Nine abietane diterpenoids (1–9) were isolated from the stems of Clerodendrum trichotomum Thunb. and identified by spectroscopic methods. Furthermore, corrected NMR data is provided for Villosin C (1) and B (2) whose absolute configurations were elucidated from circular dichroism (CD) data. All isolates were tested for cytotoxicity against four cancer cell lines (A549, HepG-2, MCF-7 and 4T1). Compounds 1, 2, 3, 4 and 8 were found to have remarkable cytotoxic effects with IC50 values ranging from 8.79 to 35.46 μM.
(a) PengJ., ChenS.L. (1982) Verbenaceae: Flora Republicae Popularis Sinicae.Science Press, Beijing, 186; (b) Nanjing University of Chinese Medicine. (2006) The Dictionary of Traditional Chinese Medicine. Shanghai Science and Technology Press, Shanghai, 2654–2655
2.
(a) ChaeS., KangK.A., KimJ.S., HyunJ.W., KangS.S. (2006) Trichotomoside: a new antioxidative phenylpropanoid glycoside from Clerodendron trichotomum. Chemistry & Biodiversity, 3, 41–48; (b) Kim HJ, Woo ER, Shin CG, Hwang DJ, Park H, Lee YS. (2001) HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum. Archives of Pharmacal Research, 24, 286–291; (c) Kim KH, Kim S, Jung MY, Ham IH, Whang WK. (2009) Anti-inflammatory phenylpropanoid glycosides from Clerodendron trichotomum leaves. Archives of Pharmacal Research, 32, 7–13; (d) Kang DG, Lee YS, Kim HJ, Lee YM, Lee HS. (2003) Angiotensin converting enzyme inhibitory phenylpropanoid glycosides from Clerodendron trichotomum. Journal of Ethnopharmacology, 89, 151–154; (e) Lee JY, Lee JG, Sim SS, Whang WK, Kim CJ. (2011) Anti-asthmatic effects of phenylpropanoid glycosides from Clerodendron trichotomum leaves and Rumex gmelini herbes in conscious guinea-pigs challenged with aerosolized ovalbumin. Phytomedicine, 18, 134–142; (f) Nagao T, Abe F, Okabe H. (2001) Antiproliferative constituents in the plants 7. Leaves of Clerodendron bungei and leaves and bark of C. trichotomum. Biological & Pharmaceutical Bulletin, 24, 1338–1341.
3.
(a) MinY.S., YimS.H., BaiK.L., ChoiH.J., JeongJ.H., SongH.J., ParkS.Y., HamI., WhangW.K., SohnU.D. (2005) The effects of apigenin-7-O-β-D-glucuronopyranoside on reflux oesophagitis and gastritis in rats. Autonomic and Autacoid Pharmacology, 25, 85–91; (b) Okigawa M, Hatanaka H, Kawano N, Matsunaga I, Tamura Z. (1970) A new glycoside, acacetin-7-glucurono-(1 lead to 2)-glucuronide from the leaves of Clerodendron trichotomum. Tetrahedron Letters, 29, 35–36.
4.
(a) KawaiK., AmanoT., NishidaR., KuwaharaY., FukamiH. (1998) Clerodendrins from Clerodendrum trichotomum and their feeding stimulant activity for the turnip sawfly. Phytochemistry, 49, 1975–1980; (b) Wang WX, Xiong J, Tang Y, Zhu JJ, Li M, Zhao Y, Yang GX. (2013) Rearranged abietane diterpenoids from the roots of Clerodendrum trichotomum and their cytotoxicities against human tumor cells. Phytochemistry, 89, 89–95.
5.
(a) IwadareS., ShizuriY., SasakiK., HirataY. (1974) Isolation and structure of trichotomine and trichotomine G1. Tetrahedron, 30, 4105–4111; (b) Irikawa H, Toyoda Y, Kumagai H, Okumura Y. (1989) Isolation of four 2,3,5,6,11,11-b-hexahydro-3-oxo-1H-indolizino[8,7-b]indole-5-carboxylic acids from Clerodendron trichotomum Thunb and properties of their derivatives. Bulletin of the Chemical Society of Japan, 62, 880–887; (c) Toyoda Y, Kumagai H, Irikawa H, Okumura Y. (1982) Isolation of four indolizino[8,7-b]indole-5-carboxylic acids from Clerodendron trichotomum Thunb. Chemistry Letters, 903–906.
6.
ChoiJ.W., ChoE.J., LeeD.G., ChoiK., KuJ., ParkK.W., LeeS. (2012) Antibacterial activity of triterpenoids from Clerodendron trichotomum. Journal of Applied Biological Chemistry, 55, 169–172.
7.
(a) KawanoN., MiuraH., KamoY. (1967) Studies on the components of Clerodendron tichotomum Thunb. Yakugaku Zasshi, 87, 1146–1148; (b) Xu RL, Wang R, Ding L, Shi YP. (2013) New cytotoxic steroids from the leaves of Clerodendrum trichotomum. Steroids, 78, 711–716.
DorsazA.C., MarstonA., Stoeckli-EvansH., MsonthiJ.D., HostettmannK. (1985) Phytochemistry of African medicinal plants. 4. Uncinatone, a new antifungal hydroquinone diterpenoid from Clerodendrum uncinatum Schinz. Helvetica Chimica Acta, 68, 1605–1610.
11.
CarreirasM.C., RodriguezB., de la TorreM.C., PeralesA., TorresM.R., SavonaG., PiozziF. (1990) Rearranged abietane diterpenoids from the root of teucrium polium subsp. vincentinum. Tetrahedron, 46, 847–860.
12.
SenguptaP., ChoudhuriS.N., KhastgirH.N. (1960) Constituents of the trunk bark of Melia azadirachta Linn. and the structure of the ketophenol, nimbiol. Tetrahedron, 10, 45–54.
13.
CuadradoM.J.S., BrunoM., De La TorreM.C., PiozziF., SavonaG., RodríguezB. (1992) Rearranged abietane diterpenoids from the root of two Teucrium species. Phytochemistry, 31, 1697–1701.
14.
(a) LemiereG., GaoM., De GrootA., DommisseR., LepoivreJ., PietersL., BussV. (1995) 3′,4-Di-O-methylcedrusin: synthesis, resolution and absolute configuration. Journal of the Chemical Society Perkin Transactions, 1, 1775–1779; (b) Matsuda N, Sato H, Yaoita Y, Kikuchi M. (1996) Isolation and absolute structures of the neolignan glycosides with the enantiometric aglycones from the leaves of Viburnum awabuki K. Koch. Chemical and Pharmaceutical Bulletin, 44, 1122–1123.
MosmannT. (1983) Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65, 55–63.