natural-products Chemistry

9 个科学问题 · 化学 Chemistry

本页目录

为什么大漆涂的器物千年不腐还发亮?

Why do lacquerware objects stay uncorrupted and shiny for millennia?

生漆含漆酚,接触空气后氧化聚合成致密漆膜,耐水耐腐蚀;但漆酚会使部分人过敏起疹。
Raw lacquer contains urushiol, which oxidizes and polymerizes into a dense, water- and corrosion-resistant film; however urushiol can cause allergic dermatitis.
难度 专业 · 适合 大众 CC BY 4.0 · 已核验 · Verified 2026-08-23 · 2 条独立证据
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邢其毅 等,《基础有机化学》第4版,北京大学出版社,2016

Xing Qiyi et al., Basic Organic Chemistry, 4th ed., Peking University Press, 2016

#大漆 #漆酚 #聚合

为什么屠呦呦用乙醚而不是水煮青蒿?

Why did Tu Youyou use ether instead of boiling water to extract artemisinin?

青蒿素受热易破坏,屠呦呦受古法启发用低沸点乙醚低温萃取,保留活性,后改造出双氢青蒿素,拯救无数疟疾病人,获2015诺贝尔奖。
Artemisinin is heat-labile; Tu Youyou used low-boiling ether for low-temperature extraction (inspired by ancient texts), preserving activity, then developed dihydroartemisinin—winning the 2015 Nobel Prize.
难度 专业 · 适合 高中(15-18) CC BY 4.0 · 已核验 · Verified 2026-08-23 · 2 条独立证据
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邢其毅 等,《基础有机化学》第4版,北京大学出版社,2016

Xing Qiyi et al., Basic Organic Chemistry, 4th ed., Peking University Press, 2016

#青蒿素 #屠呦呦 #萃取

青蒿素如何借助疟原虫体内的血红素发挥抗疟活性?

How does artemisinin exploit heme within malaria parasites to exert its antimalarial activity?

青蒿素是一种带有过氧桥的倍半萜内酯。疟原虫消化血红蛋白时会释放游离血红素,其二价铁将过氧桥还原,O-O键均裂后生成高活性碳自由基,这些自由基进而烷基化虫体蛋白质并损伤膜系统,导致疟原虫迅速死亡。过氧桥是活性必需结构,脱氧青蒿素几乎没有活性,这也解释了该药对红内期疟原虫见效快的特点。
Artemisinin is a sesquiterpene lactone containing an endoperoxide bridge. Digestion of hemoglobin by malaria parasites releases free heme, whose ferrous iron reduces the peroxide; cleavage of the O-O bond generates highly reactive carbon-centered radicals that alkylate parasite proteins and damage membranes, rapidly killing the pathogen. The endoperoxide is indispensable for activity, deoxyartemisinin being essentially inactive, which explains the drug's remarkably fast clearance of erythrocytic-stage parasites.
难度 专业 · 适合 高中(15-18) CC BY 4.0 · 已核验 · Verified 2026-11-02
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J. Wang 等,Nature Communications(《自然·通讯》),2015年,第6卷,文章号10111,DOI: 10.1038/ncomms10111

J. Wang et al., "Haem-activated promiscuous targeting of artemisinin in Plasmodium falciparum", Nature Communications, vol. 6, art. 10111, 2015, DOI: 10.1038/ncomms10111

#青蒿素 #过氧桥 #抗疟机理

青霉素为何能选择性杀灭细菌?β-内酰胺环的张力在其作用机理中扮演什么角色?

How does penicillin kill bacteria selectively, and what role does the strain of its β-lactam ring play in the mechanism?

青霉素在大小与电荷分布上酷似肽聚糖侧链末端的D-Ala-D-Ala二肽,因而能进入转肽酶(青霉素结合蛋白)的活性腔。稠合双环骨架把四元β-内酰胺的酰胺键强行扭离平面,酰胺共振被破坏,羰基异常缺电;活性位丝氨酸羟基一旦进攻便开环,生成热力学稳定的无活性酰基酶,交联中断,细菌在渗透压下胀裂。人体细胞没有细胞壁这一靶标,故药物选择性毒性很高。
Penicillin mimics the size and charge distribution of the D-Ala-D-Ala terminus of the peptidoglycan stem, so it enters the active site of transpeptidases (penicillin-binding proteins). Its fused bicyclic framework forces the four-membered β-lactam amide far out of planarity, destroying amide resonance and making the carbonyl highly electrophilic. Attack by the active-site serine opens the strained ring to a thermodynamically stable, inactive acyl–enzyme complex; cross-linking stops and the cell lyses under turgor pressure. Human cells lack a cell wall target, giving the drug its selective toxicity.
难度 专业 · 适合 高中(15-18) CC BY 4.0 · 已核验 · Verified 2026-11-04
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Tipper 与 Strominger,《Mechanism of action of penicillins: a proposal based on their structural similarity to acyl-D-alanyl-D-alanine.》,Proceedings of the National Academy of Sciences 54, 1133-1141,1965 (DOI: 10.1073/pnas.54.4.1133)

Tipper and Strominger, 'Mechanism of action of penicillins: a proposal based on their structural similarity to acyl-D-alanyl-D-alanine.', Proceedings of the National Academy of Sciences 54, 1133-1141, 1965, DOI: 10.1073/pnas.54.4.1133

#β-内酰胺 #转肽酶抑制 #选择性毒性

青蒿素分子里的过氧桥结构,为什么恰恰是它抗疟活性的关键所在?

Why is the endoperoxide bridge in the artemisinin molecule precisely the key to its antimalarial activity?

过氧桥正是青蒿素药效的核心:把这一过氧O-O键还原掉,抗疟活性几乎完全丧失。疟原虫消化血红蛋白时释放大量游离血红素,其中的亚铁离子催化过氧桥断裂,生成碳中心自由基与活性氧;这些物种迅速攻击疟原虫自身的蛋白质和膜脂,虫体随之死亡。人体细胞并不产生游离血红素,所受伤害相对轻微,药物的选择性由此而来。
The endoperoxide O-O bond is the pharmacological heart of artemisinin: reduce it away and antimalarial activity almost vanishes. As the malaria parasite digests hemoglobin it releases free heme, whose ferrous iron cleaves the peroxide bridge to spawn carbon-centered radicals and reactive oxygen species. These quickly attack the parasite's own proteins and membrane lipids, killing it. Human cells generate no free heme and suffer far less damage, which is where the selectivity comes from.
难度 专业 · 适合 高中(15-18) CC BY 4.0 · 已核验 · Verified 2026-11-02
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屠呦呦,《自然·医学(Nature Medicine)》,2011年,第17卷,1217至1220页

Y. Tu, The discovery of artemisinin (qinghaosu) and gifts from Chinese medicine, Nature Medicine, 2011, vol. 17, pp. 1217-1220

#青蒿素 #过氧桥 #自由基机理

为什么大蒜拍碎或切开后味道更冲?

Why does crushed or cut garlic taste much stronger?

蒜瓣完整时前体和酶分开;破坏细胞后酶把前体转化成大蒜素,就是那股辛辣味。
Intact cloves keep precursor and enzyme apart; crushing lets the enzyme make allicin, the pungent compound.
难度 进阶 · 适合 大众 CC BY 4.0 · 已核验 · Verified 2026-08-23 · 2 条独立证据
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邢其毅 等,《基础有机化学》第4版,北京大学出版社,2016

Xing Qiyi et al., Basic Organic Chemistry, 4th ed., Peking University Press, 2016

#大蒜 #大蒜素 #酶

为什么很多有毒植物都是苦的?

Why are many toxic plants bitter?

植物用生物碱等苦味化学物质驱赶动物,人类舌头对苦味敏感也是一种防毒预警。
Plants use bitter alkaloids to deter herbivores, and our sensitivity to bitterness is a built-in toxin warning.
难度 入门 · 适合 幼儿(3-6) CC BY 4.0 · 已核验 · Verified 2026-08-23 · 2 条独立证据
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邢其毅 等,《基础有机化学》第4版,北京大学出版社,2016

Xing Qiyi et al., Basic Organic Chemistry, 4th ed., Peking University Press, 2016

#苦味 #生物碱 #进化

切洋葱为什么会让人流泪?

Why do onions make you cry when cut?

洋葱细胞被破坏时,蒜氨酸酶把前体物质转化成催泪的丙硫醛-S-氧化物,刺激眼睛分泌泪液。
When onion cells are damaged, the enzyme alliinase converts precursors into syn-propanethial-S-oxide, a lachrymator that irritates the eyes and triggers tears.
难度 入门 · 适合 大众 CC BY 4.0 · 已核验 · Verified 2026-08-23 · 2 条独立证据
来源 · Source

邢其毅 等,《基础有机化学》第4版,北京大学出版社,2016

Xing Qiyi et al., Basic Organic Chemistry, 4th ed., Peking University Press, 2016

#洋葱 #催泪 #酶

青霉素真的是一块发霉培养皿带来的偶然吗?后来人们改了它的什么?

Was penicillin really a lucky moldy dish — and what did chemists later change about it?

偶然给了起点:1928年弗莱明休假归来,发现青霉菌落周围的葡萄球菌被溶解,命名青霉素并发表,但提纯卡住。十年后弗洛里与钱恩将其变成药物:冷冻干燥加柱层析得纯品,动物实验与1941年首例病人验证疗效,美国深罐发酵和玉米浆培养基把产量放大千倍以上。化学改造同样关键:天然青霉素F/G不耐胃酸只能注射,经前体添加与半合成改造侧链,得到耐酸的青霉素V和抗青霉素酶的甲氧西林家族。
Chance opened the door: Fleming's 1928 petri dish with bacteria dissolving around a Penicillium colony led to naming the substance, though purification stalled. A decade later Florey and Chain turned it into medicine — freeze-drying and chromatography yielded pure material, animal tests and the first patient in 1941 confirmed it, and deep-tank fermentation with corn-steep liquor in America scaled output a thousandfold. Chemists then did the fine print: natural penicillin dies in stomach acid, so side-chain semisynthesis gave acid-stable penicillin V and the methicillin family resistant to staphylococcal beta-lactamase.
难度 入门 · 适合 大众 CC BY 4.0 · 来源待核验 · Source pending review
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出处备注:此条未指向带版次的可引用著作(通识性内容、机构文件或未展开的英文书名),本库不提供独立书目出处;如需精确引用,需由编辑补全具体篇目与版次。

Fleming,《On the Antibacterial Action of Cultures of a Penicillium»,British Journal of Experimental Pathology 第10卷,1929

A. Fleming, On the Antibacterial Action of Cultures of a Penicillium, British Journal of Experimental Pathology 10, 1929

#青霉素 #半合成抗生素 #发酵工程