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Planta Med 2014; 80(05): 419-425
DOI: 10.1055/s-0034-1368252
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

New Clerodane Diterpenes from Tinospora sagittata var. yunnanensis

Zhi-Yong Jiang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Chemistry and Biotechnology, Yunnan University of Nationalities, Kunming, Yunnan, P. R. China
,
Wen-Juan Li
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Chemistry and Biotechnology, Yunnan University of Nationalities, Kunming, Yunnan, P. R. China
,
Li-Xiang Jiao
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Chemistry and Biotechnology, Yunnan University of Nationalities, Kunming, Yunnan, P. R. China
,
Jun-Ming Guo
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Chemistry and Biotechnology, Yunnan University of Nationalities, Kunming, Yunnan, P. R. China
,
Kai Tian
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Chemistry and Biotechnology, Yunnan University of Nationalities, Kunming, Yunnan, P. R. China
,
Chun-Tao Yang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Chemistry and Biotechnology, Yunnan University of Nationalities, Kunming, Yunnan, P. R. China
,
Xiang-Zhong Huang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Chemistry and Biotechnology, Yunnan University of Nationalities, Kunming, Yunnan, P. R. China
2   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, P. R. China
› Author Affiliations
Further Information

Publication History

received 25 September 2013
revised 22 January 2014

accepted 14 February 2014

Publication Date:
14 March 2014 (online)

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Abstract

Four new clerodane diterpenes, namely sagittatayunnanosides A–D (1–4), were isolated from the roots of Tinospora sagittata var. yunnanensis, together with two known compounds, tinospinoside C (5) and tinospinoside E (6). The structures of the four new compounds were well elucidated by extensive analyses of the MS, IR, and 1D and 2D NMR data. The cytotoxic and antifouling activities of compounds 1–6 were evaluated.

Key words

Tinospora sagittata var. Yunnanensis - Menispermaceae - clerodane diterpenes - cytotoxicity - antifouling activity

Supporting Information

 

  • References

  • 1 Jiangsu New Medical College. The dictionary of traditional Chinese medicine. Shanghai: Peopleʼs Publishing House; 1986: 1393-1394
    Search in Google Scholar
  • 2 Zhan ZJ, Zhang XY, Hou XR, Li CP, Shan WG. New diterpenoids from Tinospora capillipes . Helv Chim Acta 2009; 92: 790-794
    CrossrefPubMedSearch in Google Scholar
  • 3 Shi LM, Li RQ, Liu WH. Two new furanoid diterpenoids from Tinospora sagittata . Helv Chim Acta 2008; 91: 978-982
    CrossrefPubMedSearch in Google Scholar
  • 4 Liu XH, Hu ZL, Shi QR, Zeng HW, Shen YH, Jin HZ, Zhang WD. Anti-inflammatory and anti-nociceptive activities of compounds from Tinospora sagittata (Oliv.) Gagnep. Arch Pharm Res 2010; 33: 981-987
    CrossrefPubMedSearch in Google Scholar
  • 5 Li RW, Lin GD, Myers SP, Leach DN. Anti-inflammatory activity of Chinese medicinal vine plants. J Ethnopharmacol 2003; 85: 61-67
    CrossrefPubMedSearch in Google Scholar
  • 6 Castro A, Coll J. Neo-clerodane diterpenoids from Verbenaceae: Structural elucidation and biological activity. Nat Prod Commun 2008; 3: 1021-1031
    PubMedSearch in Google Scholar
  • 7 Huang XZ, Cheng CM, Dai Y, Fu GM, Guo JM, Yin Y, Liang H. A novel 18-norclerodane diterpenoid from the roots of Tinospora sagittata var. yunnanensis . Molecules 2010; 15: 8360-8365
    CrossrefPubMedSearch in Google Scholar
  • 8 Huang XZ, Cheng CM, Dai Y, Fu GM, Guo JM, Liang H, Wang C. A novel lignan glycoside with antioxidant activity from Tinospora sagittata var. yunnanensis . Nat Prod Res 2012; 26: 1876-1880
    CrossrefPubMedSearch in Google Scholar
  • 9 Li W, Huang C, Li SP, Ma FH, Li Q, Asada Y, Koike K. Clerodane diterpenoids from Tinospora sagittata (Oliv.) Gagnep. Planta Med 2012; 78: 82-85
    Thieme ConnectPubMedSearch in Google Scholar
  • 10 Huang C, Li W, Ma FH, Li Q, Asada Y, Koike K. Tinospinosides D, E and tinospin E, further clerodane diterpenoids from Tinospora sagittata . Chem Pharm Bull 2012; 60: 1324-1328
    CrossrefPubMedSearch in Google Scholar
  • 11 Muhammad I, El-Feraly FS, Mossa JS, Ramadan AF. Terpenoids from Pulicaria glutinosa . Phytochemistry 1992; 31: 4245-4248
    CrossrefPubMedSearch in Google Scholar
  • 12 Cifuente DA, Borkowski EJ, Sosa ME, Gianello JC, Giordano OS, Tonn CE. Clerodane diterpenes from Baccharis sagittalis: insect antifeedant activity. Phytochemistry 2002; 61: 899-905
    CrossrefPubMedSearch in Google Scholar
  • 13 Ceñal JP, Giordano OS, Rossomando PC, Tonn CE. Neoclerodane diterpenes from Baccharis crispa . J Nat Prod 1997; 60: 490-492
    CrossrefPubMedSearch in Google Scholar
  • 14 Achari B, Chaudhuri C, Saha CR, Dutta PK, Pakrashi SC. A clerodane diterpene and other constituents of Clerodendron inerme . Phytochemistry 1990; 29: 3671-3673
    CrossrefPubMedSearch in Google Scholar
  • 15 Manabe S, Nishino C. Stereochemistry of cis-clerodane diterpenes. Tetrahedron 1986; 42: 3461-3470
    CrossrefPubMedSearch in Google Scholar
  • 16 Li W, Wei K, Koike K. Structure and absolute configuration of clerodane diterpene glycosides and a rearranged cadinane sesquiterpene glycosides from the stems of Tinospora sinensis . J Nat Prod 2007; 70: 1971-1976
    CrossrefPubMedSearch in Google Scholar
  • 17 Maurya R, Manhas LR, Gupta P, Mishra PK, Singh G, Yadav PP. Amritosides A, B, C, and D: clerodane furano dietrpene glucosides from Tinospora cordifolia . Phytochemistry 2004; 65: 2051-2055
    CrossrefPubMedSearch in Google Scholar
  • 18 Martin TS, Ohtani K, Kasai R, Yamasaki K. Furanoid diterpene glucosides from Tinospora rumphii . Phytochemistry 1996; 42: 153-158
    CrossrefPubMedSearch in Google Scholar
  • 19 Maurya R, Wazir V, Tyagi Y, Kapil RS. Clerodane diterpenoids from Tinospora cordifolia . Phytochemistry 1995; 38: 659-661
    CrossrefPubMedSearch in Google Scholar
  • 20 Wazir V, Maurya R, Kapil RS. Cordioside, a clerodane furano diterpene glucoside from Tinospora cordifolia . Phytochemistry 1995; 38: 447-449
    CrossrefPubMedSearch in Google Scholar
  • 21 Gangan VD, Pradhan P, Sipahimalani AT, Banerji A. Norditerpene furan glycosides from Tinospora cordifolia . Phytochemistry 1995; 39: 1139-1142
    CrossrefPubMedSearch in Google Scholar
  • 22 Kiem PV, Minh CV, Dat NT, Kinh LV, Huang DT, Nam NH, Cuong NX, Huong HT, Lau TV. Aporphine alkaloids, clerodane diterpenes and other constituents from Tinospora cordifolia . Fitoterapia 2010; 81: 485-489
    CrossrefPubMedSearch in Google Scholar
  • 23 Bhatt RK, Hanuman JB, Sabata BK. A new clerodane derivative from Tinospora cordifolia . Phytochemistry 1988; 27: 1212-1216
    CrossrefPubMedSearch in Google Scholar
  • 24 Maurya R, Dhar KL, Handa SS. A sesquiterpene glucoside from Tinospora cordifolia . Phytochemistry 1997; 44: 749-750
    CrossrefPubMedSearch in Google Scholar
  • 25 Khan MA, Gray AI, Waterman PG. Tinosporaside, an 18-norclerodane glucoside from Tinospora cordifolia . Phytochemistry 1989; 28: 273-275
    CrossrefPubMedSearch in Google Scholar
  • 26 Tuntiwachwuttikul P, Boonrasri N, Bremner JB, Taylor WC. Rearranged clerodane diterpenes from Tinospora baenzigeri . Phytochemistry 1999; 52: 1335-1340
    CrossrefPubMedSearch in Google Scholar
  • 27 Yonemitsu M, Fukuda N, Kimura T, Isobe R, Komori T. Studies on the constituents of the stems of Tinospora sinensis. II. Isolation and structure elucidation of two new dinorditerpene glucosides, tinosineside A and B. Liebigs Ann Chem 1995; 2: 437-439
    PubMedSearch in Google Scholar
  • 28 Maurya R, Wazir V, Tyagi A, Kapil RS. Clerodane diterpenoids from Tinospora cordifolia . Phytochemistry 1995; 38: 659-661
    CrossrefPubMedSearch in Google Scholar
  • 29 Song CQ, Xu RS. New clerodane diterpenoids from Tinospora capillipes . Chin Chem Lett 1992; 3: 185-188
    PubMedSearch in Google Scholar
  • 30 Itokawa H, Mizuno K, Tajima R, Takeya K. Furanoditerpene glucosides from Fibraurea tinctoria . Phytochemistry 1986; 25: 905-908
    CrossrefPubMedSearch in Google Scholar
  • 31 Jiang ZY, Zhang XM, Zhou J, Chen JJ. New triterpenoid glycosides from Centella asiatica . Helv Chim Acta 2005; 88: 297-303
    CrossrefPubMedSearch in Google Scholar
  • 32 Dash S, Jin CL, Lee OO, Xu Y, Qian PY. Antibacterial and antilarval settlement potential and metabolite profiles of novel sponge-associated marine bacteria. J Indian Microbiol Biotechnol 2009; 36: 1047-1056
    PubMedSearch in Google Scholar
  • 33 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63
    CrossrefPubMedSearch in Google Scholar
  • 34 Thiyagarajan V, Harder T, Qiu JW, Qian PY. Energy content at metamorphosis and growth rate of the early juvenile barnacle Balanus amphitrite . Mar Biol 2003; 143: 543-554
    CrossrefPubMedSearch in Google Scholar
  • 35 Xu Y, He HP, Schulz S, Liu X, Fusetani N, Xiong HR, Xiao X, Qian PY. Potent antifouling compounds produced by marine Streptomyces . Bioresour Technol 2010; 101: 1331-1336
    CrossrefPubMedSearch in Google Scholar