Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Heterocyclic Communications

Editor-in-Chief: Henary, Maged


IMPACT FACTOR 2018: 0.810

CiteScore 2018: 0.77

SCImago Journal Rank (SJR) 2018: 0.208
Source Normalized Impact per Paper (SNIP) 2018: 0.264

Open Access
Online
ISSN
2191-0197
See all formats and pricing
More options …
Volume 20, Issue 2

Issues

Chemical constituents of plants from the genus Neolitsea

Xia Qing
  • School of Pharmaceutical Sciences, Hebei Key Laboratory of Forensic Medicine, Hebei Medical University, Shijiazhuang 050017, Hebei Province, China
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Ting Zhao
  • School of Pharmaceutical Sciences, Hebei Key Laboratory of Forensic Medicine, Hebei Medical University, Shijiazhuang 050017, Hebei Province, China
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Rui-Xia Guo
  • School of Pharmaceutical Sciences, Hebei Key Laboratory of Forensic Medicine, Hebei Medical University, Shijiazhuang 050017, Hebei Province, China
  • College of Chemical Engineering, Shijiazhuang University, The Yangtze River, Road No. 6, Shijiazhuang, Hebei Province, 050035, China
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Yi-Bing Wu
  • School of Pharmaceutical Sciences, Hebei Key Laboratory of Forensic Medicine, Hebei Medical University, Shijiazhuang 050017, Hebei Province, China
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Qing-Wen Shi
  • Corresponding author
  • School of Pharmaceutical Sciences, Hebei Key Laboratory of Forensic Medicine, Hebei Medical University, Shijiazhuang 050017, Hebei Province, China
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Yu-Cheng Gu / Hiromasa Kiyota
  • Corresponding author
  • Graduate School of Environmental and Life Science, Okayama University, 1-1-1 Tsushima-Naka, Kita-ku, Okayama 700-8530, Japan
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2014-03-31 | DOI: https://doi.org/10.1515/hc-2013-0239

Abstract

The genus Neolitsea (Lauraceae) contains over 85 species distributed around the world. These plants have been found to be rich in sesquiterpenes, triterpenes, steroids, and alkaloids. This review summarizes the phytochemical progress and list of all the constituents isolated from the genus Neolitsea over the past few decades. Some biological activities of compounds isolated from this genus are also included.

Keywords: biological activity; chemical composition; Neolitsea; plant

Introduction

The genus Neolitsea (Lauraceae) comprises nearly 85 species that are distributed throughout tropical and subtropical Asia and America. In particular, there are 45 species widespread in South China, East China, and Southwest China. The plants of genus Neolitsea have been found to be rich in sesquiterpenes, triterpenes, alkaloids, and steroids [1, 2]. The occurrence of a small number of flavonoids, benzenoids, monoterpenes, and benzoquinone has also been reported [3]. Constituents of the Neolitsea genus (Lauraceae) have been reported to possess diverse bioactivities, such as antioxidant, antibacterial, anti-inflammatory activities, and cytotoxicity [3].

This review summarizes the phytochemical progress involving all constituents isolated from the genus Neolitsea over the past few decades. Some biological activities of compounds isolated from this genus are also included.

Chemical constituents

The reported chemical constituents from this genus include sesquiterpenes, triterpenes, alkaloids, steroids, flavonoids, essential oils, and some other compounds. Their structures are shown in the following sections, and their names and the corresponding plant sources are collected in Tables 15.

Table 1

Sesquiterpenes.

Table 2

Triterpenes.

Table 3

Alkaloids.

Table 4

Steroids.

Table 5

Other compounds.

Sesquiterpenes (Table 1 and Figure 1)

Sesquiterpenes are the characteristic constituents within the genus Neolitsea. From 1966 to 2013, 67 compounds have been isolated. The researched plants include Neolitsea zeylanica, Neolitsea parvigemma, Neolitsea aciculata, Neolitsea acutotrinervia, Neolitsea hiiranensis, and Neolitsea sericea, among others. In 1966, six sesquiterpenes 16 were isolated from N. zeylanica [1]. In the course of further investigation on the chemical constituents of this plant, four novel sesquiterpenes of the furanogermacrane type 710 have been isolated from the stems of N. parvigemma [2]. In 2011, investigation of N. hiiranensis revealed seven new sesquiterpenoids 1218 and 12 known sesquiterpenoids 1930 from the leaves of this plant [3]. In 1983, Nozaki et al. isolated a new sesquiterpene dilactone 31, named neoliacine, from the leaves of N. aciculata, and they further examined chemical components of the same plant and isolated the sesquiterpene acid 32 [14, 15]. Four known furanosesquiterpene lactones 1, 2, 5, 6, along with a new derivative, deacetylzeylanidine 33, were isolated from N. parvigemma [5]. From N. sericea, three new elemane-type sesquiterpenoids 24, 41, 58 and two new germacrane-type sesquiterpenoids 39, 40 were isolated by column chromatography and thin layer chromatography [8]. In 1970, components of N. aciculata were investigated, and ten furan sesquiterpenes 14, 11, 3438 were isolated from the root and trunk [9]. At the same time, neosericenine 42, an isomer of sericenine 39, along with compounds 40 and 41 were isolated from the leaf of N. sericea [16, 17]. Phytochemical investigation of Neolitsea acuminatissima resulted in the isolation of three new eudesmanolide sesquiterpenes 4345 and a known eudesmanolide sesquiterpene 41 [18]. Investigation of N. acutotrinervia revealed numerous sesquiterpene lactones, including four known furanogermacranolides 2, 4, 37, 38, one known germacranediolide 35, and four new germacranediolides 4750 [10]. Chen et al. have isolated two novel sesquiterpenes of the furanogermacrane type, namely parvigemone 9 and neolitrane 10, along with six known compounds 12, 56, 11, 33 from the stems of N. parvigemma [6]. Compounds 5154 are not produced naturally in plant, but formed by oxidation of 2 [11]. Seven sesquiterpene lactones 1, 2, 11, 17, 26, 34, 38 were isolated from the roots of Neolitsea villosa, in which three compounds 17, 26, 38 are new [4]. Three new compounds 5557 were isolated from the roots of Neolitsea daibuensis [19]. In the continuing studies on Lauraseae plants, which are widely distributed in Japan, three germacranes 25, 59, 60 and two elemanes 61, 62 have been isolated from the fresh leaves of N. aciculata Koidz [13]. The major constituents of the leaf and bark oil of Neolitsea pallens are compounds 6367 [20].

Sesquiterpenoid structures.
Figure 1

Sesquiterpenoid structures.

Triterpenes (Table 2 and Figure 2)

Most of the triterpenes reported in the genus Neolitsea are tetracyclic, and a few of them are pentacyclic. These triterpenes are dammaranes, lanostanes, cycloartanes, oleananes, and lupanes. A phytochemical investigation of the crude chloroform extract of the Neolitsea dealbata bark revealed two common triterpenes 68, 69, which were reported for the first time from this plant [21]. Investigation of the ethyl acetate-soluble extract of the leaves of N. hiiranensis led to the isolation of hiiranterpenone 70 [3]. Chan and Hui isolated three C32 triterpenes 7173 by column chromatography of the light petroleum extract [23]. In addition, analysis of a larger quantity of a similar extract led to the discovery of three related minor triterpenes 7476 [22, 23]. Compound 77, a new cycloartane, was reported from N. sericea in 1993, and further investigation of this plant revealed three new lanostanes 7880, along with a known compound 81 [24, 43]. In 1992, several triterpenes 8199 were isolated from the alcohol extract of N. sericea, among which 86, 93, and 94 are new compounds [39, 40]. Lupenone 100 was isolated from the stem bark of Neolitsea fuscata [25].

Triterpenoid structures.
Figure 2

Triterpenoid structures.

Alkaloids (Table 3 and Figure 3)

In 2001, 15 alkaloids 101103, 106, 107, 124–129, 133–135, 137 were isolated from the stem bark of N. acuminatissima. Among them, compound 124 was a new benzylisoquinoline alkaloid. Their structures were established on the basis of analysis of NMR and mass spectral data [18]. The first chemical investigation of N. villosa (Bl.) Merr. led to the isolation of ten known isoquinoline alkaloids 101, 104–106, 121, 128, 133, 136, 143, 144 from the stem of this plant [26]. In 1965, three new alkaloids 115, 139, 145 were found in the ethanolic extract of the dried leaves of Neolitsea pulchella [34]. Kozuka et al. reported the isolation and identification of two alkaloids 104, 134 from Neolitsea ariculuta in 1984 [32]. Three new oxygenated noraporphine alkaloids 130, 137, 138 along with eight known aporphine alkaloids 121, 108–112, 140, 141 were isolated from the bark of the Chinese tree, Neolitsea aurata var. paraciculata, which was the first report of chemical constituents of this plant [28]. In 1998, Chen et al. reported eight alkaloids 101, 113, 114, 128, 129, 131, 132, 142 from N. parvigemma and Neolitsea konishii, and compounds 129, 113, 114, 131, 132 were isolated for the first time from this genus [31]. In 2001, 15 alkaloids were isolated from the stem bark of N. acuminatissima. Among them, compound 123 is a new benzylisoquinoline alkaloid, whose structure was established on the basis of analysis of NMR and mass spectral data [18]. By combination of centrifugal partition chromatography and common separation methods, 12 known alkaloids were isolated from N. konishii and characterized [29]. Compounds 121 and 117 were isolated from Neolitsea buisanensis, N. sericea, and N. aurata [27, 30]. In addition, compounds 118, 131, 135 were isolated from N. aurata [35]. Lu and Su isolated three alkaloids 108, 112, 147 from Neolitsea variabillima [33]. In 2010, a new aporphine alkaloid 149 was reported from the bark of N. dealbata [36]. In 2011, Wong et al. reported three new β-carboline alkaloids 120, 148, 150 from the root of N. daibuensis [19]. A total 14 new alkaloids and 37 known alkaloids were reported from this genus.

Alkaloid structures.
Figure 3

Alkaloid structures.

Steroids (Table 4 and Figure 4)

Four steroids, a mixture of 155 and 156, and a mixture of 157 and 158, were isolated from N. acuminatissima [18]. Komae and Hayashi detected phytosterols (155, 156, 159) in the wood of N. sericea by using gas chromatography [37]. Neolitsea sericea and Daemia extensa (Asclepiadaceae) seem to be the only plants containing 3α-hydroxy sterols in a higher plant. Yano et al. investigated the constituents of the stem of this plant and isolated two new 4α-methylsterols and three new 3α-hydroxy-14α-methyl-Δ9(11) sterols; they are compounds 168 and 169, 24α- and 24β-epimers of 14α,24-dimethyl-5α-cholest-9(11)-en-3α-ol, compounds 160 and 161, and 14α-methyl-24α-ethyl-5α-cholest-9(11)-en-3α-ol 162 [38, 40]. The ethyl acetate extract from the wood of N. sericea contained two new steroidal compounds 170 and 171 [41]. Further study on the sterols from N. sericea extract led to the isolation of compounds 163167 [39, 40].

Steroids (see Figure 2 for definition of the R groups).
Figure 4

Steroids (see Figure 2 for definition of the R groups).

Others (Table 5 and Figure 5)

From the fruit oil of N. pallens, Padalia et al. isolated trans-β-ocimene 200 and sabinene 201 [20]. Investigation of N. sericea var. aurata revealed occurrence of six flavone rhamnosides 187–193 [42]. In 1998, three flavonoids, kaempferol-3-O-rhamnoside 187, quercetin-3-O-rhamnoside 188, and taxifolin-3-O-rhamnoside 189, three ferulates, docosanyl ferulate 194, tetracosanyl ferulate 195, and hexacosanyl ferulate 196, two cyclohex-2-en-1-ones, blumenol A 197, and roseoside 198, and one amide, N-trans-feruloylmethoxytyramine 199 were isolated from Neolitsea pavigemma and N. konishii [31]. From the leaves of Neolitsea cassia, de Silva et al. isolated a water-soluble arabinoxylan [44]. Chang et al. isolated three lignans, (+)-lyoniresinol 179, (+)-syringaresinol 180, and (±)-glaberide I 181, four benzenoids, vanillin 182, isovanillin 183, p-methoxybenzoic acid 184, and methylparaben 185, together with one paraquinone, 2,6-dimethoxy-p-benzoquinone (186), from the stem bark of N. acuminatissima [18]. The following compounds were also isolated from the leaves of N. hiiranensis: 132-hydroxy-(132S)-pheophytin (172), α-tocopheryl quinine (173), α-tocopherol (174), ficaprenol-11 (175), linolenic acid (176), syringaldehyde (177), syringic acid (178), vanillin (182) and p-anisic acid (184) [3].

Structures of other compounds.
Figure 5

Structures of other compounds.

Biological activities

Anti-inflammatory activity

The anti-inflammatory effects of compounds 13 and 15 were evaluated by their suppression of the N-formyl- methionyl-leucyl-phenylalanine (fMLP)-induced generation of the superoxide anion, an inflammatory mediator produced by neutrophils. And the inhibitory activity against fMLP-induced superoxide production with IC50 values of 21.86±3.97 and 25.78±4.77 mm, respectively [3]. Six furanogermacranes 1, 57, 10, 11 were tested for anti-inflammatory activities. Among them, compounds 1 and 11 show significant inhibitory effects on superoxide anion generation by human neutrophils in response to fMLP/CB: the IC50 of compounds 1 and 11 were found to be 3.21 and 8.48 mg/mL, respectively [7]. Compounds 34 and 163, 7-O-methylnaringenin and prunetin, which were isolated from N. daibuensis, exhibit moderate inducible nitric oxide synthase inhibitory activity, with IC50 values of 18.41, 0.30, 19.55, and 10.50 mm, respectively [19]. The essential oil of N. aciculata exhibit moderate to strong antibacterial activity against drug-susceptible and -resistant Propionibacterium acnes and Staphylococcus epidermidis, which are known as acne-causing bacteria. In addition, the essential oil reduces the P. acnes-induced secretion of tumor necrosis factor-alpha (TNF-α) and interleukin-8 (IL-8) in THP-1 cells, highlighting its anti-inflammatory effects [45].

Antitumor activity

Neoliacine 31, a sesquiterpene lactone isolated from the leaves of N. aciculata, exhibits moderate cytotoxicity in HeLa cell culture in vitro [14]. Compounds 44, 45, and 184 selectively inhibit Hep 2,2,15 cells with IC50 values in the range of 0.24–0.04 μg/mL. 2,6-Dimethoxy-p-benzoquinone is marginally cytotoxic to Hep G2 cells [18]. A known elemane-type sesquiterpene, isolinderalactone 34, shows promising antitumor activity in vitro against all tumor cells tested: KB (EDSo=2.990 ppm), P-388 (0.816 ppm), A-549 (1.420 ppm), and HI-29 (1.528 ppm) [4]. Recently, Su et al. reported the chemical components and in vitro anticancer activities of the essential oil isolated from the leaf of N. variabillima. The anticancer activities of oil were evaluated and the results showed that the oil exhibits cytotoxic activity against human oral, liver, lung, colon, melanoma, and leukemic cancer cells [46]. The presence of β-caryophyllene, τ-cadinol, and α-cadinol significantly contributes to the anticancer activity of N. variabillima leaf oil [46]. Compound 164 selectively inhibits the growth of cervical cancer cells (HeLa) with an IC50 of 4.0 μm [40].

Vasoconstricting activity

Thaliporphine, isolated from N. konishii, has been found to possess vasoconstricting action and selectively inhibits expression of inducible, but not constitutive, nitric oxide synthase [29].

Antifungal and antibacterial activities

The hydro-distilled leaf essential oil of N. parvigemma exhibits antifungal activity against seven fungi, including Aspergillus clavatus, Aspergillus niger, Chaetomium globosum, Cladosporium cladosporioides, Myrothecium verrucaria, Penicillium citrinum, and Trichoderma viride. Besides, the oil also possesses anti-wood-decay activity induced by fungi Trametes versicolor, Phaneochaete chrysosporium, Phaeolus schweintizii, and Lenzites sulphureu [47]. The essential oil isolated from N. aciculata and N. sericea possesses antimicrobial activities [45, 48].

Others

The bark and leaves of N. cassia can be used for the treatment of fractures [44]. Several antiplatelet aggregation sesquiterpenes and alkaloids were also isolated from N. konishii, N. villosa, N. parvigemma, N. variabillima, and N. aurata and characterized [2]. Aporphine alkaloids, commonly present in this genus, have been shown to possess various pharmacological activities, such as choleretic and smooth muscle relaxing properties for boldine and hypotensive and hyperlipidemia-reducing properties in tested animals for dicentrine [12].

Conclusions

The genus Neolitsea includes 85 species, and some of them have been used as traditional herbal medicines. The chemical investigation of the Neolitsea genus has revealed that this genus contains numerous and complicated constituents, and many components with significant bioactivities have been isolated. This review reveals that only a few species have been investigated, with many species receiving little or no attention. Further phytochemical and biological studies should be carried out on these plants.

Acknowledgments

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (81072551, 81241101), Key Projects of Science and Technology of Hebei Province (11276103D-89). We also wish to extend our sincere thanks to Syngenta Ltd. (2013-Hebei Medical University-Syngenta-04) and JSPS KAKENHI (grant numbers 19580120, 22560112, 25450144) for financial support.

References

  • [1]

    Joshi, B. S.; Kamat, V. N.; Govindachari, T. R. Sesquiterpenes of Neolitsea zeylanica Merr.-I isolated of some constituents. Tetrahedron 1967, 23, 261–265.CrossrefGoogle Scholar

  • [2]

    Chen, K. S.; Wu, Y. C. Sesquiterpenoids from Neolitsea parvigemma: isolation, oxidation products and antiplatelet actions. Tetrahedron 1999, 55, 1353–1366.CrossrefGoogle Scholar

  • [3]

    Liou, B. J.; Chang, H. S.; Wang, G. J.; Chiang, M. Y.; Liao, C. H.; Lin, C. H.; Chen, I. S. Secondary metabolites from the leaves of Neolitsea hiiranensis and the anti-inflammatory activity of some of them. Phytochemistry 2011, 72, 415–422.CrossrefWeb of SciencePubMedGoogle Scholar

  • [4]

    Li, W. S.; Duh, C. Y. Sesquiterpene lactones from Neolitsea villosa. Phytochemistry 1993, 32, 1503–1507.Google Scholar

  • [5]

    Li, W. S. Chemical constituents of Neolitsea parvigemma. J. Nat. Prod. 1990, 53, 1581–1584.CrossrefGoogle Scholar

  • [6]

    Chen, K. S.; Chang, F. R. Two novel sesquiterpenes from Neolitsea parvigemma. J. Nat. Prod. 1996, 59, 704–706.CrossrefGoogle Scholar

  • [7]

    Chen, K. S.; Hsieh, P. W.; Hwang, T. L.; Chang, F. R.; Wu, Y. C. Anti-inflammatory furanogermacrane sesquiterpenes from Neolitsea parvigemma. Nat. Prod. Res. 2005, 19, 283–286.CrossrefGoogle Scholar

  • [8]

    Hayashi, N. Sesquiterpenoids in the essential oil of Neolitsea sericea. Physics Chem. 1969, 33, 107–133.Google Scholar

  • [9]

    Takeda, K.; Horibe, I.; Teraoka, M.; Minato, H. Sesquiterpenes of Lauraceae plants. Part 1. Components of Neolitsea aciculate Koidz. J. Chem. Soc. (C) 1970, 7, 973–980.Google Scholar

  • [10]

    Li, W. S. Sesquiterpene lactones from the root of Neolitsea acutotrinervia. J. Nat. Prod. 1992, 55, 1614–1619.CrossrefGoogle Scholar

  • [11]

    Li, S.; Li, W. S. Terpenoids from Neolitsea buisanensis. Phytochemistry 1991, 30, 4160–4162.Google Scholar

  • [12]

    Sun, S. W.; Lee, S. S.; Huang, H. M. Determination of lauraceous aporphine alkaloids by high-performance liquid chromatography. J. Pharm. Biomed. Anal. 1996, 14, 1383–1387.CrossrefGoogle Scholar

  • [13]

    Takaoka, D.; Tani, H.; Nozaki, H.; Tada, S.; Nakayama, M. Structures of highly oxygenated sesquiterpenoids of Lauraceae, Neolitsea aciculata Koidz. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1992, 34, 424–431.Google Scholar

  • [14]

    Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayarna, M. Neoliacine, a novel germacranolide sesquiterpene dilactone from Neolitsea acciculata Koidz.:X-ray crystal structure. J.Chem.Soc.Chem.Commun. 1983, 19, 1107–1108.CrossrefGoogle Scholar

  • [15]

    Takaoka, D.; Nozaki, H.; Nakayama, M. Structure of neoliacinic acid, a new highly oxidized sesquiterpene from Neolitsea acciculata Koidz. J. Chem. Soc. Chem. Commun. 1987, 24, 1861–1862.CrossrefGoogle Scholar

  • [16]

    Takeda, K.; Tori, K.; Horibe, I.; Minato, H. Structure of sericenine. J. Chem. Soc. (C) 1970, 7, 985.Google Scholar

  • [17]

    Takeda, K.; Horibe, I.; Minato, H. Sesquiterpenes of Lauraceae plants. Part II. Neosericenine, a component of Neolitsea sericea Koidz. J. Chem. Soc. (C) 1970, 11, 1547–1549.Google Scholar

  • [18]

    Chang, F. R.; Hsieh, T. J.; Huang, T. L.; Chen, C. Y.; Kuo, R. Y.; Chang, Y. C.; Chiu, H. F.; Wu, Y. C. Cytotoxic constituents of the stem bark of Neolitsea acuminatissima. J. Nat. Prod. 2002, 65, 255–258.CrossrefGoogle Scholar

  • [19]

    Wong, S. L.; Chang, H. S.; Wang, G. J.; Chiang, M. Y.; Huang, H. Y.; Chen, C. H.; Tsain, S. C.; Lin, C. H.; Chen, I. S. Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity. J. Nat. Prod. 2011, 74, 2489–2496.CrossrefGoogle Scholar

  • [20]

    Padalia, R. C.; Chanotiya, C. S.; Thakuri, B. C.; Mathela, C. S. Germacranolide rich essential oil from Neolitsea pallens. Nat. Prod. Commun. 2007, 2, 591–593.Google Scholar

  • [21]

    Wu, X. J.; Vogler, B.; Jackes, B. R.; Setzer, W. N. Terpenoids from Neolitsea dealbata. Nat. Prod. Commun. 2008, 3, 129–132.Google Scholar

  • [22]

    Hui, W. H.; Luk, K.; Arthur, H. R.; Loo, S. N. Structures of three C32 triterpenoids from Neolitsea puchella. J. Chem. Soc. (C) 1971, 16, 2826–2829.Google Scholar

  • [23]

    Chan, W. S.; Hui, W. H. Further C32 triterpenoids from Neolitsea puchella. J. Chem. Soc. (C) 1973, 5, 490–492.Google Scholar

  • [24]

    Sharma, M. C.; Ohira, T.; Yatagai, M. Sericeol, a cycloartane triterpene from Neolitsea sericea. Phytochemistry 1993, 33, 721–722.CrossrefGoogle Scholar

  • [25]

    Gunatilaka, A. A. L.; Sotheeswaran, S.; Sriyani, B.; Balasubramaniam, S. Isoboldine and lupenone from Neolitsea fuscata. Planta Med. 1981, 43, 309–310.CrossrefGoogle Scholar

  • [26]

    Lee, S. S.; Wang, P. H.; Chiou, C. M.; Chen, I. S.; Chen, C. H. Isoquinoline alkaloids from Litsea garciae and Neolitsea villosa. Chin. Pharmaceut. J. 1995, 47, 69–75.Google Scholar

  • [27]

    Tatsuo, N.; Shozo, N. Alkaloids of lauraceous plants. III. Alkaloids isolated from the leaves of Neolitsea sericea. Yakugaku Zasshi 1959, 79, 1267–1272.Google Scholar

  • [28]

    Buchanan, M. S.; Carroll, A. R.; Pass, D.; Quinn, R. J.; Buchanan, M. S.; Carroll, A. R.; Pass, D.; Quinn, R. J. Aporphine alkaloids from the Chinese tree Neolitsea aurata paraciculata. Nat. Prod. Commun. 2007, 2, 255–259.Google Scholar

  • [29]

    Lee, S. S.; Yang, H. C. Isoquinoline alkaloids from Neolitsea konishii. J. Chin. Chem. Soc. 1992, 39, 189–194.Google Scholar

  • [30]

    Tatsuo, N.; Shozo, A.; Yuri, K. Alkaloids of Lauraceae plants. V. Alkaloids isolated from the trunk bark of Neolitsea sericea. Yakugaku Zasshi 1966, 86, 129–134.Google Scholar

  • [31]

    Chen, K. S.; Chang, F. R.; Chia, Y. C.; Wu, T. S.; Wu, Y. C. Chemical constituents of Neolitsea parvigemma and Neolitsea konishii. J. Chin. Chem. Soc. 1998, 45, 103–110.Google Scholar

  • [32]

    Kozuka, M.; Takeuchi, M.; Sawada, T. Alkaloid from Neolitsea aciculata. J. Nat. Prod. 1984, 47, 1062.CrossrefGoogle Scholar

  • [33]

    Lu, S. T.; Su, T. L. Alkaloids of formosan Lauraceous plants. XVI. Alkaloids of Neolitsea variabillima. J. Chin. Chem. Soc. 1973, 20, 75–81.Google Scholar

  • [34]

    Hui, W. H.; Loo, S. N.; Arthur, H. R. New aporphine alkaloids from Neolitsea pulchella. J. Chem. Soc. (C) 1965, 3, 2285–2286.Google Scholar

  • [35]

    Lu, S. T.; Su, T. L.; Wang, E. C. Studies on the alkaloids of formosan lauraceous plants. XVIII. Alkaloids of Neolitsea buisanensis Yamamoto et Kamikoti and Neolitsea aurata (Hay.) Koidz. J. Chin. Chem. Soc. 1975, 22, 349–353.Google Scholar

  • [36]

    Tran, T. D.; Pham, N. B.; Fechner, G.; Quinn, R. J.; Ronald, J. Chemical investigation of drug-like compounds from the Australian tree Neolitsea dealbata. Bioorg. Med. Chem. Lett. 2010, 20, 5859–5863.CrossrefPubMedWeb of ScienceGoogle Scholar

  • [37]

    Komae, H.; Hayashi, N. Palmitone and phytosterols from Neolitsea sericea. Phytochemistry 1971, 10, 1953–1954.CrossrefGoogle Scholar

  • [38]

    Yano, K.; Akihisa, T.; Tamura, T.; Matsumoto, T. 3α-Hydroxy-14-methyl-Δ9(11) sterol from Neolitsea acicutala. Phytochemistry 1992, 31, 2902–2904.Google Scholar

  • [39]

    Yano, K.; Akihisa, T.; Kawaguchi, R.; Tamura, T.; Matsumoto, T. 24-Methylene-25-methylcycloartanol and 24α-ethyl-5α-cholestan-3α-ol from Neolitsea sericea. Phytochemistry 1992, 31, 1941–1946.Google Scholar

  • [40]

    Yano, K.; Akihisa, T.; Tamura, T.; Matsumoto, T. Four 4α-methylsterols and triterpene alkaloids from Neolitsea aciculata. Phytochemistry 1992, 31, 2093–2098.CrossrefGoogle Scholar

  • [41]

    Sharma, M. C.; Ohira, T.; Yatagai, M. Extractives of Neolitsea sericea a new hydroxy steroidal ketone, and other compounds from the heartwood of Neolitsea sericea. Mokuzai Gakkaishi 1993, 39, 939–943.Google Scholar

  • [42]

    Lam, S. H.; Chen, C. K.; Wang, J. S.; Lee, S. S. Investigation of flavonoid glycosides from Neolitsea sericea var. aurata via the general method and HPLC-SPE-NMR. J. Chin. Chem. Soc. 2008, 55, 449–455.Google Scholar

  • [43]

    Sharma, M. C.; Ohira, T.; Yatagai, M. Lanostane triterpenes from the bark of Neolitsea sericea. Phytochemistry 1994, 37, 201–203.CrossrefGoogle Scholar

  • [44]

    de Silva, S. S. M.; Kumar, N. S. Structural studies of an arabinoxylan isolated from the leaves of Neolitsea cassia. Carbohydr. Res. 1986, 152, 229–236.CrossrefGoogle Scholar

  • [45]

    Suk, K. S.; Eun, K. J.; Hyun, C. G.; Lee, N. H. Neolitsea aciculata essential oil inhibits drug-resistant skin pathogen growth and propionibacterium acnes-induced inflammatory effects of human monocyte leukemia. Nat. Prod. Commun. 2011, 8, 1193–1198.Google Scholar

  • [46]

    Su, Y. C.; Hsu, K. P.; Wang, E. I. C.; Ho, C. L. Composition and in vitro anticancer activities of the leaf essential oil of Neolitsea variabillima from Taiwan. Nat. Prod. Commun. 2013, 8, 531–532.PubMedGoogle Scholar

  • [47]

    Ho, C. L.; Liao, P. C.; Wang Eugene, I. C.; Su, Y. C. Composition and antifungal activities of the leaf essential oil of Neolitsea parvigemma from Taiwan. Nat. Prod. Commun. 2011, 6, 1357–1360.PubMedGoogle Scholar

  • [48]

    Hyun, C. G.; Yoon, W. J.; Lee, N. H. Essential oils of Neolitsea sericea having anti-inflammatory and antimicrobial activities. Korean Kongkae Taeho Kongbo 2011, KR 2011036318 A 20110407.Google Scholar

About the article

Corresponding authors: Qing-Wen Shi, School of Pharmaceutical Sciences, Hebei Key Laboratory of Forensic Medicine, Hebei Medical University, Shijiazhuang 050017, Hebei Province, China, e-mail: ; and Hiromasa Kiyota, Graduate School of Environmental and Life Science, Okayama University, 1-1-1 Tsushima-Naka, Kita-ku, Okayama 700-8530, Japan, e-mail:


Received: 2013-12-17

Accepted: 2014-02-13

Published Online: 2014-03-31

Published in Print: 2014-04-01


Citation Information: Heterocyclic Communications, Volume 20, Issue 2, Pages 61–75, ISSN (Online) 2191-0197, ISSN (Print) 0793-0283, DOI: https://doi.org/10.1515/hc-2013-0239.

Export Citation

©2014 by Walter de Gruyter Berlin/Boston.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Nor Akmalazura Jani, Hasnah Mohd Sirat, Farediah Ahmad, Nor Azah Mohamad Ali, and Muhd Hafizi Zainal
Natural Product Communications, 2016, Volume 11, Number 12, Page 1934578X1601101

Comments (0)

Please log in or register to comment.
Log in