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Planta Med 2009; 75(15): 1591-1596
DOI: 10.1055/s-0029-1185868
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Chemical Constituents of Dracocephalum forrestii

Su-Mei Li2 , 3 , Xian-Wen Yang1 , 3 , Yong-Li Li1 , Yun-Heng Shen1 , Lin Feng1 , Yue-Hu Wang2 , Hua-Wu Zeng1 , Xiao-Hua Liu1 , Chang-Sheng Zhang3 , Chun-Lin Long2 , Wei-Dong Zhang1
  • 1Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China
  • 2Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
  • 3Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, P. R. China
Further Information

Publication History

received March 24, 2009 revised May 14, 2009

accepted June 6, 2009

Publication Date:
03 July 2009 (online)

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Abstract

A systematic phytochemical examination of the whole plant Dracocephalum forrestii led to the isolation of 4 new and 65 known chemical constituents. By detailed 1D and 2D NMR spectroscopic analyses, the new compounds were identified as 4-hydroxy-3-methoxyphenylethanol 8-O-[(6-O-syringoyl)-β-D-glucopyranoside] (1), 3,4,5-trimethoxyphenylethanol β-D-glucopyranoside (2), 4-O-[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl]phenylethylcinnamamide (3), and 9″-O-n-butyl lithospermate (4). The new isolates were evaluated for inhibitory activities against LPS-induced NO production in RAW 264.7 macrophages. Compound 2 revealed a moderate effect without any cytotoxicity under the assayed concentrations.

Key words

Dracocephalum forrestii - Lamiaceae - phenylethanoids - lignans - RAW 264.7 macrophages - NO

References

  • 1 Wu Z Y, Li X W. Flora of China, Vol. 2. Beijing; Science Press 1979: 354
    Search in Google Scholar
  • 2 Yang J S, Chu-Chen J C. Tibetan medicine of Diqing, 1st edition. Kunming; The Ethnic Publishing House of Yunan 1989: 394
    Search in Google Scholar
  • 3 Yang X W, Zeng H W, Liu X H, Li S M, Xu W, Shen Y H, Zhang C, Zhang W D. Anti-inflammatory and anti-tumour effects of Abies georgei extracts.  J Pharm Pharmacol. 2008;  60 937-941
    CrossrefPubMedSearch in Google Scholar
  • 4 Yang X W. Chemical constituents and neuroprotective activities of Tarenna attenuata and Baccaurear ramiflora [dissertation]. Kunming; Kunming Institute of Botany, Chinese Academy of Sciences 2006
    Search in Google Scholar
  • 5 Li S M, Yang X W, Shen Y H, Feng L, Wang Y H, Zeng H W, Liu X H, Tian J M, Shi Y N, Zhang W D, Long C L. Chemical constituents of Aeschynanthus bracteatus and their anti-inflammatory activities.  Phytochemistry. 2008;  69 2200-2204
    CrossrefPubMedSearch in Google Scholar
  • 6 Yang G Z, Zhao S, Li Y C. Studies on the chemical constituents of Lycianthes biflora.  Acta Pharm Sin. 2002;  37 437-439
    PubMedSearch in Google Scholar
  • 7 Kelley C J, Mahajan J R, Brooks L C, Neubert L A, Breneman W R, Carmack M. Polyphenolic acids of Lithospermum ruderale Dougl. ex Lehm. (Boraginaceae). 1. Isolation and structure determination of lithospermic acid.  J Org Chem. 1975;  40 1804-1815
    CrossrefPubMedSearch in Google Scholar
  • 8 Kohda H, Takeda O, Tanaka S, Yamasaki K, Yamashita A, Kurakawa T, Ishibashi S. Isolation of inhibitors of adenylate cyclase from Dan-shen, the root of Salvia miltiorrhiza.  Chem Pharm Bull. 1989;  37 1287-1290
    PubMedSearch in Google Scholar
  • 9 Takeda Y, Mima C, Masuda T, Hirata E, Takushi A, Otsuka H. Glochidioboside, a glucoside of (7S,8R)-dihydrodehydroconiferyl alcohol from leaves of Glochidion obovatum.  Phytochemistry. 1998;  49 2137-2139
    CrossrefPubMedSearch in Google Scholar
  • 10 Du Q Z, Jerz G, Shen L Q, Xiu L L, Winterhalter P. Isolation and structure determination of a lignan from the bark of Salix alba.  Chin J Nat Med. 2007;  21 451-454
    PubMedSearch in Google Scholar
  • 11 Vermes B, Seligmann O, Wagner H. Synthesis of biologically active tetrahydro-furofuranlignan-(syringin, pinoresinol)-mono- and bis-glucosides.  Phytochemistry. 1991;  30 3087-3089
    CrossrefPubMedSearch in Google Scholar
  • 12 Wang M, Liang J Y, Chen X Y. Water-soluble constituents of Clerodendranthus spicatus.  Chin J Nat Med. 2007;  5 27-30
    PubMedSearch in Google Scholar
  • 13 Umehara K, Hattori I, Miyase T, Ueno A, Hara S. Studies on the constituents of leaves of Citrus unshiu Marcov.  Chem Pharm Bull. 1998;  36 5004-5008
    PubMedSearch in Google Scholar
  • 14 Zhou L Y, Zhang X H, Chen C X. Chemical study on Rhodiola from Lijiang.  Nat Prod Res Dev. 2004;  16 410-414
    PubMedSearch in Google Scholar
  • 15 Ly T N, Yamauchi R, Shimoyamada M, Kato K. Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga (Alpinia officinarum Hance).  J Agric Food Chem. 2002;  50 4919-4924
    CrossrefPubMedSearch in Google Scholar
  • 16 Fujita T, Nakayama M. Perilloside A, a monoterpene glucoside from Perilla frutescens.  Phytochemistry. 1992;  31 3265-3267
    CrossrefPubMedSearch in Google Scholar
  • 17 Zhao W M, Qin G W, Xu R S, Li X Y, Liu J S, Wang Y, Feng M. Constituents from the roots of Acanthopanax setchuenensis.  Fitoterapia. 1999;  70 529-531
    CrossrefPubMedSearch in Google Scholar
  • 18 Deng S M, Zhou J, Cheng Y X, Dai H F, Tan N H. Two new phenolic glycosides from Magnolia rostrata.  Chin Chem Lett. 2000;  11 1001-1002
    PubMedSearch in Google Scholar
  • 19 Kiem P V, Tri M D, Tuong L VD, Tung N H, Hanh N N, Quang T H, Cuong N X, Minh C V, Choi E M, Kim Y H. Chemical constituents from the leaves of Manglietia phuthoensis and their effects on osteoblastic MC3T3-E1 cells.  Chem Pharm Bull. 2008;  56 1270-1275
    CrossrefPubMedSearch in Google Scholar
  • 20 Yutaka S, Kazutomo O, Yoshihiro M. Studies on the chemical constituents of the bulbs of Lilium mackliniae.  Chem Pharm Bull. 1991;  39 2362-2368
    PubMedSearch in Google Scholar
  • 21 Ono M, Masuoka C, Tanaka T, Ito Y, Nohara T. Antioxidative and antihyaluronidase activities of some constituents from the aerial part of Daucus carota.  Food Sci Technol Res. 2001;  7 307-310
    CrossrefPubMedSearch in Google Scholar
  • 22 Cardona L, Fernandez I, Pedro J R, Vidal R. Polyoxygenated terpenes and cyanogenic glucosides from Centaurea aspera var. subinermis.  Phytochemistry. 1992;  31 3507-3509
    CrossrefPubMedSearch in Google Scholar
  • 23 Huang H. Phenolic compounds of Isodon oresbius.  J Nat Prod. 1996;  59 1079-1080
    CrossrefPubMedSearch in Google Scholar
  • 24 Reyes A, Muñoz M, Garcia H, Cox C. Chemistry of Myzodendraceae, I. Myzodendrone, a new phenylbutanone of Myzodendron punctulatum.  J Nat Prod. 1986;  49 318-320
    CrossrefPubMedSearch in Google Scholar
  • 25 Pabst A, Barron D, Adda J, Schreier P. Phenylbutan-2-one β-D-glucosides from raspberry fruit.  Phytochemistry. 1990;  29 3853-3858
    CrossrefPubMedSearch in Google Scholar
  • 26 Manns D. Linalool and cineole type glucosides from Cunila spicata.  Phytochemistry. 1995;  39 1115-1118
    CrossrefPubMedSearch in Google Scholar
  • 27 Abe F, Yamauchi T, Honda K, Hayashi N. Conduritol F glucosides and terpenoid glucosides from Cynanchum liukiuense and distribution of conduritol F glucosides in several asclepiadaceous plants.  Chem Pharm Bull. 2000;  48 1090-1092
    PubMedSearch in Google Scholar
  • 28 Su W C, Fang J M, Cheng Y S. Sesquiterpens from leaves of Cryptomeria japonica.  Phytochemistry. 1995;  39 603-607
    CrossrefPubMedSearch in Google Scholar
  • 29 Uchiyama T, Miyase T, Ueno A, Usmanghani K. Terpenic glycosides from Pluchea indica.  Phytochemistry. 1989;  28 3369-3372
    CrossrefPubMedSearch in Google Scholar
  • 30 Matsumura T, Ishikawa T, Kitajima J. New p-menthanetriols and their glucosides from the fruit of caraway.  Tetrahedron. 2001;  57 8067-8074
    CrossrefPubMedSearch in Google Scholar
  • 31 Someya Y, Kobayashi A, Kubota K. Isolation and identification of trans-2- and trans-3-hydroxy-1,8-cineole glucosides from Alpinia galanga.  Biosci Biotechnol Biochem. 2001;  65 950-953
    CrossrefPubMedSearch in Google Scholar
  • 32 Rustaiyan A, Habibi Z, Zdero C. Clerodane derivatives from Platychaete aucheri.  Phytochemistry. 1990;  29 985-987
    CrossrefPubMedSearch in Google Scholar
  • 33 Sanz J F, Marco J A. A germacrane derivative from Pallenis spinosa.  Phytochemistry. 1991;  30 2788-2790
    CrossrefPubMedSearch in Google Scholar
  • 34 Kalsi P S, Arora G S, Ghulati R S. New antipodal sesquiterpene alcohols from vetiver oil.  Phytochemistry. 1979;  18 1223-1224
    CrossrefPubMedSearch in Google Scholar
  • 35 Labbe C, Castillo M, Connolly J D. Mono- and sesquiterpenoids from Satureja gilliesii.  Phytochemistry. 1993;  34 441-444
    CrossrefPubMedSearch in Google Scholar
  • 36 Bruno M, de la Torre M C, Rodriguez B, Omar A A. Guaiane sesquiterpenes from Teucrium leucocladum.  Phytochemistry. 1993;  34 245-247
    CrossrefPubMedSearch in Google Scholar
  • 37 Hu J F, Bai S P, Jia Z J. Eudesmane sesquiterpenes from Artemisia eriopoda.  Phytochemistry. 1996;  43 815-817
    CrossrefPubMedSearch in Google Scholar
  • 38 Zou C, Pu X Y, Zhou J. Sesquiterpenoids from Kadsura ananosma.  Acta Bot Yunn. 1993;  15 196-200
    PubMedSearch in Google Scholar
  • 39 Sung T V, Steffan B, Steglich W, Klebe G, Adam G. Sesquiterpenoids from the roots of Homalomena aromatica.  Phytochemistry. 1992;  31 3515-3520
    CrossrefPubMedSearch in Google Scholar
  • 40 Fang N B, Yu S G, Mabry T J, Abboud K A, Simonsen S H. Terpenoids from Ageratina saltillensis.  Phytochemistry. 1988;  27 3187-3196
    CrossrefPubMedSearch in Google Scholar
  • 41 de Menezesa J ESA, Machadoa F EA, Lemosa T LG, Silveira E R, Braz Filho R, Pessoa O DL. Sesquiterpenes and a phenylpropanoid from Cordia trichotoma.  Z Naturforsch [C]. 2004;  59 19-22
    PubMedSearch in Google Scholar
  • 42 Heymann H, Tezuka Y, Kikuchi T, Supriyatna S. Constituents of Sindora sumatrana Miq. I. Isolation and NMR spectral analysis of sesquiterpenes from the dried pods.  Chem Pharm Bull. 1994;  42 138-146
    PubMedSearch in Google Scholar
  • 43 Laidlaw R A, Morgan J WW. The diterpenes of Xylia dolabriformis.  J Chem Soc. 1963;  644-650
    CrossrefPubMedSearch in Google Scholar
  • 44 Uchiyama N, Kiuchi F, Ito M, Honda G, Takeda Y, Khodzhimatov O K, Ashurmetov O A. New icetexane and 20-norabietane diterpenes with trypanocidal activity from Dracocephalum komarovi.  J Nat Prod. 2003;  66 128-131
    CrossrefPubMedSearch in Google Scholar
  • 45 Jolad S D, Hoffmann J J, Schram K H, Cole J R, Bates R B, Tempesta M S. A new diterpene from Cupressus goveniana var. abramasiana: 5-hydroxy-6-oxasugiol (cupresol).  J Nat Prod. 1984;  47 983-987
    CrossrefPubMedSearch in Google Scholar
  • 46 Tinto W F, Blair L C, Alli A. Lupane triterpenoids of Salacia cordata.  J Nat Prod. 1992;  55 395-398
    CrossrefPubMedSearch in Google Scholar
  • 47 Maillard M, Adewunmi C O, Hostettmann K. A triterpene glycoside from the fruits of Tetrapleura tetraptera.  Phytochemistry. 1992;  31 1321-1323
    CrossrefPubMedSearch in Google Scholar
  • 48 Kundu A P, Mahato S B. Triterpenoids and their glycosides from Terminalia chebula.  Phytochemistry. 1993;  32 999-1002
    CrossrefPubMedSearch in Google Scholar
  • 49 Kim D H, Han K M, Chung I S, Kim D K, Kim S H, Kwon B M, Jeong T S, Park M H, Ahn E M, Baek N I. Triterpenoids from the flower of Campsis grandiflora K. Schum. as human Acyl-CoA: cholesterol acyltransferase inhibitors.  Arch Pharm Res. 2005;  28 550-556
    CrossrefPubMedSearch in Google Scholar
  • 50 Furuya T, Orihara Y, Hayashi C. Triterpenoids from Eucalyptus perriniana cultured cells.  Phytochemistry. 1987;  26 715-719
    CrossrefPubMedSearch in Google Scholar
  • 51 Seto T, Tanaka T, Tanaka O, Naruhashi N. β-Glucosyl esters of 19α-hydroxyursolic acid derivatives in leaves of Rubus species.  Phytochemistry. 1984;  23 2829-2834
    CrossrefPubMedSearch in Google Scholar
  • 52 Ohmoto T, Nikaido T, Ikuse M. Constituents of pollen. V. Constituents of Betula platyphylla var. japonica.  Chem Pharm Bull. 1978;  26 1437-1442
    PubMedSearch in Google Scholar
  • 53 Jayasinghe L, Wannigama G P, Macleod J K. Triterpenoids from Anamirta cocculus.  Phytochemistry. 1993;  34 1111-1116
    CrossrefPubMedSearch in Google Scholar
  • 54 Li J S, Zhao Y Y, Wang B, Li X L, Ma L B. Separation and identification of the flavonoids from Buddleia officinalis Maxim.  Acta Pharm Sin. 1996;  31 849-854
    PubMedSearch in Google Scholar
  • 55 Feng Y L, Li Y Q, Xu L Z, Yang S L. Flavonoids isolated from flowers of Althaea rosea.  Chin Tradit Herb Drugs. 2006;  37 1622-1624
    PubMedSearch in Google Scholar
  • 56 Miersch O, Schneider G, Sembdner G. Hydroxylated jasmonic acid and related compounds from Botryodiplodia theobromae.  Phytochemistry. 1991;  30 4049-4051
    CrossrefPubMedSearch in Google Scholar
  • 57 Fu G M, Pang H H, Wong Y H. Naturally occuring phenylethanoid glycosides: potential leads for new therapeutics.  Curr Med Chem. 2008;  15 2592-2613
    CrossrefPubMedSearch in Google Scholar

Dr. Wei-Dong Zhang

Department of Natural Product Chemistry School of Pharmacy
Second Military Medical University

325 Guohe Rd.

Shanghai 200433

People's Republic of China

Phone: + 86 21 81 87 12 44

Fax: + 86 21 81 87 12 44

Email: wdzhangy@hotmail.com

Dr. Chun-Lin Long

Kunming Institute of Botany
Chinese Academy of Sciences

132 Lanhei Road

Heilongtan

Kunming 650204

People's Republic of China

Phone: + 86 87 15 22 32 33

Fax: + 86 87 15 21 62 01

Email: long@mail.kib.ac.cn

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