Planta Med 2013; 79(15): 1453-1460
DOI: 10.1055/s-0033-1350769
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Novel Sesquiterpenoid Glycosides and Sesquiterpenes from the Roots of Illicium henryi

Peng-Yu Zhuang
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Gui-Jie Zhang
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Xiao-Jing Wang
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Yan Zhang
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Shi-Shan Yu
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Shuang-Gang Ma
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Yun-Bao Liu
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Jing Qu
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Yong Li
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
,
Nai-Hong Chen
State Key Laboratory of Bioactive Substances and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 02 February 2013
revised 02 July 2013

accepted 22 July 2013

Publication Date:
27 August 2013 (online)

Abstract

Seven new sesquiterpenoid glycosides, consisting of one thapsan-type (1), two capnellane-type (2 and 3), four floridanolide sesquiterpene glycosides (47), and one new azulene-type sesquiterpene (8), along with six known sesquiterpenes (914) were isolated from the roots of Illicium henryi. The structures of 18 were elucidated by extensive spectroscopic analyses and chemical methods. The absolute configurations of 1, 2, and 8 were determined based on Rh2(OCOCF3)4-induced CD, Mo2(OAc)4-induced CD data, and calculated electronic circular dichroism (ECD), respectively. Compound 1 was found to exhibit weak neurotoxicant activity.

Supporting Information

 
  • References

  • 1 Huang JM, Yang CS, Kondo M, Nakade K, Takahashi H, Takaoka S, Fukuyama Y. Merrillianin, a unique seco-prezizaane-type sesquiterpene, and (6R)-pseudomajucin from Illicium merrillianum . Tetrahedron 2002; 58: 6937-6941
  • 2 Schmidt TJ. Novel seco-prezizaane sesquiterpenes from North American Illicium species. J Nat Prod 1999; 62: 684-687
  • 3 Yamada K, Takada S, Nakamura S, Hirata Y. Structures of anisatin and neoanisatin toxic sesquiterpenes from Illicium anisatum . Tetrahedron 1968; 24: 199-229
  • 4 Huang JM, Yang CS, Tanaka M, Fukuyama Y. Structures of merrilactones B and C, novel anislactone-type sesquiterpenes from Illicium merrillianum, and chemical conversion of anislactone B to merrilactone A. Tetrahedron 2001; 57: 4691-4698
  • 5 Kouno I, Mori K, Kawano N, Sato S. Structure of anislactone A: a new skeletal type of sesquiterpene from the pericarps of Illicium anisatum . Tetrahedron Lett 1989; 30: 7451-7452
  • 6 Schmidt TJ, Mueller E, Fronczek FR. New allo-cedrane type sesquiterpene hemiketals and further sesquiterpene lactones from fruits of Illicium floridanum . J Nat Prod 2001; 64: 411-414
  • 7 Huang JM, Yokoyama R, Yang CS, Fukuyama Y. Structure and neurotrophic activity of seco-prezizaane-type sesquiterpenes from Illicium merrillianum . J Nat Prod 2001; 64: 428-431
  • 8 Kubo M, Okada C, Huang JM, Harada K, Hioki H, Fukuyama Y. Novel pentacyclic seco-prezizaane-type sesquiterpenoids with neurotrophic properties from Illicium jiadifengpi . Org Lett 2009; 11: 5190-5193
  • 9 Yokoyama R, Huan JM, Yang CS, Fukuyama Y. New seco-prezizaanetype sesquiterpenes, jiadifenin with neurotrophic activity and 1, 2-dehydroneomajucin from Illicium jiadifengpi . J Nat Prod 2002; 65: 527-531
  • 10 Tang WZ, Ma SG, Yu SS, Qu J, Liu YB, Liu J. Rearranged prenylated C6-C3 compounds and a highly oxygenated seco-prezizaane-type sesquiterpene from the stem bark of Illicium oligandrum . J Nat Prod 2009; 72: 1017-1021
  • 11 Ma SG, Tang WZ, Liu YX, Hu YC, Yu SS, Zhang Y, Chen XG, Qu J, Ren JH, Liu YB, Xu S, Liu J, Liu YY, Li Y, Lu HN, Wu XF. Prenylated C6-C3 compounds with molecular diversity from the roots of Illicium oligandrum . Phytochemistry 2011; 72: 115-125
  • 12 Tang WZ, Liu YB, Yu SS, Qu J, Su DM. New sesquiterpene lactone and neolignan glycosides with antioxidant and anti-inflammatory activities from the fruits of Illicium oligandrum . Planta Med 2007; 73: 484-490
  • 13 Wu XF, Li Y, Lu HN, Yu SS, Ma SG, Liu J. Prenylated C6-C3 compounds from the fruits of Illicium simonsii . J Asian Nat Prod Res 2009; 11: 1056-1061
  • 14 Fang L, Du D, Ding GZ, Si YK, Yu SS, Liu Y, Wang WJ, Ma SG, Xu S, Qu J, Wang JM, Liu YX. Neolignans and glycosides from the stem bark of Illicium difengpi . J Nat Prod 2010; 73: 818-824
  • 15 Bai J, Chen H, Fang ZF, Yu SS, Wang WJ, Liu Y, Ma SG, Li Y, Qu J, Xu S, Liu JH, Zhao F, Zhao N. Sesquiterpenes from the roots of Illicium dunnianum . Phytochemistry 2012; 80: 137-147
  • 16 Liu JS, Zhou QR. The toxic principle of Illicium henryi Diels and structure of 6-deoxypseudoanisatin. Acta Pharmacol Sin 1988; 23: 221-223
  • 17 Liu JF, Jiang ZY, Zhang Q, Shi Y, Ma YB, Xie MJ, Zhang XM, Chen JJ. Henrylactones A–E and Anti-HBV Constituents from Illicium henryi . Planta Med 2010; 76: 152-158
  • 18 Liu JF, Zhang XM, Shi Y, Jiang ZY, Ma YB, Chen JJ. Chemical constituents from rhizomes of Illicium henryi . Zhongguo Zhongyao Zazhi 2010; 17: 2281-2284
  • 19 Liu JF, Jiang ZY, Geng CA, Zhang Q, Shi Y, Ma YB, Zhang XM, Chen JJ. Two new lignans and anti-HBV constituents from Illicium henryi . Chem Biodivers 2011; 8: 692-698
  • 20 Song TF, Zhang WD, Xia XH, Shen YH, Liu CM, Lin S, Jin HZ, Li HL. Two new acorane sesquiterpenes from Illicium henryi . Arch Pharm Res 2009; 32: 1233-1236
  • 21 Xiang WJ, Ma L, Hu LH. Neolignans and flavonoids from the root bark of Illicium henryi . Fitoterapia 2010; 81: 1228-1231
  • 22 Xie DL, Wang S, Cheng ZW, Song YS, Kong DY. Analysis of flavonoids in the root-cortex of Henry anisetree (Illicium henryi). Zhongcaoyao 1990; 21: 447-449
  • 23 Chen YD, Gao A, Gong J, Yang LJ, Wang M, Yang WH, Zhao T, Li N, Ni SF. An overview of pharmaceutical research on Illicium henryi Diels. Anhui Nongye Kexue 2011; 39: 8376-8377
  • 24 Zhuang PY, Zhang GJ, Wang XJ, Zhang Y, Yu SS, Ma SG, Liu YB, Qu J, Li Y, Xu S, Lü HN, Chen X, Li L, Si YK, Zhang D. Prenylated C6−C3 compounds from the roots of Illicium henryi . Phytochemistry 2013; 86: 176-183
  • 25 Nakamura T, Okuyama E, Yamazaki M. Neurotropic components from star anise (Illicium verum HOOK. fil.). Chem Pharm Bull 1996; 44: 1908-1914
  • 26 Hu YM, Yang ZL, Ye WC, Cheng Q. Studies on the constituents in rhizome of Homalomena occuta . Zhongguo Zhongyao Zazhi 2003; 28: 342-344
  • 27 Zaharia LI, Gai Y, Nelson KM, Ambrose SJ, Abrams SR. Oxidation of 80-hydroxy abscisic acid in Black Mexican Sweetmaize cell suspension cultures. Phytochemistry 2004; 65: 3199-3209
  • 28 Ma SG, Hu YC, Yu SS, Zhang Y, Chen XG, Liu J, Liu YX. Cytotoxic triterpenoid saponins acylated with monoterpenic acid from Pithecellobium lucidum . J Nat Prod 2008; 71: 41-46
  • 29 Minkin VI, Legrand M, Rougier MJ. Stereochemistry. Determination of configurations by dipole moments, CD or ORD. Stuttgart: Georg Thieme; 1977: 135-136
  • 30 Frelek J, Szczepek WJ. [Rh2(OCOCF3)4] as an auxiliary chromophore in chiroptical studies on steroidal alcohols. Tetrahedron 1999; 10: 1507-1520
  • 31 Wang JL, Yang CS, Yan RN, Yao B, Yang XB. Sesquiterpene lactones from Illicium minwanense . Acta Pharmacol Sin 1994; 29: 693-696
  • 32 Yokoyama R, Huang JM, Hosoda A, Kino K, Yang CS, Fukuyama Y. Seco-prezizaane-type sesquiterpenes and an abietane-type diterpene from Illicium minwanense . J Nat Prod 2003; 66: 799-803
  • 33 Hu CQ, Zhou BN. Isolation and structure of two new diterpenoid glycosides from Andrographis paniculata Nees. Acta Pharmacol Sin 1982; 17: 435-440
  • 34 Alley MC, Scudiero DA, Monks A, Hursey ML, Czerwinski MJ, Fine DL, Abbott BJ, Mayo JG, Shoemaker RH, Boyd MR. Feasibility of drugs screening with panela of human tumor cell lines using a microculture tetrazolium assay. Cancer Res 1988; 48: 589-601