Antioxidant Constituents from Pinus massoniana (Pinaceae)

doi:10.7677/ynzwyj201312104

Abstract

Abstract:

Twenty one known compounds were isolated from the twigs of Pinus massoniana. Their structures were elucidated as 7, 13, 15-abietatrien-18-oic acid (1), 12-methoxy-7, 13-abietadien-18-oic acid (2), 15-methoxy-7, 13-abietadien-18-oic acid methyl ester (3), 12-hydroxydehydroabietic acid (4), dehydroabietic acid (5), 15-hydroxydehydroabietic acid methyl ester (6), 3β-methoxyserrat-14-en-21-one (7), 3β-methoxy-30-hydroxyserrat-14-en-21-one (8), β-sitosterol (9), (±)-pinoresinol (10), (±)-matairesinol (11), (-)-nortrachelogenin (12), balanophonin (13), cedrusin (14), pinocembin (15), 5-methoxypinosylvin (16), pinos、lvin (17), 1, 2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1, 3-diol (18), cleistophostaudin (19), lignoceryl ferulate (20) and coniferaldehyde (21). Compounds 12, 14, 18 and 21 showed antioxidant activities on DPPH assay with EC50 values of 11.36, 6.76, 14.07, and 13.33μg·mL-1, respectively. Compounds 2-4, 6-8, 10, 11, 13 and 15-21 were isolated from this plant for the first time.
Key words: Pinus massoniana; Chemical constituents; Antioxidant activityPinus massoniana Lamb. belongs to the family of Pinaceae and is widely distributed in China. Its pollen and nodular branch are used as two traditional Chinese medicines, which can be used to treat traumatic hemorrhage, eczema, sprain and strain (Chinese Pharmacopoeia Commission, 2010). Previous investigations on P.massoniana led to the isolation of a series of lignans, flavones and diterpenoids (Feng et al., 2004; Bi et al., 2002; Shen and Theander, 1985; Wang et al., 2008; Yang et al., 2010), and the discovery of some antitumor diterpenes (Tanaka et al., 2008) and some antioxidant extracts (Pan et al., 2009). For the recent researches revealed that the occurrence of some chronic diseases such as cancer, cardiovascular disease and diabetes were main caused by oxidative stress, therefore antioxidant compounds might provide us some different insights for treating these severe diseases. In this paper, we report the isolation and structural elucidation of 21 known compounds from its twigs with the antioxidant activities.

Key words: Pinus massoniana, Chemical constituents, Antioxidant activity

CLC Number:

Q 946

ZHANG Yu-Mei-, GONG Qing-Fang-, YANG Jia-Qian-, CENG Guang-Zhi-, TAN Ning-Hua. Antioxidant Constituents from Pinus massoniana (Pinaceae)[J]. Plant Diversity, 2013, 35(2): 209-215.

References

Achenbach H, Waibel R, AddaeMrasah I, 1983. Lignans and other constituents from Carissa edulis［J］. Phytochemistry, 22 (3): 749—753
Agrawal PK, Rastogi RP, Osterdahl BG, 1983. 13C NMR spectral analysis of dihydrobenzofuran lignans［J］. Organic Magnetic Resonance, 21 (2): 119—121
Bi YF (毕跃峰), Zheng XK (郑晓珂), Feng WS (冯卫生) et al., 2002. Isolation and structure identification of lignan glycosides from pine needles of Pinus

massoniana Lamb［J］. Acta Pharmaceutica Sinica(药学学报), 37 (8): 626—629
Cheung HTA, Miyase T, Lenguyen MP et al., 1993. Further acidic constituents and neutral components of Pinus massoniana resin［J］. Tetrahedron, 49 (36):

7903—7915
Chinese Pharmacopoeia Commission (国家药典委员会), 2010. Pharmacopoeia of People′s Republic of China (中华人民共和国药典一部) ［M］. Beijing: Chinese

Medicine Science and Technology Press, 191—192, 211—212
Fang JM, Su WC, Cheng YS, 1988. Flavonoids and stilbenes from armand pine［J］. Phytochemistry, 27 (5): 1395—1397
Fang JM, Tsai WY, Cheng YS, 1991. Serratene triterpenes from Pinus armandii bark［J］. Phytochemistry, 30 (4): 1333—1336
Feng WS (冯卫生), Wang YZ (王彦志), Zheng XK (郑晓珂) et al., 2004. Isolation and structure identification of the chemical constituents from pine needles of

Pinus massoniana Lamb［J］. Acta Pharmaceutica Sinica (药学学报), 39 (3): 190—193
Fraga BM, Mestres T, Diaz CE et al., 1994. Dehydroabietane diterpenes from Nepeta teydea［J］. Phytochemistry, 35 (6): 1509—1512
Fonseca SF, Campello JDP, Barata LES et al., 1978. 13C NMR spectra analysis of lignans from Araucaria angustifolia［J］. Phytochemistry, 17 (3): 499—502
Guz NR, Stermitz F, 2000. Spectral comparisons of coniferyl and cinnamyl alcohol epoxide derivatives with a purported cisepoxyconiferyl alcohol isolate［J

］. Phytochemistry, 54 (8): 897—899
Kinouchi Y, Ohtsu H, Tokuda H et al., 2000. Potential antitumorpromoting diterpenoids from the stem bark of Picea glehni［J］. Journal of Natural

Products, 63 (6): 817—820
Li SS (李石生), Deng JZ (邓京振), Zhao SX (赵守训), 2000. Minor phenolic constituents of chinaberrytree (Melia azedarach) ［J］. Chinese Traditional and

Herbal Drugs (中草药), 31 (2): 86—88
Miki K, Takehara T, Sasaya T et al., 1980. Lignans of Larix leptolepis［J］. Phytochemistry, 19 (3): 449—453
Narayanan CR, Bhadane NR, 1968. The conformation of esters, acids and aldehydes in terpenoids［J］. Tetrahedron Letters, 9 (13): 1565—1568
Ohmoto T, Satto M, Yamaguchi K, 1987. Constituents of pollen. XIV. Constituents of Cedrus deodara Loud［J］. Chemical & Pharmaceutical Bulletin, 35 (6):

2443—2447
Pan X (潘炘), Chen SW (陈顺伟), Zhuang XW (庄晓伟), 2009. Antioxidative activities of extracts from Pinus massoniana needles by different extraction

processes［J］. Biomass Chemical Engineering (生物质化学工程), 43 (3): 21—24
Schultz TP, Boldin WD, Fisher TH et al., 1992. Structurefungicidal properties of some 3and 4hydroxylated stilbenes and bibenzyl analogues［J］.

Phytochemistry, 31 (11): 3801—3806
Shen Z, Theander O, 1985. The constituents of conifer needles. Part II. (-)Massoniresinol, a lignan from Pinus massoniana［J］. Phytochemistry, 24 (2):

364—365
Sy LK, Brown GD, 1999. Coniferaldehyde derivatives from tissue culture of Artemisia annua and Tanacetum parthenium［J］. Phytochemistry, 50 (5): 781—785
Tanaka R, Mun C, Usami Y et al., 1994. 3Oxoserratene triterpenoids from the stem bark of Picea jezoensis Carr. var. hondoensis［J］. Phytochemistry, 35

(6): 1517—1522
Tananka H, Ichino K, Ito K, 1985. A novel flavanone, linderatone, from lindera umbellata［J］. Chemical & Pharmaceutical Bulletin, 33 (6): 2602—2604
Tanaka R, Tokuda H, Ezaki Y, 2008. Cancer chemopreventive activity of “rosin” constituents of Pinus spez. and their derivatives in twostage mouse skin

carcinogenesis test［J］. Phytomedicine, 15 (11): 985—992
Tane P, Ayafor F, Sondengam BL, 1998. A substituted cinnamoyl ester from Cleistopholis staudth［J］. Phytochemistry, 27 (12): 3986—3988
Wang W (王巍), Wang XH (王晓华), Yin JF (尹江峰) et al., 2008. Study on the flavonoid chemical constituents from pine needles of Pinus massoniana［J］.

Chinese Journal of Hospital Pharmacy (中国医院药学杂志), 28 (7): 549—552
Yang NY, Liu L, Tao WW et al., 2010. Diterpenoids from Pinus massoniana resin and their cytotoxicity against A431 and A549 cells［J］. Phytochemistry, 71

(13): 1528—1533

[1]	LIAO PengYing, ZHANG YingJun, WANG YiFei, WANG Dong, YANG ChongRen,. Chemical Constituents of Guangdong TuNiuXi (Eupatorium chinense, Compositae) [J]. Plant Diversity, 2010, 32(02): 183-188.
[2]	LI Shi-Fei^, , HUANG Nian-Xu , HAO Xiao-Jiang , LI Ling, LI Shun-Lin. Effect of Chemical Constituents from Syzygium cumini (Myrtaceae) on Glucose Uptake in Insulin-resistant L6 Cells [J]. Plant Diversity, 2009, 31(05): 469-473.
[3]	ZHONG Rui-Min-, Zhang-Zhen-Ming-, Xiao-Zi-Jun-, Ceng-Qing-Xiao-, Wang-Yu-Mei-**. Chemical Composition and Antioxidant Activities of the Essential Oils of Five Magnoliaceae Species from South China [J]. Plant Diversity, 2006, 28(2): 208-214.
[4]	SUN WeiBang，ZHOU Jun. A New Proposal on Generic Division of the Chinese Magnoliaceae [J]. Plant Diversity, 2003, 25(06): 1-3.
[5]	MEI Wen-Li NI Wei CHEN Chang-Xiang. Two New Compounds from Dichotomanthes tristaniaecarpa [J]. Plant Diversity, 2002, 24(06): 1-3.
[6]	YANG Xiao-Sheng,ZHAO Chao,ZHOU Xin,LUO Bo,YANG Fu-Mei,HAO Xiao-Jiang. The Constituents of Volatile Oil from Ilex Kudincha [J]. Plant Diversity, 2002, 24(03): 1-3.
[7]	WANG Han-Zhang,CHEN You-Gen, FAN Cui-Sheng. REVIEW OF STUDIES ON CHEMICAL CONSTITUENTS AND PHARMACOLOGY OF GENUS ACORUS IN CHINA [J]. Plant Diversity, 1998, 20(10): 1-3.
[8]	LI Zhu-Qiang, LUO Lei, DAI Wang-Hua, HUANG Rong, ZHANG Yuan-Qing. Chemical Constituents of the Essential Oil on Amomum tsao-ko from Yunnan Province [J]. Plant Diversity, 1998, 20(01): 1-3.
[9]	YE Hai-Ya, CHEN Chang-Xiang, HAO Xiao-Jiang. THE CHEMICAL CONSTITUENTS FROM OSTRYOPSIS NOBILIS [J]. Plant Diversity, 1996, 18(04): 1-3.
[10]	RAO Gao-Xiong, WANG Xing-Wen, LIU Qi-Xi, SUN Han-Dong. THE CHEMICAL CONSTITUENTS OF CHUANMINSHEN VIOLACEUM [J]. Plant Diversity, 1996, 18(03): 1-3.
[11]	RAO Gao-Xiong LIU Qi-Xin SUN Han-Dong . CHEMICAL CONSTITUENT OF ARCUATOPTERUS FILIPEDICHLLUS [J]. Plant Diversity, 1995, 17(04): 1-3.
[12]	RAO Gao-Xiong, DAI Yun-Hua, WANG Li-Xin, CAI Feng,LIN Zhong-Wen, SUN Han-Dong. CHEMICAL CONSTITUENTS FROM LIGUSTICUM PTERIDOPHYLLUM [J]. Plant Diversity, 1991, 13(02): 1-3.
[13]	Li Heng Chen Changxiang Ding Jingkai. THE CHEMICAL CONSTITUENTS, DISTRIBUTION AND THE RESOURCE APPRAISAL OF THE GENUS PARIS [J]. Plant Diversity, 1988, 10(S1): 1-3.
[14]	Sun Handong, Lin Zhongwen, Shen Xiaoyu, Niu Fangdi and Zhou Chan. STUDIES ON THE CHEMICAL CONSTITUENTS OF SEVEN SPECIES OF LICHEN PLANTS IN YUNNAN [J]. Plant Diversity, 1986, 8(04): 1-3.