艾纳香不同提取物GC-MS分析及其抑菌活性

胡璇; 王凯; 于福来; 王丹; 谢小丽; 庞玉新; 陈鸿发

doi:10.19303/j.issn.1008-0384.2021.10.003

艾纳香不同提取物GC-MS分析及其抑菌活性

doi: 10.19303/j.issn.1008-0384.2021.10.003

胡璇^1,,
王凯¹,
于福来^1, ,,
王丹¹,
谢小丽¹,
庞玉新^2, ,,
陈鸿发³

1.
中国热带农业科学院热带作物品种资源研究所/海南省艾纳香工程技术研究中心，海南　海口　571101
2.
广东药科大学中药资源学院，广东　云浮　527500
3.
海南艾纳香生物科技发展股份有限公司，海南　海口　570208

基金项目: 中国热带农业科学院基本科研业务费专项（1630032019036）；海南省自然科学基金项目（2019CXTD414、721QN325）

详细信息

作者简介:
胡璇（1986−），女，硕士，助理研究员，研究方向：南药资源研究与开发利用（E-mail：mchuxuan@163.com）

通讯作者:
于福来（1983–），男，博士，副研究员，研究方向：中药（南药）资源定向培育及综合开发利用研究（E-mail：fulai.yu@163.com）

庞玉新（1975–），男，博士，研究员，研究方向：南药资源研究与开发利用（E-mail：pyxmarx@126.com）

中图分类号: R 284.1
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出版历程
- 收稿日期: 2021-06-03
- 修回日期: 2021-07-27
- 网络出版日期: 2021-10-23
- 刊出日期: 2021-10-28

Composition and Antibacterial Activity of Blumea balsamifera Extracts

HU Xuan^1
,,
WANG Kai¹,
YU Fulai^{1
, ,},
WANG Dan¹,
XIE Xiaoli¹,
PANG Yuxin^{2
, ,},
CHEN Hongfa³

1.
Tropical Crops Genetic Resources Institute, Chinese Academy of Tropical Agricultural Sciences/Hainan Provincial Engineering Research Center for Blumea balsamifera, Haikou, Hainan　571101, China
2.
School of Chinese Materia Medica Resources, Guangdong Pharmaceutical University, Yunfu, Guangdong　527500, China
3.
Hainan Ainaxiang Biotechnology Development Co., Ltd., Haikou, Hainan　570208, China

摘要

摘要: 目的研究艾纳香不同提取物的化学成分以及对口腔厌氧菌的体外抑菌活性，为艾纳香提取物的开发利用提供科学依据。方法采用气相色谱-质谱（GC-MS）联用技术分析了3种艾纳香提取物艾纳香油、艾粉和艾片的化学成分，并采用管碟法、微量肉汤稀释法和琼脂培养基平板法测定3种提取物对4株常见口腔厌氧菌株变形链球菌（Streptococcus mutans）、具核梭杆菌（Fusobacterium nucleatum）、牙龈卟啉单胞菌（Porphyromonas gingivalis）和中间普氏菌（Prevotella intermedia）的敏感度、最低抑菌浓度（Minimum inhibitory concentration，MIC）和最小杀菌浓度（Minimum bactericidal concentration，MBC）。结果从艾纳香油、艾粉和艾片中分别鉴别出56、19和8种化合物，艾纳香油中化学组分相对艾粉和艾片更为复杂。3种提取物仅含有左旋龙脑1个共有成分，左旋龙脑相对含量分别为13.36%、81.40%和76.07%。体外抑菌试验中艾纳香油、艾粉、艾片对变形链球菌、具核梭杆菌、中间普氏菌均有一定的药敏活性，表现出了中度敏感，3种提取物对牙龈卟啉单胞菌无明显的药敏作用。3种提取物对4种口腔厌氧菌表现出不同程度的抑制作用，MIC为8.34～100 mg·mL⁻¹，其中艾纳香油的抑菌效果最强（MIC、MBC分别为8.34～16.68、33.35～133.4 mg·mL⁻¹），艾粉和艾片的抑菌效果并无明显差异。艾粉和艾片对牙龈卟啉单胞菌、艾粉对变形链球菌、艾片对中间普氏菌的MBC值均＞200 mg·mL⁻¹，杀菌效果均不理想。结论艾纳香中不同提取物艾纳香油、艾粉和艾片对多种口腔厌氧菌均具有体外抑菌活性，尤其是对具核梭杆菌抑制作用最强，其中艾纳香油对口腔厌氧菌的抑制作用最强。
- 艾纳香提取物 /
- GC-MS /
- 体外抑菌作用 /
- 最低抑菌浓度 /
- 最低杀菌浓度
Abstract: Objective Chemical compositions andin vitro antibacterial activity of a variety of extracts from Blumea balsamifera (L.) DC were studied. Method Gas chromatography-mass spectrometry (GC-MS) was used to analyze the chemical compositions of B. blsamifera extracts in the forms of oil, powder, and camphor. Sensitivity, minimal inhibitory concentration (MIC), and minimal bactericidal concentration (MBC) against the common oral anaerobes, i.e., Streptococcus mutans, Fusobacterium nucleatum, Porphyromonas gingivalis, and Prevotella intermedia, of the products were determined by means of the cup plate, micro-broth dilution, and agar culture medium plate methods. Result There were 56 compounds identified from the oil, 19 from the power, and 8 from the camphor product. Chemically, the oil was significantly more complex than the other two, and only l-borneol was commonly found among them. The relative content of l-borneol in the oil was 13.36%, 81.40% in the powder, and 76.07% in the camphor. All 3 products exhibited varying degrees of moderate sensitivity to S. mutans, F. nucleatum, and P. intermedia, but not at all to P. gingivalis, on the in vitro antibacterial tests. They also showed varying inhibitory effects on the oral anaerobic bacteria with MICs ranging from 8.34 to 100 mg·mL⁻¹. Among them, the oil had the highest MICs ranging 8.34–16.68 mg·mL⁻¹ and MBCs 33.35–133.4 mg·mL⁻¹, but no significant difference between the powder and the camphor. In addition, since the MBCs of the powder and the camphor to P. gingivalis, the powder to S. mutans, and the camphor to P. intermedia were all greater than 200 mg·mL⁻¹, the bactericidal efficacies of the powder and the camphor were not considered highly desirable in comparison to the oil. Conclusion The various forms of B. blsamifera extracts displayed in vitro antibacterial activities against some common oral anaerobic bacteria, especially on F. nucleatum by the oil.
- Blumea balsamifera (L.) DC extracts /
- GC-MS /
- antibacterial activity /
- in vitro antibacterial activity /
- MIC

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图 1 艾纳香油（A）、艾粉（B）和艾片（C）的总离子流色谱图

Figure 1. GC-MS total ionic current chromatograms of blumea oil (A), blumea powder (B), and blumea camphor (C)

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表 1 艾纳香油中化学组成成分

Table 1. Chemical composition of blumea oil

序号 No.	化合物 Compounds	保留时间 Retention time/min	化学式 Chemical formula	分子质量 Molecular mass	相对含量 Relative amount/%
1	γ-松油烯 Gamma-terpinene	7.50	C₁₀H₁₆	136.125	0.57
2	（−）-莰烯（−）-camphene	8.02	C₁₀H₁₆	136.125	0.61
3	1-辛烯-3-醇 1-octen-3-ol	9.98	C₈H₁₆O	128.12	0.99
4	（+）-柠檬烯（+）-limonene	11.16	C₁₀H₁₆	136.125	0.33
5	罗勒烯异构体混合物 1,3,6-octatriene,3,7-dimethyl-,（Z）-	12.06	C₁₀H₁₆	136.125	0.36
6	2,6,6-三甲基双环[3.2.0]庚-2-烯-7-酮 2,6,6-trimethylbicyclo[3.2.0]hept-2-en-7-one	14.58	C₁₀H₁₄O	150.104	0.10
7	芳樟醇 Linalool	14.95	C₁₀H₁₈O	154.136	1.66
8	合成樟脑 Synthetic camphor	16.54	C₁₀H₁₆O	152.120	7.18
9	左旋龙脑 l-borneol	18.35	C₁₀H₁₈O	154.136	13.36
10	4-异丙基苯甲醛 Benzaldehyde,4-（1-methylethyl）-	21.16	C₁₀H₁₂O	148.089	0.16
11	1,7,7-三甲基双环[2.2.1]庚-2-醋酸酯（1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl-ester）-acetic acid	22.69	C₁₂H₂₀O₂	196.146	0.90
12	silphiperfol-5-ene	24.22	C₁₅H₂₄	204.188	3.43
13	缬草稀醛-4,7（11）-二烯 Valerena-4,7（11）-diene	25.08	C₁₅H₂₄	204.188	6.77
14	Silphiperfola-4,7（14）-diene	25.60	C₁₅H₂₂	202.172	0.48
15	（10S,11S）-himachala-3（12）,4-diene	26.02	C₁₅H₂₄	204.188	0.12
16	Naphthalene,decahydro-4a-methyl-1-methylene-7-（1-methylethylidene）-,（4aR,8aS）-	26.38	C₁₅H₂₄	204.188	0.20
17	1aR-1aβ,2,3,3a,4,5,6,7bβ-octahydro-1,1,3aβ,7-tetramethyl-1H-cyclopropa[a]naphthalene	27.82	C₁₅H₂₄	204.188	0.95
18	长叶烯-（V4）Longifolene-（V4）	28.49	C₁₅H₂₄	204.188	13.45
19	（Z,Z,Z）-1,5,9,9-四甲基-1,4,7-环十一碳三烯（Z,Z,Z）-1,5,9,9-tetramethyl-1,4,7-cycloundecatriene	29.73	C₁₅H₂₄	204.188	1.80
20	Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-,（1R,4E,9R）-	30.03	C₁₅H₂₄	204.188	3.41
21	（6S）-6-乙烯-6-甲基-1-丙烷-2-基-3-丙烷-2-基-环己烯（6S）-6-ethenyl-6-methyl-1-propan-2-yl-3-propan-2-ylidene-cyclohexene	30.65	C₁₅H₂₄	204.188	0.30
22	长叶蒎烯（+）-alpha-longipinene	30.93	C₁₅H₂₄	204.188	0.94
23	（+）-环苜蓿烯（+）-cyclosativene	31.58	C₁₅H₂₄	204.188	0.70
24	α-布藜烯 α-bulnesene	31.79	C₁₅H₂₄	204.188	0.11
25	γ-杜松烯 γ-cadinene	32.18	C₁₅H₂₄	204.188	0.34
26	δ-杜松烯 δ-cadinene	32.54	C₁₅H₂₄	204.188	0.90
27	（+）-γ-古芸烯（+）-gamma-gurjunene	32.90	C₁₅H₂₄	204.188	0.11
28	喇叭茶醇（1aR,7aα,7bβ）-decahydro-1,1,4α,7β-tetramethyl-4aH-cycloprop[e]azulen-4aα-ol	34.41	C₁₅H₂₆O	222.198	0.75
29	12-oxabicyclo[9.1.0]dodeca-4,7-diene,1,5,9,9-tetramet	35.65	C₁₅H₂₄O	220.183	0.29
30	愈创醇 Guaiol	35.88	C₁₅H₂₆O	222.198	2.16
31	（2R）-2,3,4,4a,5,6,7,8-八氢-α,α,4aβ,8β-四甲基-2-萘甲醇（2R）-2,3,4,4a,5,6,7,8-octahydro-α,α,4aβ,8β-tetramethyl-2-naphthalenemethanol	36.26	C₁₅H₂₆O	222.198	0.57
32	2-（4aR）-1,2,3,4,4alpha,5,6,7-octahydro-4alpha,8-dimethylnaphthalen-2-yl）-propan-2-ol	36.60	C₁₅H₂₆O	222.198	1.92
33	2-（4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl）propan-2-ol	37.20	C₁₅H₂₆O	222.198	1.47
34	（4alpha,5alpha,10beta）-6-eudesmen-4-ol	38.16	C₁₅H₂₆O	222.198	4.32
35	十五醛 Pentadecanal	44.46	C₁₅H₃₀O	226.23	0.17
36	1H-Indene,1-ethylideneoctahydro-7a-methyl-,（3aR,7aR）-rel-	44.80	C₁₂H₂₀O₂	164.157	0.25
37	4a,8a-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol	76.83	C₁₂H₁₈O	178.136	0.17

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表 2 艾粉中各化学成分

Table 2. Chemical composition of blumea powder （$ \overline { X}\pm { \rm {s}}$, n=3）

序号 No.	化合物　　　　　　　 Compounds	保留时间 Retention time/min	化学式 Chemical formula	分子质量 Molecular mass	相对含量 Relative amount/%
1	2-蒈烯 2-carene	8.05	C₁₀H₁₆	136.125	0.38
2	月桂烯 Beta.-myrcene	9.09	C₁₀H₁₆	136.125	0.32
3	左旋樟脑 l--camphor	16.47	C₁₀H₁₆O	152.12	8.27
4	左旋龙脑 l-borneol	18.49	C₁₀H₁₈O	154.136	81.40
5	Silphiperfol-5-ene	24.18	C₁₅H₂₄	204.188	0.22
6	1,1′-（4,6-二羟基苯）二乙酮 4,6-diacetyl-1,3-benzenediol	28.81	C₁₀H₁₀O₄	194.058	0.13
7	silphiperfol-6-en-5-one	36.62	C₁₅H₂₂O	218.167	0.26
8	4′,6-二甲基-2-羟基苯乙酮 xanthoxylin	39.70	C₁₀H₁₂O₄	196.074	0.18
9	（3S,3aS,6R,7R,9aS）-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulene-3,6-diol	47.39	C₁₅H₂₆O₂	238.193	0.41
10	2,2′-亚甲基双-（4-甲基-6-叔丁基苯酚） phenol,2,2′-methylenebis[6-（1,1-dimethylethyl）-4-methyl-	67.49	C₂₃H₃₂O₂	340.24	0.14

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表 3 艾片中各化学成分

Table 3. Chemical composition of blumea camphor

序号 No.	化合物 Compounds	保留时间 Retention time/min	化学式 Chemical formula	分子质量 Molecular mass	相对含量 Relative amount/%
1	右旋樟脑 d-camphor	16.51	C₁₀H₁₆O	152.12	20.53
2	左旋龙脑 l-borneol	18.45	C₁₀H₁₈O	154.136	76.07
3	2,2′-亚甲基双-（4-甲基-6-叔丁基苯酚） 2,2′-methylenebis（6-tert-butyl-4-methylphenol）	67.45	C₂₃H₃₂O₂	340.24	0.14

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表 4 3种艾纳香提取物对4株厌氧菌的平均抑菌圈直径测定结果

Table 4. Average antibacterial circle diameters of blumea products on 4 oral anaerobes

提取物 Extracts	抑菌圈 Inhibition zone/mm
提取物 Extracts	牙龈卟啉单胞菌 Porphyromonas gingivalis	中间普氏菌 Prevotella intermedia	变形链球菌 Streptococcus mutans	具核梭杆菌 Fusobacterium nucleatum
艾纳香油 Blumea Balsamifera oil	−	13.27±1.41	10.97±0.39	10.79±0.60
艾粉 Blumea Balsamifera powder	−	13.72±0.21	12.71±1.33	12.48±0.91
艾片 Blumea Balsamifera camphor	−	11.06±0.40	11.85±1.23	12.01±1.08
注：“−”为无抑菌圈。 Note：“−” means no average antibacterial circle.

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表 5 3种艾纳香提取物对4株厌氧菌的MIC和MBC测定结果

Table 5. MICs and MBCs of blumea products against 4 oral anaerobes （单位：mg·mL⁻¹）

提取物 Extracts	牙龈卟啉单胞菌 P. gingivalis		中间普氏菌 P. intermedia		变形链球菌 S. mutans		具核梭杆菌 F. nucleatum
提取物 Extracts	MIC	MBC	MIC	MBC	MIC	MBC	MIC	MBC
艾纳香油 Blumea Balsamifera oil	8.34	133.4	8.34	133.4	16.68	133.4	16.68	33.35
艾粉 Blumea Balsamifera powder	100	＞200	100	100	100	＞200	50	50
艾片 Blumea camphor	50	＞200	50	＞200	100	100	50	50
氨苄青霉素 AMP	1.25	/	2.5	/	5	/	2.5	/
95%乙醇 95% Ethanol	−	/	−	/	−	/	−	/
注: “−”表示无抑菌圈；“/”表示无，MBC无对照样品。 Note: “−” indicates no inhibition zone; “/” indicates doing nothing，MBC with no control sample.

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