Download PDF
Planta Med 2016; 82(08): 742-746
DOI: 10.1055/s-0042-104349
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Diterpenoids from the Roots of Aralia melanocarpa

Zhi-Yong Jiang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
,
Chun-Tao Yang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
,
Shu-Qun Hou
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
,
Kai Tian
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
,
Wei Wang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
,
Qiu-Fen Hu
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
,
Xiang-Zhong Huang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
2   Key Laboratory of Comprehensive Utilization of Mineral Resources in Ethnic Regions, Yunnan Minzu University, Kunming, Yunnan, P. R. China
3   Key Laboratory of Yi Medicine Resources & Pharmacodynamics Research, Kunming, Yunnan, P. R. China
› Author Affiliations
Further Information

Publication History

received 23 September 2015
revised 12 February 2016

accepted 27 February 2016

Publication Date:
19 April 2016 (online)

    Permissions and Reprints

Abstract

Five new diterpenoids (1–5) were isolated from the roots of Aralia melanocarpa, together with four known compounds, 7β-hydroxy-ent-pimara-8(14),15-diene-19-oic acid (6), 18-norpimara-8(14),15-dien-4-ol (7), ent-16βH,17-isovalerate-kauran-19-oic acid (8), and ent-16α,17-dihydroxykauran-19-oic acid (9). Based on the MS, IR, and NMR spectral analysis, the structures of the five new diterpenoids (1–5) were elucidated. The cytotoxic activities of compounds 1–9 were assayed, and compounds 1 and 2 showed cytotoxicity in four cancer cell lines with IC50s from 4.2 to 8.2 µM.

Key words

Aralia melanocarpa - Araliaceae - ent-pimarane - diterpenoid - cytotoxicity

Supporting Information

 

  • References

  • 1 Flora of China Editorial Committee, Chinese Academy of Sciences. Flora of China, Vol. 54. Beijing: Science Press; 1978: 173-174
    Google Scholar
  • 2 Collection of Chinese Herbal Medicines Compilation Group. Collection of Chinese Herbal Medicines, Vol. 2. Beijing: Peopleʼs Medical Publishing House; 1978: 197
    Google Scholar
  • 3 Hanson JR, White AF. Diterpenes of spikenard root (Aralia racemosa). Phytochemistry 1970; 9: 1359-1361
    CrossrefPubMedGoogle Scholar
  • 4 Kang OH, Chae HS, Choi JG, Oh YC, Lee YS, Kim JH, Seung MJ, Jang HJ, Bae KH, Lee JH, Shin DW, Kwon DY. ent-Pimara-8(14), 15-dien-oic acid isolated from the roots of Aralia cordata inhibits induction of inflammatory mediators by blocking NF-κB activation and mitogen-activated protein kinase pathways. Eur J Pharmacol 2008; 601: 179-185
    CrossrefPubMedGoogle Scholar
  • 5 Choi RJ, Shin EM, Jung HA, Choi JS, Kim YS. Inhibitory effects of kaurenoic acid from Aralia continentalis on LPS-induced inflammatory response in RAW264.7 macrophages. Phytomedicine 2011; 18: 677-682
    CrossrefPubMedGoogle Scholar
  • 6 Cho JH, Lee JY, Sim SS, Whang WK, Kim CJ. Inhibitory effects of diterpene acids from root of Aralia cordata on IgE-mediated asthma in guinea pigs. Pulm Pharmacol Ther 2010; 23: 190-199
    CrossrefPubMedGoogle Scholar
  • 7 Lyu JH, Lee GS, Kim KH, Kim HW, Cho SI, Jeong SI, Kim HJ, Ju YS, Kim HK, Sadikot RT, Christman JW, Oh SR, Lee HK, Ahn KS, Joo M. ent-Kaur-16-en-19-oic acid, isolated from the roots of Aralia continentalis, induces activation of Nrf2. J Ethnopharmacol 2011; 137: 1442-1449
    CrossrefPubMedGoogle Scholar
  • 8 Wang QH, Zhang J, Ma X, Ye XY, Yang BY, Xia YG, Kuang HX. A new triterpenoid saponin from the leaves of Aralia elata . Chin J Nat Med 2011; 9: 17-21
    PubMedGoogle Scholar
  • 9 Hsiao JJ, Chiang HC. Lignans from the wood of Aralia bipinnata . Phytochemistry 1995; 39: 899-902
    CrossrefPubMedGoogle Scholar
  • 10 Miyase T, Sutoh N, Zhang DM, Ueno A. Araliasaponins XII–XVIII, triterpene saponins from the roots of Aralia chinensis . Phytochemistry 1996; 42: 1123-1130
    CrossrefPubMedGoogle Scholar
  • 11 Nhiem NX, Lim HY, Kiem PV, Minh CV, Thu VK, Tai BH, Quang TH, Song SB, Kim YH. Oleanane-type triterpene saponins from the bark of Aralia elata and their NF-κB inhibition and PPAR activation signal pathway. Bioorg Med Chem Lett 2011; 21: 6143-6147
    CrossrefPubMedGoogle Scholar
  • 12 Satoh Y, Sakai S, Katsumata M, Nagasao M, Miyakoshi M, Ida Y, Shoji J. Oleanolic acid saponins from root-bark of Aralia elata . Phytochemistry 1994; 36: 147-152
    CrossrefPubMedGoogle Scholar
  • 13 Hu M, Ogawa K, Sashida Y, Xiao PG. Triterpenoid glucuronide saponins from root-bark of Aralia armata . Phytochemistry 1995; 39: 179-184
    CrossrefPubMedGoogle Scholar
  • 14 Lee MK, Hung TM, Min BS, Lee IS, Na MK, Woo MH, Son JK, Kim YH, Choi JS, Bae KH. Quantitative determination of diterpenoids from the roots of Aralia cordata . Nat Prod Sci 2009; 15: 50-54
    PubMedGoogle Scholar
  • 15 Oh HL, Lim HY, Park Y, Lim Y, Koh HC, Cho YH, Lee CH. HY253, a novel compound isolated from Aralia continentalis, induces apoptosis via cytochrome c-mediated intrinsic pathway in HeLa cells. Bioorg Med Chem Lett 2009; 19: 797-799
    CrossrefPubMedGoogle Scholar
  • 16 Oh HL, Lee CH. HY251, a novel decahydrocyclopenta[a]indene analog, from Aralia continentalis induces apoptosis via down-regulation of AR expression in human prostate cancer LNCaP cells. Bioorg Med Chem Lett 2011; 21: 1347-1349
    CrossrefPubMedGoogle Scholar
  • 17 Lee JH, Jeong CS, Lee JH, Jeong C. Suppressive effects on the biosynthesis of inflammatory mediators by Aralia elata extract fractions in macrophage cells. Environ Toxicol Pharmacol 2009; 28: 333-341
    CrossrefPubMedGoogle Scholar
  • 18 Chung YS, Choi YH, Lee SJ, Choi S, Lee J, Kim H, Hong EK. Water extract of Aralia elata prevents cataractogenesis in vitro and in vivo . J Ethnopharmacol 2005; 101: 49-54
    CrossrefPubMedGoogle Scholar
  • 19 Jung HA, Lee EJ, Kim JS, Kang SS, Lee JH, Min BS, Choi JS. Cholinesterase and BACE1 inhibitory diterpenoids from Aralia cordata . Arch Pharm Res 2009; 32: 1399-1408
    CrossrefPubMedGoogle Scholar
  • 20 Lee CK, Fang JM, Cheng YS. Norditerpenes from Juniperus chinensis . Phytochemistry 1995; 39: 391-394
    CrossrefPubMedGoogle Scholar
  • 21 Kim YH, Kim HS, Lee SW, Uramoto M, Lee JJ. Kaurane derivatives from Acanthopanax koreanum . Phytochemistry 1995; 39: 449-451
    CrossrefPubMedGoogle Scholar
  • 22 Lin AS, Lin CR, Du YC, Lübken T, Chiang MY, Chen IH, Wu CC, Hwang TL, Chen SL, Yen MH, Chang FR, Wu YC. Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana . Planta Med 2009; 75: 256-261
    Article in Thieme ConnectPubMedGoogle Scholar
  • 23 Rudi A, Kashman Y. Chelodane, barekoxide, and zaatirin- three new diterpenoids from the marine sponge Chelonaplysilla erecta . J Nat Prod 1992; 55: 1408-1414
    CrossrefPubMedGoogle Scholar
  • 24 Kuniyoshi M, Marma MS, Higa T, Bernardinelli G, Jefford CW. 3-Bromobarekoxide, an unusual diterpene from Laurencia luzonensis . Chem Commun 2000; 13: 1155-1156
    PubMedGoogle Scholar
  • 25 Zinkel DF, Spalding BR. Structure of strobic acid. Tetrahedron 1973; 29: 1441-1444
    CrossrefPubMedGoogle Scholar
  • 26 Demaro PV, Farkas E, Doddrell D, Mylari BL, Wenkert E. Pyridine-induced solvent shifts in the nuclear magnetic resonance spectra of hydroxylic compounds. J Am Chem Soc 1968; 90: 5480-5486
    CrossrefPubMedGoogle Scholar
  • 27 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63
    CrossrefPubMedGoogle Scholar