Subscribe to RSS
DOI: 10.1055/s-0031-1298215
© Georg Thieme Verlag KG Stuttgart · New York
Three New Diterpenoids from the Leaves of Thuja orientalis
Publication History
received July 19, 2011
revised November 28, 2011
accepted January 9, 2012
Publication Date:
31 January 2012 (online)

Abstract
Three new diterpenoids, 18-formyloxy-8β-hydroxysandaracopimar-15-ene (1), 15(R)-n-butoxypinusolidic acid (2), and 15,16-dihydro-15,16-dimethoxylambertianic acid (3), along with twelve known compounds (4–15) were isolated from MeOH extracts of leaves of Thuja orientalis L. The structures of the three new compounds were elucidated on the basis of spectroscopic analyses, including extensive 2D-NMR data. The absolute stereochemistry of compound 2 was clarified by a CD spectroscopic study. The isolated compounds were evaluated for cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines in vitro using the sulforhodamin B (SRB) bioassay.
Key words
Thuja orientalis - Cupressaceae - diterpene - cytotoxicity
References
- 1
Sung S H, Koo K A, Lim H K, Lee H S, Cho J H, Kim H S, Kim Y C.
Diterpenes of Biota orientalis leaves.
Korean J Pharmacognosy.
1998;
29
347-352
MissingFormLabel
- 2
Lee M K, Yang H, Yoon J S, Jeong E J, Kim D Y, Ha N R, Sung S H, Kim Y C.
Antifibrotic activity of diterpenes from Biota orientalis leaves on hepatic stellate cells.
Arch Pharm Res.
2008;
31
866-871
MissingFormLabel
- 3
Guleria S, Kumar A, Tiku A K.
Chemical composition and fungitoxic activity of essential oil of Thuja orientalis L. grown in the north-western Himalaya.
Z Naturforsch C.
2008;
63
211-214
MissingFormLabel
- 4
Yoon J S, Koo K A, Ma C J, Sung S H, Kim Y C.
Neuroprotective lignans from Biota orientalis leaves.
Nat Prod Sci.
2008;
14
167-170
MissingFormLabel
- 5
Xu G H, Ryoo I J, Kim Y H, Choo S J, Yoo I D.
Free radical scavenging and antielastase activities of flavonoids from the fruits
of Thuja orientalis.
Arch Pharm Res.
2009;
32
275-282
MissingFormLabel
- 6
Yang H O, Han B H.
Pinusolidic acid: A Platelet-activating factor inhibitor from Biota orientalis.
Planta Med.
1998;
64
73-74
MissingFormLabel
- 7
Aldesanmi A J.
The stem constituents of Dysoxylum lenticellare.
Tetrahedron.
1988;
44
3749-3756
MissingFormLabel
- 8
Demarco P V, Farkas E, Doddrell D, Mylari B L, Wenkert E.
Pyridine-induced solvent shifts in the nuclear magnetic resonance spectra of hydroxylic
compounds.
J Am Chem Soc.
1968;
90
5480-5486
MissingFormLabel
- 9
Chien S C, Liu H K, Kuo Y H.
Two new compounds from the leaves of Calocedrus microlepic var. formosana.
Chem Pharm Bull.
2004;
52
762-763
MissingFormLabel
- 10
Frischmuth K, Samson E, Kranz A, Welzel P, Meuer H, Sheldrick W S.
Routes to derivatives of strigol (the witchweed germination factor) modified in the
5-position.
Tetrahedron.
1991;
47
9793-9806
MissingFormLabel
- 11
Asili J, Lambert M, Ziegler H L, Stærk D, Sairafianpour M, Witt M, Asghari G, Ibrahimi I S, Jaroszewski J W.
Labdanes and isopimaranes from Platycladus orientalis and their effects on erythrocyte membrane and on Plasmodium falciparum growth in the erythrocyte host cells.
J Nat Prod.
2004;
67
631-637
MissingFormLabel
- 12
Mori K, Waku M.
Synthesis of oryzalexins A, B and C, the diterpenoidal phytoalexins isolated from
rice blast leaves infected with Pyricularia oryzae.
Tetrahedron.
1985;
41
5653-5660
MissingFormLabel
- 13
Block S, Baccelli C, Tinant B, Meervelt L V, Rozenberg R, Jiwan J H, Llabrès G, De Pauw-Gillet M C, Quetin-Leclercq J.
Diterpenes from the leaves of Croton zambesicus.
Phytochemistry.
2004;
65
1165-1171
MissingFormLabel
- 14
Urones J G, Sanchez M I, Fernandez F J, Barcala B.
Terpenoids from Nepeta tuberosa subsp. reticulata (II).
Phytochemistry.
1988;
27
523-526
MissingFormLabel
- 15
Muto N, Tomokuni T, Haramoto M, Tatemoto H, Nakanishi T, Inatomi Y, Murata H, Inada A.
Isolation of apoptosis- and differentiation-inducing substances toward human promyelocytic
leukemia HL-60 cells from leaves of Juniperus taxifolia.
Biosci Biotechnol Biochem.
2008;
72
477-484
MissingFormLabel
- 16
Yang H O, Suh D Y, Han B H.
Isolation and characterization of platelet-activating factor receptor binding antagonists
from Biota orientalis.
Planta Med.
1995;
61
37-40
MissingFormLabel
- 17
Fukushima J, Yatagai M, Ohira T.
Abietane-type and labdane-type diterpenoids from the cones of Chamaecyparis obtuse.
J Wood Sci.
2002;
48
326-330
MissingFormLabel
- 18
Shimizu M, Tsuji H, Shogawa H, Fukumura H, Tanaami S, Hayashi T, Arisawa M, Morita N.
Anti-inflammatory constituents of topically applied crude drugs. II. Constituents
and anti-inflammatory effect of Cryptomeria japonica D. Don.
Chem Pharm Bull.
1988;
36
3967-3973
MissingFormLabel
- 19
Popova M P, Chinou I B, Marekov I N, Bankova V S.
Terpenes with antimicrobial activity from Cretan propolis.
Phytochemistry.
2009;
70
1262-1271
MissingFormLabel
- 20
Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren J T, Bokesch H, Kenney S, Boyd M R.
New colorimetric cytotoxicity assay for anticancer-drug screening.
J Natl Cancer Inst.
1990;
82
1107-1112
MissingFormLabel
Prof. Dr. Kang Ro Lee
Natural Products Laboratory, School of Pharmacy
Sungkyunkwan University
300 Cheoncheon-dong
Jangan-gu
Suwon-si 440–746
Korea
Phone: +82 3 12 90 77 10
Fax: +82 3 12 90 77 30
Email: krlee@skku.ac.kr