無(wú)花果亞屬植物異戊烯基類(lèi)黃酮及其生物活性研究進(jìn)展

盛智麗, 劉俊梅, 高潔, 楊寶

無(wú)花果亞屬植物異戊烯基類(lèi)黃酮及其生物活性研究進(jìn)展

盛智麗1,2, 劉俊梅2, 高潔3, 楊寶1*

(1.中國(guó)科學(xué)院華南植物園，廣東省應(yīng)用植物學(xué)重點(diǎn)實(shí)驗(yàn)室，廣州 510650；2. 吉林農(nóng)業(yè)大學(xué)食品科學(xué)與工程學(xué)院，長(zhǎng)春 130118；3. 華南理工大學(xué)食品科學(xué)與工程學(xué)院，廣州 510641)

無(wú)花果亞屬隸屬于?？疲仁侵匾乃Y源，也是優(yōu)良的中藥資源，廣泛種植于熱帶、亞熱帶地區(qū)，因含有豐富的生物活性成分和保健功效，經(jīng)濟(jì)價(jià)值突出。無(wú)花果亞屬植物中異戊烯基類(lèi)黃酮含量豐富，結(jié)構(gòu)多樣，已報(bào)道有37種異黃酮、2種黃烷酮、7種黃酮和1種查爾酮。無(wú)花果異戊烯基類(lèi)黃酮具有突出的抗氧化活性，能夠緩解更年期癥狀，保護(hù)骨骼、預(yù)防炎癥、預(yù)防癌癥等。從化學(xué)結(jié)構(gòu)和生物活性?xún)煞矫鎸?duì)無(wú)花果亞屬植物的異戊烯基黃酮類(lèi)化合物的研究概況進(jìn)行總結(jié)，以期為該屬植物的開(kāi)發(fā)和利用提供參考。

異戊烯基類(lèi)黃酮；生物活性；?？?；無(wú)花果亞屬；綜述

無(wú)花果亞屬(subgenus)是榕屬(genus)中最大的開(kāi)花植物屬，包含700余種植物[1]。原產(chǎn)于西南亞和地中海地區(qū)，現(xiàn)已在熱帶、亞熱帶及溫帶地區(qū)廣泛種植[2]。無(wú)花果亞屬植物具有重要的食用和藥用價(jià)值[3–4], 其果實(shí)在很多國(guó)家可食用,根和葉則被應(yīng)用于傳統(tǒng)醫(yī)藥。在越南，地果()廣泛用于治療水腫、痢疾、膿皰等病癥[5]，因其提取物具有顯著的抗菌活性[6]，常被用來(lái)提取精油。在印度，對(duì)葉榕()常用于治療皮膚、呼吸系統(tǒng)和泌尿系統(tǒng)等的疾病[7]。作為無(wú)花果亞屬中最具商業(yè)價(jià)值的水果，無(wú)花果()既是口感甜美的水果食品，同時(shí)也具有祛痰、疏肝、消炎、抗癌功效并用于治療肝脾疾病等[8–9]。查閱近年來(lái)國(guó)內(nèi)外對(duì)無(wú)花果亞屬植物化學(xué)成分和生物活性的報(bào)道, 該亞屬植物富含類(lèi)黃酮[10]、三萜、香豆素等活性成分[11–12]。其中，一些香豆素類(lèi)成分，如馬豆素、補(bǔ)骨脂素、香檸檬烯等可減少氧化應(yīng)激，防止胰島細(xì)胞損傷，表現(xiàn)出降血糖活性[13]。部分萜類(lèi)成分,如鮑爾烯醇、羽扇豆醇、齊墩果酸等具有抗氧化、抗炎、保肝等功效[11]。此外，異戊烯基黃酮類(lèi)物質(zhì)是該類(lèi)植物的特征性物質(zhì)，已成為近年來(lái)學(xué)者們關(guān)注的熱點(diǎn)，具有重要的藥用價(jià)值。本文對(duì)無(wú)花果亞屬中異戊烯基黃酮類(lèi)化合物進(jìn)行綜述。

1 結(jié)構(gòu)類(lèi)型

無(wú)花果亞屬植物中，已報(bào)道47個(gè)異戊烯基黃酮類(lèi)化合物。異戊烯基主要存在形式有13種(圖1)，其中二甲基烯丙基是主要的結(jié)構(gòu)類(lèi)型。取代位點(diǎn)發(fā)生在類(lèi)黃酮A環(huán)或B環(huán)，以A-異戊烯基化為主, 最常見(jiàn)的取代位點(diǎn)為A-6位和A-8位；部分取代發(fā)生在B環(huán)上，主要取代位點(diǎn)為B-2?和B-4?處。除異戊烯基取代外，黃酮母核上通常還連有羥基和甲氧基。無(wú)花果亞屬植物異戊烯基黃酮的類(lèi)黃酮骨架類(lèi)型主要以異黃酮為主，還包含少量的黃烷酮、黃酮、查爾酮(圖2, 3)。

2 異戊烯基黃酮類(lèi)成分和生物活性

黃酮類(lèi)化合物是重要天然活性物質(zhì)，安全性好，具有抗腫瘤、抗病毒、抗炎、抗菌等活性。已有化學(xué)及生物活性研究結(jié)果表明，大多數(shù)情況下,異戊烯基基團(tuán)的引入會(huì)增加類(lèi)黃酮的親脂性，改善對(duì)生物膜的親和性，顯著提高生物活性[14–15]。表1列出了已報(bào)道的無(wú)花果亞屬植物異戊烯基類(lèi)黃酮的生物活性。

2.1 雌激素受體調(diào)節(jié)活性

異戊烯基異黃酮是無(wú)花果異戊烯基類(lèi)黃酮的主要結(jié)構(gòu)形式，在結(jié)構(gòu)上與雌激素相似[16]，可以與雌激素、受體結(jié)合，并具有選擇性。通過(guò)發(fā)揮雌激素受體調(diào)節(jié)活性，異戊烯基異黃酮可緩解更年期癥狀，保護(hù)骨骼，預(yù)防乳腺癌[17]等疾病。在已經(jīng)報(bào)道的47種異戊烯基類(lèi)黃酮中，37種為異戊烯基異黃酮。因此，無(wú)花果亞屬植物是豐富的異戊烯基異黃酮資源，可用于功能食品或藥物開(kāi)發(fā)。

圖1 異戊烯基結(jié)構(gòu)

圖2 無(wú)花果亞屬植物異戊烯基類(lèi)黃酮成分結(jié)構(gòu)(1～29)

2.2 抗氧化

氧化損傷是引發(fā)癌癥、心血管疾病、動(dòng)脈粥樣硬化等多種慢性病的重要因素[18]，常常伴隨炎癥的產(chǎn)生。通過(guò)抑制或延遲氧化反應(yīng)來(lái)預(yù)防和治療疾病十分重要[19]。作為膳食抗氧化劑，食源性黃酮類(lèi)成分在減緩氧化損傷中具有重要作用。已有研究表明[5,7,11,20–21]，無(wú)花果中大部分異戊烯基類(lèi)黃酮成分(化合物17、18、21、22、29、35、37、42、45、46、47)表現(xiàn)出優(yōu)良的清除DPPH自由基活性。抗氧化活性強(qiáng)弱和異戊烯基類(lèi)黃酮的母核結(jié)構(gòu)、官能團(tuán)排列、酚羥基數(shù)目直接相關(guān)。B環(huán)羥基與2,3-烯基的存在是影響抗氧化活性的重要因素[22]。此外, Popoola等[23]的研究表明，化合物26還可以抑制酪氨酸酶活性，減少體內(nèi)自由基的積累，進(jìn)而預(yù)防皮膚衰老。

2.3 預(yù)防炎癥

炎癥，通常是機(jī)體對(duì)抗外界感染而產(chǎn)生的防御性免疫反應(yīng)[24]。炎癥失衡可引發(fā)哮喘、糖尿病等多種急、慢性并發(fā)癥[15]。在無(wú)花果異戊烯基類(lèi)黃酮中，17種成分通過(guò)調(diào)節(jié)促炎分子合成和炎癥相關(guān)細(xì)胞因子分泌而表現(xiàn)出抗炎活性。其中，化合物1～15通過(guò)抑制NO的產(chǎn)生而緩解炎癥反應(yīng)[25]?；衔?7對(duì)抑制單核細(xì)胞/巨噬細(xì)胞活化具有重要作用[26]。在這些具有抗炎活性的化合物中，9～11、13表現(xiàn)出強(qiáng)抗炎活性(IC50值<2mol/L)[25]。這幾個(gè)物質(zhì)的類(lèi)黃酮骨架結(jié)構(gòu)與異戊烯基結(jié)構(gòu)特征是影響其抗炎活性的關(guān)鍵因素。

2.4 預(yù)防癌癥

抗炎治療是治療早期腫瘤進(jìn)展和惡性轉(zhuǎn)化的一種有效的治療方法。無(wú)花果異戊烯基類(lèi)黃酮在發(fā)抗炎活性的同時(shí)，也具有抗癌細(xì)胞增殖作用[27]。

圖3 無(wú)花果亞屬植物異戊烯基類(lèi)黃酮成分結(jié)構(gòu)(30～47)

此外，異戊烯基類(lèi)黃酮通過(guò)調(diào)節(jié)不同分子靶點(diǎn)發(fā)揮癌癥預(yù)防作用。主要機(jī)制包括誘導(dǎo)細(xì)胞凋亡、抑制血管生成、調(diào)控遺傳因子、轉(zhuǎn)錄因子等[28]。如化合物16可通過(guò)誘導(dǎo)細(xì)胞中ROS和ERK抑制癌細(xì)胞增殖[29]；化合物44可抑制A549和NCI-292細(xì)胞的增殖[30]?；衔?8通過(guò)誘導(dǎo)肺細(xì)胞、食管鱗狀細(xì)胞、腎細(xì)胞凋亡抗癌[21]；化合物20對(duì)TPA誘導(dǎo)的Raji細(xì)胞中EBV-EA活化的抑制作用明顯[31];化合物35可抑制前列腺癌細(xì)胞系(DU-145)和靜脈內(nèi)皮細(xì)胞系(HUVEC)實(shí)現(xiàn)抗腫瘤和抗血管生成作用[32]；化合物42通過(guò)MAPK和AKT信號(hào)傳導(dǎo)途徑誘導(dǎo)HeLa細(xì)胞凋亡預(yù)防癌癥[33]。

2.5 抗菌活性

不同于常規(guī)藥物，植物類(lèi)黃酮在發(fā)揮抗菌活性的同時(shí)具有較好的安全性，可以選擇性地靶向細(xì)菌細(xì)胞，抑制毒性因子和微生物威脅的同時(shí)，不會(huì)引發(fā)抗生素耐藥性等問(wèn)題[53]，已成為目前最受歡迎的生物抗菌劑之一。無(wú)花果異戊烯基類(lèi)黃酮物質(zhì)中, 化合物18和30對(duì)金黃色葡萄球菌，大腸桿菌、李斯特菌具有抑制作用[30–31]?；衔?7可抑制結(jié)核分岐桿菌[38], 表現(xiàn)出抗結(jié)核作用，可用于開(kāi)發(fā)肺部感染的抗菌藥物。Lopes等[28,33]的研究表明，化合物2和4具有明顯抗真菌活性，可能是由于羥基化程度的增加導(dǎo)致對(duì)微生物的抑制能力提升。此外，化合物21和22也表現(xiàn)出抗菌活性[11]，其抗菌機(jī)理還需進(jìn)一步研究。

2.6 其他活性

Sakat等[7]報(bào)道，化合物31～34和38可通過(guò)抑制-葡萄糖苷酶活性預(yù)防糖尿病。與目前在T2D的治療中使用的-葡萄糖苷酶抑制劑(如阿卡波糖)相比，不產(chǎn)生胃腸道副作用，有希望成為新型和更安全的治療藥物。Jung-Hae等[43]報(bào)道，化合物28可通過(guò)抑制血小板來(lái)預(yù)防血栓。Matsuda等[42]的研究表明，化合物24可抑制d-半乳糖胺誘導(dǎo)的小鼠原代肝細(xì)胞的細(xì)胞毒性，具有保肝作用。Williams等[35]的研究表明，化合物3、25和33可通過(guò)抑制BACE1活性預(yù)防阿爾茲海默癥。

表1 無(wú)花果亞屬植物異戊烯基類(lèi)黃酮

續(xù)表(Continued)

①: 抗炎; ②: 抗細(xì)胞增殖; ③: 抗皮膚炎癥; ④: 預(yù)防阿爾茲海默癥; ⑤: 抗真菌; ⑥: 抗菌; ⑦: 預(yù)防癌癥; ⑧: 保肝作用; ⑨: 預(yù)防糖尿病; ⑩: 預(yù)防血栓; ?: 促進(jìn)骨細(xì)胞增殖; ?: 抗氧化。

①: Anti-inflammatory; ②: Cell proliferation-inhibitory; ③: Anti-dermatitis; ④: Alzheimer’s disease prevention; ⑤: Antifungal activity; ⑥: Antibacterial; ⑦: Cancer prevention; ⑧: Hepatoprotective activity; ⑨: Anti-diabetic; ⑩: Thromboprophylaxis; ?: Proliferation-promote of osteoblast; ?: Antioxidant.

3 展望

因?yàn)楦缓Y(jié)構(gòu)多樣、活性突出的異戊烯基類(lèi)黃酮物質(zhì)，無(wú)花果亞屬植物已成為功能食品、天然藥物領(lǐng)域的重要原料來(lái)源。在未來(lái)研究中，仍需加強(qiáng)對(duì)無(wú)花果亞屬植物的化學(xué)成分發(fā)掘，深入闡明其生物活性作用機(jī)理以及構(gòu)效關(guān)系。相關(guān)研究結(jié)果對(duì)于該亞屬植物的綜合開(kāi)發(fā)與利用具有重要意義。

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Prenylated Flavonoids insubgenus: Chemistry and Bioactivities

SHENG Zhili1,2, LIU Junmei2, GAO Jie3, YANG Bao1*

(1. Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences,Guangzhou 510650, China; 2. College of Food Science and Engineering, Jilin Agricultural University, Changchun 130118, China; 3. College of Food Science and Engineering, South China University of Technology,Guangzhou 510641, China)

Subgenusbelongs to Moraceae, which is an important resource of fruit and herbal medicine.subgenus is widely planted in tropical and subtropical areas. It has outstanding economic value because of abundant bioactive compounds and multiple health benefits. Prenylated flavonoids are the characteristic bioactive compounds ofsubgenus, including 37 isoflavones, 2 flavanones, 7 flavones, and 1 chalcone. Numerous biological activities have been reported for these prenylated flavonoids, such as menopause relief, bone protection, anti-inflammation, anti-oxidation, cancer prevention and anti-bacteria activities. The updated information regarding the prenylated flavonoids insubgenus was summarized, and also their chemical structures and biological activities. The information is helpful for the development and utilization of this subgenus.

Prenylated flavonoid; Biological activity; Moraceae;subgenus; Review

10.11926/jtsb.4496

2021-08-16

2021-10-08

國(guó)家自然科學(xué)基金項(xiàng)目(31871851)資助

This work was supported by the National Natural Science Foundation of China (Grant No. 31871851).

盛智麗, 女，碩士研究生。E-mail: shengzl@scbg.ac.cn

E-mail: yangbao@scbg.ac.cn