温新潮, 李于益, 等. 交趾黄檀化学成分研究[J]. 中药材, 2015, 38(9):1868-1871. doi:10.13863/j.issn1001-4454.2015.09.017.
    [12] LIU R H, WEN X C, ZHANG P Z, et al. Chemical constituents of isofla-vonoids from Dalbergia cochinchinensis[J]. Chin Trad Herb Drugs, 2015, 46(19):2851-2855. doi:10.7501/j.issn.0253-2670.2015.19.006.刘荣华, 温新潮, 张普照, 等. 交趾黄檀异黄酮类化学成分研究[J]. 中草药, 2015, 46(19):2851-2855. doi:10.7501/j.issn.0253-2670.2015. 19.006.
    [13] LIU R H, WEN X C, SHAO F, et al. Flavonoids from heartwood of Dalbergia cochinchinensis[J]. Chin Herb Med, 2016, 8(1):89-93. doi:10.1016/S1674-6384(16)60014-X.
    [14] LIU R H, LI Y Y, SHAO F, et al. A new chalcone from the heartwood of Dalbergia cochinchinensis[J]. Chem Nat Compd, 2016, 52(3):405-408. doi:10.1007/s10600-016-1659-7.
    [15] EL-SEBAKHY N A, ASAAD A M, ABDALLAH R M, et al. Anti-microbial isoflavans from Astragalus species[J]. Phytochemistry, 1994, 36(6):1387-1389. doi:10.1016/S0031-9422(00)89728-9.
    [16] MUANGNOICHAROEN N, FRAHM A W. Neoflavanoids of Dal-bergia parviflora[J]. Phytochemistry, 1982, 21(3):767-772. doi:10. 1016/0031-9422(82)83184-1.
    [17] KHAN W N, LODHI M A, ALI I, et al. New natural urease inhibitors from Ranunculus repens[J]. J Enzyme Inhib Med Chem, 2006, 21(1):17-19. doi:10.1080/14756360500319210.
    [18] FULLAS F, KORNBERG L J, WANI M C, et al. Two new aromatic constituents from the rootwood of Aeschynomene mimosifolia[J]. J Nat Prod, 1996, 59(2):190-192. doi:10.1021/np960052v.
    [19] SEKINE N, ASHITANI T, MURAYAMA T, et al. Bioactivity of latifolin and its derivatives against termites and fungi[J]. J Agric Food Chem, 2009, 57(13):5707-5712. doi:10.1021/jf900719p.
    [20] PARK J A, JA KIM H, JIN C, et al. A new pterocarpan, (-)-maackiain sulfate, from the roots of Sophora subprostrata[J]. Arch Pharm Res, 2003, 26(12):1009-1013. doi:10.1007/BF02994750.
    [21] TIAN F, MCLAUGHLIN J L. Bioactive flavonoids from the black locust tree, Robinia pseudoacacia[J]. Pharm Biol, 2000, 38(3):229-234. doi:10.1076/1388-0209(200007)3831-SFT229.
    [22] TANG L N, PANG Y L, YAN Q, et al. Synthesis of coumestan deriva-tives via FeCl3-mediated oxidative ring closure of 4-gydroxy coumarins[J]. J Org Chem, 2011, 76(8):2744-2752. doi:10.1021/jo2000644.
    [23] GONG T, WANG D X, YANG Y, et al. A novel 3-arylcoumarin and three new 2-arylbenzofurans from Mucuna birdwoodiana[J]. Chem Pharm Bull, 2010, 58(2):254-256. doi:10.1248/cpb.58.254.
    [24] KUMAR N, SESHADRI T R. Triterpenoids of Pterocarpus santalinus:constitution of a new lupene diol[J]. Phytochemistry, 1975, 14(2):521-523. doi:10.1016/0031-9422(75)85121-1.
    [25] PAN Z H, WANG Y Y, LI M M, et al. Terpenoids from Salvia trijuga[J]. J Nat Prod, 2010, 73(6):1146-1150. doi:10.1021/np100250w.
    [26] KUMAR P, KUSHWAHA P, KHEDGIKAR V, et al. Neoflavonoids as potential osteogenic agents from Dalbergia sissoo heartwood[J]. Bioorg Med Chem Lett, 2014, 24(12):2664-2668. doi:10.1016/j.bmcl. 2014.04.056.
    [27] LIU R H, LIN S, ZHANG P Z, et al. Neoflavonoids and their phar-macological activities in Dalbergia genus[J]. China J Chin Mat Med, 2017, 42(24):4707-4715. doi:10.19540/j.cnki.cjcmm.20170928.013.刘荣华, 林帅, 张普照, 等. 黄檀属植物新黄酮类化学成分与药理活性研究进展[J]. 中国中药杂志, 2017, 42(24):4707-4715. doi:10. 19540/j.cnki.cjcmm.20170928.013.
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钟艳霞,陈郊,莫新良,徐志防,邱声祥,刘新红.交趾黄檀心材的黄酮类和三萜类成分[J].热带亚热带植物学报,2021,29(5):573~578

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History
  • Received:April 26,2021
  • Revised:June 08,2021
  • Online: September 23,2021
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