Biochemical Systematics and Ecology最新文献

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Chemophenetically relevant iridoids and phenolics from Betonica and Stachys (Lamioideae, Lamiaceae) 川芎科、川芎科中环烯醚萜和酚类化合物的化学表型研究

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-26 DOI: 10.1016/j.bse.2025.105113

Isabelle Herre , Thomas Stegemann , Christian Zidorn

Betonica L. and Stachys L. are closely related genera within the Lamiaceae family, yet comparative phytochemical data on their secondary metabolites remain limited. In this study, we investigated and compared the iridoid and phenolic profiles of selected species from both genera to better understand their secondary metabolite diversity. RP-UHPLC-DAD-HRMS analyses of the methanolic extracts of three Betonica species (B. alopecuros L., B. macrantha K.Koch, and B. officinalis L.) and three Stachys species [S. arvensis (L.) L., S. byzantina K.Koch, and S. sylvatica L.] revealed pronounced differences in their secondary metabolite profiles. Chlorogenic acid, harpagide, and martynoside were detected in all investigated species. The iridoid glycoside allobetonicoside was present exclusively in the examined Betonica species, while flavone glycosides showed genus-specific patterns: isoscutellarein and hypolaetin derivatives occurred only in Stachys, whereas tricin and tricetin glucuronides were restricted to Betonica. These differences highlight distinct secondary metabolite profiles between the two genera. Allobetonicoside, tricin 7-O-glucuronide, and tricetin 3′,4′,5′-trimethyl ether-7-O-glucuronide might therefore serve as chemophenetic markers for the genus Betonica, while the presence of hypolaetin 4′-methylether 7-O-[6‴-acetylallosyl (1→2) glucoside] and isoscutellarein 7-O-[6‴-acetylallosyl (1→2) glucoside] exclusively in Stachys supports their value as marker compounds for this genus.

Tricetin 3′,4′,5′-trimethyl ether-7-O-glucuronide, which had previously only been reported from Artemisia frigida Willd. (Asteraceae) as friginoside A, was isolated from B. officinalis. A detailed analysis of the methanolic extract of B. officinalis confirmed the presence of known compounds, including the phenylpropanoids verbascoside, forsythoside B, leucosceptoside B, martynoside, betonyoside F, and stachysoside B; the iridoids harpagide, 8-O-acetylharpagide, and allobetonicoside; and the flavonoid isoorientin. These findings might contribute to chemophentically characterize the genera Betonica and Stachys.

Betonica L.和Stachys L.在Lamiaceae家族中是密切相关的属，但它们的次生代谢产物的比较植物化学数据仍然有限。在本研究中，我们研究并比较了两属植物的环烯醚萜类和酚类化合物，以更好地了解它们的次生代谢物多样性。三种Betonica （B. alopecuros L.， B. macrantha k.k koch， B. officinalis L.）和三种Stachys的甲醇提取物的RP-UHPLC-DAD-HRMS分析[j]。薄荷(l)L.， S. byzantina K.Koch和S. sylvatica L.]揭示了它们次生代谢物谱的显著差异。在所有被调查的物种中均检测到绿原酸、哈弗苷和马丁苷。环烯醚萜苷只存在于甜菜属中，而黄酮类苷则具有属特异性：异花蓟苷和次花蓟苷衍生物仅存在于Stachys中，而tricin和tricetin glucuronides仅存在于甜菜属中。这些差异突出了两个属之间不同的次生代谢物谱。因此，同种异体甜菜糖苷、tricin 7-O-葡糖苷和tricin 3 ',4 ',5 ' -三甲基醚-7-O-葡糖苷可以作为Betonica属的化学标记物，而在Stachys中只存在hypaetin 4 ' -甲基醚7-O-[6′-乙酰氨基乙基（1→2）葡萄糖苷]和异花蓟苷7-O-[6′-乙酰氨基乙基（1→2）葡萄糖苷]支持它们作为该属标记物的价值。曲西汀3 ',4 ',5 ' -三甲基醚-7- o -葡糖苷，此前仅报道从冷蒿中分离得到。（Asteraceae）为friginoside A，从officinalis中分离得到。对牛头草的甲醇提取物进行了详细分析，证实了已知化合物的存在，包括苯丙素毛蕊花苷、连珠合苷B、白藜芦醇苷B、马丁花苷、皂荚苷F和水苏糖苷B；环烯醚萜类化合物哈巴苷、8- o -乙酰哈巴苷和异素甜菜甙；还有类黄酮异荭草苷。这些发现可能有助于Betonica属和Stachys属的化学化学特征。

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引用次数: 0

Corrigendum to “Biomarker identification in warehouse beetle (Trogoderma variabile) larvae: Tracking metabolic shifts across grain hosts” [Biochem. Systemat. Ecol. 120 (2025) 104983] 仓库甲虫（Trogoderma可变）幼虫的生物标志物鉴定：跟踪谷物寄主的代谢变化[生物化学]。Systemat。生态学报。120 (2025)104983]

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-25 DOI: 10.1016/j.bse.2025.105116

Thamer Al-Shuwaili , Khalid Mohammed , Pushpendra Koli , Sonu Kumar Mahawer , Anup Kumar

引用次数: 0

Chemical constituents with chemotaxonomic value from Yunnanopilia longistaminaea 云南云母属植物具有化学分类价值的化学成分

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-22 DOI: 10.1016/j.bse.2025.105112

Liangrui Yang , Yan Wu , Shengqi Zhang , Yaxin Liu , Lifu Wu , Yongfan Zi , Tianpeng Yin , Le Cai

A systematic investigation was conducted on the chemical constituents of Yunnanopilia longistaminaea, a wild edible woody plant endemic to China. Twenty-two compounds, including one lactone (1), one phenolic acid (2), three phenylpropanoids (3–5), five terpenoids (6–10), eight nitrogen-containing heterocyclic compounds (11–18), three steroids (19–21), and one aliphatic chain compound (22), were isolated and identified. Among these, 18 compounds were isolated from this plant for the first time. An evaluating of the chemotaxonomic significance of these compounds revealed that compounds 1, 5, 6, 7, 11, and 22 exhibit notable distribution specificity within the genus Yunnanopilia, serving as characteristic chemotaxonomic markers for both the genus and the family Opiliaceae. These findings provide new chemical evidence for the taxonomy and phylogenetic studies of Y. longistaminaea.

对中国特有野生食用木本植物云母的化学成分进行了系统的研究。共分离鉴定了22个化合物，包括1个内酯(1)、1个酚酸(2)、3个苯丙酸（3-5）、5个萜类（6-10）、8个含氮杂环化合物（11-18）、3个甾体（19-21）和1个脂肪链化合物（22）。其中18个化合物为首次从该植物中分离得到。对化合物1、5、6、7、11和22的化学分类意义进行了评价，发现化合物1、5、6、7、11和22在云芝属中具有显著的分布特异性，可作为云芝科和云芝属的特征化学分类标记。这些发现为长绒芽孢杆菌的分类和系统发育研究提供了新的化学依据。

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引用次数: 0

Chemical constituents from Magnolia grandiflora Linn leaves and their chemotaxonomic significance 大玉兰叶化学成分及其化学分类意义

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-19 DOI: 10.1016/j.bse.2025.105110

Fang Liu , Zhongqin Zhang , Chunmao Yuan , Jun Jin

A phytochemical investigation of the leaves of Magnolia grandiflora Linn. afforded eighteen compounds, including six sequiterpenes (1–6), six alkaloids (7–12), four phenylpropanoids (13–16), and two benzaldehyde derivatives (17–18). Their structural elucidation was achieved by comprehensive NMR analysis as well as by comparison of their spectroscopic date with the literature. Among them, 2 and 3 are firstly isolated and identified as nature products from plant source, 11 and 12 are being firstly reported from the family Magnoliaceae, and 4–6 and 15 were obtained from the genus Magnolia for the first time. This work contributes to the understanding of the chemical diversity of M. grandiflora and also the chemotaxonomic significance of these isolated compounds is discussed.

大玉兰叶的植物化学研究。得到18个化合物，包括6个四萜（1-6）、6个生物碱（7-12）、4个苯丙素（13-16）和2个苯甲醛衍生物（17-18）。它们的结构是通过全面的核磁共振分析以及与文献的光谱数据比较来实现的。其中，2个和3个为首次从植物源分离鉴定的天然产物，11个和12个为首次从木兰科中分离报道，4-6个和15个为首次从木兰属中分离得到。本研究有助于了解桔梗属植物的化学多样性，并对这些分离化合物的化学分类意义进行了探讨。

引用次数: 0

The chemotypes of Ethiopian Echinops kebericho accessions 衣索比亚棘猴材料的化学型分析

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-18 DOI: 10.1016/j.bse.2025.105111

Bekri Melka Abdo , Bizuayehu Tesfaye Asfaw , M. Iqbal Choudhary , Sammer Yousuf , Solomon Abate Mekonnen , Wendawek Abebe Mengesha

The chemotype of essential oils plays a crucial role in classifying plant subspecies with similar morphological traits and optimizing their biological activities. This study characterized and classified the chemotype of 45 accessions of Echinops kebericho, collected from different geographical areas of Ethiopia, based on 15 major chemical constituents of their root essential oil. The chemical composition was analyzed using GC-MS, and chemotype classification was performed through multivariate statistical analysis. Principal component analysis and hierarchical clustering formed the accessions into four groups, leading to the identification of three distinct chemotypes. Chemotype A was characterized by a high concentration of dehydrocostus lactone, β-guaiene, and δ-cadinene, while chemotype B contained dehydrocostus lactone, β-guaiene, and caryophyllene oxide. Chemotype C, designated as the dehydrocostus lactone type, was dominated by dehydrocostus lactone. The north Ethiopia kebericho population was uniformly classified as chemotype C, whereas the other populations exhibited chemotypic diversity, encompassing all three chemotypes. These findings highlight significant chemical variability among kebericho accessions, which originated from various geographical locations of Ethiopia. This chemophenetic approach provides a valuable foundation for the targeted improvement, sustainable production, utilization, and conservation of kebericho plant.

精油的化学型在分类具有相似形态特征的植物亚种和优化其生物活性方面起着至关重要的作用。本研究基于15种主要化学成分，对采自埃塞俄比亚不同地理区域的45份石竹（Echinops kebericho）进行了化学型鉴定和分类。采用GC-MS分析化学成分，采用多元统计分析进行化学型分类。主成分分析和层次聚类将这些材料分为四组，从而鉴定出三种不同的化学型。化学型A含有高浓度的脱氢木香内酯、β-愈创木烯和δ-癸二烯，而化学型B含有脱氢木香内酯、β-愈创木烯和氧化石竹烯。化学型C为脱氢木香内酯型，以脱氢木香内酯为主。埃塞俄比亚北部kebericho种群被统一归类为C型，而其他种群则表现出化学型多样性，包括所有三种化学型。这些发现突出了产自埃塞俄比亚不同地理位置的kebericho材料之间显著的化学差异。这一化学表型分析方法为kebericho植物的定向改良、可持续生产、利用和保护提供了有价值的基础。

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引用次数: 0

Chemical, chemophenetic and antiproliferative studies of Cattleya purpurata 紫癜的化学、化学表型和抗增殖研究

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-17 DOI: 10.1016/j.bse.2025.105114

Diego Luiz Lucca , Gredson Keiff de Souza , Silas Halede de Carvalho , Silvana Maria de Oliveira , Melyssa Fernanda Norman Negri , Deisiany Gomes , Paula Derksen Macruz , Eduardo Jorge Pilau , Maria Auxiliadora Milaneze-Gutierre , Armando Mateus Pomini

This study investigates the phytochemical composition, cytotoxic activity, and chemophenetic relationships of Cattleya purpurata, a prominent Brazilian orchid. Despite its widespread cultivation for ornamental and commercial purposes, the phytochemical profile of C. purpurata remains underexplored. Phytochemical analysis led to the isolation and identification of 12 compounds using nuclear magnetic resonance (NMR) spectroscopy: the triterpene 24-methylenecycloartanol (1), the steroids β-sitosterol (2), stigmasterol (3), and campesterol (4), the phenanthrenequinones phocanthone (5) and ephemeranthoquinone (8), the stilbenoids stilbostemin J (6) and 3′-O-methylbatatasin III (10), the dihydrophenanthrenes coelonin (11) and lusianthridin (12), and the phenolic acids salicylic acid (7) and phloretic acid (9). Dereplication studies employing ultra-high-performance liquid chromatography coupled with high-resolution time-of-flight mass spectrometry (UHPLC-QToF-HR-MS/MS) enabled the putative identification of additional compounds, the alkaloid feruloytyramine (13), the monoterpene lactone loliolide (14), the nucleoside methylsulfinyladenosine (15), the stilbene gigantol (16), and the phenolic compounds methoxyhydroxytyrosol (17) and syringic acid glucosyl ester (18). Cytotoxicity assays were conducted on human HeLa cancer cells and non-tumor VERO cell lines using the crude extract and fractions. Chemophenetic analysis suggests a close relationship between C. purpurata and the related species C. tigrina and C. intermedia, supported by shared morphological and genetic traits that facilitate even natural hybridization. These findings underscore C. purpurata as a valuable taxon for chemophenetic studies within the Cattleya genus.

本文研究了巴西著名兰科植物紫花兰（catleya purpurata）的植物化学成分、细胞毒活性和化学亲缘关系。尽管紫癜广泛种植用于观赏和商业用途，但紫癜的植物化学特征仍未得到充分研究。植物化学分析导致使用核磁共振（NMR）光谱分离和鉴定了12种化合物：三萜24-亚甲基环醇(1)，甾体β-谷甾醇(2)、豆甾醇(3)和油菜甾醇(4)，菲三醌类化合物phocanthone(5)和ephemeranthoquinone(8)，二苯乙烯类化合物stilbostemin J(6)和3 ' - o -甲基batatasin III(10)，二氢菲酮coelonin（11）和柳绿蓟素（12），酚酸类化合物水杨酸(7)和苯二酚酸(9)。利用超高效液相色谱和高分辨率飞行时间质谱（uhplc - qtof - hrms /MS）进行重复研究，可以推测鉴定出其他化合物，生物碱阿铁酰酪胺（13）、单萜内酯油橄榄内酯（14）、核苷甲基亚砜ladenosine（15）、二苯乙烯巨糖醇（16）、酚类化合物甲氧羟基酪醇（17）和丁香酸葡萄糖基酯（18）。用粗提物和馏分对人HeLa癌细胞和非肿瘤VERO细胞株进行细胞毒性试验。化学遗传学分析表明，紫癜与近缘种C. tigrina和C. intermedia亲缘关系密切，具有共同的形态和遗传特征，有利于自然杂交。这些发现强调了紫癜属植物作为一种有价值的化学遗传学研究分类单元。

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引用次数: 0

Triterpenoid saponins from the seeds of Aralia elata (Miq.) Seem. and their chemotaxonomic significance 楤木种子中的三萜皂苷（Miq.）似乎。以及它们的化学分类意义

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-16 DOI: 10.1016/j.bse.2025.105115

Wu-Di Zhai , Wen-Hao Zong , Bo-Yue Xiao , Chen-Yang Liu , Xiao-Ping Zhang , Yan Zhang

Phytochemical research was conducted on the seeds of Aralia elata (Miq.) Seem., resulting in the isolation of twelve compounds. The chemical structures of the compounds were elucidated through spectral analysis, and the obtained nuclear magnetic resonance (NMR) spectra were systematically compared with published literature values. Among the isolated compounds, compound 1 was an undescribed compound, while compound 6 was isolated for the first time from the genus Aralia. The chemotaxonomic significance was further analyzed and discussed.

对楤木（Aralia elata）种子进行了植物化学研究。似乎。，分离出12个化合物。通过波谱分析对化合物的化学结构进行了解析，并将得到的核磁共振波谱与已发表的文献值进行了系统比较。其中化合物1为未从该属植物中分离得到，化合物6为首次从该属植物中分离得到。进一步分析和讨论了其化学分类学意义。

引用次数: 0

A new norlignan and other compounds from Artemisia frigida Willd 一种新的冷蒿去甲脂素及其它化合物

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-05 DOI: 10.1016/j.bse.2025.105102

Xin-Ya Dong , Ru-Ya Li , Hong-Xia Tang , Ya-Jie Li , Jun Chen , Jin-Guo Luo , Na Yu , Xiang-Wei Xu , Xu-Dong Zhou

Artemisia frigida is an endemic plant that only grows in China and its phytochemistry has never been fully appreciated and sufficiently studied. In the present study, a phytochemical investigation on the aerial parts of A. frigida resulted in the isolation of a new norlignan (1), together with twelve known constituents (2–13). Their structures were established by NMR spectroscopic analysis and comparison of their data with previous literature. Compound 1 existed as racemic mixtures, and all of the compounds were isolated from A. frigida for the first time except compounds 2–5. Moreover, the chemotaxonomic significance corresponding to the above compounds was investigated.

冷蒿（Artemisia frigida）是中国特有的植物，其植物化学性质尚未得到充分认识和研究。在本研究中，对冷田中气生部分进行了植物化学研究，分离出一种新的褐皮素(1)，以及12种已知成分（2-13）。通过核磁共振波谱分析和与文献数据的比较，确定了它们的结构。化合物1为外消旋混合物，除化合物2 ~ 5外，其余化合物均为首次从冷蒿中分离得到。并对上述化合物的化学分类意义进行了探讨。

引用次数: 0

Unveiling chemical and morphological variation in Pimpinella deverroides Boiss.: Insights into Iranian populations and essential oil chemotypes 揭示了斑蝽的化学和形态变异。：了解伊朗人口和精油化学型

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-04 DOI: 10.1016/j.bse.2025.105108

Negin Salahi , Pooran Golkar , Mohammad Hossein Mirjalili

Pimpinella deverroides Boiss. is an important aromatic plant belonging to the Apiaceae family. This study aimed to evaluate the morphological, phytochemical, and essential oils (EOs) variations among nine Iranian Pimpinella deverroides populations (PDPs). Significant variation was observed in morphological traits, as well as in the total contents of phenols, anthocyanins, carotenoids, and chlorophyll. Among the studied populations, PDP4 exhibited superior performance in terms of plant height (108 ± 1.15 cm), number of umbellate (212.3 ± 4.05), plant fresh weight (1048 ± 5.77 g), and plant dry weight (592 ± 4.61 g). The EOs and phenolic acids extracted from air-dried aerial parts were analyzed using chromatographic techniques including GC, GC/MS and HPLC. The highest contents of rutin (2.57 ± 0.035 mg/g DW) and chlorogenic acid (12.43 ± 0.057 mg/g DW) were found in PDP3 and PDP5, respectively. In total, thirty-one compounds representing 90.34–96.73 % of the total EOs composition were identified, with twenty-two compounds shared across all populations. Spathulenol (2.07–17.31 %), γ-eudesmol (1.63–11.91 %), oleic acid (5.02–10.73 %), and δ-cadinene (1.00–7.73 %) were the major compounds identified in the EOs. Oxygenated sesquiterpenes (28.71–47.36 %) and hydrocarbon sesquiterpenes (21.78–35.45 %) were the main groups of compounds in the studied EOs. Three main chemotypes were found to be Chemotype I (spiro[4.4] nona-1,6-diene, valernanone), Chemotype II (oleic acid/spathulenol) and Chemotype III (δ-cadinene, δ-elemene). These findings provide valuable insights for the conservation, utilization, and breeding of superior PDPs for further exploitation and the production of attributed herbal products.

Pimpinella verroides Boiss。是蜂科重要的芳香植物。本研究旨在评价9个伊朗黑毛小蠊种群（pdp）形态、植物化学和精油（EOs）的差异。在形态性状、酚类物质、花青素、类胡萝卜素和叶绿素的总含量方面存在显著差异。其中，PDP4在株高（108±1.15 cm）、伞形花序数（212.3±4.05）、鲜重（1048±5.77 g）和干重（592±4.61 g）方面表现优异。采用气相色谱（GC）、气相色谱/质谱（GC/MS）和高效液相色谱（HPLC）等色谱技术对风干航空部件中提取的EOs和酚酸进行分析。其中芦丁（2.57±0.035 mg/g DW）和绿原酸（12.43±0.057 mg/g DW）含量最高的是PDP3和PDP5。共鉴定出31种化合物，占总成分的90.34 - 96.73%，其中22种化合物为所有种群共有。主要化合物为Spathulenol（2.07 - 17.31%）、γ-eudesmol（1.63 - 11.91%）、油酸（5.02 - 10.73%）和δ-cadinene（1.00 - 7.73%）。氧化倍半萜（28.71 ~ 47.36%）和烃类倍半萜（21.78 ~ 35.45%）是所研究的EOs中主要的化合物类群。三种主要的化学型分别是化学型I（螺[4.4]nona-1,6-二烯，缬草纳米酮），化学型II（油酸/spathulenol）和化学型III （δ-cadine， δ-榄香烯）。这些发现为优质pdp的保护、利用和育种提供了有价值的见解，为进一步开发和生产特色草药产品提供了依据。

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引用次数: 0

Chemical constituents of the vines of Fibraurea recisa Pierre and their chemotaxonomic significance 白纤维藤的化学成分及其化学分类意义

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology

Pub Date : 2025-08-01 DOI: 10.1016/j.bse.2025.105107

Ying Zhang , Huiwen Pang , Tao Wang , Shankui Liu

Phytochemical analysis of the vines of Fibraurea recisa Pierre resulted in the isolation of 12 compounds, including a new degraded sesquiterpene (1), three known degraded sesquiterpenes (2–4), two diterpenes (5–6), four alkaloids (7–10), and two lignans (11–12). Structural elucidation was achieved through comprehensive spectroscopic analysis. Notably, compounds 1–2, 4, 6–7, and 11–12 represent new additions to the Menispermaceae family. This study further evaluates the chemotaxonomic relevance of these isolates, emphasizing their potential as biochemical markers for phylogenetic classification within the genus.

通过植物化学分析，分离得到12个化合物，包括1个新降解倍半萜(1)、3个已知降解倍半萜（2-4）、2个二萜（5-6）、4个生物碱（7-10）和2个木脂素（11-12）。通过全面的光谱分析实现了结构解析。值得注意的是，化合物1-2、4、6-7和11-12是menispermacae科的新成员。本研究进一步评估了这些分离株的化学分类相关性，强调了它们作为该属系统发育分类的生化标记的潜力。

引用次数: 0

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