Chemical constituents from the fruits of Vitex trifolia L. (Verbenaceae) and their chemotaxonomic significance

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Highlights

  • One new labdane-type diterpenoid and twenty-three known compounds were isolated from the fruits of Vitex trifolia.

  • Compounds 2, 9, and 10 were firstly found from Vitex trifolia.

  • Compounds 1, 6, 14, 15, 17, and 22 were firstly found from the family Verbenaceae.

  • Diterpenoids could be obviously considered as chemotaxonomic markers for the genus Vitex.

Abstract

One new labdane-type diterpenoid (1) named viterotulin D, along with twenty-three known compounds, including fourteen diterpenoids (215), one monoterpenoid (16), three steroids (1719), one flavonoid (20), and four phenols (2124) were isolated from the fruits of Vitex trifolia L. The structures of these compounds were identified based on spectroscopic data interpretation and comparison with previously reported values in the literature. This is the first report on the isolation of compounds (1, 6, 14, 15, 17, and 22) and (2, 9, and 10) from the family Verbenaceae and Vitex trifolia, respectively. The chemotaxonomic significant of the isolates was also discussed.

Section snippets

Subject and source

The genus Vitex belongs to the family Verbenaceae and comprises about 250 species distributed in tropical and subtropical areas around the world (Rani and Sharma, 2013). Only fourteen of them are widely distributed in China. Vitex trifolia L. is a small deciduous shrub, and the fruits of this plant are used in folk medicine for the treatment of headache, eye pain, migraine, cold, and cancer (Wu et al., 2009). In this present study, the fruits of V. trifolia were purchased from Anguo, Hebei

Previous work

Previous phytochemical studies on V. trifolia have reported the isolation of diverse second metabolites such as sesquiterpenoids (Suksamrarn et al., 1991), diterpenoids (Ono et al., 2000; Zheng et al., 2013; Luo et al. 2017a, 2017b; Tiwari et al., 2013), triterpenoids (Jangwan et al., 2013), flavonoids (Li et al., 2005), and iridoids (Bao et al., 2018).

Present study

The air-dried and powdered fruits of V. trifolia (30 kg) were extracted with 95% ethanol (100 L) at room temperature once a week during three weeks successively. After removing the organic solvent under reduced pressure, the residue (941 g) was suspended in H2O and partitioned with EtOAc. The EtOAc extract (450 g) was subjected to silica gel column chromatography (CC) using petroleum ether-acetone mixtures (40:1, 20:1, 10:1, 5:1, 2:1, 1:1, V/V) to afford fractions A-F. Monitored by thin-layer

Chemotaxonomic significance

Terpenoids are the characteristic constituents of the genus Vitex, and diterpenoids are the most dominants. In the present study, fifteen diterpenoids (115) were isolated from the fruits of V. trifolia, which included eight labdane-type (18), two norlabdane-type (9 and 10), two halimane-type (11 and 12), two abietane-type (13 and 14) and one cyclophytane-type (15) diterpenoids.

Viterotulin D (1), a new labdane-type diterpenoid, was isolated and reported from the family Verbenaceae for the

CRediT authorship contribution statement

Komi Djimabi: Investigation, Methodology, Data curation, Formal analysis, Writing – original draft, Writing – review & editing. Bing Li: Investigation, Methodology, Formal analysis. Xiao-Han Chen: Methodology, Formal analysis, Data curation. Pan-Jie Su: Methodology, Formal analysis, Data curation. Xu Liu: Methodology, Formal analysis, Data curation. Ru-Yue Wang: Investigation, Formal analysis, Data curation. Feng-Ming Qi: Data curation, Formal analysis. Mei-Jie Wang: Formal analysis, Data

Declaration of competing interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgment

This work was financially supported by the National Natural Science Foundation of China (No. 31870324 and No. 31670350).

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