Norditerpenes from Juniperus chinensis

Ching Kuo Lee; Jim Min Fang; Yu Shia Cheng

doi:10.1016/0031-9422(94)00868-T

Norditerpenes from Juniperus chinensis

Ching Kuo Lee, Jim Min Fang, Yu Shia Cheng

Research output: Contribution to journal › Article › peer-review

46 Citations (Scopus)

Abstract

One norpimarane and 11 norabietanes were isolated from the leaves of Juniperus chinensis. The new compounds include 19-norabieta-8,11,13-trien-4-yl formate, 18-norabieta-8,11,13-triene-4-hydroperoxide, 19-norabieta-8,11,13-triene-4-hydroperoxide, 4-hydroxy-18-norabieta-8,11,13-trien-7-one, 4-hydroxy-19-norabieta-8,11,13-trien-7-one, 4-hydroperoxy-19-norabieta-8,11,13-trien-7-one, 7α-hydroxy-19-norabieta-8,11,13-trien-4-hydroperoxide, 19-norabieta-7,13-dien-4-ol and 13β,14β-epoxy-4-hydroxy-19-norabiet-7-en-6-one.

Original language	English
Pages (from-to)	391-394
Number of pages	4
Journal	Phytochemistry
Volume	39
Issue number	2
DOIs	https://doi.org/10.1016/0031-9422(94)00868-T
Publication status	Published - May 1995
Externally published	Yes

Keywords

Cupressaceae
Juniperus chinensis
norabietane-type
norditerpenes
norpimarane-type

ASJC Scopus subject areas

Horticulture
Plant Science
Biochemistry
Molecular Biology
Organic Chemistry
Drug Discovery

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10.1016/0031-9422(94)00868-T

Cite this

@article{b6fbb7bbf5b74bcf8ad5b2a54f88f959,

title = "Norditerpenes from Juniperus chinensis",

abstract = "One norpimarane and 11 norabietanes were isolated from the leaves of Juniperus chinensis. The new compounds include 19-norabieta-8,11,13-trien-4-yl formate, 18-norabieta-8,11,13-triene-4-hydroperoxide, 19-norabieta-8,11,13-triene-4-hydroperoxide, 4-hydroxy-18-norabieta-8,11,13-trien-7-one, 4-hydroxy-19-norabieta-8,11,13-trien-7-one, 4-hydroperoxy-19-norabieta-8,11,13-trien-7-one, 7α-hydroxy-19-norabieta-8,11,13-trien-4-hydroperoxide, 19-norabieta-7,13-dien-4-ol and 13β,14β-epoxy-4-hydroxy-19-norabiet-7-en-6-one.",

keywords = "Cupressaceae, Juniperus chinensis, norabietane-type, norditerpenes, norpimarane-type, Cupressaceae, Juniperus chinensis, norabietane-type, norditerpenes, norpimarane-type",

author = "Lee, {Ching Kuo} and Fang, {Jim Min} and Cheng, {Yu Shia}",

note = "Funding Information: 16, 17), 1.29 (s, H-20), 1.32 (s, H-18), 2.08 (dd,J = 12.3, stirred at 18 ° in the air for 5 days. Solvent was removed, 5.7 Hz, H-5), 2.84 (dd,J = 18.2, 12.3 Hz, H-6), 2.87 (dd, the residue was taken up with CHCI 3 and the compo-J = 18.2, 5.7 Hz, H-6), 2.90 (septJ, = 6.9 Hz, H-15), 7.27 nents were separated by HPLC with elution of (d, J = 8.2 Hz, H-11), 7.37 (dd,J = 8.2, 1.9 Hz, H-12), 7.84 hexane-EtOAc (5: 2) to give 4-epidehydroabietic acid (d, J = 1.9 Hz, H-14). El-MS (70 eV) m/z (rel. int.): 302 (12 mg), norditerpenes 2 (3 rag), 3 (3 mg), 8 (2 mg) and \[M\+] (8), 286 (26), 271 (49), 253 (84), 211 (63), 201 (70), 4 (2 mg). 185 (42), 43 (100). Exact mass \[M\+] for C19H2603 requires 302.1883. Found 302.1872. 7ct-Hy droxy1-9-norabieta-8,11,13-triene-4-hydropAecrokxn-o wledgement--Waree grateful to the National Neat ide (10). An oil, \[ct\]2s+16.°0 (CHCI3; c0.75). Science Council of the Republic of China for financial IR Vma~ cm-l: 3363. 1HNMR (CDC13): 61.20 (s, H-20), support (NSC 83-0208-M-002-095). 1.21 (d, J = 6.9 Hz, H-16, 17), 1.23 (m, H-3ct), 1.40 (ddd, J = 14.0, 14.0, 3.6 Hz, H-I~), 1.37 (s, H-18), 1.94 (dd, J = 12.0, 3.1 Hz, H-5), 2.10 (ddd,J = 13.6, 12.0, 3.8 Hz, H-6fl), 2.14 (m, H-6ct), 2.20 (m, H-3fl), 2.23 (m, H-lfl), 2.85 (septJ, = 6.9 Hz, H-15), 4.81 (dd,J = 3.8, 3.8 Hz, H-7), 7.10 (dd, J = 8.1, 2.0 Hz, H-12), 7.14 (d, J = 2.0 Hz, H-14), 7.19 (d, J = 8.1 Hz, H-11). EI-MS (70 eV) m/z (rel. int.): 304 \[M\+] (40), 287 (9), 271 (7), 269 (8), 254 (27), 253 (100), 211 (45), 187 (26). Exact mass \[M\+] for C19H2803 requires 304.2039. Found 304.2050. 19-Norabieta-7,13-dien-(411-)o. lA n oil, \[c~2\]5 + 62.1 ° (CHCI3; c0.1). IRvmNae{\~a}t Cm -1. . 3484 (OH). 1HNMR (CDCI3): 60.92 (s, H-20), 0.99 (d, J = 6.8 Hz, H-16), 1.00 (d, J=6.8Hz, H-17), 1.14 (s, H-18), 2.21 (sept, J = 6.8 Hz, H-15), 5.43 (br s, H-7), 5.77 (s, H-14). El-MS (70 eV) m/z (rel. int.): 274 I-M\]÷ (34), 256 (83), 241 (100), 213 (36), 199 (14), 185 (86), 157 (11), 143 (17). Exact mass \[M\÷] for C19H3oO requires 274.2298. Found 274.2297. 13fl,14fl-Epoxy-4-hydroxy-19-norabiet-7-e(1n2-)6. -on7e. An oil, I-~\2] 5 - 57.1 ° (MeOH; c0.14). IR VmaxNeact m-l{"} 3525 (-OH). 1661 (conjugated C=O): UV 2mueaox nm (e): 246 (10810). IHNMR (CDCI3): 60.96 (d, J=7.0Hz, H-16), 0.99 (s, H-20), 1.01 (d, J = 7.0 Hz, H-17), 1.32 (s, H-18), 1.66 (septJ, -=-7.0 Hz, H-15), 2.30 (s, H-5), 3.22 (s, H-14), 3.40 (d, J = 2.5 Hz, -OH), 6.11 (d, J = 3.0 Hz, H-7). El-MS (70 eV) m/z (rel. iiit.): 304 \[M\+] (77), 290 (21), 289 (100), 286 (19), 271 (20), 243 (29), 219 (22), 147 (30). Exact mass \[M\÷] for C19 H28 03 requires 304.2037. Found 304.2045. Autoxidationo f abieta-8,11,13-trien-19T-hael . title compound (24 mg) was dissolved in benzene (15 ml) and Copyright: Copyright 2014 Elsevier B.V., All rights reserved.",

year = "1995",

month = may,

doi = "10.1016/0031-9422(94)00868-T",

language = "English",

volume = "39",

pages = "391--394",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Limited",

number = "2",

}

TY - JOUR

T1 - Norditerpenes from Juniperus chinensis

AU - Lee, Ching Kuo

AU - Fang, Jim Min

AU - Cheng, Yu Shia

N1 - Funding Information: 16, 17), 1.29 (s, H-20), 1.32 (s, H-18), 2.08 (dd,J = 12.3, stirred at 18 ° in the air for 5 days. Solvent was removed, 5.7 Hz, H-5), 2.84 (dd,J = 18.2, 12.3 Hz, H-6), 2.87 (dd, the residue was taken up with CHCI 3 and the compo-J = 18.2, 5.7 Hz, H-6), 2.90 (septJ, = 6.9 Hz, H-15), 7.27 nents were separated by HPLC with elution of (d, J = 8.2 Hz, H-11), 7.37 (dd,J = 8.2, 1.9 Hz, H-12), 7.84 hexane-EtOAc (5: 2) to give 4-epidehydroabietic acid (d, J = 1.9 Hz, H-14). El-MS (70 eV) m/z (rel. int.): 302 (12 mg), norditerpenes 2 (3 rag), 3 (3 mg), 8 (2 mg) and \[M\+] (8), 286 (26), 271 (49), 253 (84), 211 (63), 201 (70), 4 (2 mg). 185 (42), 43 (100). Exact mass \[M\+] for C19H2603 requires 302.1883. Found 302.1872. 7ct-Hy droxy1-9-norabieta-8,11,13-triene-4-hydropAecrokxn-o wledgement--Waree grateful to the National Neat ide (10). An oil, \[ct\]2s+16.°0 (CHCI3; c0.75). Science Council of the Republic of China for financial IR Vma~ cm-l: 3363. 1HNMR (CDC13): 61.20 (s, H-20), support (NSC 83-0208-M-002-095). 1.21 (d, J = 6.9 Hz, H-16, 17), 1.23 (m, H-3ct), 1.40 (ddd, J = 14.0, 14.0, 3.6 Hz, H-I~), 1.37 (s, H-18), 1.94 (dd, J = 12.0, 3.1 Hz, H-5), 2.10 (ddd,J = 13.6, 12.0, 3.8 Hz, H-6fl), 2.14 (m, H-6ct), 2.20 (m, H-3fl), 2.23 (m, H-lfl), 2.85 (septJ, = 6.9 Hz, H-15), 4.81 (dd,J = 3.8, 3.8 Hz, H-7), 7.10 (dd, J = 8.1, 2.0 Hz, H-12), 7.14 (d, J = 2.0 Hz, H-14), 7.19 (d, J = 8.1 Hz, H-11). EI-MS (70 eV) m/z (rel. int.): 304 \[M\+] (40), 287 (9), 271 (7), 269 (8), 254 (27), 253 (100), 211 (45), 187 (26). Exact mass \[M\+] for C19H2803 requires 304.2039. Found 304.2050. 19-Norabieta-7,13-dien-(411-)o. lA n oil, \[c~2\]5 + 62.1 ° (CHCI3; c0.1). IRvmNaeãt Cm -1. . 3484 (OH). 1HNMR (CDCI3): 60.92 (s, H-20), 0.99 (d, J = 6.8 Hz, H-16), 1.00 (d, J=6.8Hz, H-17), 1.14 (s, H-18), 2.21 (sept, J = 6.8 Hz, H-15), 5.43 (br s, H-7), 5.77 (s, H-14). El-MS (70 eV) m/z (rel. int.): 274 I-M\]÷ (34), 256 (83), 241 (100), 213 (36), 199 (14), 185 (86), 157 (11), 143 (17). Exact mass \[M\÷] for C19H3oO requires 274.2298. Found 274.2297. 13fl,14fl-Epoxy-4-hydroxy-19-norabiet-7-e(1n2-)6. -on7e. An oil, I-~\2] 5 - 57.1 ° (MeOH; c0.14). IR VmaxNeact m-l" 3525 (-OH). 1661 (conjugated C=O): UV 2mueaox nm (e): 246 (10810). IHNMR (CDCI3): 60.96 (d, J=7.0Hz, H-16), 0.99 (s, H-20), 1.01 (d, J = 7.0 Hz, H-17), 1.32 (s, H-18), 1.66 (septJ, -=-7.0 Hz, H-15), 2.30 (s, H-5), 3.22 (s, H-14), 3.40 (d, J = 2.5 Hz, -OH), 6.11 (d, J = 3.0 Hz, H-7). El-MS (70 eV) m/z (rel. iiit.): 304 \[M\+] (77), 290 (21), 289 (100), 286 (19), 271 (20), 243 (29), 219 (22), 147 (30). Exact mass \[M\÷] for C19 H28 03 requires 304.2037. Found 304.2045. Autoxidationo f abieta-8,11,13-trien-19T-hael . title compound (24 mg) was dissolved in benzene (15 ml) and Copyright: Copyright 2014 Elsevier B.V., All rights reserved.

PY - 1995/5

Y1 - 1995/5

N2 - One norpimarane and 11 norabietanes were isolated from the leaves of Juniperus chinensis. The new compounds include 19-norabieta-8,11,13-trien-4-yl formate, 18-norabieta-8,11,13-triene-4-hydroperoxide, 19-norabieta-8,11,13-triene-4-hydroperoxide, 4-hydroxy-18-norabieta-8,11,13-trien-7-one, 4-hydroxy-19-norabieta-8,11,13-trien-7-one, 4-hydroperoxy-19-norabieta-8,11,13-trien-7-one, 7α-hydroxy-19-norabieta-8,11,13-trien-4-hydroperoxide, 19-norabieta-7,13-dien-4-ol and 13β,14β-epoxy-4-hydroxy-19-norabiet-7-en-6-one.

AB - One norpimarane and 11 norabietanes were isolated from the leaves of Juniperus chinensis. The new compounds include 19-norabieta-8,11,13-trien-4-yl formate, 18-norabieta-8,11,13-triene-4-hydroperoxide, 19-norabieta-8,11,13-triene-4-hydroperoxide, 4-hydroxy-18-norabieta-8,11,13-trien-7-one, 4-hydroxy-19-norabieta-8,11,13-trien-7-one, 4-hydroperoxy-19-norabieta-8,11,13-trien-7-one, 7α-hydroxy-19-norabieta-8,11,13-trien-4-hydroperoxide, 19-norabieta-7,13-dien-4-ol and 13β,14β-epoxy-4-hydroxy-19-norabiet-7-en-6-one.

KW - Cupressaceae

KW - Juniperus chinensis

KW - norabietane-type

KW - norditerpenes

KW - norpimarane-type

KW - Cupressaceae

KW - Juniperus chinensis

KW - norabietane-type

KW - norditerpenes

KW - norpimarane-type

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U2 - 10.1016/0031-9422(94)00868-T

DO - 10.1016/0031-9422(94)00868-T

M3 - Article

AN - SCOPUS:0029161399

SN - 0031-9422

VL - 39

SP - 391

EP - 394

JO - Phytochemistry

JF - Phytochemistry

IS - 2

ER -

Norditerpenes from Juniperus chinensis

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